ORCID Profile
0000-0001-8490-0628
Current Organisation
DyStar (Germany)
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Publisher: University of Queensland Library
Publisher: American Chemical Society (ACS)
Date: 28-10-2014
DOI: 10.1021/OL502003A
Abstract: We report the synthesis of a new class of molecules which are hybrids of long-lived tetramethylisoindolinoxyl (TMIO) radicals and the pyrido[1,2-a]benzimidazole (PyrImid) scaffold. These compounds represent a new lead for noncovalently binding nucleic acid probes, as they interact with nucleic acids with previously unreported C (DNA) and C/U (RNA) complementarity, which can be detected by electron paramagnetic resonance (EPR) techniques. They also have promising properties for fluorimetric analysis, as their fluorescent spin-quenched derivatives exhibit a significant Stokes shift.
Publisher: Elsevier BV
Date: 11-2018
DOI: 10.1016/J.FREERADBIOMED.2018.03.008
Abstract: Here we describe new fluorescent probes based on fluorescein and rhodamine that provide reversible, real-time insight into cellular redox status. The new probes incorporate bio-imaging relevant fluorophores derived from fluorescein and rhodamine linked with stable nitroxide radicals such that they cannot be cleaved, either spontaneously or enzymatically by cellular processes. Overall fluorescence emission is determined by reversible reduction and oxidation, hence the steady state emission intensity reflects the balance between redox potentials of critical redox couples within the cell. The permanent positive charge on the rhodamine-based probes leads to their rapid localisation within mitochondria in cells. Reduction and oxidation also leads to marked changes in the fluorophore lifetime, enabling monitoring by fluorescence lifetime imaging microscopy. Finally, we demonstrate that administration of a methyl ester version of the rhodamine-based probe can be used at concentrations as low as 5 nM to generate a readily detected response to redox stress within cells as analysed by flow cytometry.
Publisher: Wiley
Date: 05-02-2016
Abstract: Pharmaceutical and agrochemical discovery programs are under considerable pressure to meet increasing global demand and thus require constant innovation. Classical hydrocarbon scaffolds have long assisted in bringing new molecules to the market place, but an obvious omission is that of the Platonic solid cubane. Eaton, however, suggested that this molecule has the potential to act as a benzene bioisostere. Herein, we report the validation of Eaton's hypothesis with cubane derivatives of five molecules that are used clinically or as agrochemicals. Two cubane analogues showed increased bioactivity compared to their benzene counterparts whereas two further analogues displayed equal bioactivity, and the fifth one demonstrated only partial efficacy. Ramifications from this study are best realized by reflecting on the number of bioactive molecules that contain a benzene ring. Substitution with the cubane scaffold where possible could revitalize these systems, and thus expedite much needed lead candidate identification.
Publisher: Royal Society of Chemistry (RSC)
Date: 2013
DOI: 10.1039/C3SC51396C
Publisher: Wiley
Date: 05-02-2016
Publisher: MDPI AG
Date: 10-09-2016
DOI: 10.3390/S16091457
Publisher: Wiley
Date: 22-12-2021
Abstract: 1,1,3,3‐Tetramethylisoindolin‐2‐yloxyl (TMIO) is a well‐known stable 2,3‐dihydroisoindoline aminoxyl radical, which is thermally generated (at °C) from literature alkoxyamine derivatives. Herein is the synthesis of visible light activated benzimidazolequinone alkoxyamines of TMIO using oxidative methods and the first room temperature nitroxide‐exchange experiments with 2,2,6,6‐tetramethylpiperidine‐1‐oxyl (TEMPO) analogues. For the alkoxyamine TMIO‐Vis dissociation rate constants are provided using TEMPO and oxygen as radical traps.
Publisher: Wiley
Date: 27-02-2014
Publisher: CSIRO Publishing
Date: 2010
DOI: 10.1071/CH10107
Abstract: Cubane can be considered the ideal internal standard for reactions observed by NMR, due to an almost complete benign reactivity and uniquely reliable 1H and 13C NMR resonances, in wide variety of deuterated solvents.
Publisher: Royal Society of Chemistry (RSC)
Date: 2013
DOI: 10.1039/C3CC46146G
Abstract: Protecting a nitroxide as the methyl ether is highly effective. It can be de-protected in good yield using a peracid.
Publisher: Wiley
Date: 29-02-2016
Publisher: Wiley
Date: 29-02-2016
Publisher: Wiley
Date: 06-07-2018
Publisher: Royal Society of Chemistry (RSC)
Date: 2019
DOI: 10.1039/C8OB02959H
Abstract: An enantioselective synthesis of the non-proteinogenic amino acid ( R )-2-cubylglycine and the first ex les of cubane C–H insertion are reported.
Publisher: CSIRO Publishing
Date: 2009
DOI: 10.1071/CH09447
Abstract: 3- and 4-Pyridyliminopropadienones were prepared by flash vacuum thermolysis of Meldrum’s acid derivatives and characterized by low temperature IR spectroscopy. They react with dimethylamine to afford 1,5-, 1,6-, and 1,7-naphthyridones. The same naphthyridones are also obtained by microwave irradiation of the Meldrum’s acid derivatives. Quinolones were obtained by microwave irradiation of phenylaminomethylene-Meldrum’s acids and 1-phenylpyrrole-2,3-diones.
Publisher: Wiley
Date: 08-01-2013
Publisher: Georg Thieme Verlag KG
Date: 17-02-2014
Publisher: Royal Society of Chemistry (RSC)
Date: 2018
DOI: 10.1039/C8OB00811F
Abstract: Schiff base salts are characterized and form N -amino methylated acrylamides and methacrylamides.
Publisher: Wiley
Date: 25-04-2017
DOI: 10.1002/POLA.28607
Publisher: Wiley
Date: 05-07-2018
Publisher: Royal Society of Chemistry (RSC)
Date: 2019
DOI: 10.1039/C9OB01238A
Abstract: Trials and tribulations of the cubane paradigm in biomolecule discovery highlight synthetic limitations, culminating in a continuing guide for practitioners, which includes cyclooctatetraene.
Publisher: Elsevier BV
Date: 12-2017
Location: Australia
No related grants have been discovered for Benjamin Chalmers.