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

Lookup NU author(s): Dr John Perry, Dr Vindhya Salwatura

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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 beta-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. (C) 2011 Elsevier Ltd. All rights reserved.

Publication metadata

Author(s): Cellier M, Fabrega OJ, Fazackerley E, James AL, Orenga S, Perry JD, Salwatura VL, Stanforth SP

Publication type: Article

Publication status: Published

Journal: Bioorganic & Medicinal Chemistry

Year: 2011

Volume: 19

Issue: 9

Pages: 2903-2910

Print publication date: 24/03/2011

ISSN (print): 0968-0896

ISSN (electronic): 1464-3391

Publisher: Pergamon

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

DOI: 10.1016/j.bmc.2011.03.043

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