Synthesis and evaluation of halogenated nitrophenoxazinones as nitroreductase substrates for the detection of pathogenic bacteria

Bedernjak, Alexandre, Groundwater, Paul, Gray, Mark, Orenga, S, Perry, J D and Anderson, Rosaleen (2013) Synthesis and evaluation of halogenated nitrophenoxazinones as nitroreductase substrates for the detection of pathogenic bacteria. Tetrahedron, 69 (39). pp. 8456-8462. ISSN 0040-4020

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Abstract

The synthesis and microbiological evaluation of 7-, 8- and 9-nitro-1,2,4-trihalogenophenoxazin-3-one substrates with potential in the detection of nitroreductase-expressing pathogenic microorganisms are described. The 7- and 9-nitrotrihalogenophenoxazinone substrates were reduced by most Gram negative microorganisms and were inhibitory to the growth of certain Gram positive bacteria; however, the majority of Gram positive strains that were not inhibited by these agents, along with the two yeast strains evaluated, did not reduce the substrates. These observations suggest there are differences in the active site structures and substrate requirements of the nitroreductase enzymes from different strains; such differences may be exploited in the future for differentiation between pathogenic microorganisms. The absence of reduction of the 8-nitrotrihalogenophenoxazinone substrates is rationalized according to their electronic properties and correlates well with previous findings.

Item Type: Article
Subjects: Sciences > Pharmacy and Pharmacology
Divisions: Faculty of Applied Sciences
Faculty of Applied Sciences > Department of Pharmacy Health and Wellbeing
Health Sciences and Wellbeing Beacon
Health Sciences and Wellbeing Beacon > Drug Discovery and Application Workstream
Depositing User: Glenda Young
Date Deposited: 18 Apr 2013 11:23
Last Modified: 20 Sep 2017 14:32
URI: http://sure.sunderland.ac.uk/id/eprint/3810

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