An altered zinc-binding site confers resistance to a covalent inactivator of New Delhi metallo-beta-lactamase-1 (NDM-1) discovered by high-throughput screening

Bioorganic and Medicinal Chemistry

Volumn 21, Issue 11, 2013, Pages 3138-3146

  Thomas, Pei W ^a   Spicer, Timothy ^b   Cammarata, Michael ^a   Brodbelt, Jennifer S ^a   Hodder, Peter ^a,b   Fast, Walter ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

^b SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

Antibiotic resistance; High throughput screening; Metallo beta lactamase

Indexed keywords

2 (2,4 DICHLOROPHENYL) 3 (1 METHYL 3 INDOLYL)MALEIMIDE; 4 AMINO 1,8 NAPHTHALIMIDE A; 4 CHLOROMECURIBENZOATE; BETA LACTAMASE; CYSTINE; DIPYRIDAMOLE; ELLIPTICINE; ENZYME INHIBITOR; IDARUBICIN; LISURIDE MALEATE; NEW DELHI METALLO BETA LACTAMASE 1; NITROPRUSSIDE SODIUM; RECOMBINANT ENZYME; TERGURIDE; UNCLASSIFIED DRUG; ZINC;

AMINO ACID SEQUENCE; ANTIBIOTIC RESISTANCE; ARTICLE; AUTOMATION; BINDING SITE; CONTROLLED STUDY; COVALENT BOND; DRUG DESIGN; ENZYME ACTIVE SITE; ENZYME ACTIVITY; ENZYME ASSAY; ENZYME INACTIVATION; FALSE POSITIVE RESULT; HIGH THROUGHPUT SCREENING; NONHUMAN; PILOT STUDY; SCREENING TEST;

ANTI-BACTERIAL AGENTS; BETA-LACTAM RESISTANCE; BETA-LACTAMASES; CATALYTIC DOMAIN; CYSTEINE; ENTEROBACTERIACEAE; HIGH-THROUGHPUT SCREENING ASSAYS; MICROBIAL SENSITIVITY TESTS; MUTATION; NITROPRUSSIDE; P-CHLOROMERCURIBENZOIC ACID; RECOMBINANT PROTEINS; TANDEM MASS SPECTROMETRY; ZINC;

EID: 84877797475     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2013.03.031     Document Type: Article

References (34)

1. L.S. Goodman, A. Gilman, and L.L. Brunton Goodman & Gilman's Manual of Pharmacology and Therapeutics 2008 McGraw-Hill Medical New York
2. J.C. Gallagher, and C. MacDougall Antibiotics, Simplified 2009 Jones and Bartlett Publishers Sudbury, MA
3. M. Shahid, F. Sobia, A. Singh, A. Malik, H.M. Khan, D. Jonas, and P.M. Hawkey Crit. Rev. Microbiol. 35 2009 81
4. P. Oelschlaeger, N. Ai, K.T. Duprez, W.J. Welsh, and J.H. Toney J. Med. Chem. 53 2010 3013
5. D. Yong, M.A. Toleman, C.G. Giske, H.S. Cho, K. Sundman, K. Lee, and T.R. Walsh Antimicrob. Agents Chemother. 53 2009 5046
6. K.K. Kumarasamy, M.A. Toleman, T.R. Walsh, J. Bagaria, F. Butt, R. Balakrishnan, U. Chaudhary, M. Doumith, C.G. Giske, S. Irfan, P. Krishnan, A.V. Kumar, S. Maharjan, S. Mushtaq, T. Noorie, D.L. Paterson, A. Pearson, C. Perry, R. Pike, B. Rao, U. Ray, J.B. Sarma, M. Sharma, E. Sheridan, M.A. Thirunarayan, J. Turton, S. Upadhyay, M. Warner, W. Welfare, D.M. Livermore, and N. Woodford Lancet Infect. Dis. 10 2010 597
7. T.R. Walsh Int. J. Antimicrob. Agents 36 2010 S8
8. M.W. Crowder, J. Spencer, and A.J. Vila Acc. Chem. Res. 39 2006 721
9. D.M. Livermore, S. Mushtaq, A. Morinaka, T. Ida, K. Maebashi, and R. Hope J. Antimicrob. Chemother. 68 2013 153
10. Y. Guo, J. Wang, G. Niu, W. Shui, Y. Sun, H. Zhou, Y. Zhang, C. Yang, Z. Lou, and Z. Rao Protein Cell 2 2011 384
11. H. Boerzel, M. Koeckert, W. Bu, B. Spingler, and S.J. Lippard Inorg. Chem. 42 2003 1604
12. P.W. Thomas, M. Zheng, S. Wu, H. Guo, D. Liu, D. Xu, and W. Fast Biochemistry 50 2011 10102
13. Minond, D.; Saldanha, S. A.; Spicer, T.; Qin, L.; Mercer, B. A.; Roush, W. R.; Hodder, P. Probe Reports from the NIH Molecular Libraries Program, 2010; PMID 21961119.
14. J.H. Zhang, T.D. Chung, and K.R. Oldenburg J. Biomol. Screen. 4 1999 67
15. P. Zuck, G.T. O'Donnell, J. Cassaday, P. Chase, P. Hodder, B. Strulovici, and M. Ferrer Anal. Biochem. 342 2005 254
16. P. Hodder, J. Cassaday, R. Peltier, K. Berry, J. Inglese, B. Feuston, C. Culberson, L. Bleicher, N.D. Cosford, C. Bayly, C. Suto, M. Varney, and B. Strulovici Anal. Biochem. 313 2003 246
17. I. Massova, and S. Mobashery Antimicrob. Agents Chemother. 42 1998 1
18. H. Adachi, T. Ohta, and H. Matsuzawa J. Biol. Chem. 266 1991 3186
19. H. Yang, M. Aitha, A.M. Hetrick, T.K. Richmond, D.L. Tierney, and M.W. Crowder Biochemistry 51 2012 3839
20. L.B. Horton, S. Shanker, R. Mikulski, N.G. Brown, K.J. Phillips, E. Lykissa, B.V. Venkataram Prasad, and T. Palzkill Antimicrob. Agents Chemother. 56 2012 5667
21. D. Minond, S.A. Saldanha, P. Subramaniam, M. Spaargaren, T. Spicer, J.R. Fotsing, T. Weide, V.V. Fokin, K.B. Sharpless, M. Galleni, C. Bebrone, P. Lassaux, and P. Hodder Bioorg. Med. Chem. 17 2009 5027
22. R.A. Copeland Evaluation of Enzyme Inhibitors in Drug Discovery: A Guide for Medicinal Chemists and Pharmacologists 2005 Wiley-Interscience Hoboken, NJ
23. D.T. King, L.J. Worrall, R. Gruninger, and N.C. Strynadka J. Am. Chem. Soc. 134 2012 11362
24. B.K. Shoichet J. Med. Chem. 49 2006 7274
25. R. Parkesh, T. Clive Lee, and T. Gunnlaugsson Org. Biomol. Chem. 5 2007 310
26. R.L. Lundblad Chemical Reagents for Protein Modification 2005 CRC Press Boca Raton
27. P.G. Wang, T.B. Cai, and N. Taniguchi Nitric Oxide Donors: For Pharmaceutical and Biological Applications 2005 Wiley-VCH Weinheim
28. Y. Yang, and K. Bush FEMS Microbiol. Lett. 137 1996 193
29. A. Zervosen, M.H. Valladares, B. Devreese, C. Prosperi-Meys, H.W. Adolph, P.S. Mercuri, M. Vanhove, G. Amicosante, J. van Beeumen, J.M. Frere, and M. Galleni Eur. J. Biochem. 268 2001 3840
30. P.S. Mercuri, I. Garcia-Saez, K. De Vriendt, I. Thamm, B. Devreese, J. Van Beeumen, O. Dideberg, G.M. Rossolini, J.M. Frere, and M. Galleni J. Biol. Chem. 279 2004 33630
31. D.J. Payne, J.H. Bateson, B.C. Gasson, D. Proctor, T. Khushi, T.H. Farmer, D.A. Tolson, D. Bell, P.W. Skett, A.C. Marshall, R. Reid, L. Ghosez, Y. Combret, and J. Marchand-Brynaert Antimicrob. Agents Chemother. 41 1997 135
32. Y. Yang, D. Keeney, X. Tang, N. Canfield, and B.A. Rasmussen J. Biol. Chem. 274 1999 15706
33. Z. Wang, W. Fast, and S.J. Benkovic Biochemistry 38 1999 10013
34. E.F. Pettersen, T.D. Goddard, C.C. Huang, G.S. Couch, D.M. Greenblatt, E.C. Meng, and T.E. Ferrin J. Comput. Chem. 25 2004 1605