Inactivation of a class A and a class C β-lactamase by 6β-(hydroxymethyl)penicillanic acid sulfone

Biochemical Pharmacology

Volumn 83, Issue 4, 2012, Pages 462-471

  Papp Wallace, Krisztina M ^a,c   Bethel, Christopher R ^a   Gootz, Thomas D ^b   Shang, Wenchi ^b   Stroh, Justin ^b   Lau, William ^b   McLeod, Dale ^b   Price, Loren ^b   Marfat, Anthony ^b   Distler, Anne ^e   Drawz, Sarah M ^a,c   Chen, Hansong ^f   Harry, Emily ^f   Nottingham, Micheal ^f   Carey, Paul R ^d   Buynak, John D ^f   Bonomo, Robert A ^a,c  

^a LOUIS STOKES CLEVELAND VA MEDICAL CENTER   (United States)

^b PFIZER INC   (United States)

^c CASE WESTERN RESERVE UNIVERSITY SCHOOL OF MEDICINE   (United States)

^d CASE WESTERN RESERVE UNIVERSITY   (United States)

^e Cuyahoga Community College   (United States)

^f SOUTHERN METHODIST UNIVERSITY   (United States)

Author keywords

Lactam; Lactamase; Lactamase inhibitor; PDC 3; Sulfone; TEM 1

Indexed keywords

AMPICILLIN; BETA LACTAMASE AMPC; BETA LACTAMASE TEM 1; CEPHALOSPORINASE; CLAVULANIC ACID; NITROCEFIN; POTASSIUM SALT; SODIUM; SULBACTAM; TAZOBACTAM; WATER;

ARTICLE; CONTROLLED STUDY; COVALENT BOND; DRUG EFFICACY; DRUG INACTIVATION; ENZYME INACTIVATION; ENZYME STABILITY; FRAGMENTATION REACTION; HYDROLYSIS; IC 50; MASS SPECTROMETRY; NONHUMAN; PRIORITY JOURNAL; PSEUDOMONAS AERUGINOSA;

ANTI-BACTERIAL AGENTS; BACTERIAL PROTEINS; BETA-LACTAMASES; CATALYTIC DOMAIN; COMPUTER SIMULATION; ESCHERICHIA COLI; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PROTEIN CONFORMATION; PSEUDOMONAS AERUGINOSA; SULBACTAM;

EID: 84855764882     PISSN: 00062952     EISSN: 18732968     Source Type: Journal    
DOI: 10.1016/j.bcp.2011.11.015     Document Type: Article

References (29)

1. E. Chain Chemical properties and structure of the penicillins Endeavour 7 1948 83 passim
2. E. Chain The chemistry of penicillin Annu Rev Biochem 17 1948 657 704
3. H. Florey Penicillin other antibiotics Adv Sci 4 1948 281 286
4. R.P. Ambler, and R.J. Meadway Chemical structure of bacterial penicillinases Nature 222 1969 24 26
5. K. Bush, G.A. Jacoby, and A.A. Medeiros A functional classification scheme for β-lactamases and its correlation with molecular structure Antimicrob Agents Chemother 39 1995 1211 1233
6. R.P. Ambler The structure of β-lactamases Philos Trans R Soc Lond B: Biol Sci 289 1980 321 331
7. S.M. Drawz, and R.A. Bonomo Three decades of β-lactamase inhibitors Clin Microbiol Rev 23 2010 160 201
8. K. Bush, and G.A. Jacoby Updated functional classification of β-lactamases Antimicrob Agents Chemother 54 2010 969 976
9. J.D. Buynak The discovery and development of modified penicillin- and cephalosporin-derived β-lactamase inhibitors Curr Med Chem 11 2004 1951 1964 (Pubitemid 38821350)
10. J.D. Buynak, A.S. Rao, V.R. Doppalapudi, G. Adam, P.J. Petersen, and S.D. Nidamarthy The synthesis and evaluation of 6-alkylidene-2′β- substituted penam sulfones as β-lactamase inhibitors Bioorg Med Chem Lett 9 1999 1997 2002 (Pubitemid 29336389)
11. G. Bou, E. Santillana, A. Sheri, A. Beceiro, J.M. Sampson, and M. Kalp Design, synthesis, and crystal structures of 6-alkylidene-2'-substituted penicillanic acid sulfones as potent inhibitors of Acinetobacter baumannii OXA-24 carbapenemase J Am Chem Soc 132 2010 13320 13331
12. L. Maveyraud, I. Massova, C. Birck, K. Miyashita, J.-P. Samama, and S. Mobashery Crystal structure of 6α-(hydroxymethyl)penicillanate complexed to the TEM-1 β-lactamase from Escherichia coli: evidence on the mechanism of action of a novel inhibitor designed by a computer-aided process J Am Chem Soc 118 1996 7435 7440 (Pubitemid 26279797)
13. Kellog MS, Hamanaka ES. Process for converting 6,6-disubstituted penicillanic acid derivatives to the 6-β-congeners. Patent#4,397,783, USA; 1983.
14. J.D. Buynak, H. Chen, L. Vogeti, V.R. Gadhachanda, C.A. Buchanan, and T. Palzkill Penicillin-derived inhibitors that simultaneously target both metallo- and serine-β-lactamases Bioorg Med Chem Lett 14 2004 1299 1304 (Pubitemid 38229875)
15. M. Nottingham, C.R. Bethel, S.R. Pagadala, E. Harry, A. Pinto, and Z.A. Lemons Modifications of the C6-substituent of penicillin sulfones with the goal of improving inhibitor recognition and efficacy Bioorg Med Chem Lett 21 2011 387 393
16. S.M. Drawz, M. Taracila, E. Caselli, F. Prati, and R.A. Bonomo Exploring sequence requirements for C(3)/C(4) carboxylate recognition in the Pseudomonas aeruginosa cephalosporinase: insights into plasticity of the AmpC β-lactamase Protein Sci 20 2011 941 958
17. CLSI methods for dilution antimicrobial susceptibility tests for bacteria that grow aerobically. Approved Standard, 1st ed. Wayne, PA: Clinical and Laboratory Standards Institute. CLSI M7-A1.
18. CLSI. CLSI performance standards for antimicrobial susceptibility testing. Eighteen informational supplement. Wayne, PA: Clinical and Laboratory Standards Institute. CLSI M100-S17; 2007.
19. K. Bush, and S.B. Singer Biochemical characteristics of extended broad spectrum β-lactamases Infection 17 1989 429 433 (Pubitemid 20013479)
20. S.J. Cartwright, and S.G. Waley Purification of β-lactamases by affinity chromatography on phenylboronic acid-agarose Biochem J 221 1984 505 512
21. K. Bush, C. Macalintal, B.A. Rasmussen, V.J. Lee, and Y. Yang Kinetic interactions of tazobactam with β-lactamases from all major structural classes Antimicrob Agents Chemother 37 1993 851 858 (Pubitemid 23096890)
22. R.A. Powers, and B.K. Shoichet Structure-based approach for binding site identification on AmpC β-lactamase J Med Chem 45 2002 3222 3234 (Pubitemid 34774273)
23. B. Stec, K.M. Holtz, C.L. Wojciechowski, and E.R. Kantrowitz Structure of the wild-type TEM-1 β-lactamase at 1.55 A and the mutant enzyme Ser70Ala at 2.1 A suggest the mode of noncovalent catalysis for the mutant enzyme Acta Crystallogr D: Biol Crystallogr 61 2005 1072 1079 (Pubitemid 43951489)
24. Y. Yang, K. Janota, K. Tabei, N. Huang, M.M. Siegel, and Y.I. Lin Mechanism of inhibition of the class A β-lactamases PC1 and TEM-1 by tazobactam Observation of reaction products by electrospray ionization mass spectrometry J Biol Chem 275 2000 26674 26682
25. A.P. Kuzin, M. Nukaga, Y. Nukaga, A. Hujer, R.A. Bonomo, and J.R. Knox Inhibition of the SHV-1 β-lactamase by sulfones: crystallographic observation of two reaction intermediates with tazobactam Biochemistry 40 2001 1861 1866 (Pubitemid 32144059)
26. P. Bitha, Z. Li, G.D. Francisco, B.A. Rasmussen, and Y.I. Lin 6-(1-Hydroxyalkyl)penam sulfone derivatives as inhibitors of class A and class C β-lactamases I Bioorg Med Chem Lett 9 1999 991 996 (Pubitemid 29179895)
27. J. Fisher, R.L. Charnas, S.M. Bradley, and J.R. Knowles Inactivation of the RTEM β-lactamase from Escherichia coli. Interaction of penam sulfones with enzyme Biochemistry 20 1981 2726 2731 (Pubitemid 11038333)
28. A. Bulychev, I. Massova, K. Miyashita, and S. Mobashery Nuances of mechanisms and their implications for evolution of the versatile β-lactamase activity: from biosynthetic enzymes to drug resistance factors J Am Chem Soc 119 1997 7619 7625 (Pubitemid 27376374)
29. A. Patera, L.C. Blaszczak, and B.K. Shoichet Crystal structures of substrate and inhibitor complexes with AmpC β-lactamase: possible implications for substrate-assisted catalysis J Am Chem Soc 122 2000 10504 10512