title: 2-Arylbenzothiazole, benzoxazole and benzimidazole derivatives as fluorogenic substrates for the detection of nitroreductase and aminopeptidase activity in clinically important bacteria.
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 β-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.
authors.affiliation: Research & Development Microbiology, bioMérieux SA, 3 route de Port Michaud, 38 390 La-Balme-les-Grottes, France.
authors.forename: Marie
authors.initials: M
authors.lastname: Cellier
authors.forename: Olivier J
authors.initials: OJ
authors.lastname: Fabrega
authors.forename: Elizabeth
authors.initials: E
authors.lastname: Fazackerley
authors.forename: Arthur L
authors.initials: AL
authors.lastname: James
authors.forename: Sylvain
authors.initials: S
authors.lastname: Orenga
authors.forename: John D
authors.initials: JD
authors.lastname: Perry
authors.forename: Vindhya L
authors.initials: VL
authors.lastname: Salwatura
authors.forename: Stephen P
authors.initials: SP
authors.lastname: Stanforth
mesh_terms: D000626:Aminopeptidases / Q000737:chemistry / Q000378:metabolism*; D001419:Bacteria / Q000201:enzymology* / Q000302:isolation & purification; D001562:Benzimidazoles / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D052160:Benzothiazoles / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D001583:Benzoxazoles / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D005456:Fluorescent Dyes / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D009601:Nitroreductases / Q000737:chemistry / Q000378:metabolism*; D013379:Substrate Specificity
chemical_list: D001562:Benzimidazoles; D052160:Benzothiazoles; D001583:Benzoxazoles; D005456:Fluorescent Dyes; C031000:benzimidazole; D009601:Nitroreductases; D000626:Aminopeptidases; C005465:benzothiazole