Synthesis of 2-arylbenzothiazole derivatives and their application in bacterial detection |
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| Institution: | 1. Research & Development Microbiology, bioMérieux SA, 3 route de Port Michaud, 38 390 La-Balme-les-Grottes, France;2. Department of Applied Sciences, Northumbria University, Newcastle upon Tyne NE1 8ST, UK;3. Department of Microbiology, Freeman Hospital, Newcastle upon Tyne NE7 7DN, UK;1. Physics Department, Ural Federal University, Lenina str. 51, 620000 Ekaterinburg, Russia;2. Kutateladze Institute of Thermophysics SB RAS, 630090 Novosibirsk, Russia;3. James Weir Fluids Laboratory, Department of Mechanical and Aerospace Engineering, University of Strathclyde, Glasgow G1 1XJ, UK;4. Aix Marseille Université – Polytech Marseille, Département de Mécanique Energétique – IUSTI, UMR CNRS 7343, 5 rue Enrico Fermi, 13453 Marseille cedex 13, France;1. College of Chemistry, Jilin University, Qianjin Street 2699, Changchun, 130012, China;2. College of Life Sciences, Jilin University, Qianjin Street 2699, Changchun, 130012, China;1. Departmento de Química, Universidade Federal de Viçosa, Viçosa, Minas Gerais, Brazil;2. Instituto de Química, Universidade Federal de Uberlândia, Uberlândia, Minas Gerais, Brazil;3. Departamento de Química, Universidade Federal de Lavras, Lavras, Minas Gerais, Brazil;4. Departamento de Química, Instituto de Ciências Exatas, Universidade Federal de Minas Gerais, Belo Horizonte, Minas Gerais, Brazil;5. Instituto de Física de São Carlos, Universidade de São Paulo, São Carlos, SP, Brazil;6. Department of Life Science and Biotechnology, University of Ferrara, Ferrara, Italy;1. School of Chemistry and Chemical Engineering, University of Jinan, Jinan, 250022, China;2. Institute for Advanced Interdisciplinary Research, University of Jinan, Jinan, 250022, China |
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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). |
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| Keywords: | Fluorogenic substrates Aminopeptidase Esterase Phosphatase β-Galactosidase Bacteria detection |
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