ORCID Profile
0000-0002-3425-6552
Current Organisations
The University of Auckland
,
Sekolah Tinggi Ilmu Komunikasi AWS
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Publisher: Elsevier BV
Date: 02-2020
Publisher: Royal Society of Chemistry (RSC)
Date: 2019
DOI: 10.1039/C9MD00305C
Abstract: Close-shelled carbocations DNA intercalators Pr-ADOTA and Pr-DAOTA are very cytotoxic against the cancer cell lines MDA-MB-231 (breast) and HCT116 (colon).
Publisher: Royal Society of Chemistry (RSC)
Date: 27-02-2002
DOI: 10.1039/B200073N
Publisher: MDPI AG
Date: 10-08-2015
DOI: 10.3390/MD13085102
Publisher: Wiley
Date: 26-06-2006
Abstract: The synthesis of several ABE tricyclic analogues 5 , 31 and 32 of the alkaloid methyllycaconitine ( 1 ) is reported. The analogues contain two key pharmacophores: a tertiary N ‐(3‐phenylpropyl) substituent attached to a 3‐azabicyclo[3.3.1]nonane ring system and a 2‐(3‐methyl‐2,5‐dioxopyrrolidin‐1‐yl)benzoate ester. Double Mannich reaction of the cyclic β‐keto esters 6 and 1 7 with the bis(aminol) ether 7 using methyltrichlorosilane as an activating agent provided an efficient method for the construction of the 3‐azabicyclo[3.3.1]nonanes 8 and 18 . Ring‐closing metathesis of the derived dienes 11 , 19 , and 20 afforded the tricyclic ethers 12 , 21 , and 22 , respectively, the C‐8 ester of which was reduced to a hydroxymethyl group to form the ABE tricyclic analogues 13 , 23 , and 24 . Conversion of the alcohol 13 to the anthranilate ester 14 using N ‐(trifluoroacetyl)anthranilic acid followed by fusion with methylsuccinic anhydride afforded the analogue 5 containing the key N ‐(methylsuccinimido)anthranilate pharmacophore. In the case of the alcohols 23 and 24 the 2‐(3‐methyl‐2,5‐dioxopyrrolidin‐1‐yl)benzoate ester pharmacophore was appended by direct esterification with unsaturated acid 28 followed by hydrogenation to the ABE tricyclic compounds 33 and 34 . (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)
Publisher: Elsevier BV
Date: 03-2016
DOI: 10.1016/J.BMC.2016.01.047
Abstract: Seventy nine derivatives of thieno[2,3-b]quinolines, tetrahydrothieno[2,3-b]quinoline, dihydrocyclopenta[b]thieno[3,2-e]pyridine, cyclohepta[b]thieno[3,2-e]pyridine and hexahydrocycloocta[b]thieno[3,2-e]pyridine were either synthesized or obtained commercially and tested for their antiproliferative activity against HCT116, MDA-MB-468 and MDA-MB-231 human cancer cell lines. The most potent eight compounds were active against all cell lines with IC50 values in the 80-250nM range. In general hexahydrocycloocta[b]thieno[3,2-e]pyridines were most active with increasing activity observed as larger cycloalkyl rings were fused to the pyridine ring.
Publisher: Wiley
Date: 26-11-2007
DOI: 10.1002/MRC.2100
Abstract: The 1H and 13C NMR data for 3-azabicyclo[3.3.1]nonanes with OH and OMe substituents at C-6 and C-9 were measured using 1D (DEPT) and 2D (COSY, HSQC, HMBC, NOESY) experiments. Comparison of this NMR data illustrates the effects of stereochemistry and substitution at these positions.
Publisher: International Union of Crystallography (IUCr)
Date: 24-09-2008
Publisher: Elsevier BV
Date: 08-2012
Publisher: Elsevier BV
Date: 2021
Publisher: MDPI AG
Date: 27-10-2022
DOI: 10.3390/MOLECULES27217294
Abstract: C13-norisoprenoids are of particular importance to grapes and wines, as these molecules influence wine aroma and have been shown to significantly contribute to the distinct character of various wine varieties. Blumenol B is a putative precursor to a number of important wine aroma compounds, including the well-known compounds theaspirone and vitispirane. The enantioselective synthesis of (R,R)-blumenol B from commercially available 4-oxoisophorone was achieved using a short and easily scaleable route, which was then successfully applied to the synthesis of poly-deuterated d9-blumenol B.
Publisher: American Chemical Society (ACS)
Date: 22-07-2011
DOI: 10.1021/JO200968F
Abstract: The enantioselective synthesis of three structurally distinct classes of lignan from a single, aza-Claisen-derived, chiral morpholine amide is reported. The class of lignan formed is dependent on the substitution pattern in the aryl rings and choice of protecting group on a key benzylic hydroxyl group. The methodology has been used to asymmetrically synthesize and determine the absolute stereochemistry of lignans (+)-cyclogalgravin 3, (-)-pycnanthulignene A 4, (-)-pycnanthulignene B 5, and (-)-kadangustin J 8.
Publisher: Elsevier BV
Date: 04-2015
Publisher: Georg Thieme Verlag KG
Date: 19-04-2017
Abstract: 1-Arylnaphthalene lignans such as (–)-isoguaiacin and (–)-isogalbulin have been reported to exhibit notable biological properties. While (–)-isoguaiacin has not been previously synthesized, syntheses of (–)-isogalbulin are generally long and produce a mixture of stereoisomers. We herein present the efficient total synthesis of (±)-isoguaiacin and (±)-isogalbulin in seven and eight steps with an overall yield of 46% and 36%, respectively. The reported approach harnesses a hydrogenolysis reaction in acidic conditions, to convert a furan into an arylnaphthalen structure.
Publisher: Wiley
Date: 06-2013
Publisher: American Chemical Society (ACS)
Date: 10-12-2012
DOI: 10.1021/NP300790G
Abstract: A biomimetic synthesis of the biologically active ascidian metabolites thiaplidiaquinones A and B is described. Reaction of geranylbenzoquinone with Et(3)N in CH(2)Cl(2) yielded two isomeric quinones, comprising the benzo[c]chromene-7,10-dione core of the natural products. Subsequent reaction with hypotaurine yielded the title compounds and their dioxothiazino regioisomers.
Publisher: Elsevier BV
Date: 02-2016
DOI: 10.1016/J.BMCL.2015.12.090
Abstract: A range of di- and triaryl benzamides were synthesised to investigate the effect of the presence and nature of a polar sidechain, bonding and substitution patterns and functionalisation of benzylic substituents. These compounds were tested for their antiproliferative activity as well as their DNA binding activity. The most active compounds in all assays were unsymmetrical triaryl benzamides with a bulky or alkylating benzylic substituent and a polar amino sidechain.
Publisher: American Chemical Society (ACS)
Date: 05-12-2022
Publisher: Elsevier BV
Date: 02-2001
Publisher: Royal Society of Chemistry (RSC)
Date: 2019
DOI: 10.1039/C9PY01428D
Abstract: A multifunctional conjugated polymer (CP) of poly(3-hexylthiophene) grafted with photo-patternable and stretchable side chains is reported.
Publisher: Elsevier BV
Date: 04-2022
DOI: 10.1016/J.MSARD.2022.103688
Abstract: Eliciting the research priorities of people affected by a condition, carers and health care professionals can increase research value and reduce research waste. The Cochrane Multiple Sclerosis and Rare Disease of CNS Group, in collaboration with the Cochrane Neurological Sciences Field, launched a priority setting exercise with the aim of prioritizing pressing questions to ensure that future systematic reviews are as useful as possible to the people who need them, in all countries, regardless of their economic status. Sixteen high priority questions on different aspects of MS were developed by members of a multi-stakeholder priority setting Steering Group (SG). In an anonymous online survey translated into 12 languages researchers, clinicians, people with MS (PwMS) and carers were asked to identify and rank, 5 out of 16 questions as high priority and to provide an explanation for their choice. An additional free-text priority research topic suggestion was allowed. The survey was accessible through MS advocacy associations' social media and Cochrane web pages from October 20, 2020 to February 6, 2021. 1.190 responses (86.73% of all web contacts) were evaluable and included in the analysis. Responses came from 55 countries worldwide, 7 of which provided >75% of respondents and 95% of which were high and upper-middle income countries. 58.8% of respondents live in the EU, 23% in the Americas, 8.9% in the Western Pacific, 2.8% in the Eastern Mediterranean and 0.3% in South Eastern Asia. About 75% of the respondents were PwMS. The five research questions to be answered with the highest priority were: Question (Q)1 "Does MRI help predict disability worsening of PwMS?" (19.9%), Q5 "What are the benefits and harms of treating PwMS with one disease-modifying drug compared to another?" (19.3%), Q3 "Does multidisciplinary care by teams of different social and health professionals improve health outcomes and experiences for PwMS?" (11.9%), Q16 "Does psychological health affect disease progression in PwMS?" (9.2%) and Q10 "What are the benefits and harms of exercise for PwMS?" (7.2%). The multivariable logistic regression analysis indicated a significant influence of geographic area and income level on the ranking of Q1 and a marginal for Q16 as top a priority after accounting for the effect of all other predictors. Approximately 50% of the respondents indicated that they had an important additional suggestion to be considered. This international collaborative initiative in the field of MS offers a worldwide perspective on the research questions perceived as pivotal by a geographically representative s le of multiple stakeholders in the field of MS. The results of the survey could guide the prioritization of research on pharmacological and non-pharmacological interventions which could be meaningful and useful for PwMS and carers, avoiding the duplication of efforts and research waste. High quality systematic reviews elicited by priority setting exercises may offer the best available evidence and inform decisions by healthcare providers and policy-makers which can be adapted to the different realities around the world.
Publisher: Royal Society of Chemistry (RSC)
Date: 2019
DOI: 10.1039/C9CC03020D
Abstract: Polysulfides, potential signalling molecules, were synthesised and then found and explored for the first time in yeast.
Publisher: Elsevier BV
Date: 12-2018
Publisher: Elsevier BV
Date: 05-2012
DOI: 10.1016/J.BIOS.2012.03.022
Abstract: There has been an enormous demand for commercial label-free DNA sensors in a erse range of fields including pre-emptive medicine, diagnostics, environmental monitoring, and food industry. Addressing the need for sensitive, selective and facile DNA sensors, we demonstrate a novel switch on/off sensor design that utilizes sandwich hybridization between photoluminescent anionic conjugated polyelectrolyte (CPE) bound captureprobe coated onto magnetic beads, target and the signaling probe. The hybridization-readout in our sensor was monitored by either fluorescence resonance energy transfer (FRET, switch-on) or superquenching (switch-off) depending on the type of signaling probe used. Moreover recent designs that utilize beads for sensing DNA have been limited towards using electrostatic interactions or intercalation of dyes to observe FRET. To our knowledge this is the first report of a switch on/off sensor utilizing either FRET or superquenching thus providing flexibility for future development of such rapid, facile and sensitive DNA sensors. The FRET-based sensor was investigated by optimizing the reaction parameters and selectivity. A low detection limit of 240 fmol in 2 mL of SSC buffer was achieved.
Publisher: Georg Thieme Verlag KG
Date: 10-2008
Publisher: Future Science Ltd
Date: 02-2023
Abstract: Background: It has been demonstrated that the lead compound 2-phenylimidazo[1,2- a]quinoline 1a selectively inhibits CYP1 enzymes. Additionally, CYP1 inhibition has been linked to inducing antiproliferative effects in various breast cancer cell lines as well as relieving drug resistance caused by CYP1 upregulation. Materials & methods: Herein, 54 novel analogs of 2-phenylimidazo[1,2- a]quinoline 1a have been synthesized with varied substitution on the phenyl and imidazole rings. Antiproliferative testing was conducted using 3 H thymidine uptake assays. Results: 2-Phenylimidazo[1,2- a]quinoline 1a and phenyl-substituted analogs 1c (3-OMe), 1n (2,3-napthalene) displayed excellent anti-proliferative activities, demonstrating their potency against cancer cell lines for the first time. Molecular modeling suggested that 1c and 1n bind similarly to 1a in the CYP1 binding site.
Publisher: Elsevier BV
Date: 2018
DOI: 10.1016/J.EJMECH.2017.11.014
Abstract: Drugs which inhibit platelet function are commonly used to prevent blood clot formation in patients with Acute Coronary Syndromes (ACS) or those at risk of stroke. The thieno[3,2-c]pyridine class of therapeutic agents, of which clopidogrel is the most commonly used, target the P2Y
Publisher: Elsevier BV
Date: 2017
DOI: 10.1016/J.BMCL.2016.12.009
Abstract: 3-Amino-2-arylcarboxamide-thieno[2,3-b]pyridines are a known class of antiproliferative compounds with activity against the phospholipase C enzyme. To further investigate the structure activity relationships of these derivatives a series of analogues were prepared modifying key functional groups. It was determined that modification of the 3-amino and 2-aryl carboxamide functionalities resulted in complete elimination of activity, whilst modification at C-5 allowed compounds of greater activity to be prepared.
Publisher: Elsevier BV
Date: 03-2015
Publisher: Wiley
Date: 07-07-2017
Abstract: Ovafolinins A and B, isolated from Lyonia ovalifolia var. elliptica, are lignans that contain a unique bridged structure containing a penta- and tetracyclic benzoxepin and an aryl tetralin. We report the first total synthesis of these natural products in which an acyl-Claisen rearrangement was initially utilized to construct the lignan backbone with correct relative stereochemistry. Judicious use of a bulky protecting group placed reactive moieties in the correct orientation, thereby resulting in a cascade reaction to form the bridged benzoxepin/aryl tetralin from a linear precursor in a single step. Modification of this route allowed the enantioselective synthesis of (+)-ovafolinins A and B, which confirmed the absolute stereochemistry, and comparison of optical rotation suggests that these compounds are found as scalemic mixtures in nature.
Publisher: American Chemical Society (ACS)
Date: 05-08-2021
Publisher: Elsevier BV
Date: 03-2008
Publisher: Wiley
Date: 21-03-2019
Publisher: Elsevier BV
Date: 07-2015
Publisher: Wiley
Date: 06-2018
Publisher: MDPI AG
Date: 27-09-2022
Abstract: This review surveys and summarizes the materials and methods used to make liquid filtration membranes. Ex les of each method including phase inversion, electrospinning, interfacial polymerization, thin film composites, stretching, lithography and templating techniques, are given and the pros and cons of each method are discussed. Trends of recent literature are also discussed and their potential direction is deliberated. Furthermore, the polymeric materials used in the fabrication process of liquid filtration membranes are also reviewed and trends and similarities are shown and discussed. Thin film composites and selective filtration applications appear to be a growing area of research for membrane technology. Other than the required mechanical properties (tensile strength, toughness and chemical and thermal stability), it becomes apparent that polymer solubility and hydropathy are key factors in determining their applicability for use as a membrane material.
Publisher: Elsevier BV
Date: 02-2018
DOI: 10.1016/J.CHROMA.2017.12.065
Abstract: Sesquiterpenes are a widespread class of compounds of increasing interest found in grapes and wines, amongst many other natural sources. Due to a lack of standards and the complexity of the mass spectra fragmentation, accurate quantification of these low concentration compounds had not previously been accomplished. The current paper presents a new method for the concurrent quantification of several sesquiterpenes. The multivariate method optimisation is presented. Synthesised isotopic standards were utilised in conjunction with solid phase microextraction (SPME) and gas chromatography-tandem mass spectrometry (GC-MS/MS) to perform a standard isotope dilution assay (SIDA). The method was successfully applied to several grape must s les of four different cultivar. To the best of our knowledge this was the first time some of these sesquiterpenes were quantified in grape.
Publisher: Beilstein Institut
Date: 26-10-2015
DOI: 10.3762/BJOC.11.215
Abstract: The first total synthesis of the unusual aromatic sesquiterpene panicein A 2 is reported and the structure of the natural product has been confirmed. When tested by the NCI against a range of human cancer cell lines, it was found that panicein A 2 exhibits very little antiproliferative activity at 10 μM – an observation that is at odds with the earlier report that stated panicein A 2 exhibits in vitro cytotoxicity against a number of tumour cell lines.
Publisher: MDPI AG
Date: 13-07-2023
Abstract: 3-Amino-2-arylcarboxamido-thieno[2-3-b]pyridines have been previously described as having potent anti-proliferative activity against MDA-MB-231 and HCT116 cancer cell lines. The mechanism by which these molecules prevent cancer cell growth is proposed to be through interfering with phospholipid metabolism via inhibition of PI-PLC, along with other cellular processes. Previously, 5-cinnamyl derivatives of these thieno[2-3-b]pyridines have been shown to have enhanced anti-proliferative activity compared to compounds lacking this moiety, indicating a tethered aromatic ring is important for this western region of the pharmacophore. Herein, we report the synthesis and biological evaluation of a library of 40 novel thieno[2-3-b]pyridine analogues containing shorter benzoyl or secondary benzyl alcohol tethers at the 5-position, in addition to various substituents on the two phenyl rings present on the molecule. Compounds bearing alcohol functionality had improved efficacy compared to their benzoyl counterparts, in addition to a 2-methyl-3-halogen substitution on the 2-arylcarboxamide ring being important for maximising anti-proliferative activity. The most potent molecules 7h and 7i demonstrated IC50 concentrations of 25–50 nM against HCT116 and MDA-MB-231 cells, a similar level of activity as previous thienopyridine compounds bearing cinnamyl moieties, suggesting that these novel derivatives with shorter tethers were able to maintain potent anti-proliferative activity, while allowing for a more concise synthesis.
Publisher: Elsevier BV
Date: 10-2013
DOI: 10.1016/J.CHROMA.2013.08.066
Abstract: Varietal thiols [3-mercaptohexan-1-ol (3MH), 3-mercaptohexyl acetate (3MHA) and 4-mercapto-4-methylpentan-2-one (4MMP)] have been extensively studied in the recent literature. Nonetheless the hardest obstacle for research focussing on this class of compounds is the lack of quick, user-friendly and sensitive analytical methods. The current paper presents the use of ethyl propriolate (ETP) as a novel derivatising agent to quantify varietal thiols and the first time quantification of the thiol-ETP adducts via gas chromatography-mass spectrometry. Method optimisation including choice of the best SPE cartridge, derivatisation pH and adducts stability is presented. Validation of the method via stable isotope dilution was carried out. Detection limits in both model wine (4MMP 7.2ng/L, 3MHA 40.0ng/L and 3MH 91.2ng/L) and white wine (4MMP 24.5ng/L, 3MHA 120.9ng/L and 3MH 194.6ng/L) for the novel ETP-based method were lower than those obtained with the p-HMB method. Finally, 14 New Zealand Sauvignon blanc were analysed with both the new method and the organo-mercury based procure: good correlations were obtained for 3MH and 3MHA. Detection limits obtained with the new methods, its rapidity and reproducibility make this protocol perfectly suitable for oenological purposes.
Publisher: American Chemical Society (ACS)
Date: 03-03-2022
Abstract: Lyoniresinol and its derivatives are lignans which have been isolated from a plethora of plant species. In addition to exhibiting a range of interesting biological activities including anticancer, anti-inflammatory, antimicrobial, and others, these compounds have also been discovered in wines and spirits and shown to have gustatory effects in these alcoholic matrices. (+)-Lyoniresinol
Publisher: Elsevier BV
Date: 07-2004
Publisher: Elsevier BV
Date: 2016
Publisher: Georg Thieme Verlag KG
Date: 17-01-2017
Publisher: Informa UK Limited
Date: 07-2016
Publisher: MDPI AG
Date: 28-09-2022
Abstract: Due to the role of cancer stem cells (CSCs) in tumor resistance and glycosphingolipid (GSL) involvement in tumor pathogenesis, we investigated the effect of a newly synthesized compound (3-amino-N-(3-chloro-2-methylphenyl)-5-oxo-5,6,7,8-tetrahydrothieno[2,3-b]quinoline-2-carboxamide 1 on the percentage of CSCs and the expression of six GSLs on CSCs and non-CSCs on breast cancer cell lines (MDA-MB-231 and MCF-7). We also investigated the effect of 1 on the metabolic profile of these cell lines. The MTT assay was used for cytotoxicity determination. Apoptosis and expression of GSLs were assessed by flow cytometry. A GC–MS-coupled system was used for the separation and identification of metabolites. Compound 1 was cytotoxic for both cell lines, and the majority of cells died by treatment-induced apoptosis. The percentage of CSCs was significantly lower in the MDA-MB-231 cell line. Treatment with 1 caused a decrease of CSC IV6Neu5Ac-nLc4Cer+ MDA-MB-231 cells. In the MCF-7 cell line, the percentage of GalNAc-GM1b+ CSCs was increased, while the expression of Gg3Cer was decreased in both CSC and non-CSC. Twenty-one metabolites were identified by metabolic profiling. The major impact of the treatment was in glycolysis/gluconeogenesis, pyruvate and inositol metabolism. Compound 1 exhibited higher potency in MBA-MB-231 cells, and it deserves further examination.
Publisher: American Chemical Society (ACS)
Date: 29-08-2012
DOI: 10.1021/JO3011914
Abstract: Nucleophilic addition of Grignard reagents and organolithium species to a 3-silyloxy-3,4,5,6-tetrahydropyridine N-oxide provides trans-2,3-disubstituted N-hydroxypiperidines exclusively. The application of this methodology to the preparation of a ersity of useful trans-2-substituted-3-hydroxypiperidines, a concise synthesis of (+)-swainsonine, and an enantiopure 1-substituted quinolizidine of utility in target-directed synthesis is reported.
Publisher: Elsevier BV
Date: 08-2018
Publisher: International Union of Crystallography (IUCr)
Date: 22-10-2008
Publisher: Springer Science and Business Media LLC
Date: 28-07-2020
Publisher: American Chemical Society (ACS)
Date: 28-11-2018
DOI: 10.1021/ACS.JNATPROD.8B00416
Abstract: 1,4-Benzodioxane lignans are a class of bioactive compounds that have received much attention through the years. Herein research pertaining to both 1,4-benzodioxane flavonolignans and 1,4-benzodioxane neolignans is presented. A novel synthesis of both traditional 1,4-benzodioxane flavonolignans and 3-deoxyflavonolignans is described. The antiviral and cytotoxic activities of 1,4-benzodioxane neolignans were then investigated eusiderins A, B, G, and M, deallyl eusiderin A, and nitidanin, which contain the 1,4-benzodioxane motif but lack the chromanone motif found in the known antiviral flavonolignans, were tested. Notably, it was found that all eusiderin 1,4-benzodioxane neolignans exhibited greater antiviral activity than the potent and well-known silybin flavonolignans. While most modifications of the C-1' side chain did not significantly alter the cytotoxicity or antiviral activity, eusiderin M and nitidanin, which contain an allylic alcohol side chain, had lower cytotoxicity. All the eusiderins had similar antiviral activities, with eusiderin B having the best selectivity index. These results show that the chromanone moiety of the flavonolignans is not essential for bioactivity.
Publisher: American Chemical Society (ACS)
Date: 13-06-2018
DOI: 10.1021/ACS.ACCOUNTS.7B00596
Abstract: The field of bioelectronics involves the fascinating interplay between biology and human-made electronics. Applications such as tissue engineering, biosensing, drug delivery, and wearable electronics require biomimetic materials that can translate the physiological and chemical processes of biological systems, such as organs, tissues. and cells, into electrical signals and vice versa. However, the difference in the physical nature of soft biological elements and rigid electronic materials calls for new conductive or electroactive materials with added biomimetic properties that can bridge the gap. Soft electronics that utilize organic materials, such as conjugated polymers, can bring many important features to bioelectronics. Among the many advantages of conjugated polymers, the ability to modulate the biocompatibility, solubility, functionality, and mechanical properties through side chain engineering can alleviate the issues of mechanical mismatch and provide better interface between the electronics and biological elements. Additionally, conjugated polymers, being both ionically and electrically conductive through reversible doping processes provide means for direct sensing and stimulation of biological processes in cells, tissues, and organs. In this Account, we focus on our recent progress in molecular engineering of conjugated polymers with tunable biomimetic properties, such as biocompatibility, responsiveness, stretchability, self-healing, and adhesion. Our approach is general and versatile, which is based on functionalization of conjugated polymers with long side chains, commonly polymeric or biomolecules. Applications for such materials are wide-ranging, where we have demonstrated conductive, stimuli-responsive antifouling, and cell adhesive biointerfaces that can respond to external stimuli such as temperature, salt concentration, and redox reactions, the processes that in turn modify and reversibly switch the surface properties. Furthermore, utilizing the advantageous chemical, physical, mechanical and functional properties of the grafts, we progressed into grafting of the long side chains onto conjugated polymers in solution, with the vision of synthesizing solution-processable conjugated graft copolymers with biomimetic functionalities. Ex les of the developed materials to date include rubbery and adhesive photoluminescent plastics, biomolecule-functionalized electrospun biosensors, thermally and dually responsive photoluminescent conjugated polymers, and tunable self-healing, adhesive, and stretchable strain sensors, advanced functional biocidal polymers, and filtration membranes. As outlined in these ex les, the applications of these biomimetic, conjugated polymers are still in the development stage toward truly printable, organic bioelectronic devices. However, in this Account, we advocate that molecular engineering of conjugated polymers is an attractive approach to a versatile class of organic electronics with both ionic and electrical conductivity as well as mechanical properties required for next-generation bioelectronics.
Publisher: MDPI AG
Date: 22-11-2018
DOI: 10.3390/MOLECULES23123057
Abstract: Dibenzyl butyrolactone lignans are well known for their excellent biological properties, particularly for their notable anti-proliferative activities. Herein we report a novel, efficient, convergent synthesis of dibenzyl butyrolactone lignans utilizing the acyl-Claisen rearrangement to stereoselectively prepare a key intermediate. The reported synthetic route enables the modification of these lignans to give rise to 5-hydroxymethyl derivatives of these lignans. The biological activities of these analogues were assessed, with derivatives showing an excellent cytotoxic profile which resulted in programmed cell death of Jurkat T-leukemia cells with less than 2% of the incubated cells entering a necrotic cell death pathway.
Publisher: MDPI AG
Date: 26-10-2021
Abstract: Inhibition of phosphatidylcholine-specific phospholipase C (PC-PLC) has previously been shown to be a potential target for novel cancer therapeutics. One downstream consequence of PC-PLC activity is the activation of NF-κB, a nuclear transcription factor responsible for transcribing genes related to oncogenic traits, such as proliferation, angiogenesis, metastasis, and cancer cell survival. Another biological pathway linked to NF-κB is the exogenous delivery of nitric oxide (NO), which decreases NF-κB activity through an apparent negative-feedback loop. In this study, we designed and synthesised 13 novel NO-releasing derivatives of our previously reported class of PC-PLC inhibitors, 2-morpholinobenzoic acids. These molecules contained a secondary benzylamine group, which was readily nitrosylated and subsequently confirmed to release NO in vitro using a DAF-FM fluorescence-based assay. It was then discovered that these NO-releasing derivatives possessed significantly improved anti-proliferative activity in both MDA-MB-231 and HCT116 cancer cell lines compared to their non-nitrosylated parent compounds. These results confirmed that the inclusion of an exogenous NO-releasing functional group onto a known PC-PLC inhibitor enhances anti-proliferative activity and that this relationship can be exploited in order to further improve the anti-proliferative activity of current/future PC-PLC inhibitors.
Publisher: Elsevier BV
Date: 10-2016
Publisher: Elsevier BV
Date: 07-2005
DOI: 10.1016/J.BMC.2005.04.054
Abstract: Bicyclic analogues of methyllycaconitine (MLA), such as 12, have been synthesised that incorporate the C1-OMe substituent present in the natural product. Electrophysiology experiments using Xenopus oocytes expressing nicotinic acetylcholine receptors (nAChRs) were conducted on these analogues and a related tricyclic analogue 2. The most potent compound, 2, was an antagonist at all receptors studied but displayed different antagonist effects at each receptor subtype. This study more clearly defines the biological effects of MLA analogues at nAChRs and demonstrates that these analogues are not selective ligands for the alpha7 nAChR subtype.
Publisher: Royal Society of Chemistry (RSC)
Date: 2018
DOI: 10.1039/C8RA02673D
Abstract: The rise in multidrug resistant bacteria is an area of growing concern and it is essential to identify new biocidal agents.
Publisher: Walter de Gruyter GmbH
Date: 25-03-2012
Abstract: The acyl-Claisen rearrangement, also called a zwitterionic aza-Claisen rearrangement, allows for the synthesis of 2,3- syn -substituted morpholine pent-4-eneamides with high levels of diastereoselectivity. A wide variety of alkyl and aryl substituents can be introduced with yields highly dependent on the stoichiometry of the Lewis acid catalyst. The use of these morpholine amides in the synthesis of the tetrasubstituted tetrahydrofuran lignans fragransin A 2 , talaumidin, and galbelgin is summarized. The conversion of the Claisen-derived amides into aryl tetraline and 1,1-diarylbutanol lignans via alteration of the protecting groups is also described. Nucleophilic addition of an organometallic reagent to the morpholine amide followed by Wacker oxidation of the alkene gives highly substituted 1,4-diketones, which can be easily converted into fully substituted pyrroles.
Publisher: Wiley
Date: 12-12-2007
Publisher: Georg Thieme Verlag KG
Date: 30-09-2010
Publisher: No publisher found
Date: 2022
Abstract: The conformation of a fluorescent polymer, in the solid state or in solution, plays a critical role in the polymer's fluorescent properties. Thus, grafted side chains on a fluorescent polymer can directly influence its optical properties. In this study, the effect of grafted polymeric side chains on the photoluminescent properties of poly(para-phenylene vinylene) (PPV) and poly(para-phenylene ethynylene) (PPE) were investigated. Low- and high-molecular-weight grafts of neutral poly(n-butyl acrylate), cationic poly(trimethylaminoethyl methacrylate) and anionic poly(sulfopropyl acrylate) were grafted onto PPVs and PPEs, and the effect of the grafting on the graft copolymer's absorption and emission wavelengths, the fluorescence intensity and the quantum yield were studied. The results indicate that in the case of the ionic grafts, contrary to the expectations, the polymers have a reduced quantum yield. This contrasts with the copolymers with uncharged side chains (P
Publisher: American Chemical Society (ACS)
Date: 22-12-2020
Publisher: Springer Science and Business Media LLC
Date: 23-06-2021
Publisher: American Chemical Society (ACS)
Date: 13-08-2020
Publisher: American Chemical Society (ACS)
Date: 13-09-2017
DOI: 10.1021/ACS.ORGLETT.7B02644
Abstract: The first total synthesis of (-)-bicubebin A, and two previously unreported dilignans, (-)-bicubebin B and (+)-bicubebin C has been achieved through the dimerization of (-)-cubebin, confirming the structure and absolute stereochemistry of (-)-bicubebin A. Analysis of the data for (-)-bicubebin B showed it matched that of reported compound (-)-cis-cubebin. The NMR data of the subsequently synthesized proposed structure of cis-cubebin confirmed that its original proposed structure was incorrect.
Publisher: Springer Science and Business Media LLC
Date: 27-02-2018
DOI: 10.1007/S10886-018-0936-2
Abstract: Volatiles emitted from unpollinated in situ flowers were collected from two male cultivars, 'M33', 'M91', and one female cultivar 'Zesy002' (Gold3) of kiwifruit (Actinidia chinensis var. chinensis). The s les were found to contain 48 compounds across the three cultivars with terpenes and straight chain alkenes dominating the headspace. Electrophysiological responses of honey bees (Apis mellifera) and bumble bees (Bombus terrestris) to the headspace of the kiwifruit flowers were recorded. Honey bees consistently responded to 11 floral volatiles from Gold3 pistillate flowers while bumble bees consistently responded to only five compounds from the pistillate flowers. Nonanal, 2-phenylethanol, 4-oxoisophorone and (3E,6E)-α-farnesene from pistillate flowers elicited responses from both bee species. Overall, honey bees were more sensitive to the straight chain hydrocarbons of the kiwifruit flowers than the bumble bees, which represented one of the main differences between the responses of the two bee species. The floral volatiles from staminate flowers of the male cultivars 'M33' and 'M91' varied greatly from those of the pistillate flowers of the female cultivar Gold3, with most of the bee active compounds significantly different from those in the Gold3 flower headspace. The total floral emissions of 'M33' flowers were significantly less than those of the Gold3 flowers, while the total floral emissions of the 'M91' flowers were significantly greater than those of the Gold3 flowers.
Publisher: American Chemical Society (ACS)
Date: 17-12-2015
Abstract: Efficient bioinspired syntheses of the biologically active pyridoacridine marine alkaloids demethyldeoxy himedine, deoxy himedine, and himedine are reported. Reaction of styelsamine D, prepared via an optimized route starting from Boc-dopamine, with paraformaldehyde afforded demethyldeoxy himedine and deoxy himedine. Oxidation of the latter using either K3[Fe(CN)6] or DMSO/conc. HCl gave himedine in 8 steps from tryptamine with an overall yield of 14%. The versatility of the method was demonstrated by the synthesis of non-natural ethyl and benzyl congeners of deoxy himedine and himedine.
Publisher: MDPI AG
Date: 11-06-2020
DOI: 10.3390/MOLECULES25112713
Abstract: In an effort to gain more understanding on the structure activity relationship of pseudoceratidine 1, a di-bromo pyrrole spermidine alkaloid derived from the marine sponge Pseudoceratina purpurea that has been shown to exhibit potent biofouling, anti-fungal, antibacterial, and anti-malarial activities, a large series of 65 compounds that incorporated several aspects of structural variation has been synthesised through an efficient, ergent method that allowed for a number of analogues to be generated from common precursors. Subsequently, all analogues were assessed for their antibacterial activity against both Gram-positive (Staphylococcus aureus) and Gram-negative (Escherichia coli) bacteria. Overall, several compounds exhibited comparable or better activity than that of pseudoceratidine 1, and it was found that this class of compounds is generally more effective against Gram-positive than Gram-negative bacteria. Furthermore, altering several structural features allowed for the establishment of a comprehensive structure activity relationship (SAR), where it was concluded that several structural features are critical for potent anti-bacterial activity, including di-halogenation (preferable bromine, but chlorine is also effective) on the pyrrole ring, two pyrrolic units in the structure and with one or more secondary amines in the chain adjoining these units, with longer chains giving rise to better activities.
Publisher: American Chemical Society (ACS)
Date: 11-04-2018
DOI: 10.1021/ACS.BIOMAC.8B00341
Abstract: This research focuses on the design of biocompatible materials/scaffold suitable for use for tissue engineering. Porous fiber mats were produced through electrospinning of polythiophene phenylene (PThP) conducting polymers blended with poly(lactide- co-glycolic acid) (PLGA). A peptide containing an arginylglycylaspartic acid (RGD) fragment was synthesized using solid phase peptide synthesis and subsequently grafted onto a PThP polymer using azide-alkyne "click" chemistry. The obtained RGD functionalized PThP was also electrospun into a fiber mat. The electrospun mats' morphology, roughness and stiffness were studied by means of scanning electron microscopy (SEM) and atomic force microscopy (AFM) and their electroactivity by cyclic voltammetry. The fibers show excellent cytocompatibility in culture assays with human dermal fibroblasts-adult (HDFa) and human epidermal melanocytes-adult (HEMa) cells. The electrospun fibers' roughness and stiffness changed after exposing the fiber mats to the cell culture medium (measured in dry state), but these changes did not affect the cell proliferation. The cytocompatibility of our porous scaffolds was established for their applicability as cell culture scaffolds by means of investigating mitochondrial activity of HDFa and HEMa cells on the scaffolds. The results revealed that the RGD moieties containing PThP scaffolds hold a promise in biomedical applications, including skin tissue engineering.
Publisher: Inderscience Publishers
Date: 2014
Publisher: Elsevier BV
Date: 03-2015
Publisher: Elsevier BV
Date: 08-2002
Publisher: Elsevier BV
Date: 09-2013
Publisher: International Union of Crystallography (IUCr)
Date: 03-05-2008
Publisher: Georg Thieme Verlag KG
Date: 22-06-2005
Publisher: American Chemical Society (ACS)
Date: 10-11-2016
Abstract: The enantioselective synthesis of 2,3-disubstituted benzomorpholines, analogues of 1,4-benzodioxane natural products, has been achieved via addition of electron-rich aromatic donors to acyl-iminium ions derived from benzomorpholine aminols. Subsequent modification of the benzomorpholine scaffold allows side chains mimicking those found in 1,4-benzodioxane lignans to be added. Antiproliferative testing of the prepared analogues showed promising results against MDA-MB-231 and HCT116 cancer cell lines.
Publisher: Elsevier BV
Date: 11-2023
Publisher: Beilstein Institut
Date: 17-02-2015
DOI: 10.3762/BJOC.11.29
Abstract: The synthesis of the unique furo[2,3- b ]chromene ring system found in hyperaspidinols A and B, acylphloroglucinols from Hypericum chinense has been achieved in twelve steps. By comparison of the NMR spectra of the synthesized compounds with those of the natural products, a relative stereochemistry is suggested, especially that of the ketal carbon.
Publisher: American Chemical Society (ACS)
Date: 03-10-2011
DOI: 10.1021/JO201654H
Abstract: Bioassay-directed fractionation of an extract of the New Zealand ascidian Aplidium scabellum has afforded the anti-inflammatory secondary metabolite 2-geranyl-6-methoxy-1,4-hydroquinone-4-sulfate (1) and a family of pseudodimeric meroterpenoids scabellones A (2)-D (5). The benzo[c]chromene-7,10-dione scaffold contained within scabellones A-D is particularly rare among natural products. The structures were elucidated by interpretation of NMR data. Scabellone B was also identified as a moderately potent, nontoxic inhibitor of Plasmodium falciparum.
Publisher: Elsevier BV
Date: 07-2006
Publisher: Elsevier BV
Date: 10-2014
DOI: 10.1016/J.EJMECH.2014.09.001
Abstract: Forty seven thieno[2,3-b]pyridines-2-carboxamides, furo[2,3-b]pyridines-2-carboxamides and tetrahydrothieno[2,3-b]quinolones-2-carboxamides derivatives were synthesized and tested for their antiproliferative activity against the NCI-60 cell lines. The 5-keto-tetrahydrothieno[2,3-b]quinolones-2-carboxamides (series 17) were found to have the greatest activity, with the compound containing a 3-methoxyphenylcarboxamide (compound 17d) being the most active, with GI50 values in the low nanomolar range against a range of cell lines, in particular the melanoma cell line MDA-MD-435 (GI50 - 23 nM) and the breast cancer cell line MDA-MB-468 (GI50 - 46 nM). Molecular modelling of series 17 against phosphoinositide specific-phospholipase C reveals that the side chains of the amino acids His356, Glu341, Arg549 and Lys438 are involved in hydrogen bonding with the ligands as well as a lipophilic pocket is occupied by the phenyl carboxamide moiety.
Publisher: Georg Thieme Verlag KG
Date: 07-09-2015
Publisher: American Chemical Society (ACS)
Date: 19-02-2023
Publisher: MDPI AG
Date: 06-07-2022
Abstract: A process for using grape (Pinot noir) pomace to produce products with improved health-promoting effects was investigated. This process integrated a solid–liquid extraction (SLE) method and a method to acylate the polyphenolics in the extract. This report describes and discusses the methods used, including the rationale and considerations behind them, and the results obtained. The study begins with the work to optimize the SLE method for extracting higher quantities of (+)-catechin, (−)-epicatechin and quercetin by trialing 28 different solvent systems on small-scale s les of Pinot noir pomace. One of these systems was then selected and used for the extraction of the same flavonoids on a large-scale mass of pomace. It was found that significantly fewer quantities of flavonoids were observed. The resultant extract was then subject to a method of derivatization using three different fatty acylating agents. The antiproliferative activities of these products were measured however, the resulting products did not display activity against the chosen cancer cells. Limitations and improvements to the methods in this process are also discussed.
Publisher: Elsevier BV
Date: 03-2003
Publisher: Royal Society of Chemistry (RSC)
Date: 2019
DOI: 10.1039/C9TC00709A
Abstract: This review discusses recent development of conjugated polymer (CP)-based composites, hydrogels and intrinsically stretchable CPs for stretchable organic electronics.
Publisher: Royal Society of Chemistry (RSC)
Date: 2013
DOI: 10.1039/C3PY21090A
Publisher: Elsevier BV
Date: 02-2013
DOI: 10.1016/J.EJMECH.2012.12.013
Abstract: The asymmetric synthesis of 8,4'-oxyneolignans (-)-virolin, (-)-surinamensin and a number of analogues has been achieved. A ergent synthesis was used, with all compounds being elaborated from a single chiral aldehyde derived from ethyl lactate. In the 15 compounds that were tested, the level of substitution on the A-ring was found to directly influence the activity against Leishmania donovani whilst the activity against Plasmodium falciparum was influenced by numerous substitution and stereochemical factors.
Publisher: American Chemical Society (ACS)
Date: 31-08-2020
Publisher: Springer Science and Business Media LLC
Date: 10-03-2016
Publisher: Royal Society of Chemistry (RSC)
Date: 2022
DOI: 10.1039/D2OB00336H
Abstract: A flexible approach to C7 keto dibenzyl butyrolactone lignans was developed and the synthesis of several natural products and their related derivatives is described herein. The developed pathway proceeds through enantioenriched β-substituted butyrolactones, from which facile aldol addition and subsequent oxidation affords the desired benzylic ketone moiety. This methodology was used to complete the first enantioselective total syntheses of three natural products, (+)-7-oxohinokinin, (+)-7-oxoarcitin and (+)-conicaol B, and a further five analogues. The utility of this method was further demonstrated through a 1-2 step modification to access another class of natural product, aryltetralin lignans, allowing the asymmetric total synthesis of (-)-isopolygamain and a polygamain derivative. Anti-proliferative testing determined (-)-isopolygamain was the most active of the compounds prepared, with IC
Publisher: MDPI AG
Date: 07-12-2022
DOI: 10.3390/BIOS12121143
Abstract: Biofouling on surfaces, caused by the assimilation of proteins, peptides, lipids and microorganisms, leads to contamination, deterioration and failure of biomedical devices and causes implants rejection. To address these issues, various antifouling strategies have been extensively studied, including polyethylene glycol-based polymer brushes. Conducting polymers-based biointerfaces have emerged as advanced surfaces for interfacing biological tissues and organs with electronics. Antifouling of such biointerfaces is a challenge. In this study, we fabricated electrospun fibre mats from sulphonated polystyrene-block-poly(ethylene-ran-butylene)-block-polystyrene (sSEBS), infused with conducting polymer poly(3,4-ethylenedioxythiophene) (PEDOT) (sSEBS-PEDOT), to produce a conductive (2.06 ± 0.1 S/cm), highly porous, fibre mat that can be used as a biointerface in bioelectronic applications. To afford antifouling, here the poly(oligo (ethylene glycol) methyl ether methacrylate) (POEGMA) brushes were grafted onto the sSEBS-PEDOT conducting fibre mats via surface-initiated atom transfer radical polymerization technique (SI-ATRP). For that, a copolymer of EDOT and an EDOT derivative with SI-ATRP initiating sites, 3,4-ethylenedioxythiophene) methyl 2-bromopropanoate (EDOTBr), was firstly electropolymerized on the sSEBS-PEDOT fibre mat to provide sSEBS-PEDOT/P(EDOT-co-EDOTBr). The POEGMA brushes were grafted from the sSEBS-PEDOT/P(EDOT-co-EDOTBr) and the polymerization kinetics confirmed the successful growth of the brushes. Fibre mats with 10-mers and 30-mers POEGMA brushes were studied for antifouling using a BCA protein assay. The mats with 30-mers grafted brushes exhibited excellent antifouling efficiency, ~82% of proteins repelled, compared to the pristine sSEBS-PEDOT fibre mat. The grafted fibre mats exhibited cell viability %, comparable to the standard cell culture plate controls. Such conducting, porous biointerfaces with POEGMA grafted brushes are suitable for applications in various biomedical devices, including biosensors, liquid biopsy, wound healing substrates and drug delivery systems.
Publisher: Royal Society of Chemistry (RSC)
Date: 2014
DOI: 10.1039/C3MD00320E
Publisher: American Chemical Society (ACS)
Date: 12-07-2022
Abstract: Electrochemical techniques offer great opportunities for the capture of chemical and biological entities from complex mixtures and their subsequent release into clean buffers for analysis. Such methods are clean, robust, rapid, and compatible with a wide range of biological fluids. Here, we designed an electrochemically addressable system, based on a conducting terpolymer [P(EDOT
Publisher: Elsevier BV
Date: 04-2020
Publisher: Elsevier BV
Date: 2012
Publisher: Elsevier BV
Date: 12-2015
Publisher: MDPI AG
Date: 18-12-2017
Publisher: American Chemical Society (ACS)
Date: 18-08-2016
Publisher: Springer Science and Business Media LLC
Date: 13-06-2023
DOI: 10.1007/S00216-023-04789-2
Abstract: γ-Nonalactone is a linear aliphatic lactone ubiquitous in wine, associated with coconut, sweet, and stone fruit aroma descriptors. Little research has been conducted looking at the importance of this compound to New Zealand (NZ) wine aroma. 2 H 2 13 C 2 -γ-Nonalactone, a novel isotopologue of γ-nonalactone, was synthesised in this work for use in a stable isotope dilution assay (SIDA) for quantification of γ-nonalactone in NZ Pinot noir wines for the first time. Synthesis was carried out using heptaldehyde as the starting material, and 13 C atoms and 2 H atoms were introduced via Wittig olefination and deuterogenation steps, respectively. The suitability of this compound as an internal standard was demonstrated by spiking model wine at normal and elevated conditions during s le preparation, with subsequent analysis via mass spectrometry showing stability of 2 H 2 13 C 2 -γ-nonalactone. A model wine calibration, with concentrations of γ-nonalactone from 0 to 100 µg L −1 , was shown to have excellent linearity ( R 2 0.99), reproducibility (0.72%), and repeatability (0.38%). Twelve NZ Pinot noir wines, representative of a range of NZ Pinot noir–producing regions, prices, and vintages, were analysed by solid-phase extraction–gas chromatography–mass spectrometry (SPE-GC–MS). The concentrations of γ-nonalactone ranged from 8.3 to 22.5 µg L −1 , the latter of which was close to the odour detection threshold of this compound. These findings provide a basis for further research into γ-nonalactone and its impact on NZ Pinot noir aroma and provide a robust method for the quantification of this compound in Pinot noir. Graphical abstract
Publisher: International Union of Crystallography (IUCr)
Date: 12-07-2008
Publisher: Royal Society of Chemistry (RSC)
Date: 2014
DOI: 10.1039/C3MD00290J
Publisher: American Chemical Society (ACS)
Date: 11-02-2015
DOI: 10.1021/ACS.ORGLETT.5B00189
Abstract: The enantioselective synthesis and chiroptic analysis of all members of the rodgersinine family of 1,4-benzodioxane neolignans has been achieved. ECD spectra and optical rotation analysis determined that the previously published stereochemistry of trans-rodgersinines A and B was incorrect. The cis-rodgersinines A and B did not follow the model ECD study commonly used to assign the absolute stereochemistry of 1,4-benzodioxane natural products. This finding has implications on the absolute stereochemistry of other natural products of this type. Additionally, the rodgersinines were found to have anti-HCV activities.
Publisher: Elsevier BV
Date: 07-2016
DOI: 10.1016/J.BMC.2016.05.024
Abstract: Biological screening of a library of synthesized benzo[c]chromene-7,10-dione natural products against human farnesyltransferase (FTase) has identified tecomaquinone I (IC50 of 0.065±0.004μM) as being one of the more potent natural product inhibitors identified to date. Anti-plasmodial screening of the same library against a drug-resistant strain of Plasmodium falciparum identified the structurally-related dichromenol tectol as a moderately active growth inhibitor with an IC50 3.44±0.20μM. Two novel series of analogues, based on the benzo[c]chromene-7,10-dione scaffold, were subsequently synthesized, with one analogue exhibiting farnesyltransferase inhibitory activity in the low micromolar range. A preliminary structure-activity relationship (SAR) study has identified different structural requirements for anti-malarial activity in comparison to FTase activities for these classes of natural products. Our results identify tecomaquinone I as a novel scaffold from which more potent inhibitors of human and parasitic FTase could be developed.
Publisher: Royal Society of Chemistry (RSC)
Date: 2015
DOI: 10.1039/C5NP00048C
Abstract: This review describes the evolution of synthetic methods towards 1,4-benzodioxane lignan natural products, from early biomimetic approaches to recent enantiospecific syntheses. Additionally, a comprehensive report of their biosynthesis and significant biological activities is detailed.
Publisher: Walter de Gruyter GmbH
Date: 20-05-2015
Abstract: The development of highly sensitive and selective DNA sensors has fuelled applications in a wide range of fields including medical diagnostics, forensics, biodefense, food contamination and environment monitoring. We demonstrate a novel superquenching based DNA sensor with “switch-on” readout using poly( p -phenylenevinylene) (PPV) coated magnetic beads (PPV-MagSi) and quencher functionalized tentacle probes (TP). The sensor design utilizes signal lification properties of PPV and cooperativity of TPs to monitor hybridization of target oligonucleotides (ONs). The switch-on sensor exhibits excellent sensitivity and selectively discriminates mismatches in the target DNA sequence. Two novel anionic PPVs – poly (6,6′-((2-methyl-5-(( E )-4-(( E )-prop-1-en-1-yl)styryl)-1,4-phenylene)-bis(oxy) dihexanoic acid) ( PMDH ) and poly (6,6′-((2-(( E )-2,5-bis(2-methoxyethoxy)-4-(( E )-prop-1-en-1-yl)styryl)-5-methyl-1,4-phenylene)-bis-(oxy)) di-hexanoic acid) ( PDMonoG ) were tested and compared against each other as part of the sensor design. The employed hairpin TPs possess further advantages of avoiding labelling of target ON, increased selectivity and sensitivity faster assay time, and capability of magnetically controlled deployment and separation of PPV-MagSi beads.
Publisher: Wiley
Date: 17-09-2019
DOI: 10.1002/JSFA.9983
Abstract: Dimethyl sulfide (DMS) is a small sulfur-containing impact odorant, imparting distinctive positive and / or negative characters to food and beverages. In white wine, the presence of DMS at perception threshold is considered to be a fault, contributing strong odors reminiscent of asparagus, cooked cabbage, and creamed corn. The source of DMS in wine has long been associated with S-methyl-l-methionine (SMM), a derivative of the amino acid methionine, which is thought to break down into DMS through chemical degradation, particularly during wine ageing. We developed and validated a new liquid chromatography-tandem mass spectrometry (LC-MS/MS) method with a stable isotope dilution assay (SIDA) to measure SMM in grape juice and wine. The application of this new method for quantitating SMM, followed by the quantitation of DMS using headspace-solid phase micro-extraction coupled with gas chromatography-mass spectrometry (HS-SPME/GC-MS), confirmed that DMS can be produced in wine via the chemical breakdown of SMM to DMS, with greater degradation observed at 28 °C than at 14 °C. Further investigation into the role of grape juice and yeast strain on DMS formation revealed that the DMS produced from three different Sauvignon blanc grape juices, either from the SMM naturally present or SMM spiked at 50 mmol L This study confirms the existence of a chemical pathway to the formation of DMS and reveals a yeast-mediated mechanism towards the formation of DMS from SMM during alcoholic fermentation. © 2019 Society of Chemical Industry.
Publisher: Wiley
Date: 2007
DOI: 10.1002/MRC.2027
Abstract: The 1H and 13C NMR data for 3-azabicyclo[3.3.1]nonanes having C-1 methylsuccinimidoanthranilate esters and C-6 methyl ethers were measured and assigned using 1D (DEPT) and 2D (COSY, HSQC, HMBC, NOESY) experiments. Comparison of this with previously published data illustrates the effects of stereochemistry and substitution on the basic heterocyclic framework.
Publisher: Elsevier BV
Date: 07-2016
DOI: 10.1016/J.BMCL.2016.05.026
Abstract: A series of pyrrole analogues of combretastatin (CA-4) were synthesized and tested for their anti-proliferative activity. The highly diastereoselective acyl-Claisen rearrangement was used to provide 2,3-syn disubstituted morpholine amides which were used as precursors for the various analogues. This synthesis allows for the preparation of 1,2- and 2,3-diaryl-1H-pyrroles which are both geometrically similar to CA-4. These pyrrolic analogues were tested for their anti-proliferative activity against two human cell lines, K562 and MDA-MB-231 with 2,3-diaryl-1H-pyrrole 35 exhibiting the most potent activity with IC50 value of 0.07μM against MDA-MB-231 cell line.
Publisher: Elsevier BV
Date: 12-2015
Publisher: Elsevier BV
Date: 04-2017
Publisher: International Union of Crystallography (IUCr)
Date: 08-09-2007
Publisher: Elsevier BV
Date: 09-2017
DOI: 10.1016/J.PHYTOCHEM.2017.05.011
Abstract: In situ flower volatiles from six kiwifruit cultivars (Actinidia chinensis var. deliciosa) 'Hayward', 'Chieftain', 'M56', 'Zes007' (Green11), 'M36', and 'M43' were collected by dynamic headspace s ling. Forty-five compounds were detected in the headspace of the flowers, with straight chain hydrocarbons and terpenes accounting for >98% of the volatiles emitted quantitatively across the six cultivars. Of these hydrocarbons, (3Z,6Z,9Z)-heptadecatriene is reported for the first time from a floral source while (8Z)-hexadecene and (9Z)-nonadecene are reported for the first time from kiwifruit flowers. All three hydrocarbons were verified by synthesis. Quantitative comparison of the six honey bee perceived compounds from the headspace of the cultivars showed that the males 'M36' and 'M43' closely matched the female cultivar Green11 that they are used to pollinate. Males 'M56' and 'Chieftain' were not as closely matched to the female cultivar 'Hayward' that they are used to pollinate. The male 'M56' in particular differed significantly from the female 'Hayward' in four of the six honey bee perceived compounds.
Publisher: MDPI AG
Date: 06-01-2023
DOI: 10.3390/IJMS24021167
Abstract: Dibenzylbutyrolactone lignans (DBLs) are a class of natural products with a wide variety of biological activities. Due to their potential for the development of human therapeutic agents, DBLs have been subjected to various SAR studies in order to optimise activity. Previous reports have mainly considered changes on the aromatic rings and at the benzylic carbons of the compounds, whilst the effects of substituents in the lactone, at the C-9′ position, have been relatively unexplored. This position has an unexploited potential for the development of novel dibenzyl butyrolactone derivatives, with previous preliminary findings revealing C-9′-hydroxymethyl analogues inducing programmed cell cycle death. Using the core structure of the bioactive natural product arctigenin, C-9′ derivatives were synthesised using various synthetic pathways and with prepared derivatives providing more potent anti-proliferative activity than the C-9′-hydroxymethyl lead compound.
Publisher: Georg Thieme Verlag KG
Date: 13-11-2012
Publisher: MDPI AG
Date: 22-06-2021
Abstract: The adhesion of cancer cells to vascular endothelium is a critical process in hematogenous metastasis and might be similar to the recruitment of leukocytes at the site of inflammation. It is mediated by E-selectin and its ligands, of which the most stereospecific is a glycoconjugate sialyl Lewis x (CD15s), which may be expressed as an oligosaccharide branch of the CD44 glycoprotein, as well as a self-contained glycosphingolipid. It is also known that increased sialylation of glycoconjugates is a feature of malignant cells. The aim of the study was to analyse the effect of a novel thieno[2,3-b]pyridine, compound 1, in MDA-MB-231 triple-negative breast cancer cells (TNBCs) upon CD15s and CD44 expression in different cell subpopulations using flow cytometry. CD15s expression was compared between mesenchymal-like cancer stem cells (CSC, CD44+CD24−), epithelial cells without CD44 (CD44−CD24+ and CD44−CD24−), and CD44+CD24+ cells that exhibit mesenchymal and epithelial features. In addition, expression of CD44 in CD15s+CSC and CD15s−CSC was determined. Compound 1 significantly decreased the percentage of CD15s+CSC, CD15s+CD44+CD24+, and CD15s+CD44− subpopulations, as well as the expression of CD15s in CD44+CD24+ and CD44− cells, and therefore shows potential as a treatment for TNBC.
Publisher: Royal Society of Chemistry (RSC)
Date: 2017
DOI: 10.1039/C7PY00919D
Abstract: Polymers with thermoresponsive properties have received a strong interest due to their potential applications.
Publisher: American Chemical Society (ACS)
Date: 14-12-2020
Publisher: Elsevier BV
Date: 10-2015
Publisher: Elsevier BV
Date: 03-2020
Publisher: Royal Society of Chemistry (RSC)
Date: 2021
DOI: 10.1039/D0AY02208J
Abstract: In this manuscript, we report our work in the development and optimisation of a MALDI-TOF mass spectrometry assay to monitor the kinetics and inhibition of PC-PLC, a phospholipase that catalyses the hydrolysis of phosphatidylcholines.
Publisher: MDPI AG
Date: 26-11-2021
DOI: 10.3390/PHARMACEUTICS13122020
Abstract: The compounds 2-amino-3-carboxamido-thieno[2,3-
Publisher: Royal Society of Chemistry (RSC)
Date: 2004
DOI: 10.1039/B401119H
Abstract: The synthesis of several ABE tricyclic analogues of the alkaloid methyllycaconitine 1 is reported. The analogues contain two key pharmacophores: a homocholine motif formed from a tertiary N-ethyl amine in a 3-azabicyclo[3.3.1]nonane ring system and a 2-(3-methyl-2,5-dioxopyrrolidin-1-ly)benzoate ester 4. The synthesis of the ABE tricyclic analogues of MLA 1 began with selective allylation at C-3 of 3 to produce allyl beta-keto ester 4. Double Mannich reaction of 4 with ethylamine and formaldehyde produced bicyclic amine 5 The C-9 ketone of bicyclic amine 5 was selectively reduced to form bicyclic alcohols 6 and 7 which were subsequently allylated to form dienes 8 and 9. Ring closing metathesis of dienes 8 and 9 afforded tricyclic ethers 11 and 12, respectively, the C-8 ester of which was reduced to a hydroxymethyl group to form ABE tricyclic analogues 13 and 14. Addition of allylmagnesium bromide to the C-9 ketone of 20 afforded dienes 21 and 22, which underwent ring closing metathesis to form tricyclic esters 23 and 24, respectively. Reduction of the C-8 ethyl ester of 23 and 24 to a hydroxymethyl group afforded diols 25 and 26 respectively. The 2-(3-methyl-2,5-dioxopyrrolin-1-ly)benzoate ester was introduced by conversion of alcohols 13, 14, 25 and 26, to the anthranilate esters 16, 17, 27 and 28 using N-(trifluoroacetyl)anthranilic acid 15 followed by fusion with methylsuccinic anhydride to afford the substituted anthranilates 18, 19, 29 and 30 containing the key 2-(3-methyl-2,5-dioxopyrrolidin-1-ly)benzoate ester pharmacophore.
Publisher: Georg Thieme Verlag KG
Date: 11-10-2016
Publisher: Wiley
Date: 09-12-2013
Publisher: Wiley
Date: 04-12-2019
Abstract: Here, the synthesis of a novel poly(pyrrole phenylene) (PpyP) that is both modular in ways of functionalization and soluble in organic solvents is reported, and therefore solution processable. This is achieved through the functionalization of the side-chain substituents in pyrrole phenylene (PyP) repeating units.
Publisher: Elsevier BV
Date: 02-2020
DOI: 10.1016/J.EJMECH.2019.111919
Abstract: Phosphatidylcholine-specific phospholipase C (PC-PLC) is a promising target for new anticancer treatment. Herein, we report our work in the discovery of novel drug-like PC-PLC inhibitors. Virtual screening led to the identification of promising hits from four different structural series that contain the molecular scaffold of benzenesulphonamides (10), pyrido[3,4-b]indoles (22), morpholinobenzoic acid (84) and benzamidobenzoic acid (80). 164 structural analogues were tested to investigate the chemical space around the hit series and to generate preliminary structurally activity relationships (SAR). Two of the pyrido[3,4-b]indoles (22_10 and 22_15) had comparable or better potency as D609, an established but non-drug-like PC-PLC inhibitor. Furthermore, three morpholinobenzoic acids (84, 84_4 and 84_5) had superior potency than D609. Therefore, this study paves the way towards the development of drug-like PL-PLC inhibitors as potential anticancer agents.
Publisher: International Union of Crystallography (IUCr)
Date: 08-09-2007
Publisher: Elsevier BV
Date: 08-2016
Publisher: Elsevier BV
Date: 02-2012
Publisher: Elsevier BV
Date: 05-2021
Publisher: Elsevier BV
Date: 2018
Publisher: Springer Science and Business Media LLC
Date: 19-05-2023
Publisher: Elsevier BV
Date: 08-2010
Publisher: Elsevier BV
Date: 10-2012
DOI: 10.1016/J.JPHOTOBIOL.2012.07.003
Abstract: Most of the clinically used anticancer drugs exert their antitumor effect by damaging the replication machinery of DNA either by covalent or non-covalent binding. Intercalation and groove fitting are the major modes of non-covalent interaction. Small crescent shaped molecules have been claimed to bind with DNA via minor grooves. A plethora of hybrid molecules based on distamycin or netropsin have been synthesised with the objectives of improved selectivity and specificity with no/reduced unwanted side effects. This review critically and objectively describes the previously known hybrid DNA minor groove binding agents based on five membered, distamycin or netropsin. Moreover, the future use of six-membered benzamides has also been highlighted. Special emphasis has been put on developing structure-activity relationships of DNA minor groove binding agents.
Publisher: International Union of Crystallography (IUCr)
Date: 13-06-2008
Publisher: Elsevier BV
Date: 06-2009
Publisher: American Chemical Society (ACS)
Date: 11-04-2019
Abstract: Aristolactams are an important subgroup of aporphinoids, which all share a common phenanthrene chromophore motif that is thought to be responsible for the range of interesting physicochemical and biological properties exhibited by these compounds. Among all of the aristolactams discovered, (+)-aristolactam GI displays a unique structural feature of having the aristolactam scaffold linked via a benzodioxane ring to a phenyl propanoid unit, resulting in the compound being an aporphinoid-lignan hybrid. The synthesis of (+)-aristolactam GI was achieved first by synthesis of an orthogonally protected aristolactam, which was prepared using a Suzuki/aldol cascade to convert a differentially protected isoindolin-1-one to the required phenanthrene. The required enantiopure phenyl propanoid unit was prepared from readily available ( R)-methyl lactate. A selective Mitsunobu reaction was used to combine these two key fragments, prior to the formation of the linking benzodioxane in the final step. The absolute stereochemistry of the natural product was confirmed to be 7' S, 8' S.
Publisher: Wiley
Date: 25-07-2006
DOI: 10.1002/MRC.1878
Abstract: The 1H and 13C NMR spectra of 3-azabicyclo[3.3.1]nonanes with various oxygenated substituents at C-6 were assigned using 1D (DEPT) and 2D (COSY, HSQC, HMBC, NOESY) experiments. Close examination of this NMR data details the effects of substitution and stereochemistry at C-6 in these compounds.
Publisher: MDPI AG
Date: 11-04-2019
DOI: 10.3390/MOLECULES24071424
Abstract: The 13 research articles/communications, six reviews, and one perspective that comprise this Special Issue on Lignans, highlight the most recent research and investigations into this erse and important class of bioactive natural products [...]
Publisher: MDPI AG
Date: 27-01-2022
DOI: 10.3390/MOLECULES27030836
Abstract: 3-Amino-2-arylcarboxamido-thieno[2,3-b]pyridines have been shown to have anti-proliferative activity, but are also known to have poor solubility. This has been previously proposed to be due to their extensive planarity, which allows for intermolecular stacking and crystal packing. We herein report the synthesis of fifteen novel thieno[2,3-b]pyridines that have incorporated bulky, but easily cleavable, ester and carbonate functional groups in an effort to decrease crystal packing. The addition of these ‘prodrug-like’ moieties into the thieno[2,3-b]pyridine resulted in compounds with increased activity against HCT-116 colon cancer cells and the triple-negative breast cancer cell line MDA-MB-231.
Publisher: Elsevier BV
Date: 07-2012
Publisher: American Chemical Society (ACS)
Date: 06-08-2020
Publisher: MDPI AG
Date: 14-03-2021
DOI: 10.3390/MOLECULES26061608
Abstract: Quercetin is a flavonoid that is found in many plant materials, including commonly eaten fruits and vegetables. The compound is well known for its wide range of biological activities. In this study, 5-O-acyl derivatives of quercetin were synthesised and assessed for their antiproliferative activity against the HCT116 colon cancer and MDA-MB-231 breast cancer cell lines and their radical scavenging activity against the 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) (ABTS) radical cation and 2,2-diphenyl-1-picrylhydrazyl (DPPH) radical species. Four derivatives were found to have improved the antiproliferative activity compared to quercetin whilst retaining radical scavenging activity.
Publisher: MDPI AG
Date: 11-01-2018
Publisher: Wiley
Date: 09-08-2018
DOI: 10.1002/POLA.29087
Publisher: MDPI AG
Date: 18-10-2016
DOI: 10.3390/POLYM8100365
Publisher: Wiley
Date: 30-03-2009
Abstract: The synthesis of AE and BE analogues of the alkaloid methyllycaconitine is reported. The analogues contain two key pharmacophores: a 2‐(2‐methylmaleimido)benzoate ester and a homocholine motif formed from a tertiary N ‐(3‐phenylpropyl)amine incorporated into either a 3‐azabicyclo[3.3.1]nonane (AE) or octahydroquinoline (BE) ring system. An additional aromatic group is introduced into the AE bicyclic system using a Horner–Wadsworth–Emmons reaction. The BE analogues are synthesised by a one‐pot cyclisation using ethyl α‐(bromomethyl)acrylate, a primary amine and cyclohexanone leading to an efficient assembly of an octahydroquinoline ring system that mimics the BE‐rings of methyllycaconitine. In both the AE and BE analogues, the key 2‐(2‐methylsuccinimido)benzoate ester pharmacophore is introduced by esterification of the alcohol precursors with 2‐(2‐methylmaleimido)benzoic acid ( 10 ) under Steglich conditions followed by hydrogenation over palladium on charcoal.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
Publisher: American Chemical Society (ACS)
Date: 04-12-2020
DOI: 10.1021/ACS.JMEDCHEM.9B01694
Abstract: Cell-penetrating peptide conjugated peptide aldehydes
Publisher: Elsevier BV
Date: 04-2013
Publisher: Informa UK Limited
Date: 03-2017
DOI: 10.2147/DDDT.S121122
Publisher: Georg Thieme Verlag KG
Date: 11-11-2009
Publisher: Elsevier BV
Date: 11-2018
Publisher: Elsevier BV
Date: 10-2011
Publisher: American Chemical Society (ACS)
Date: 18-04-2023
Publisher: Royal Society of Chemistry (RSC)
Date: 2015
DOI: 10.1039/C5MD00245A
Abstract: The thieno[2,3- b ]pyridines bind to TDP1 with the best analogue 9d with IC 50 at 0.5 μM.
Publisher: American Chemical Society (ACS)
Date: 30-08-2012
DOI: 10.1021/JO3015006
Abstract: The enantioselective synthesis of (-)-eusiderins A (1), B (2), G (25), L (23), M (5) and (+)-eusiderin C (20) and a range of analogues was undertaken using an efficient, ergent synthesis all from a single chiral aldehyde 15, which was derived from (S)-ethyl lactate 9. A comprehensive set of NMR data along with ECD spectra and optical rotation measurements of the synthesized natural products and analogues were then obtained. This data confirmed the absolute stereochemistry of eusiderins A (1) and C (20) and for the first time gives the ECD and optical rotation for eusiderins B (2), G (25), L (23), and M (5) and a range of other substituted 1,4-benzodioxanes. This data will now allow for the determination of absolute stereochemistry of other members in this class of compound.
Publisher: American Chemical Society (ACS)
Date: 13-10-2017
Publisher: Elsevier BV
Date: 08-2017
DOI: 10.1016/J.BMC.2017.06.029
Abstract: Marine meroterpenoids, thiaplidiaquinones A and B and their respective non-natural dioxothiazine regioisomers have been shown to inhibit mammalian and protozoal farnesyltransferase (FTase) with the regioisomers exhibiting activity in the nanomolar range. In order to explore the structure-activity relationship (SAR) of this class of marine natural products, analogues of thiaplidiaquinones A and B and their regioisomers were synthesised, with variation in the number of isoprene units present in their side chains to afford prenyl and farnesyl analogues. The previously reported geranyl series of compounds were found to be the most potent FTase inhibitors closely followed by the novel farnesyl series. The prenyl series exhibited the most potent anti-plasmodial activity but the series was also the most cytotoxic. Overall, the farnesyl series exhibited moderate anti-plasmodial activity with one analogue, 14 also exhibiting low cytotoxicity, identifying it as a scaffold worthy of further exploration.
Publisher: International Union of Crystallography (IUCr)
Date: 27-09-2008
Publisher: Royal Society of Chemistry (RSC)
Date: 2018
DOI: 10.1039/C8SM00777B
Abstract: We investigate the effect of side chain length on the chain shape and thin film behaviour of conjugated graft copolymers.
Publisher: Royal Society of Chemistry (RSC)
Date: 2017
DOI: 10.1039/C7OB01122A
Abstract: Synthesis of the antimicrobial marine natural product halocyamine A has been achieved utilizing a combination of Sonogashira coupling, ruthenium complex/ytterbium triflate catalyzed hydroamidation and solid-phase peptide synthesis (SPPS) chemistry. The synthetic natural product exhibited only modest levels of antibacterial activities but significant antioxidant activity.
Start Date: 2016
End Date: 2019
Funder: Marsden Fund
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