Thiomandelic acid, a broad spectrum inhibitor of zinc β-lactamases. Kinetic and spectroscopic studies

Journal of Biological Chemistry

Volumn 276, Issue 48, 2001, Pages 45015-45023

  Mollard, Claire ^a   Moali, Catherine ^b   Papamicael, Cyril ^c   Damblon, Christian ^a   Vessilier, Sandrine ^d   Amicosante, Gianfranco ^d   Schofield, Christopher J ^c   Galleni, Moreno ^b   Frère, Jean Marie ^d   Roberts, Gordon C K ^a  

^a UNIVERSITY OF LEICESTER   (United Kingdom)

^b UNIVERSITY OF LIÈGE   (Belgium)

^c UNIVERSITY OF OXFORD   (United Kingdom)

^d UNIVERSITY OF L'AQUILA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIBODIES; ENZYMES; POSITIVE IONS; SYNTHESIS (CHEMICAL);

BROAD SPECTRUM INHIBITORS;

ZINC;

ARGININE; BACTERIAL ENZYME; BETA LACTAM ANTIBIOTIC; BETA LACTAMASE; BETA LACTAMASE INHIBITOR; CARBOXYLIC ACID; CARBOXYLIC ACID DERIVATIVE; MANDELIC ACID DERIVATIVE; PRODRUG; THIOESTER; THIOMANDELIC ACID; UNCLASSIFIED DRUG; ZINC ION; BETA LACTAMASES; ENZYME INHIBITOR; THIOL DERIVATIVE; ZINC;

AEROMONAS HYDROPHILA; ARTICLE; BACILLUS CEREUS; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME KINETICS; ISOMERISM; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; PROTEIN BINDING; PROTON NUCLEAR MAGNETIC RESONANCE; SPECTROSCOPY; STRUCTURE ACTIVITY RELATION; BINDING SITE; CHEMICAL MODEL; CHEMICAL STRUCTURE; CHEMISTRY; KINETICS; METABOLISM; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SPECTROPHOTOMETRY; SYNTHESIS;

AEROMONAS; AEROMONAS HYDROPHILA; BACILLUS CEREUS; BACTERIA (MICROORGANISMS); NEGIBACTERIA; POSIBACTERIA;

ARGININE; BETA-LACTAMASES; BINDING SITES; ENZYME INHIBITORS; KINETICS; MAGNETIC RESONANCE SPECTROSCOPY; MANDELIC ACIDS; MODELS, CHEMICAL; MODELS, MOLECULAR; PROTEIN BINDING; SPECTROPHOTOMETRY; STRUCTURE-ACTIVITY RELATIONSHIP; SULFHYDRYL COMPOUNDS; SUPPORT, NON-U.S. GOV'T; ZINC;

EID: 0035976960     PISSN: 00219258     EISSN: None     Source Type: Journal    
DOI: 10.1074/jbc.M107054200     Document Type: Article

References (57)

1. Frère, J. M. (1995) Mol. Microbiol. 16, 385-395
2. Matagne, A., Dubus, A., Galleni, M., and Frère, J. M. (1999) Nat. Prod. Rep. 16, 1-19
3. Wang, Z., Fast, W., Valentine, A. M., and Benkovic, S. J. (1999) Curr. Opin. Chem. Biol. 3, 614-622
4. Kuwabara, S., and Abraham, E. P. (1967) Biochem. J. 103, 27C-30C
5. Payne, D. J. (1993) J. Med. Microbiol. 39, 93-99
6. Laraki, N., Franceschini, N., Rossolini, G. M., Santucci, P., Meunier, C., de Pauw, E., Amicosante, G., Frère, J. M., and Galleni, M. (1999) Antimicrob. Agents Chemother. 43, 902-906
7. Riccio, M. L., Franceschini, N., Boschi, L., Caravelli, B., Cornaglia, G., Fontana, R., Amicosante, G., and Rossolini, G. M. (2000) Antimicrob. Agents Chemother. 44, 1229-1235
8. Iyobe, S., Kusadokoro, H., Ozaki, J., Matsumura, N., Minami, S., Haruta, S., Sawai, T., and O'Hara, K. (2000) Antimicrob. Agents Chemother. 44, 2023-2027
9. Chu, Y. W., Afzal-Shah, M., Houang, E. T., Palepou, M. F., Lyon, D. J., Woodford, N., and Livermore, D. M. (2001) Antimicrob. Agents Chemother. 45, 710-714
10. Yano, H., Kuga, A., Okamoto, R., Kitasato, H., Kobayashi, T., and Inoue, M. (2001) Antimicrob. Agents Chemother. 45, 1343-1348
11. Fabiane, S. M., Sohi, M. K., Wan, T., Payne, D. J., Bateson, J. H., Mitchell, T., and Sutton, B. J. (1998) Biochemistry 37, 12404-12411
12. Paul-Soto, R., Bauer, R., Frère, J. M., Galleni, M., Meyer-Klaucke, W., Nolting, H., Rossolini, G. M., de Seny, D., Hernandez-Valladares, M., Zeppezauer, M., and Adolph, H. W. (1999) J. Biol. Chem. 274, 13242-13249
13. Concha, N. O., Rasmussen, B. A., Bush, K., and Herzberg, O. (1996) Structure 4, 823-836
14. Paul-Soto, R., Hernadez-Valladares, M., Galleni, M., Bauer, R., Zeppezauer, M., Frère, J. M., and Adolph, H. W. (1998) FEBS Lett. 438, 137-140
15. Franceschini, N., Caravelli, B., Docquier, J. D., Galleni, M., Frère, J. M., Amicosante, G., and Rossolini, G. M. (2000) Antimicrob. Agents Chemother. 44, 3003-3007
16. Rossolini, G. M., Franceschini, N., Riccio, M. L., Mercuri, P. S., Perilli, M., Galleni, M., Frère, J. M., and Amicosante, G. (1998) Biochem. J. 332, 145-152
17. Hernandez Valladares, M., Felici, A., Weber, G., Adolph, H. W., Zeppezauer, M., Rossolini, G. M., Amicosante, G., Frère, J. M., and Galleni, M. (1997) Biochemistry 36, 11534-11541
18. Walsh, T. R., Hall, L., Assinder, S. J., Nichols, W. W., Cartwright, S. J., MacGowan, A. P., and Bennett, P. M. (1994) Biochim. Biophys. Acta 1218, 199-201
19. Crowder, M. W., Walsh, T. R., Banovic, L., Pettit, M., and Spencer, J. (1998) Antimicrob. Agents Chemother. 42, 921-926
20. Mercuri, P. S., Bouillenne, F., Boschi, L., Lamotte-Brasseur, J., Amicosante, G., Devreese, B., Van Beeumen, J., Frère, J. M., Rossolini, G. M., and Galleni, M. (2001) Antimicrob. Agents Chemother. 45, 921-926
21. Bellais, S., Aubert, D., Naas, T., and Nordmann, P. (2000) Antimicrob. Agents Chemother. 44, 1878-1886
22. Carfi, A., Duée, E., Galleni, M., Frère, J. M., and Dideberg, O. (1998) Acta Crystallogr. Sect. D Biol. Crystallogr. 54, 313-323
23. Carfi, A., Duée, E., Paul-Soto, R., Galleni, M., Frere, J. M., and Dideberg, O. (1998) Acta Crystallogr. Sect. D Biol. Crystallogr. 54, 45-57
24. Fitzgerald, P. M., Wu, J. K., and Toney, J. H. (1998) Biochemistry 37, 6791-6800
25. Concha, N. O., Janson, C. A., Rowling, P., Pearson, S., Cheever, C. A., Clarke, B. P., Lewis, C., Galleni, M., Frère, J. M., Payne, D. J., Bateson, J. H., and Abdel-Meguid, S. S. (2000) Biochemistry 39, 4288-4298
26. Ullah, J. H., Walsh, T. R., Taylor, I. A., Emery, D. C., Verma, C. S., Gamblin, S. J., and Spencer, J. (1998) J. Mol. Biol. 284, 125-136
27. Galleni, M., Lamotte-Brasseur, J., Rossolini, G. M., Spencer, J., Dideberg, O., and Frère, J. M. (2001) Antimicrob. Agents Chemother. 45, 660-663
28. Bounaga, S., Laws, A. P., Galleni, M., and Page, M. I. (1998) Biochem. J. 331, 703-711
29. Wang, Z. G., Fast, W., and Benkovic, S. J. (1999) Biochemistry 38, 10013-10023
30. Baldwin, G. S., Galdes, A., Hill, H. A., Waley, S. G., and Abraham, E. P. (1980) J. Inorg. Biochem. 13, 189-204
31. Orellano, E. G., Girardini, J. E., Cricco, J. A., Ceccarelli, E. A., and Vila, A. J. (1998) Biochemistry 37, 10173-10180
32. Toney, J. H., Fitzgerald, P. M., Grover-Sharma, N., Olson, S. H., May, W. J., Sundelof, J. G., Vanderwall, D. E., Cleary, K. A., Grant, S. K., Wu, J. K., Kozarich, J. W., Pompliano, D. L., and Hammond, G. G. (1998) Chem. Biol. 5, 185-196
33. Nagano, R., Adachi, Y., Imamura, H., Yamada, K., Hashizume, T., and Morishima, H. (1999) Antimicrob. Agents Chemother. 43, 2497-2503
34. Walter, M. W., Felici, A., Galleni, M., Paul-Soto, R., Adlington, R. M., Baldwin, J. E., Frère, J. M., Gololobov, M., and Schofield, C. J. (1996) Bioorg. Med. Chem. Lett. 6, 2455-2458
35. Walter, M. W., Hernandez Valladres, M., Adlington, R. M., Amicosante, G., Baldwin, J. E., Frère, J. M., Galleni, M., Rossolini, G. M., and Schofield, C. J. (1999) Bioorg. Chem. 27, 35-40
36. Toney, J. H., Hammond, G. G., Fitzgerald, P. M. D., Sharma, N., Balkovec, J. M., Rouen, G. P., Olson, S. H., Hammond, M. L., Greenlee, M. L., and Gao, Y.-D. (2001) J. Biol. Chem. 276, 31913-31918
37. Goto, M., Takahashi, T., Yamashita, F., Koreeda, A., Mori, H., Ohta, M., and Arakawa, Y. (1997) Biol. Pharm. Bull. 20, 1136-1140
38. Payne, D. J., Bateson, J. H., Gasson, B. C., Proctor, D., Khushi, T., Farmer, T. H., Tolson, D. A., Bell, D., Skett, P. W., Marshall, A. C., Reid, R., Ghosez, L., Combret, Y., and Marchand-Brynaert, J. (1997) Antimicrob. Agents Chemother. 41, 135-140
39. Page, M. I., and Laws, A. P. (1998) Chem. Commun. 1609-1617
40. Scrofani, S. D., Chung, J., Huntley, J. J., Benkovic, S. J., Wright, P. E., and Dyson, H. J. (1999) Biochemistry 38, 14507-14514
41. Payne, D. J., Bateson, J. H., Gasson, B. C., Khushi, T., Proctor, D., Pearson, S. C., and Reid, R. (1997) FEMS Microbiol. Lett. 157, 171-175
42. Greenlee, M. L., Laub, J. B., Balkovec, J. M., Hammond, M. L., Hammond, G. G., Pompliano, D. L., and Epstein-Toney, J. H. (1999) Bioorg. Med. Chem. Lett. 9, 2549-2554
43. Hammond, G. G., Huber, J. L., Greenlee, M. L., Laub, J. B., Young, K., Silver, L. L., Balkovec, J. M., Pryor, K. D., Wu, J. K., Leiting, B., Pompliano, D. L., and Toney, J. H. (1999) FEMS Microbiol. Lett. 179, 289-296
44. Huntley, J. J. A., Scrofani, S. D. B., Osborne, M. J., Wright, P. E., and Dyson, H. J. (2000) Biochemistry 39, 13356-13364
45. Eloy, F., and Lenaers, R. (1962) Chem. Rev. 62, 155-183
46. Bonner, W. A. (1968) J. Org. Chem. 33, 1831-1836
47. Iranpoor, N., and Zeynizadeh, B. (1999) Synthesis 1, 49-50
48. Strijtveen, B., and Kellog, R. M. (1986) J. Org. Chem. 51, 3664-3671
49. Damblon, C., Prosperi, C., Lian, L. Y., Barsukov, I., Paul-Soto, R., Galleni, M., Frère, J. M., and Roberts, G. C. K. (1999) J. Am. Chem. Soc. 121, 11575-11576
50. Grassetti, D. R., and Murray, J. F. (1967) Arch. Biochem. Biophys. 119, 41-49
51. Kay, L. E., Keifer, P., and Saarinen, T. (1992) J. Am. Chem. Soc. 114, 10663-10665
52. Lian, L.-Y., Barsukov, I., Golovanov, A., Hawkins, D., Sze, K.-H., Badil, R., Keep, N. H., and Roberts, G. C. K. (2000) Structure 8, 47-55
53. Piotto, M., Saudek, V., and Sklenar, V. (1992) J. Biomol. NMR 2, 661-665
54. Kuboniwa, H., Grzesiek, S., Delaglio, F., and Bax, A. (1994) J. Biomol. NMR 4, 871-878
55. Farmer, B. T. (1996) Nat. Struct. Biol. 3, 995-997
56. Williamson, R. A., Carr, M. D., Frenkiel, T. A., Feeney, J., and Freedman, R. B. (1997) Biochemistry 36, 13882-13889
57. Muskett, F. W., Frenkiel, T. A. Feeney, J., Freedman, R. B., Carr, M. D., and Williamson, R. A. (1998) J. Biol. Chem. 273, 21736-21743