NH-1,2,3-triazole inhibitors of the VIM-2 metallo-β-lactamase

ACS Medicinal Chemistry Letters

Volumn 1, Issue 4, 2010, Pages 150-154

  Weide, Timo ^a   Saldanha, S Adrian ^b   Minond, Dmitriy ^b   Spicer, Timothy P ^b   Fotsing, Joseph R ^a,d   Spaargaren, Michael ^b   Frère, Jean Marie ^c   Bebrone, Carine ^c   Sharpless, K Barry ^a   Hodder, Peter S ^b   Fokin, Valery V ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

^b SCRIPPS RESEARCH INSTITUTE   (United States)

^c UNIVERSITY OF LIÈGE   (Belgium)

^d Senomyx Inc   (United States)

Author keywords

bacterial resistance; Escherichia coli; Metallo lactamases; NH 1,2,3 triazole based inhibitors; VIM 2

Indexed keywords

1,2,3 TRIAZOLE DERIVATIVE; BETA LACTAMASE INHIBITOR; IMIPENEM; METALLO BETA LACTAMASE; METALLO BETA LACTAMASE INHIBITOR; UNCLASSIFIED DRUG;

ARTICLE; DRUG EFFICACY; DRUG SYNTHESIS; ESCHERICHIA COLI; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; PRIORITY JOURNAL; STRUCTURE ACTIVITY RELATION;

BACTERIA (MICROORGANISMS); ESCHERICHIA COLI;

EID: 77955915532     PISSN: None     EISSN: 19485875     Source Type: Journal    
DOI: 10.1021/ml900022q     Document Type: Article

References (12)

1. Jacoby, G. A.; Munoz-Price, L. S. The new beta-lactamases N. Engl. J. Med. 2005, 352, 380-391
2. Cornaglia, G.; Akova, M.; Amicosante, G.; Canton, R.; Cauda, R.; Docquier, J. D.; Edelstein, M.; Frere, J. M.; Fuzi, M.; Galleni, M.; Giamarellou, H.; Gniadkowski, M.; Koncan, R.; Libisch, B.; Luzzaro, F.; Miriagou, V.; Navarro, F.; Nordmann, P.; Pagani, L.; Peixe, L.; Poirel, L.; Souli, M.; Tacconelli, E.; Vatopoulos, A.; Rossolini, G. M. Metallo-beta- lactamases as emerging resistance determinants in Gram-negative pathogens: Open issues Int. J. Antimicrob. Agents 2007, 29, 380-388
3. Livermore, D. M. The threat from the pink corner Ann. Med. 2003, 35, 226-234
4. Bebrone, C. Metallo-beta-lactamases (classification, activity, genetic organization, structure, zinc coordination) and their superfamily Biochem. Pharmacol. 2007, 74, 1686-1701
5. Walsh, T. R.; Toleman, M. A.; Poirel, L.; Nordmann, P. Metallo-beta-lactamases: The quiet before the storm? Clin. Microbiol. Rev. 2005, 18, 306-325
6. Docquier, J. D.; Lamotte-Brasseur, J.; Galleni, M.; Amicosante, G.; Frere, J. M.; Rossolini, G. M. On functional and structural heterogeneity of VIM-type metallo-beta-lactamases J. Antimicrob. Chemother. 2003, 51, 257-266
7. Lienard, M. A.; Strandh, M.; Hedenstrom, E.; Johansson, T.; Lofstedt, C. Key biosynthetic gene subfamily recruited for pheromone production prior to the extensive radiation of Lepidoptera BMC Evol. Biol. 2008, 8, 270
8. Olsen, L.; Jost, S.; Adolph, H. W.; Pettersson, I.; Hemmingsen, L.; Jorgensen, F. S. New leads of metallo-beta-lactamase inhibitors from structure-based pharmacophore design Bioorg. Med. Chem. 2006, 14, 2627-2635
9. Jin, W.; Arakawa, Y.; Yasuzawa, H.; Taki, T.; Hashiguchi, R.; Mitsutani, K.; Shoga, A.; Yamaguchi, Y.; Kurosaki, H.; Shibata, N.; Ohta, M.; Goto, M. Comparative study of the inhibition of metallo-beta-lactamases (IMP-1 and VIM-2) by thiol compounds that contain a hydrophobic group Biol. Pharm. Bull. 2004, 27, 851-856
10. Minond, D.; Saldanha, S. A.; Subramaniam, P.; Spaargaren, M.; Spicer, T.; Fotsing, J. R.; Weide, T.; Fokin, V. V.; Sharpless, K. B.; Galleni, M.; Frère, J.-M.; Hodder, P. Inhibitors of VIM-2 by Screening Pharmacogically Active and Click-Chemistry Compound Libraries Bioorg. Med. Chem. 2009, 15, 5027-5037
11. Loren, J. C.; Sharpless, K. B. The banert cascade: A synthetic sequence to polyfunctional NH-1,2,3-triazoles Synthesis-Stuttgart 2005, 1514-1520
12. See the Supporting Information for docking studies with compound 44.