Identification of products of inhibition of GES-2 β-lactamase by tazobactam by X-ray crystallography and spectrometry

Journal of Biological Chemistry

Volumn 286, Issue 16, 2011, Pages 14396-14409

  Frase, Hilary ^a   Smith, Clyde A ^b   Toth, Marta ^a   Champion, Matthew M ^a   Mobashery, Shahriar ^a   Vakulenko, Sergei B ^a  

^a UNIVERSITY OF NOTRE DAME   (United States)

^b SLAC NATIONAL ACCELERATOR LABORATORY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BACTERIAL PATHOGENS; CARBAPENEM ANTIBIOTIC; CLASS A; INHIBITION PROCESS; INHIBITION PROFILE; LACTAMASES; MASS SPECTROSCOPY; SHEDDING LIGHT; TAZOBACTAM; UV SPECTROMETRY; X-RAY STRUCTURE;

ANTIBIOTICS; ENZYMES; MASS SPECTROMETRY; MINERALOGY; X RAY CRYSTALLOGRAPHY; X RAYS;

ENZYME INHIBITION;

BETA LACTAMASE; PIPERACILLIN; PROTEIN GES 2; TAZOBACTAM; UNCLASSIFIED DRUG;

ARTICLE; COMPLEX FORMATION; CONTROLLED STUDY; ENZYME INHIBITION; ENZYME STRUCTURE; ESCHERICHIA COLI; HYDROLYSIS; MASS SPECTROMETRY; NONHUMAN; PRIORITY JOURNAL; ULTRAVIOLET SPECTROPHOTOMETRY; X RAY CRYSTALLOGRAPHY;

ALDEHYDES; AMINO ACID MOTIFS; BACTERIA; BETA-LACTAMASES; CATALYSIS; CATALYTIC DOMAIN; CROSS-LINKING REAGENTS; CRYSTALLOGRAPHY, X-RAY; KINETICS; MASS SPECTROMETRY; MODELS, CHEMICAL; PENICILLANIC ACID; PROTEIN CONFORMATION; SPECTROPHOTOMETRY, ULTRAVIOLET;

BACTERIA (MICROORGANISMS);

EID: 79954599167     PISSN: 00219258     EISSN: 1083351X     Source Type: Journal    
DOI: 10.1074/jbc.M110.208744     Document Type: Article

References (61)

1. Testero, S. A., Fisher, J. F., and Mobashery, S. (2010) in Burger's Medicinal Chemistry, Drug Discovery and Development (Abraham, D. J., and Rotella, D. P., eds) pp. 259-404 Wiley-Blackwell, Oxford
2. Poole, K. (2004) Cell. Mol. Life Sci. 61, 2200-2223
3. Fisher, J. F., and Mobashery, S. (2010) J. Med. Chem. 53, 4813-4829
4. Goffin, C., and Ghuysen, J. M. (2002) Microbiol. Mol. Biol. Rev. 66, 702-738
5. Fisher, J. F., Meroueh, S. O., and Mobashery, S. (2005) Chem. Rev. 105, 395-424
6. Bush, K., and Jacoby, G. A. (2010) Antimicrob. Agents Chemother. 54, 969-976
7. Bradford, P. A. (2001) Clin. Microbiol. Rev. 14, 933-951
8. Perez, F., Endimiani, A., Hujer, K. M., and Bonomo, R. A. (2007) Curr. Opin. Pharmacol. 7, 459-469
9. Baughman, R. P. (2009) J. Intensive Care Med. 24, 230-241
10. Shahid, M., Sobia, F., Singh, A., Malik, A., Khan, H. M., Jonas, D., and Hawkey, P. M. (2009) Crit. Rev. Microbiol. 35, 81-108
11. Kattan, J. N., Villegas, M. V., and Quinn, J. P. (2008) Clin. Microbiol. Infect. 14, 1102-1111
12. Walther-Rasmussen, J., and Høiby, N. (2007) J. Antimicrob. Chemother. 60, 470-482
13. Girlich, D., Poirel, L., and Nordmann, P. (2010) Antimicrob. Agents Chemother. 54, 328-332
14. Poirel, L., Le Thomas, I., Naas, T., Karim, A., and Nordmann, P. (2000) Antimicrob. Agents Chemother. 44, 622-632
15. Moubareck, C., Brémont, S., Conroy, M. C., Courvalin, P., and Lambert, T. (2009) Antimicrob. Agents Chemother. 53, 3579-3581
16. Poirel, L., Weldhagen, G. F., Naas, T., De Champs, C., Dove, M. G., and Nordmann, P. (2001) Antimicrob. Agents Chemother. 45, 2598-2603
17. Vourli, S., Giakkoupi, P., Miriagou, V., Tzelepi, E., Vatopoulos, A. C., and Tzouvelekis, L. S. (2004) FEMS Microbiol. Lett. 234, 209-213
18. Ambler, R. P., Coulson, A. F., Frère, J. M., Ghuysen, J. M., Joris, B., Forsman, M., Levesque, R. C., Tiraby, G., and Waley, S. G. (1991) Biochem. J. 276, 269-270
19. Frase, H., Shi, Q., Testero, S. A., Mobashery, S., and Vakulenko, S. B. (2009) J. Biol. Chem. 284, 29509-29513
20. Clinical and Laboratory Standards Institute (2006) Methods for Dilution Antimicrobial Susceptibility Tests for Bacteria That Grow Aerobically: Approved Standard, 7th Ed., Clinical and Laboratory Standards Institute, Wayne, PA
21. Dixon, M. (1953) Biochem. J. 55, 170-171
22. Silverman, R. B. (1988) Mechanism-based Enzyme Inactivation: Chemistry and Enzymology, CRC Press, Boca Raton, FL
23. Bush, K., Macalintal, C., Rasmussen, B. A., Lee, V. J., and Yang, Y. (1993) Antimicrob. Agents Chemother. 37, 851-858
24. Padayatti, P. S., Sheri, A., Totir, M. A., Helfand, M. S., Carey, M. P., Anderson, V. E., Carey, P. R., Bethel, C. R., Bonomo, R. A., Buynak, J. D., and van den Akker, F. (2006) J. Am. Chem. Soc. 128, 13235-13242
25. Rizwi, I., Tan, A. K., Fink, A. L., and Virden, R. (1989) Biochem. J. 258, 205-209
26. Cartwright, S. J., and Coulson, A. F. (1979) Nature 278, 360-361
27. Sulton, D., Pagan-Rodriguez, D., Zhou, X., Liu, Y., Hujer, A. M., Bethel, C. R., Helfand, M. S., Thomson, J. M., Anderson, V. E., Buynak, J. D., Ng, L. M., and Bonomo, R. A. (2005) J. Biol. Chem. 280, 35528-35536
28. Bonomo, R. A., Liu, J., Chen, Y., Ng, L., Hujer, A. M., and Anderson, V. E. (2001) Biochim. Biophys. Acta 1547, 196-205
29. Matthews, B. W. (1968) J. Mol. Biol. 33, 491-497
30. Kabsch, W. (1993) J. Appl. Crystallogr. 26, 795-800
31. Collaborative Computational Project, N. (1994) Acta Crystallogr. D Biol. Crystallogr. 50, 760-763
32. Murshudov, G. N., Vagin, A. A., Lebedev, A., Wilson, K. S., and Dodson, E. J. (1999) Acta Crystallogr. D Biol. Crystallogr. 55, 247-255
33. Emsley, P., and Cowtan, K. (2004) Acta Crystallogr. D Biol. Crystallogr. 60, 2126-2132
34. Adams, P. D., Afonine, P. V., Bunkóczi, G., Chen, V. B., Davis, I. W., Echols, N., Headd, J. J., Hung, L. W., Kapral, G. J., Grosse-Kunstleve, R. W., McCoy, A. J., Moriarty, N. W., Oeffner, R., Read, R. J., Richardson, D. C., Richardson, J. S., Terwilliger, T. C., and Zwart, P. H. (2010) Acta Crystallogr. D Biol. Crystallogr. 66, 213-221
35. Berman, H. M., Westbrook, J., Feng, Z., Gilliland, G., Bhat, T. N., Weissig, H., Shindyalov, I. N., and Bourne, P. E. (2000) Nucleic Acids Res. 28, 235-242
36. Krissinel, E., and Henrick, K. (2004) Acta Crystallogr. D Biol. Crystallogr. 60, 2256-2268
37. DeLano, W. L. (2002) The PyMOL Molecular Graphics System, DeLano Scientific LLC, San Carlos, CA
38. Drawz, S. M., and Bonomo, R. A. (2010) Clin. Microbiol. Rev. 23, 160-201
39. Ostercamp, D. L. (1970) J. Org. Chem. 35, 1632-1641
40. Yang, Y., Janota, K., Tabei, K., Huang, N., Siegel, M. M., Lin, Y. I., Rasmussen, B. A., and Shlaes, D. M. (2000) J. Biol. Chem. 275, 26674-26682
41. Pagan-Rodriguez, D., Zhou, X., Simmons, R., Bethel, C. R., Hujer, A. M., Helfand, M. S., Jin, Z., Guo, B., Anderson, V. E., Ng, L. M., and Bonomo, R. A. (2004) J. Biol. Chem. 279, 19494-19501
42. Smith, C. A., Caccamo, M., Kantardjieff, K. A., and Vakulenko, S. (2007) Acta Crystallogr. D Biol. Crystallogr. 63, 982-992
43. Meroueh, S. O., Fisher, J. F., Schlegel, H. B., and Mobashery, S. (2005) J. Am. Chem. Soc. 127, 15397-15407
44. Kuzin, A. P., Nukaga, M., Nukaga, Y., Hujer, A., Bonomo, R. A., and Knox, J. R. (2001) Biochemistry 40, 1861-1866
45. Sun, T., Bethel, C. R., Bonomo, R. A., and Knox, J. R. (2004) Biochemistry 43, 14111-14117
46. Papp-Wallace, K. M., Bethel, C. R., Distler, A. M., Kasuboski, C., Taracila, M., and Bonomo, R. A. (2010) Antimicrob. Agents Chemother. 54, 890-897
47. Mariotte-Boyer, S., Nicolas-Chanoine, M. H., and Labia, R. (1996) FEMS Microbiol. Lett. 143, 29-33
48. Kalp, M., Bethel, C. R., Bonomo, R. A., and Carey, P. R. (2009) Biochemistry 48, 9912-9920
49. Kalp, M., Totir, M. A., Buynak, J. D., and Carey, P. R. (2009) J. Am. Chem. Soc. 131, 2338-2347
50. Padayatti, P. S., Helfand, M. S., Totir, M. A., Carey, M. P., Hujer, A. M., Carey, P. R., Bonomo, R. A., and van den Akker, F. (2004) Biochemistry 43, 843-848
51. Totir, M. A., Padayatti, P. S., Helfand, M. S., Carey, M. P., Bonomo, R. A., Carey, P. R., and van den Akker, F. (2006) Biochemistry 45, 11895-11904
52. Ibuka, A., Taguchi, A., Ishiguro, M., Fushinobu, S., Ishii, Y., Kamitori, S., Okuyama, K., Yamaguchi, K., Konno, M., and Matsuzawa, H. (1999) J. Mol. Biol. 285, 2079-2087
53. Tranier, S., Bouthors, A. T., Maveyraud, L., Guillet, V., Sougakoff, W., and Samama, J. P. (2000) J. Biol. Chem. 275, 28075-28082
54. Jelsch, C., Mourey, L., Masson, J. M., and Samama, J. P. (1993) Proteins 16, 364-383
55. Brown, N. G., Shanker, S., Prasad, B. V., and Palzkill, T. (2009) J. Biol. Chem. 284, 33703-33712
56. Nukaga, M., Mayama, K., Hujer, A. M., Bonomo, R. A., and Knox, J. R. (2003) J. Mol. Biol. 328, 289-301
57. Toth, M., Smith, C., Frase, H., Mobashery, S., and Vakulenko, S. (2010) J. Am. Chem. Soc. 132, 816-823
58. Swarén, P., Maveyraud, L., Raquet, X., Cabantous, S., Duez, C., Pédelacq, J. D., Mariotte-Boyer, S., Mourey, L., Labia, R., Nicolas-Chanoine, M. H., Nordmann, P., Frère, J. M., and Samama, J. P. (1998) J. Biol. Chem. 273, 26714-26721
59. Sougakoff, W., L'Hermite, G., Pernot, L., Naas, T., Guillet, V., Nordmann, P., Jarlier, V., and Delettré, J. (2002) Acta Crystallogr. D Biol. Crystallogr. 58, 267-274
60. Ke, W., Bethel, C. R., Thomson, J. M., Bonomo, R. A., and van den Akker, F. (2007) Biochemistry 46, 5732-5740
61. Knox, J. R., and Moews, P. C. (1991) J. Mol. Biol. 220, 435-455