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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

Item Type: Article

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.

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More Information

Depositing User: Glenda Young

Identifiers

Item ID: 3810
ISSN: 0040-4020
URI: http://sure.sunderland.ac.uk/id/eprint/3810
Official URL: http://www.sciencedirect.com/science/article/pii/S...

Users with ORCIDS

ORCID for Mark Gray: ORCID iD orcid.org/0000-0002-0674-1999

Catalogue record

Date Deposited: 18 Apr 2013 11:23
Last Modified: 18 Dec 2019 15:35

Contributors

Author: Mark Gray ORCID iD
Author: Alexandre Bedernjak
Author: Paul Groundwater
Author: S Orenga
Author: J D Perry
Author: Rosaleen Anderson

University Divisions

Faculty of Health Sciences and Wellbeing
Faculty of Health Sciences and Wellbeing > School of Pharmacy and Pharmaceutical Sciences

Subjects

Sciences > Pharmacy and Pharmacology

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