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

Cellier, Marie, Fazackerley, Elizabeth, James, Arthur, Orenga, Sylvain, Perry, John, Turnbull, Graeme and Stanforth, Stephen (2014) Synthesis of 2-arylbenzothiazole derivatives and their application in bacterial detection. Bioorganic & Medicinal Chemistry, 22 (4). pp. 1250-1261. ISSN 09680896

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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).

Item Type: Article
Uncontrolled Keywords: Fluorogenic substrates, aminopeptidase, esterase, phosphatase, β-Galactosidase, bacteria detection
Subjects: C500 Microbiology
Department: Faculties > Health and Life Sciences > Applied Sciences
Depositing User: Ellen Cole
Date Deposited: 13 Feb 2014 17:17
Last Modified: 12 Oct 2019 18:29

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