Antibiotic sensitization using biphenyl tetrazoles as potent inhibitors of Bacteroides fragilis metallo-β-lactamase

Chemistry and Biology

Volumn 5, Issue 4, 1998, Pages 185-196

  Toney, Jeffrey H ^a   Fitzgerald, Paula M D ^a   Grover Sharma, Nandini ^a   Olson, Steven H ^a   May, Walter J ^a   Sundelof, Jon G ^a   Vanderwall, Dana E ^a   Cleary, Kelly A ^a   Grant, Stephan K ^a   Wu, Joseph K ^a   Kozarich, John W ^a   Pompliano, David L ^a   Hammond, Gail G ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

Antibiotic resistance; Biphenyl tetrazoles; Crystal structure; Enzyme inhibitors; Metallo lactamase

Indexed keywords

BACTEROIDES FRAGILIS; NEGIBACTERIA;

EID: 13144295022     PISSN: 10745521     EISSN: None     Source Type: Journal    
DOI: 10.1016/S1074-5521(98)90632-9     Document Type: Article

References (42)

1. Jacobs, R.F. (1986). Imipenem-cilastatin: the first thienamycin antibiotic. Pediatr. Infect. Dis. J. 5, 444-448.
2. Clissold, S.P., Todd, P.A. & Campoli-Richards, D.M. (1987). Imipenem/cilastatin: a review of its antibacterial activity, pharmacokinetic properties and therapeutic efficacy. Drugs 33, 183-241.
3. Buckley, M. M., Brogden, R.N., Barradell, L.B. & Goa, K.L. (1992). Imipenem/cilastatin: a reappraisal of its antibacterial activity, pharmacokinetic properties and therapeutic efficacy. Drugs 44, 408-444.
4. de Lancastre, H., de Jonge, B.L.M., Matthews, P.R. & Tomasz, A. (1994). Molecular aspects of methicillin resistance in Staphylococcus aureus. J. Antimicrob. Chemother. 33, 7-24.
5. Mulligan, M.E., et al., & Yu, V.L. (1993). Methicillin-resistant Staphylococcus aureus: A consensus review of the microbiology, pathogenesis, and epidemiology with implications for prevention and management. Am. J. Med. 94, 313-328.
6. Knox, J.R., Moews, P.C. & Frère, J.-M. (1996). Molecular evolution of bacterial β-lactam resistance. Chem. Biol. 3, 937-947.
7. Rasmussen, B.A. & Bush, K. (1997). Carbapenem-hydrolyzing β-lactamases. Antimicrob. Agents Chemother. 41, 223-232.
8. Rasmussen, B.A., Bush, K. & Tally, F.P. (1993). Antimicrobial resistance in Bacteroides. Clin. Infect. Dis. 16, S390-S400.
9. Hedberg, M. & Nord, C.E. (1996). Beta-lactam resistance in anaerobic bacteria: a review. J. Chemother. 8, 3-16.
10. Turner, P., Edwards, R., Weston, V., Grazis, A., Ispahani, P. & Greenwood, D. (1995). Simultaneous resistance to metronidazole, co-amoxiclav, and imipenem in a clinical isolate of Bacteroides fragilis. Lancet 345, 1275-1277.
11. Mandell, G.L. & Sande, M.A. (1985). Antimicrobial Agents. In Goodman and Gilman's The Pharmacological Basis of Therapeutics. (Goodman Gilman, A., Goodman, L.S., Rail, T.W. & Murad, F., eds), p.1145, Macmillan Publishing Co., New York.
12. Concha, N.O., Rasmussen, B.A., Bush, K. & Herzberg, O. (1996). Crystal structure of wide-spectrum binuclear zinc β-lactamase from Bacteroides fragilis. Structure 4, 823-836.
13. Carfi, A., et al., & Dideberg, O. (1995). The 3-D structure of a zinc metallo-β-lactamase from Bacillus cereus reveals a new type of protein fold. EWBO J. 14, 4914-4921.
14. Crowder, M.W., Wang, Z., Franklin, S.L., Zovinka, E.P. & Benkovic, S.J. (1996). Characterization of the metal-binding sites of the β-lactamase from Bacteroides fragilis. Biochemistry 35, 12126-12132.
15. Lippard, S.J. & Berg, J.M. (1994). Principles of Bioinorganic Chemistry, pp. 25 and 271, University Science Books, Mill Valley, CA.
16. Hartmann, M., Clark, T. & van Eldik, R. (1997). Hydration and water exchange of Zinc (II) ions. Application of density functional theory. J. Am. Chem. Soc. 119, 7843-7850.
17. Harper, C., Rene, A. & Campbell, B.J. (1971). Renal dipeptidase: localization and inhibition. Biochim. Biophys. Acta 242, 446-458.
18. Welch, C.L. & Campbell, B.J. (1980). Uptake of glycine from L-alanylglycine into renal brush border vesicles. J. Membr. Biol. 54, 39-50.
19. Mitsuhashi, S., Fuse, A., Mikami, H., Saino, Y. & Inoue, M. (1988). Purification and characterization of human renal dehydropeptidase I. Antimicrob. Agents Chemother. 32, 587-588.
20. Fitzgerald, P.M.D., Wu, J.K. & Toney, J.H. (1998). Unanticipated inhibition of the metallo-β-lactamase from Bacteroides fragilis by 4-morpholineethanesulfonic acid (MES): a crystallographic study at 1.85 Å resolution. Biochemistry, in press.
21. Miller, M.D., Kearsley, S.K., Underwood, D.J. & Sheridan, R.P. (1994). FLOG: A system to select 'quasi-flexible' ligands complementary to a receptor of known three-dimensional structure. J. Comput. Aided Mol. Des. 8, 153-174.
22. Miller, M.D., Sheridan, R.P., Kearsley, S.K. & Underwood, D.J. (1994). Advances in automated docking applied to human immunodeficiency virus type protease. Methods Enzymol. 241, 354-370.
23. Kearsley, S.K., Underwood, D.J., Sheridan, R.P. & Miller, M.D. (1994). Flexibases: a way to enhance the use of molecular docking methods. J. Comput.-Aided Mol. Design 8, 565-582.
24. Meng, E.C., Shoichet, B.K. & Kuntz, I.D. (1992). Automated docking with grid-based energy evaluation. J. Comput. Chem. 13, 505-524.
25. Lawrence, M. C. & Davis, P. C. (1992). CLIX: A search algorithm for finding novel ligands capable of binding proteins of known three-dimensional structure. Proteins: Struct. Funct Genet 12, 13-41.
26. ∥ β-lactamase from Bacteroides fragilis in an orthorhombic crystal form. Acta Crystallogr. D 54, 47-57.
27. Ashton, W.T., et al., & Siegl, P.K.S. (1993). Nonpeptide angiotensin II antagonists derived from 1H-pyrazole-5-carboxylates and 4-aryl-1H-imidazole-5-carboxylates. J. Med. Chem. 36, 3595-3605.
28. Noda, K., et al., & Karnik, S. (1995). Tetrazole and carboxylate groups of angiotensin receptor antagonists bind to the same subsite by different mechanisms. J. Biol. Chem. 270, 2284-2289.
29. Payne, D.J., et al., & Marchand-Brynaert, J. (1997). Inhibition of metallo-β-lactamases by a series of mercaptoacetic acid thiol ester derivatives. Antimicrob. Agents Chemother. 41, 135-140.
30. Walter, M.W., et al., & Schofield, C.J. (1996). Trifluoromethyl alcohol and ketone inhibitors of metallo-β-lactamases. Bioorg. Med. Chem. Lett. 6, 2455-2458.
31. Christianson, D.W. & Lipscomb, W.N. (1986). The complex between carboxypeptidase A and a possible transition state analogue: mechanistic inferences from high resolution X-ray structures of enzyme-inhibitor complexes. J. Am. Chem. Soc. 108, 4998-5003.
32. Williams, R.J. & Heymann, D.L. (1998). Containment of antibiotic resistance. Science 279, 1153-1154.
33. Guerrier-Takada, C., Salavati, R. & Altman, S. (1997). Phenotypic conversion of drug-resistant bacteria to drug sensitivity. Proc. Natl Acad. Sci. USA 94, 8468-8472.
34. Toney, J.H., Wu, J.K., Overbye, K.M., Thompson, C.M. & Pompliano, D.L. (1997). High-yield expression, purification, and characterization of active, soluble Bacteroides fragilis metallo-β-lactamase, CcrA. Protein Expr. Purif. 9, 355-362.
35. O'Callaghan, C.H., Morris, A., Kirby, S.M. & Shingler, A.H. (1972). Novel method for detection of β-lactamases using a chromogenic cephalosporin substrate. Antimicrob. Agents Chemother. 1, 283-288.
36. Kitz, R. & Wilson, I.B. (1962). Esters of methanesulfonic acid as irreversible inhibitors of acetylcholinterase. J. Biol. Chem. 237, 3245-3249.
37. Silverman, R.B. (1988). Mechanism-Based Enzyme Inhibition: Chemistry and Enzymology. (Volume 1), pp 12-23, CRC Press, Boca Raton, Fl.
38. Kropp, H., Sundelof, J.G., Hadju, R. & Kahan, F.M. (1982). Metabolism of thienamycin and related carbapenem antibiotics by the renal dipeptidase, dehydropeptidase I. Antimicrob. Agents Chemother. 22, 62-70.
39. Mantlo, N.B., et al., & Greenlee, W.J. (1991). Potent, orally active imidazo[4,5-b]pyridine-based angiotensin II receptor antagonists. J. Med. Chem. 34, 2919-2922.
40. Fitzgerald, P.M.D. (1988). MERLOT, an integrated package of computer programs for the determination of crystal structures by molecular replacement. J. Appl. Cryst. 21, 273-278.
41. Hendrickson, W.A. (1985). Stereochemically restrained refinement of macromolecular structures. Methods Enzymol. 115, 252-270.
42. Carson, M. (1997). Ribbons. Methods Enzymol. 277, 493-505.