2-Arylbenzothiazole, benzoxazole and benzimidazole derivatives as fluorogenic substrates for the detection of nitroreductase and aminopeptidase activity in clinically important bacteria

Cellier, Marie, Fabrega, Olivier, Fazackerley, Elizabeth, James, Arthur, Orenga, Sylvain, Perry, John, Salwatura, Vindhya and Stanforth, Stephen (2011) 2-Arylbenzothiazole, benzoxazole and benzimidazole derivatives as fluorogenic substrates for the detection of nitroreductase and aminopeptidase activity in clinically important bacteria. Bioorganic & Medicinal Chemistry, 19 (9). pp. 2903-2910. ISSN 0968-0896

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Official URL: http://dx.doi.org/10.1016/j.bmc.2011.03.043

Abstract

A series of 2-(2-nitrophenyl)benzothiazole 7, 2-(2-nitrophenyl)benzoxazole 10 and 2-(2-nitrophenyl)benzimidazole 13 derivatives have been synthesised and assessed as indicators of nitroreductase activity across a range of clinically important Gram negative and Gram positive bacteria. The majority of Gram negative bacteria produced strongly fluorescent colonies with substrates 7 and 10 whereas fluorescence production in Gram positive bacteria was less widespread. The l-alanine 16 and 19 and ?-alanine 21 and 23 derivatives have been prepared from 2-(2-aminophenyl)benzothiazole 14 and 2-(2-aminophenyl)benzoxazole 17. These four compounds have been evaluated as indicators of aminopeptidase activity. The growth of Gram positive bacteria was generally inhibited by these substrates but fluorescent colonies were produced with the majority of Gram negative bacteria tested.

Item Type: Article
Uncontrolled Keywords: Fluorgenic substrates, nitroreductase, aminopeptidase, benzothiazoles, benzoxazoles, benzimidazoles, bacteria detection
Subjects: A100 Pre-clinical Medicine
F100 Chemistry
Department: Faculties > Health and Life Sciences > School of Life Sciences > Applied Sciences
Depositing User: EPrint Services
Date Deposited: 06 May 2011 10:28
Last Modified: 10 Aug 2015 11:38
URI: http://nrl.northumbria.ac.uk/id/eprint/2807

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