2-Arylbenzothiazole, benzoxazole and benzimidazole derivatives as fluorogenic substrates for the detection of nitroreductase and aminopeptidase activity in clinically important bacteria

Bioorganic and Medicinal Chemistry

Volumn 19, Issue 9, 2011, Pages 2903-2910

  Cellier, Marie ^a   Fabrega, Olivier J ^b   Fazackerley, Elizabeth ^b   James, Arthur L ^b   Orenga, Sylvain ^a   Perry, John D ^c   Salwatura, Vindhya L ^b   Stanforth, Stephen P ^b  

^a BIOMÉRIEUX   (France)

^b NORTHUMBRIA UNIVERSITY   (United Kingdom)

^c FREEMAN HOSPITAL   (United Kingdom)

Author keywords

Aminopeptidase; Bacteria detection; Benzimidazoles; Benzothiazoles; Benzoxazoles; Fluorgenic substrates; Nitroreductase

Indexed keywords

1 METHYL 2 (2 NITROPHENYL)BENZIMIDAZOLE; 1 METHYL 2 (3 CHLORO 6 NITROPHENYL)BENZIMIDAZOLE; 2 (2 NITROPHENYL) 2,3 DIHYDROBENZOTHIAZOLE; 2 (2 NITROPHENYL)BENZIMIDAZOLE DERIVATIVE; 2 (2 NITROPHENYL)BENZOTHIAZOLE; 2 (2 NITROPHENYL)BENZOTHIAZOLE DERIVATIVE; 2 (2 NITROPHENYL)BENZOXAZOLE; 2 (2 NITROPHENYL)BENZOXAZOLE DERIVATIVE; 2 (3 CHLORO 6 NITROPHENYL)BENZOTHIAZOLE; 2 (3 CHLORO 6 NITROPHENYL)BENZOXAZOLE; 2 (3 FLUORO 6 NITROPHENYL) 2,3 DIHYDROBENZOTHIAZOLE; 2 (3 FLUORO 6 NITROPHENYL)BENZOTHIAZOLE; 2 (3 FLUORO 6 NITROPHENYL)BENZOXAZOLE; 2 (3,4 DIMETHOXY 6 NITROPHENYL) 2,3 DIHYDROBENZOTHIAZOLE; 2 (3,4 DIMETHOXY 6 NITROPHENYL)BENZOTHIAZOLE; 2 (3,4 DIMETHOXY 6 NITROPHENYL)BENZOXAZOLE; 2 [(2 ALANYLAMINO)PHENYL]BENZOTHIAZOLE 2 [(2 ALANYLAMINO)PHENYL]BENZOXAZOLE DERIVATIVE; 2 [(2 NITROBENZYLIDINE)AMINO]PHENOL; 2 [(3 CHLORO 6 NITROBENZYLIDENE)AMINO]PHENOL; 2 [(3 FLUORO 6 NITROBENZYLIDENE)AMINO]PHENOL; 2 [(3,4 DIMETHOXY 6 NITROBENZYLIDENE)AMINO]PHENOL; 2 ARYLBENZOTHIAZOLE DERIVATIVE; ALANINE; AMINOPEPTIDASE; BENZIMIDAZOLE DERIVATIVE; BENZOTHIAZOLE DERIVATIVE; BENZOXAZOLE DERIVATIVE; BETA ALANINE; NITROREDUCTASE; UNCLASSIFIED DRUG;

ARTICLE; BACTERIAL GROWTH; BACTERIUM COLONY; BACTERIUM DETECTION; CULTURE MEDIUM; DRUG SYNTHESIS; ENTEROBACTER CLOACAE; ENZYME ACTIVITY; ENZYME STRUCTURE; ENZYME SUBSTRATE; ESCHERICHIA COLI; GRAM NEGATIVE BACTERIUM; GRAM POSITIVE BACTERIUM; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; METHICILLIN RESISTANT STAPHYLOCOCCUS AUREUS; MORGANELLA MORGANII; NONHUMAN; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PROVIDENCIA RETTGERI; PSEUDOMONAS AERUGINOSA; SALMONELLA TYPHIMURIUM; SERRATIA MARCESCENS; STAPHYLOCOCCUS AUREUS; STAPHYLOCOCCUS EPIDERMIDIS;

AMINOPEPTIDASES; BACTERIA; BENZIMIDAZOLES; BENZOTHIAZOLES; BENZOXAZOLES; FLUORESCENT DYES; NITROREDUCTASES; SUBSTRATE SPECIFICITY;

NEGIBACTERIA; POSIBACTERIA;

EID: 79955480790     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmc.2011.03.043     Document Type: Article

References (19)

1. S. Orenga, A.L. James, M. Manfi, J.D. Perry, and D.H. Pincus J. Microbiol. Methods 79 2009 139
2. R.P. Haughland Handbook of Fluorescent Probes and Research Products 9th ed. 2002 Molecular Probes Inc. Eugene, OR
3. J.-L. Reymond, V.S. Flux, and N. Maillard Chem. Commun. 2009 34
4. M.D. Roldán, E. Pérez-Reinado, F. Castillo, and C. Moreno-Vivián FEMS Microbiol. Rev. 32 2008 474
5. A.L. James, J.D. Perry, C. Jay, D. Monget, J.W. Rasburn, and F.K. Gould Lett. Appl. Microbiol. 33 2001 403
6. James, A.; Monget, D. European Patent EP 1124986, 2001.
7. A.L. James, J.D. Perry, and S.P. Stanforth J. Heterocycl. Chem. 43 2006 515
8. A.V. Zaytsev, R.J. Anderson, A. Bedernjak, P.W. Groundwater, Y. Huang, J.D. Perry, S. Orenga, C. Roger-Dalbert, and A.L. James Org. Biomol. Chem. 6 2008 682
9. A.L. James, J.D. Perry, A. Rigby, and S.P. Stanforth Bioorg. Med. Chem. Lett. 17 2007 1418
10. Haughland, R. P.; Zhang, Y. -z.; Yue, S. T.; Terpetschnig, E.; Olsen, N. A.; Naleway, J. J.; Larison, K. D.; Huang, Z. U.S. Patent 5316,906, 1994.
11. T.-I. Kim, H.J. Kang, G. Han, S.J. Chung, and Y. Kim Chem. Commun. 2009 5895
12. Fabrega, O.; James, A.; Salwatura, V. L.; Orenga, S.; Stanforth, S. P. Patent WO 152305, 2008.
13. Fabrega, O.; James, A.; Salwatura, V. L.; Orenga, S.; Stanforth, S. P. Patent WO 152306, 2008.
14. E. Uhlemann, and V. Pohl Z. Chem. 9 1969 385
15. D. Hawkins, J.M. Lindley, I.M. McRobbie, and O. Meth-Cohn J. Chem. Soc., Perkin Trans. 1 1980 2387
16. K. Nakagawa, H. Onue, and J. Sugita Chem. Pharm. Bull. 12 1964 1135
17. M.F.G. Stevens, D.-F. Shi, and A. Castro J. Chem. Soc., Perkin Trans. 1 1996 83
18. T.H. Haskell, F.E. Peterson, D. Watson, N.R. Plessas, and T. Culbertson J. Med. Chem. 13 1970 697
19. a values of the parent heterocycles suggests that the benzothiazoles will give bis TFA salts whereas the benzoxazoles will produce mono TFA salts.