ORCID Profile
0000-0002-0475-0605
Current Organisation
Boron Molecular Pty Ltd
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Publisher: Elsevier BV
Date: 03-2002
DOI: 10.1016/S0031-9422(02)00009-2
Abstract: Extracts of stems of growing shoots of Populus deltoides and P. trichocarpa, and developing capsules of P. deltoides were analysed for gibberellins (GAs) by gas chromatography-mass spectrometry. The following known GAs were identified by comparison of their Kovats retention indices (KRIs) and mass spectra with those of standards: GA1, GA8, GA9, GA19, GA20, 16 beta,17-dihydro-17-hydroxy GA20, GA23, GA28, GA29, GA34, GA44, and GA97. Several of these have not been previously reported from Populus. In addition, two new GAs were identified as 12 beta-hydroxy GA53 (GA127) and 16 beta,17-dihydro-17-hydroxy GA53 and their structures were confirmed by partial synthesis. Evidence was found of 16,17-dihydro-16,17-dihydroxy GA9, 16,17-dihydro-16,17-dihydroxy GA12, 12-hydroxy GA14, and GA34-catabolite by comparison of mass spectra and KRIs with published data. Several putative GAs (hydroxy- and dihydroxy-GA12-like) were also found. The catabolites of active GAs or of key precursors, hydroxylated at C-2 in stems and either C-2, C-12, C-17, or C-16,17 in capsules, were the major proportion of the GAs.
Publisher: American Chemical Society (ACS)
Date: 21-11-2007
DOI: 10.1021/JO701995U
Abstract: The construction of the hetisane group of alkaloids, of which the extensively bridged nominine 17 is the simplest member, poses the ultimate challenge for those interested in the synthesis of the C20 diterpene alkaloids. We describe the synthesis of an advanced intermediate toward this goal. The key steps include reductive acylation, reductive deoxygenation, Birch reduction, and an intramolecular Lewis acid-catalyzed 1,6-addition of a carbamate to a dienone.
Publisher: American Chemical Society (ACS)
Date: 14-07-2014
DOI: 10.1021/LA5007296
Abstract: The purpose of this work was to synthesize and screen, for their effectiveness to act as T1-enhancing magnetic resonance imaging (MRI) contrast agents, a small library of nitroxide lipids incorporated into cubic-phase lipid nanoparticles (cubosomes). The most effective nitroxide lipid was then formulated into lower-toxicity lipid nanoparticles (hexosomes), and effective MR contrast was observed in the aorta and spleen of live rats in vivo. This new class of lower-toxicity lipid nanoparticles allowed for higher relaxivities on the order of those of clinically used gadolinium complexes. The new hexosome formulation presented herein was significantly lower in toxicity and higher in relaxivity than cubosome formulations previously reported by us.
Publisher: CSIRO Publishing
Date: 2011
DOI: 10.1071/CH11204
Abstract: A high yielding practical three-step procedure, which relies on an extractive work-up procedure, has been developed to convert N-phenylsulfonyl-trans-4-hydroxy-l-proline to N-phenylsulfonyl-cis-4-hydroxy-l-proline methyl ester in 82 % yield over three steps.
Publisher: American Chemical Society (ACS)
Date: 28-09-2012
DOI: 10.1021/CO300080G
Abstract: A small library of hiphilic compounds was synthesized in an array using the Huisgen 1,3-dipolar cycloaddition of terminal alkynes with azides (CuAAC or click reaction). The self-assembling properties of these compounds were evaluated by polarizing microscopy and synchrotron small-angle X-ray scattering analysis.
Publisher: Elsevier BV
Date: 06-2009
Publisher: Beilstein Institut
Date: 10-07-2014
DOI: 10.3762/BJOC.10.163
Abstract: Amphiphilic compounds are used in a variety of applications due to their lyotropic liquid-crystalline phase formation, however only a limited number of compounds, in a potentially limitless field, are currently in use. A library of organic hiphilic compounds was synthesised consisting of glucose, galactose, lactose, xylose and mannose head groups and double and triple-chain hydrophobic tails. A modular, high-throughput approach was developed, whereby head and tail components were conjugated using the copper-catalysed azide–alkyne cycloaddition (CuAAC) reaction. The tails were synthesised from two core alkyne-tethered intermediates, which were subsequently functionalised with hydrocarbon chains varying in length and degree of unsaturation and branching, while the five sugar head groups were selected with ranging substitution patterns and anomeric linkages. A library of 80 hiphiles was subsequently produced, using a 24-vial array, with the majority formed in very good to excellent yields. A preliminary assessment of the liquid-crystalline phase behaviour is also presented.
Publisher: Elsevier BV
Date: 11-2015
Publisher: Elsevier BV
Date: 03-2017
DOI: 10.1016/J.COLSURFB.2016.12.004
Abstract: The lyotropic phase behaviour of a library of sugar-based hiphiles was investigated using high-throughput small-angle X-ray scattering (SAXS). Double unsaturated-chain monosaccharide hiphiles formed inverse hexagonal and cubic micellar (Fd3m) lyotropic phases under excess water conditions. A galactose-oleyl hiphile from the library was subsequently formulated into hexosome nanoparticles, which have potential uses as drug delivery vehicles. The nanoparticles were shown to be stable at elevated temperatures and non-cytotoxic up to at least 200μgmL
Publisher: American Chemical Society (ACS)
Date: 05-11-2013
DOI: 10.1021/OL4029308
Abstract: Iodobenzene-catalyzed 1,2-olefin functionalization via C-C and C-O bond formation has been achieved with electron rich aromatic groups and vinylogous esters acting as independent nucleophiles. The reaction provides oxabicyclo[3.2.1]octanes and [4.2.1]nonanes from commercially available 3-alkoxy cycohexen-2-ones in three steps.
Publisher: American Chemical Society (ACS)
Date: 24-09-2019
Publisher: Royal Society of Chemistry (RSC)
Date: 2023
DOI: 10.1039/D2YA00348A
Abstract: Investigation of the thermodynamic and transport properties of four novel ether-functionalised piperidinium and morpholinium ionic liquids with LiFSI and LiTFSI salts, and Li-ion coordination in ionic liquids.
Publisher: American Chemical Society (ACS)
Date: 23-05-2008
DOI: 10.1021/JO800173H
Abstract: A method has been developed for the methylation of the C3' amide of taxol C and paclitaxel. Taxol C and paclitaxel were sequentially silylated at the 2', 7, and 1-hydroxyl groups with tert-butyldimethylsilyl chloride, triethylsilyl chloride, and dimethylsilyl chloride, respectively. Subsequent reaction with potassium tert-butoxide and methyl iodide provided the corresponding N-methylated taxane derivatives. Removal of the silyl protecting groups furnished N-methyltaxol C and N-methylpaclitaxel.
Publisher: Royal Society of Chemistry (RSC)
Date: 2021
DOI: 10.1039/D1QM00648G
Abstract: The synthesis and characterisation of a series of new oxazolidinium-based salts shows that ether functionality in the ring can have beneficial impacts on properties including ionic conductivity.
Publisher: American Chemical Society (ACS)
Date: 09-11-2017
DOI: 10.1021/ACS.BIOMAC.7B01168
Abstract: Achieving efficient and targeted delivery of short interfering (siRNA) is an important research challenge to overcome to render highly promising siRNA therapies clinically successful. Challenges exist in designing synthetic carriers for these RNAi constructs that provide protection against serum degradation, extended blood retention times, effective cellular uptake through a variety of uptake mechanisms, endosomal escape, and efficient cargo release. These challenges have resulted in a significant body of research and led to many important findings about the chemical composition and structural layout of the delivery vector for optimal gene silencing. The challenge of targeted delivery vectors remains, and strategies to take advantage of nature's self-selective cellular uptake mechanisms for specific organ cells, such as the liver, have enabled researchers to step closer to achieving this goal. In this work, we report the design, synthesis, and biological evaluation of a novel polymeric delivery vector incorporating galactose moieties to target hepatic cells through clathrin-mediated endocytosis at asialoglycoprotein receptors. An investigation into the density of carbohydrate functionality and its distance from the polymer backbone is conducted using reversible addition-fragmentation chain transfer polymerization and postpolymerization modification.
Publisher: CSIRO Publishing
Date: 2013
DOI: 10.1071/CH12347
Abstract: The formation of functional liposomes by the self assembly of a peptide– hiphile that comprises the neuroprotective tripeptide motif glycyl-prolyl-glutamic acid linked to a hydrophobic moiety is reported. The self-assembled peptide–lipid conjugate displays long range order and can be dispersed as nanometre sized particles.
Publisher: Royal Society of Chemistry (RSC)
Date: 2011
DOI: 10.1039/C1CC15015D
Abstract: Vinylogous esters bearing para or meta methoxy benzyl groups undergo oxidative cyclisation with 5-20 mol% iodobenzene and m-CPBA to give spirofuran or benzopyran containing heterocycles. The reaction allows rapid generation of skeletal complexity in good to excellent yields via a novel oxidative cyclisation.
Publisher: Elsevier BV
Date: 10-2011
DOI: 10.1016/J.BMC.2011.08.011
Abstract: We report a 3D QSAR study of almost 300 structurally erse small molecule antagonists of the integrin α4β1 whose biological activity spans six orders of magnitude. The alignment of the molecules was based on the conformation of a structurally related ligand bound to the αIIBβ3 and αvβ3 integrins in X-ray crystallographic studies. The molecular field method, CoMSIA, was used to generate the 3D QSAR models. The resulting models showed that the lipophilic properties were the most important, with hydrogen bond donor and steric properties less relevant. The models were highly significant (r(2)=0.89, q2(LOO)=0.67, r(2) (test set)=0.76), and could make robust predictions of the data (SEE=0.46, SEP=0.78, SEP (test set)=0.66). We predicted the antagonist activities of a further ten compounds with useful accuracy. The model appears capable of predicting α4β1 integrin antagonist activity to within a factor of five for compounds within its domain of applicability. The implications for design of improved integrin antagonists will be discussed.
Publisher: Royal Society of Chemistry (RSC)
Date: 2018
DOI: 10.1039/C8SC01862F
Abstract: A one step modification of RAFT polymers to give functionalised materials.
Publisher: American Chemical Society (ACS)
Date: 19-09-2016
Abstract: Pyrethrum is a natural insecticide extracted from Tanacetum cinerariifolium. Six esters, the pyrethrins, are responsible for the extract's insecticidal activity. The oxidative degradation of pyrethrins through contact with aerial oxygen is a potential cause of pyrethrin losses during pyrethrum manufacture. Described here is the first investigation of the autoxidation chemistry of the six pyrethrin esters isolated from pyrethrum. It was found that pyrethrins I and II, the major pyrethrin esters present in pyrethrum, undergo autoxidation more readily than the minor pyrethrin esters, the jasmolins and cinerins. Chromatographic analysis of pyrethrin I and II autoxidation mixtures showed some correlation with a similar analysis performed on extracts from T. cinerariifolium crop, which had been stored for 12 weeks without added antioxidants. Two pyrethrin II autoxidation products were isolated, characterized, and shown to be present in extracts of stored T. cinerariifolium crop, confirming that autoxidation of pyrethrin esters does occur during crop storage.
Publisher: Royal Society of Chemistry (RSC)
Date: 2014
DOI: 10.1039/C3PY01015E
Publisher: Royal Society of Chemistry (RSC)
Date: 2014
DOI: 10.1039/C3OB42332H
Abstract: A fluorescent α 9 β 1 integrin antagonist with nanomolar binding affinities has been demonstrated to bind bone marrow haemopoietic stem and progenitor cells in vivo .
Publisher: CSIRO Publishing
Date: 2008
DOI: 10.1071/CH07428
Abstract: As a result of recent investigations into the total synthesis of the complex diterpene alkaloid nominine, the preparation of two new heterocyclic intermediates is now described. The cyclic ether 10 was derived from an intramolecular Mitsunobu reaction. The precursor hydroxylated compound 9 was the minor product of the hydroboration of alkene 7, which proceeded with an unexpected stereochemical outcome. The lactam 3 was derived from the hydrogenation of oxime 18 through presumed cyclization of the amino ester.
Publisher: Wiley
Date: 13-02-2014
Abstract: A new method for the discovery of hiphiles by using high-throughput (HT) methods to synthesise and characterise a library of galactose- and glucose-containing hiphilic compounds is presented. The copper-catalysed azide–alkyne cycloaddition (CuAAC) “click” reaction between azide-tethered simple sugars and alkyne-substituted hydrophobic tails was employed to synthesise a library of compounds with systematic variations in chain length and unsaturation in a 24-vial array format. The liquid–crystalline phase behaviour was characterised in a HT manner by using synchrotron small-angle X-ray scattering (SSAXS). The observed structural variation with respect to chain parameters, including chain length and degree of unsaturation, is discussed, as well as hydration effects and degree of hydrogen bonding between head groups. The validity of our HT screening approach was verified by resynthesising a short-chain glucose hiphile. A separate phase analysis of this compound confirmed the presence of numerous lyotropic liquid–crystalline phases.
Publisher: Springer Science and Business Media LLC
Date: 03-05-2019
DOI: 10.1038/S42003-019-0397-3
Abstract: Atovaquone-proguanil (Malarone®) is used for malaria prophylaxis and treatment. While the cytochrome bc1-inhibitor atovaquone has potent activity, proguanil’s action is attributed to its cyclization-metabolite, cycloguanil. Evidence suggests that proguanil has limited intrinsic activity, associated with mitochondrial-function. Here we demonstrate that proguanil, and cyclization-blocked analogue tBuPG, have potent, but slow-acting, in vitro anti-plasmodial activity. Activity is folate-metabolism and isoprenoid biosynthesis-independent. In yeast dihydroorotate dehydrogenase-expressing parasites, proguanil and tBuPG slow-action remains, while bc1-inhibitor activity switches from comparatively fast to slow-acting. Like proguanil, tBuPG has activity against P. berghei liver-stage parasites. Both analogues act synergistically with bc1-inhibitors against blood-stages in vitro, however cycloguanil antagonizes activity. Together, these data suggest that proguanil is a potent slow-acting anti-plasmodial agent, that bc1 is essential to parasite survival independent of dihydroorotate dehydrogenase-activity, that Malarone® is a triple-drug combination that includes antagonistic partners and that a cyclization-blocked proguanil may be a superior combination partner for bc1-inhibitors in vivo.
Publisher: American Chemical Society (ACS)
Date: 17-02-2020
DOI: 10.1021/ACSCOMBSCI.9B00186
Abstract: The readily available natural product stevioside provides a unique diterpene core structure that can be explored for small molecule library development by ersity-oriented synthesis and functional group transformations. Validation arrays were prepared from steviol, isosteviol, and related analogues, derived from stevioside, to produce over 90 compounds. These compounds were submitted to the NIH Molecular Libraries Small Molecule Repository for screening in the Molecular Libraries Screening Center Network. Micromolar hits were identified in multiple high-throughput assays for several library members. A cheminformatics analysis of the compounds was performed that verified the expected ersity and complexity of this set of compounds. The screening results indicate that scaffolds-derived natural products can provide screening hits against multiple target proteins.
Publisher: Elsevier BV
Date: 07-2005
Publisher: American Chemical Society (ACS)
Date: 26-03-2013
DOI: 10.1021/OL400385W
Publisher: Elsevier BV
Date: 09-2008
Location: Australia
Start Date: 2020
End Date: 2022
Funder: Australian Research Council
View Funded ActivityStart Date: 2018
End Date: 2020
Funder: National Health and Medical Research Council
View Funded ActivityStart Date: 2016
End Date: 2018
Funder: National Health and Medical Research Council
View Funded ActivityStart Date: 2016
End Date: 2018
Funder: National Health and Medical Research Council
View Funded ActivityStart Date: 2016
End Date: 2016
Funder: Australian Research Council
View Funded Activity