Bioactivation of antituberculosis thioamide and thiourea prodrugs by bacterial and mammalian flavin monooxygenases

Chemico-Biological Interactions

Volumn 192, Issue 1-2, 2011, Pages 21-25

  Nishida, Clinton R ^a   Ortiz De Montellano, Paul R ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Antituberculosis drugs; Drug metabolism; Ethionamide; Flavin monooxygenases; Isoxyl; Thiacetazone

Indexed keywords

2,4 DIENOYL COENZYME A REDUCTASE (NADPH); BACTERIAL ENZYME; DRUG METABOLITE; ETHIONAMIDE; FLAVIN MONOOXYGENASE; ISONIAZID; NICOTINAMIDE ADENINE DINUCLEOTIDE; PRODRUG; PROTEIN INHA; PROTIONAMIDE; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE; THIOACETAZONE; THIOAMIDE; THIOUREA; TUBERCULOSTATIC AGENT; UNCLASSIFIED DRUG; UNSPECIFIC MONOOXYGENASE;

ANTIBACTERIAL ACTIVITY; ANTIBIOTIC RESISTANCE; CATALYSIS; CONFERENCE PAPER; CROSS RESISTANCE; DRUG ACTIVATION; DRUG OXIDATION; DRUG STRUCTURE; DRUG TARGETING; DRUG TRANSFORMATION; ELECTROPHILICITY; ENZYME ACTIVITY; HUMAN; MAMMAL; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN;

ANTITUBERCULAR AGENTS; BIOTRANSFORMATION; FLAVINS; HUMANS; MIXED FUNCTION OXYGENASES; OXIDATION-REDUCTION; PRODRUGS; THIOAMIDES; THIOUREA;

BACTERIA (MICROORGANISMS); MAMMALIA; MYCOBACTERIUM TUBERCULOSIS;

EID: 79958032042     PISSN: 00092797     EISSN: 18727786     Source Type: Journal    
DOI: 10.1016/j.cbi.2010.09.015     Document Type: Conference Paper

References (24)

1. B. Sahbazian, and S.E. Weis Treatment of active tuberculosis: challenges and prospects Clin. Chest Med. 26 2005 273 282
2. S.K. Sharma, and A. Mohan Multidrug-resistant tuberculosis. A menace that threatens to destabilize tuberculosis control Chest 130 2006 261 272 (Pubitemid 44116869)
3. Y. Zhang, B. Heym, B. Allen, D. Young, and S. Cole The catalase-peroxidase gene and isoniazid resistance of Mycobacterium tuberculosis Nature 358 1992 591 593
4. D.A. Rozwarski, G.A. Grant, D.H.R. Barton, W.R. Jacobs Jr., and J.C. Sacchettini Modification of the NADH of the isoniazid target (InhA) from Mycobacterium tuberculosis Science 279 1998 98 102 (Pubitemid 28079164)
5. A. Argyrou, L. Jin, L. Siconilfi-Baez, R.H. Angeletti, and J.S. Blanchard Proteome-wide profiling of isoniazid targets in Mycobacterium tuberculosis Biochemistry 45 2006 13947 13953 (Pubitemid 44846183)
6. A. Argyrou, M.W. Veetting, B. Aladegbami, and J.S. Blanchard Mycobacterium tuberculosis dihydrofolate reductase is a target for isoniazid Nat. Struct. Mol. Biol. 13 2006 408 413 (Pubitemid 43881580)
7. A.R. Baulard, J.C. Betts, J. Engohang-Ndong, S. Quan, R.A. McAdam, P.J. Brennan, C. Locht, and G.S. Besra Activation of the pro-drug ethionamide is regulated in mycobacteria J. Biol. Chem. 275 2000 28326 28331
8. A.E. DeBarber, K. Mdluli, M. Bosman, L.G. Bekker, and C.E. Barry 3rd. Ethionamide activation and sensitivity in multidrug-resistant Mycobacterium tuberculosis Proc. Natl. Acad. Sci. U.S.A. 97 2000 9677 9682 (Pubitemid 30650835)
9. T.A. Vannelli, A. Dykman, and P.R. Ortiz de Montellano The antituberculosis drug ethionamide is activated by a flavoprotein monooxygenase J. Biol. Chem. 277 2002 12824 12829 (Pubitemid 34952646)
10. A.A. Francois, C.R. Nishida, P.R. Ortiz de Montellano, I.R. Phillips, and E.A. Shephard Human flavin-containing monooxygenase 2.1 catalyzes oxygenation of the antitubercular drugs thiacetazone and ethionamide Drug Metab. Dispos. 37 2009 178 186
11. X. Hanoulle, J.-M. Wieruszeski, P. Rousselot-Pailley, I. Landrieu, C. Locht, G. Lippens, and A.R. Baulard Selective intracellular accumulation of the major metabolite issued from the activation of the prodrug ethionamide in mycobacteria J. Antimicrob. Chemother. 58 2006 768 772 (Pubitemid 44390950)
12. 1H high resolution magic angle spinning NMR Biochem. Biophys. Res. Commun. 331 2005 452 458 (Pubitemid 40602658)
13. M. Wilson, J. DeRisi, J. Kirsensen, H.-H. Imboden, S. Rane, P.O. Brown, and G.K. Schoolnik Exploring drug-induced alterations in gene expression in Mycobacterium tuberculosis by microarray hybridization Proc. Natl. Acad. Sci. U.S.A. 96 1999 12833 12838 (Pubitemid 29513588)
14. A. Banerjee, E. Dubnau, A. Quemard, V. Balasubramanian, K.S. Um, T. Wilson, D. Collins, G. de Lisle, and W.R. Jacobs Jr. InhA, a gene encoding a target for isoniazid and ethionamide in Mycobacterium tuberculosis Science 263 1994 227 230 (Pubitemid 24067929)
15. G.P Morlock, B. Metchock, D. Sikes, J.T. Crawford, and R.C. Cooksey EthA, inhA, and katG loci of ethionamide-resistant clinical Mycobacterium tuberculosis isolates Antimicrob. Agents Chemother. 47 2003 3799 3805 (Pubitemid 37484992)
16. F. Wang, R. Langley, G. Gulten, L.G. Dover, G.S. Besra, W.R. Jacobs Jr., and J.C. Sacchettini Mechanism of thioamide drug action against tuberculosis and leprosy J. Exp. Med. 204 2007 73 78 (Pubitemid 46148758)
17. L. Qian, and P.R. Ortiz de Montellano Oxidative activation of thiacetazone by the Mycobacterium tuberculosis flavin monooxygenase EtaA and human FMO1 and FMO3 Chem. Res. Toxicol. 19 2006 443 449
18. S.R. Pattyn, and M.J. Colston Cross-resistance amongst thiambutosine, thiacetazone, ethionamide and prothionamide with Mycobacterium leprae Lepr. Rev. 49 1978 324 326 (Pubitemid 9087455)
19. T. Osato, K. Tsukagoshi, and H. Shimizu Studies on thiacetazone resistance of tubercle bacilli. 3. Cross resistance between thiacetazone and ethionamide Kekkaku 46 1971 89 92
20. L.G. Dover, A. Alahari, P. Gratraud, J.M. Gomex, V. Bhowruth, R.C. Reynolds, G.S. Besra, and L. Kremer EthA, a common activator of thiocarbamide-containing drugs acting on different mycobacterial targets Antimicrob. Agents Chemother. 51 2007 1055 1063 (Pubitemid 46355295)
21. J. Kordulákova, Y.L. Janin, A. Liav, N. Barilone, T.D. Vultos, J. Rauzier, P.J. Brennan, B. Gicquel, and M. Jackson Isoxyl activation is required for bacteriostatic activity against Mycobacterium tuberculosis Antimicrob. Agents Chemother. 51 2007 3824 3829 (Pubitemid 350057777)
22. B. Phetsuksiri, M. Jackson, H. Scherman, M. McNeil, G.S. Besra, A.R. Baulard, R.A. Slayden, A.E. DeBarver, C.E. Barry III, M.S. Baird, D.C. Crick, and P.J. Brennan Unique mechanism of action of the thiourea drug isoxyl on Mycobacterium tuberculosis J. Biol. Chem. 52 2003 53123 53130 (Pubitemid 38035916)
23. S.K. Krueger, and D.E. Williams Mammalian flavin-containing monooxygenases: structure/function, genetic polymorphisms and role in drug metabolism Pharmacol. Ther. 106 2005 357 387 (Pubitemid 40726294)
24. M.C. Henderson, S.K. Krueger, J.F. Stevens, and D.E. Williams Human flavin-containing monooxygenase form 2 S-oxygenation: sulfenic acid formation from thioureas and oxidation of glutathione Chem. Res. Toxicol. 17 2004 633 640 (Pubitemid 38669520)