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

Autor: Cellier M; Research & Development Microbiology, bioMérieux SA, 3 route de Port Michaud, 38 390 La-Balme-les-Grottes, France., Fazackerley E; Department of Applied Sciences, Northumbria University, Newcastle upon Tyne NE1 8ST, UK., James AL; Department of Applied Sciences, Northumbria University, Newcastle upon Tyne NE1 8ST, UK., Orenga S; Research & Development Microbiology, bioMérieux SA, 3 route de Port Michaud, 38 390 La-Balme-les-Grottes, France., Perry JD; Department of Microbiology, Freeman Hospital, Newcastle upon Tyne NE7 7DN, UK., Turnbull G; Department of Applied Sciences, Northumbria University, Newcastle upon Tyne NE1 8ST, UK., Stanforth SP; Department of Applied Sciences, Northumbria University, Newcastle upon Tyne NE1 8ST, UK. Electronic address: steven.stanforth@northumbria.ac.uk.
Jazyk: angličtina
Zdroj: Bioorganic & medicinal chemistry [Bioorg Med Chem] 2014 Feb 15; Vol. 22 (4), pp. 1250-61. Date of Electronic Publication: 2014 Jan 15.
DOI: 10.1016/j.bmc.2014.01.013
Abstrakt: 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).
(Copyright © 2014 Elsevier Ltd. All rights reserved.)
Databáze: MEDLINE
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