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Synthesis of 2-arylbenzothiazole derivatives and their application in bacterial detection

Lookup NU author(s): Dr John Perry

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Abstract

A series of 2-arylbenzothiazole derivatives have been prepared as fluorogenic enzyme substrates in order to detect aminopeptidase, esterase, phosphatase and β-galactosidase activity in clinically important Gram-negative and Gram-positive bacteria. Substrates were incorporated into an agar-based culture medium and this allowed growth of intensely fluorescent bacterial colonies based on hydrolysis by specific enzymes. Substrate 20 targeted l-alanine aminopeptidase activity and was hydrolysed exclusively by a range of Gram-negative bacteria and inhibited the growth of a range of Gram-positive bacteria. Substrate 19a targeted β-alanyl aminopeptidase activity and generated fluorescent colonies of selected Gram-negative species including Pseudomonas aeruginosa. Substrate 21b targeted C8-esterase activity and resulted in strongly fluorescent colonies of selected species known to harbour such enzyme activity (e.g., Salmonella and Pseudomonas). Most Gram-negative species produced colonies with an intense blue fluorescence due to hydrolysis of phosphatase substrates 24a-c and substrate 24c was also hydrolysed by strains of Staphylococcus aureus. Compounds 26b and 26c targeted β-galactosidase activity and generated strongly fluorescent colonies with coliform bacteria that produced this enzyme (e.g., Escherichia coli). © 2014 Elsevier Ltd. All rights reserved.

Publication metadata

Author(s): Cellier M, Fazackerley E, James AL, Orenga S, Perry JD, Turnbull G, Stanforth SP

Publication type: Article

Publication status: Published

Journal: Bioorganic and Medicinal Chemistry

Year: 2014

Volume: 22

Issue: 4

Pages: 1250-1261

Print publication date: 15/02/2014

Online publication date: 15/01/2014

Acceptance date: 08/01/2014

ISSN (print): 0968-0896

ISSN (electronic): 1464-3391

Publisher: Pergamon Press

URL: https://doi.org/10.1016/j.bmc.2014.01.013

DOI: 10.1016/j.bmc.2014.01.013

PubMed id: 24480653

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