Inhibition of peroxidase-catalyzed lodination by cephalosporins: Metallo-β-lactamase-lnduced antithyroid activity of antibiotics

ChemMedChem

Volumn 4, Issue 4, 2009, Pages 512-516

  Tamilselvi, A ^a   Mugesh, Govindasamy ^a  

^a INDIAN INSTITUTE OF SCIENCE   (India)

Author keywords

Antibiotics; Antithyroid drugs; Drug resistance; Metallo lactamase; Peroxidase

Indexed keywords

1 METHYL 1H TETRAZOLE 5 THIOL; 2 METHYL 1,2,4 TRIAZINE 5,6 DIONE 3 THIOL; 2 METHYL 1,3,4 THIADIAZOLE 2 THIOL; ANTIBIOTIC AGENT; ANTITHYROID AGENT; BACTERIAL ENZYME; BETA LACTAM ANTIBIOTIC; CEFAMANDOLE; CEFAZOLIN; CEFMETAZOLE; CEFOPERAZONE; CEFOTAXIME; CEFTRIAXONE; CEPHALOSPORIN DERIVATIVE; HYDROGEN PEROXIDE; IODOTYROSINE; LACTOPEROXIDASE; LATAMOXEF; METALLO BETA LACTAMASE; METHYLIMIDAZOLE; PENICILLIN G; PROPYLTHIOURACIL; THIADIAZOLE DERIVATIVE; THIOKETONE; THIOL; THYROGLOBULIN; THYROID PEROXIDASE; UNCLASSIFIED DRUG;

ANTIBIOTIC RESISTANCE; ANTIMICROBIAL ACTIVITY; ANTITHYROID ACTIVITY; ARTICLE; BACILLUS CEREUS; CONCENTRATION RESPONSE; CONTROLLED STUDY; DRUG ACTIVITY; DRUG DESIGN; DRUG HYDROLYSIS; ENZYME INHIBITION; ENZYME SYNTHESIS; HYDROLYSIS; IODINATION; PHARMACOPHORE; PRIORITY JOURNAL; THYROID FUNCTION; THYROID HORMONE RELEASE;

ANTI-BACTERIAL AGENTS; BETA-LACTAMASES; BIOCATALYSIS; CEPHALOSPORINS; ENZYME INHIBITORS; HYDROLYSIS; IODINE; MOLECULAR STRUCTURE; PEROXIDASES; THYMUS GLAND;

EID: 65549114711     PISSN: 18607179     EISSN: 18607187     Source Type: Journal    
DOI: 10.1002/cmdc.200800371     Document Type: Article

References (42)

1. R. B. Woodward in Recent Advances in the Chemistry of β-Lactam Antibiotics (Ed.: J. Elks), Chemical Society, London, 1977, pp. 167-180;
2. S. G. Waley in The Chemistry of β-Lactams (Ed.: M. I. Page), Chapman and Hall, London, 1992, pp. 198-228.
3. D. M. Livermore, Clin. Microbiol. Rev. 1995, 8, 557-584;
4. B. A. Rasmussen, K. Bush, Antimicrob. Agents Chemother. 1997, 41, 223-232;
5. A. A. Medeires, Br. Med. Bull. 1984, 46, 18-27.
6. J. F. Fisher, S. O. Meroueh, S. Mobashery, Chem. Rev. 2005, 105, 395-424.
7. D. M. Llvermore, J. Antimicrob. Chemother. 1998, 41, 25-41.
8. M. W. Crowder, J. Spencer, A.J. Vila, Ace. Chem. Res. 2006, 39, 721-728 and references therein;
9. A. Tamilselvi, G. Mugesh, J. Biol. Inorg. Chem. 2008, 13, 1039-1053.
10. K. Bush, Clin. Infect. Dis. 1998, 27, S48-S53;
11. J. A. Cricco, E. G. Orellano, R. M. Rasia, E. A. Ceccarelli, A.J. Vila, Coord. Chem. Rev. 1999, 190/92, 519-535.
12. T. R. Walsh, M. A. Toleman, L. Poirel, P. Nordmann, Clin. Microbiol. Rev. 2005, 18, 306-325.
13. J. J. Lipsky, Biochem. Pharmacol. 1989, 38, 773-779;
14. J. Shimada, T. Miyahara, S. Otsubo, N. Yoshimatsu, T. Oguma, T. Matsubara, Japan J. Pharmacol. 1987, 45, 533-544.
15. R. Hochman, J. Clark, A. Rolla, S. Thomas, A. Kaldany, J. A. D'Elia, Arch. Intern. Med. 1982, 142, 1440-1442;
16. J.J. Lipsky, J.C. Lewis, W.J. Nov¡ck, Jr., Antimicrob. Agents Chemother. 1984, 25, 380-381;
17. G. Agnelli, A. D. Favero, P. Parise, R. Guerciolini, B. Pasticci, G. G. Nend, F. Ofosu, Antimicrob. Agents Chemother. 1986, 29, 1108-1109;
18. R. L. Nichols, M. A. Wlkler, J. T. McDevitt, A. L. Lentnek, J. A. Hosutt, Antimicrob. Agents Chemother. 1987, 31, 281-1285;
19. J.J. Lipsky, J. Antimicrob. Chemother. 1988, 21, 281-300;
20. J.F. Westphal, D. Vetter, J. M. Brogard, J. Antimicrob. Chemother. 1994, 33, 387-401;
21. T.C Wood, K. L. Johnson, S. Naylor, R. M. Weinshllboum, Drug Metab. Dispos. 2002, 30, 1123-1128.
22. R. Calesnick, W. D. Harris, R. S. Jones, Science 1954, 119, 128-129.
23. D. A. Libby J. Meites, Science 1954, 120, 354-355.
24. W. C. Grant, Science 1954, 120, 724-725.
25. D. R. Doerge, Xenobiotica 1995, 25, 761-767;
26. A. Taurog, Hormone synthesis: Thyroid iodine metabolism in Werner and Ingbar's The Thyroid, 8th Edition (Eds.: L. E. Braverman, R. D. Utiger), Lippincott Williams & Wilklns, Philadelphia, 2000, pp. 61-84;
27. A. Taurog, M. L. Dorrls, D. R. Doerge, Arch. Biochem. Biophys. 1994, 315, 82-89;
28. D. R. Doerge, A. Taurog, M. L. Dorris, Arch. Biochem. Biophys. 1994, 315, 90-99;
29. A. Taurog, M. L. Dorris, D. R. Doerge, Arch. Biochem. Biophys. 1996, 330, 24-32.
30. D. S. Cooper, Lancet 2003, 362, 459-468;
31. D. S. Cooper, N. Engl. J. Med. 2005, 352, 905-917 and references therein.
32. A. Taurog, M. L. Dorris, L. Lamas, Endocrinology 1974, 94, 1286-1294.
33. G. Roy, G. Mugesh, J. Am. Chem. Soc. 2005, 127, 15207-15217;
34. G. Roy, M. Nethaji, G. Mugesh, Org. Blomol. Chem. 2006, 4, 2883-2887;
35. G. Roy, D. Das, G. Mugesh, Inorg. Chim. Acta 2007, 360, 303-316.
36. H. G. Grimm, Z. Elektrochem. 1925, 31, 474-480;
37. H. G. Grimm, Naturwissenschaften 1929, 17, 557-564;
38. G. A. Patani, EJ. LaVoie, Chem. Rev. 1996, 96, 3147-3176.
39. K. Tsuchiya, M. Kida, M. Kondo, H. Ono, M. Takeuchi, T. Nishi, Antimicrob. Agents Chemother. 1978, 14, 557-568.
40. N. Kiesel, M. Limberti, K. Seeger, G. Seibert, I. Winkler, E. Schrinner, J. Antibiot. 1984, 37, 901-909.
41. Our preliminary computational data indicate that the thiones are more stable than the thiol tautomers; A. Tamilselvi, G. Mugesh, unpublished results.
42. There are numerous examples of antibiotics that contain MTT, MDT, and related heterocyclic side chains. Some of these compounds are summarized in figure S24 (Supporting Information).