An Improved Synthesis of CENTA, a Chromogenic Substrate for β-Lactamases

Synlett

Volumn 27, Issue 17, 2016, Pages 2447-2450

  Quotadamo, Antonio ^a   Linciano, Pasquale ^b   Davoli, Paolo ^b   Tondi, Donatella ^b   Costi, Maria Paola ^b   Venturelli, Alberto ^a  

^a Tydock Pharma   (Italy)

^b UNIVERSITY OF MODENA AND REGGIO EMILIA   (Italy)

Author keywords

CENTA; chromogenic substrate; synthesis; lactamase detection; lactamase kinetics

Indexed keywords

7 BETA THIEN 2 YL ACETAMIDO 3 [(4 NITRO 3 CARBOXYPHENYL)THIOMETHYL] 3 CEPHEM 4 CARBOXYLIC ACID; BETA LACTAMASE; CHROMOGENIC SUBSTRATE; NITROCEFIN; UNCLASSIFIED DRUG;

ARTICLE; BIOCHEMICAL COMPOSITION; CHEMICAL ANALYSIS; CHEMICAL STRUCTURE; CLINICAL PROTOCOL; HYDROLYSIS; NUCLEOPHILICITY; PHYSICAL CHEMISTRY; QUALITATIVE ANALYSIS; SYNTHESIS;

EID: 84978077115     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0035-1562454     Document Type: Article

References (27)

1. Livermore D. M., Brown D. F. J. Antimicrob. Chemother.: 2001; 48 59; Suppl. 1
2. van Berkel S. S., Brem J., Rydzik A. M., Salimraj R., Cain R., Verma A., Owens R. J., Fishwick C. W. G, Spencer J., Schofield C. J. J. Med. Chem.: 2013; 56 6945
3. Bidya S., Suman R. Open J. Clin. Diagn.: 2014; 4 47
4. Montgomery K., Raymundo L., Drew W. L. J. Clin. Microbiol.: 1979; 9 205
5. Papanicolaou G. A., Medeiros A. A. Antimicrob. Agents Chemother.: 1990; 34 2184
6. Kobayashi S., Arai S., Hayashi S., Sakaguchi T. Antimicrob. Agents Chemother.: 1988; 32 1040
7. O'Callaghan C. H., Morris A., Kirby S. M., Shingler A. H. Antimicrob. Agents Chemother.: 1972; 1 283
8. http://www.merckmillipore.com/FR/fr/product/Nitrocefin--CAS-41906-86-9--Calbiochem,EMD_BIO-484400?bd=1.
9. Pitkälä A., Salmikivi L., Bredbacka P., Myllyniemi A.-L, Koskinen M. T. J. Clin. Microbiol.: 2007; 45 2031
10. Marshall S. A., Sutton L. D., Jones R. N. Diagn. Microbiol. Infect. Dis.: 1995; 22 353
11. Uri J. V. Acta Microbiol. Hung.: 1985; 32 133
12. Bebrone C., Moali C., Mahy F., Rival S., Docquier J. D., Rossolini G. M., Fastrez J., Pratt R. F., Frere J. M., Galleni M. Antimicrob. Agents Chemother.: 2001; 45 1868
13. http://www.merckmillipore.com/FR/fr/product/CENTA%E2%84%A2-%CE%B2-Lactamase-Substrate--CAS-9073-60-3--Calbiochem,EMD_BIO-219475.
14. Morin S., Clouthier C. M., Gobeil S., Pelletier J. N., Gagne S. M. Biomol. NMR Assignments: 2010; 4 127
15. Padiolleau-Lefevre S., Debat H., Thomas D., Friboulet A., Avalle B. Biocatal. Biotransform.: 2003; 21 79
16. Hugonnet J.-E, Blanchard J. S. Biochemistry: 2007; 46 11998
17. Mandal S., Maharjan M., Ganguly S., Chatterjee M., Singh S., Buckner F. S., Madhubala R. Indian J. Exp. Biol.: 2009; 47 475
18. Yang-Woytowitz M., Yu C., Wiles T. WO 2009051838 A1: 2009
19. Bebrone C., Anne C., De Vriendt K., Devreese B., Rossolini G. M., Van Beeumen J., Frere J. M., Galleni M. J. Biol. Chem.: 2005; 280 28195
20. Page M. G. P. Biochim. Biophys. Acta: 1994; 1205 199
21. Vella P., Hussein W. M., Leung E. W. W, Clayton D., Ollis D. L., Mitić N., Schenk G., McGeary R. P. Bioorg. Med. Chem. Lett.: 2011; 21 3282
22. Perumal S. K., Pratt R. F. J. Org. Chem.: 2006; 71 4778
23. Makena A., van Berkel S. S., Lejeune C., Owens R. J., Verma A., Salimraj R., Spencer J., Brem J., Schofield C. J. ChemMedChem: 2013; 8 1923
24. Hailu T. T., Foit L., Bardwell J. C. A. Anal. Biochem.: 2013; 434 181
25. Kristiansen A., Grgic M., Altermark B., Leiros I. J. Antimicrob. Chemother.: 2015; 70 766
26. Jones R. N., Wilson H. W., Novick W. J., Barry A. L., Thornsberry C. J. Clin. Microbiol.: 1982; 15 954
27. Saikawa, I.; Takano, S.; Momonoi, K.; Takakura, I.; Tanaka, K.; Kutani, C. Chem. Pharm. Bull. 1985, 33, 5534.