Structural basis for the interaction of lactivicins with serine β-lactamases

Journal of Medicinal Chemistry

Volumn 53, Issue 15, 2010, Pages 5890-5894

  Brown Jr , Tom ^a   Charlier, Paulette ^b   Herman, Raphaël ^b   Schofield, Christopher J ^a   Sauvage, Eric ^b  

^a UNIVERSITY OF OXFORD   (United Kingdom)

^b UNIVERSITY OF LIÈGE   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

BETA LACTAM ANTIBIOTIC; BETA LACTAMASE; GAMMA LACTAM DERIVATIVE; LACTIVICIN;

ARTICLE; CRYSTAL STRUCTURE; DRUG PROTEIN BINDING; DRUG STRUCTURE; ENZYME BINDING;

ANTI-BACTERIAL AGENTS; BACILLUS; BETA-LACTAMASES; CRYSTALLOGRAPHY, X-RAY; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PEPTIDES; SERINE;

EID: 77955353169     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm100437u     Document Type: Article

References (35)

1. Sauvage, E.; Kerff, F.; Terrak, M.; Ayala, J. A.; Charlier, P. The Penicillin-Binding Proteins: Structure and Role in Peptidoglycan Biosynthesis FEMS Microbiol. Rev. 2008, 32, 234-258
2. Zapun, A.; Contreras-Martel, C.; Vernet, T. Penicillin-Binding Proteins and beta-Lactam Resistance FEMS Microbiol. Rev. 2008, 32, 361-385
3. Harada, S.; Tsubotani, S.; Hida, T.; Ono, H.; Okazaki, H. Structure of Lactivicin, an Antibiotic Having a New Nucleus and Similar Biological Activities to beta-Lactam Antibiotics Tetrahedron Lett. 1986, 27, 6229-6232
4. Harada, S.; Tsubotani, S.; Hida, T.; Koyama, K.; Kondo, M.; Ono, H. Chemistry of a New Antibiotic-Lactivicin Tetrahedron 1988, 44, 6589-6606
5. Tipper, D. J.; Strominger, J. L. Mechanism of Action of Penicillins: A Proposal Based on Their Structural Similarity to Acyl- d -alanyl- d -alanine Proc. Natl. Acad. Sci. U.S.A. 1965, 54, 1133-1141
6. Westwood, N. J.; Claridge, T. D. W.; Edwards, P. N.; Schofield, C. J. Reversible Acylation of Elastase by gamma-Lactam Analogues of beta-Lactam inhibitors Bioorg. Med. Chem. Lett. 1997, 7, 2973-2978
7. Imming, P.; Klar, B.; Dix, D. Hydrolytic Stability Versus Ring Size in Lactams: Implications for the Development of Lactam Antibiotics and Other Serine Protease Inhibitors J. Med. Chem. 2000, 43, 4328-4331
8. Wilmouth, R. C.; Westwood, N. J.; Anderson, K.; Brownlee, W.; Claridge, T. D. W.; Clifton, I. J.; Pritchard, G. J.; Aplin, R. T.; Schofield, C. J. Inhibition of Elastase by N -Sulfonylaryl beta-Lactams: Anatomy of a Stable Acyl-Enzyme Complex Biochemistry 1998, 37, 17506-17513
9. Wilmouth, R. C.; Kassamally, S.; Westwood, N. J.; Sheppard, R. J.; Claridge, T. D. W.; Aplin, R. T.; Wright, P. A.; Pritchard, G. J.; Schofield, C. J. Mechanistic Insights into the Inhibition of Serine Proteases by Monocyclic Lactams Biochemistry 1999, 38, 7989-7998
10. Wright, P. A.; Wilmouth, R. C.; Clifton, I. J.; Schofield, C. J. "pH-Jump" Crystallographic Analyses of gamma-Lactam Porcine Pancreatic Elastase Complexes Biochem. J. 2000, 351 (Part 2) 335-340
11. Baldwin, J. E.; Lynch, G. P.; Pitlik, J. Gamma-Lactam Analogues of beta-Lactam Antibiotics J. Antibiot. 1991, 44, 1-24
12. Macheboeuf, P.; Fischer, D. S.; Brown, T., Jr.; Zervosen, A.; Luxen, A.; Joris, B.; Dessen, A.; Schofield, C. J. Structural and Mechanistic Basis of Penicillin-Binding Protein Inhibition by Lactivicins Nat. Chem. Biol. 2007, 3, 565-569
13. Nozaki, Y.; Katayama, N.; Ono, H.; Tsubotani, S.; Harada, S.; Okazaki, H.; Nakao, Y. Binding of a Non-beta-Lactam Antibiotic to Penicillin-Binding Proteins Nature 1987, 325, 179-180
14. Tamura, N.; Matsushita, Y.; Kawano, Y.; Yoshioka, K. Synthesis and Antibacterial Activity of Lactivicin Derivatives Chem. Pharm. Bull. 1990, 38, 116-122
15. Macheboeuf, P.; Di Guilmi, A. M.; Job, V.; Vernet, T.; Dideberg, O.; Dessen, A. Active Site Restructuring Regulates Ligand Recognition in Class A Penicillin-Binding Proteins Proc. Natl. Acad. Sci. U.S.A. 2005, 102, 577-582
16. Nozaki, Y.; Katayama, N.; Harada, S.; Ono, H.; Okazaki, H. Lactivicin, a Naturally-Occurring Non-beta-Lactam Antibiotic Having beta-Lactam-like Action. Biological Activities and Mode of Action J. Antibiot. 1989, 42, 84-93
17. Fisher, J. F.; Meroueh, S. O.; Mobashery, S. Bacterial Resistance to beta-Lactam Antibiotics: Compelling Opportunism, Compelling Opportunity Chem. Rev. 2005, 105, 395-424
18. Wilmouth, R. C.; Clifton, I. J.; Robinson, C. V.; Roach, P. L.; Aplin, R. T.; Westwood, N. J.; Hajdu, J.; Schofield, C. J. Structure of a Specific Acyl-Enzyme Complex formed between beta-Casomorphin-7 and Porcine Pancreatic Elastase Nat. Struct. Biol. 1997, 4, 456-462
19. Wilmouth, R. C. Structural Studies on the Mechanism and Inhibition of Elastase. D.Phil. Thesis, University of Oxford, Oxford, U.K., 1998.
20. Knox, J. R.; Moews, P. C. beta-Lactamase of Bacillus licheniformis 749/C. Refinement at 2 Å Resolution and Analysis of Hydration J. Mol. Biol. 1991, 220, 435-455
21. Leszczynski, J. F.; Rose, G. D. Loops in Globular Proteins. A Novel Category of Secondary Structure Science 1986, 234, 849-855
22. Fonze, E.; Vanhove, M.; Dive, G.; Sauvage, E.; Frere, J. M.; Charlier, P. Crystal Structures of the Bacillus licheniformis BS3 Class A beta-Lactamase and of the Acyl-Enzyme Adduct Formed with Cefoxitin Biochemistry 2002, 41, 1877-1885
23. Hermann, J. C.; Hensen, C.; Ridder, L.; Mulholland, A. J.; Holtje, H. D. Mechanisms of Antibiotic Resistance: QM/MM Modeling of the Acylation Reaction of a Class A beta-Lactamase with Benzylpenicillin J. Am. Chem. Soc. 2005, 127, 4454-4465
24. Chen, C. C. H.; Herzberg, O. Inhibition of beta-Lactamase by Clavulanate: Trapped Intermediates in Cryocrystallographic Studies J. Mol. Biol. 1992, 224, 1103-1113
25. Padayatti, P. S.; Helfand, M. S.; Totir, M. A.; Carey, M. P.; Carey, P. R.; Bonomo, R. A.; van den Akker, F. High Resolution Crystal Structures of the trans-Enamine Intermediates Formed by Sulbactam and Clavulanic Acid and E166A SHV-1 beta-Lactamase J. Biol. Chem. 2005, 280, 34900-34907
26. Tremblay, L. W.; Hugonnet, J. E.; Blanchard, J. S. Structure of the Covalent Adduct formed between Mycobacterium tuberculosis beta-Lactamase and Clavulanate Biochemistry 2008, 47, 5312-5316
27. Brown, R. P.; Aplin, R. T.; Schofield, C. J. Inhibition of TEM-2 beta-Lactamase from Escherichia coli by Clavulanic Acid: Observation of Intermediates by Electrospray Ionization Mass Spectrometry Biochemistry 1996, 35, 12421-12432
28. Sulton, D.; Pagan-Rodriguez, D.; Zhou, X.; Liu, Y. D.; Hujer, A. M.; Bethel, C. R.; Helfand, M. S.; Thomson, J. M.; Anderson, V. E.; Buynak, J. D.; Ng, L. M.; Bonomo, R. A. Clavulanic Acid Inactivation of SHV-1 and the Inhibitor-Resistant S130G SHV-1 beta-Lactamase. Insights into the Mechanism of Inhibition J. Biol. Chem. 2005, 280, 35528-35536
29. Hugonnet, J. E.; Blanchard, J. S. Irreversible Inhibition of the Mycobacterium tuberculosis beta-Lactamase by Clavulanate Biochemistry 2007, 46, 11998-12004
30. Sauvage, E.; Zervosen, A.; Dive, G.; Herman, R.; Amoroso, A.; Joris, B.; Fonze, E.; Pratt, R. F.; Luxen, A.; Charlier, P.; Kerff, F. Structural Basis of the Inhibition of Class beta-Lactamases and Penicillin-Binding Proteins by 6-beta-Iodopenicillanate J. Am. Chem. Soc. 2009, 131, 15262-15269
31. Ledent, P.; Duez, C.; Vanhove, M.; Lejeune, A.; Fonze, E.; Charlier, P.; Rhazi-Filali, F.; Thamm, I.; Guillaume, G.; Samyn, B.; Devreese, B.; Van Beeumen, J.; Lamotte-Brasseur, J.; Frere, J.-M. Unexpected Influence of a C-Terminal-Fused His-Tag on the Processing of an Enzyme and on the Kinetic and Folding Parameters FEBS Lett. 1997, 413, 194-196
32. The CCP4 suite: programs for protein crystallography. Acta Crystallogr., Sect. D.: Biol. Crystallogr. 1994, 50, 760 - 763.
33. Murshudov, G. N.; Vagin, A. A.; Dodson, E. J. Refinement of Macromolecular Structures by the Maximum-Likelihood Method Acta Crystallogr., Sect. D: Biol. Crystallogr. 1997, 53, 240-255
34. Painter, J.; Merritt, E. A. Optimal Description of a Protein Structure in Terms of Multiple Groups Undergoing TLS motion Acta Crystallogr., Sect. D: Biol. Crystallogr. 2006, 62, 439-450
35. Emsley, P.; Cowtan, K. Coot: Model-Building Tools for Molecular Graphics Acta Crystallogr., Sect. D: Biol. Crystallogr. 2004, 60, 2126-2132