The mode of inhibition of Mycobacterium tuberculosis wild-type and isoniazid-resistant 2-trans-enoyl-ACP(CoA) reductase enzymes by an inorganic complex

Anti-Infective Agents in Medicinal Chemistry

Volumn 7, Issue 1, 2008, Pages 50-62

  Vasconcelos, I B ^a   Meyer, E ^b   Sales, F A M ^b   Moreira, I S ^b   Basso, Luiz A ^a   Santos, Diogene S ^a  

^a PONTIFICAL CATHOLIC UNIVERSITY OF RIO GRANDE DO SUL   (Brazil)

^b FEDERAL UNIVERSITY OF CEARÁ   (Brazil)

Author keywords

Drug resistance; InhA; Inorganic complex; Isoniazid; Mycolic acids; Slow onset inhibition; Tuberculosis

Indexed keywords

ENOYL ACYL CARRIER PROTEIN REDUCTASE (NADH); ISONIAZID DERIVATIVE; KATG PROTEIN; MYCOLIC ACID;

ANTIBACTERIAL ACTIVITY; ANTIBIOTIC RESISTANCE; ARTICLE; BACTERIAL MEMBRANE; DRUG MECHANISM; ENZYME ACTIVE SITE; ENZYME INHIBITION; FATTY ACID SYNTHESIS; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN; TUBERCULOSIS; TUBERCULOSIS CONTROL; WILD TYPE;

EID: 41149106795     PISSN: 18715214     EISSN: None     Source Type: Journal    
DOI: 10.2174/187152108783329799     Document Type: Article

References (76)

1. Bloom, B.R.; Myrray, C.J.L. Science, 1992, 257, 1055.
2. Gutierrez, M.C.; Brisse, S.; Brosch, R.; Fabre, M.; Omaïs B,; Marmiesse, M.; Supply, P.; Vincent, V. Plos Pathog., 2005, 1(e5), 55.
3. Young, D.B.; Marshall, B.; Smet, K.D. The return of the resistant microbes, in: The Diagnostic Challeng, E.P. Fischer and S. Klose, eds., Boehringer Mannheim Grub, Mannheim, 1996.
4. Raviglione, M.C. Tuberculosis, 2003, 83, 4.
5. World Health Organization. Global Tuberculosis Control Report, 2006.
6. Dye, C.; Scheele, S.; Dolin, P.; Pathania, V.; Raviglione, M.C. JAMA, 1999, 282, 677.
7. Reid, A.; Scano, F.; Getahun, H.; Willians, B.; Dye, C.; Nunn, P.; De Cock, K.M.; Hankins, C.; Miller, B.; Castro, K.G.; Raviglione, M.C. Lancet Infect Dis., 2006, 6, 483.
8. Corbett, E.L.; Watt, C.J.; Walker, N.; Maher, D.; Williams, B.G.; Raviglione, M.C.; Dye, C. Arch Intern. Med., 2003, 163, 1009.
9. World Health Organization. Guidelines for the programmatic management of drug-resistant tuberculosis, 2006.
10. World Health Organization. XDR-TB - Extensive Drug Resistant TB. 2006.
11. Duncan, K. Tuberculosis, 2003, 83, 201.
12. Grosset, J. Clin, Chest Med., 1980, 1, 231241.
13. Hiriyanna, K.T.; Ramakrishnan, T. Arch. Microbiol., 1986, 144, 105.
14. Russel, D.G. Nat. Rev. Mol. Cell Biol., 2001, 2, 1.
15. Hingley-Wilson, S.M.; Sambandamurthy, V.K.; Jacobs, W.R.Jr. Nat. Immunol., 2003, 4, 949.
16. Schatz, A.; Waksman, S.A. Proc. Soc. Exp. Biol. Med., 1994, 57, 244.
17. Kushner, S.; Dalalian, H.; Sanjurjo, J.L.; Bach, F.L.; Safu, S.R.; Smith, V.K.Jr.; Williams, J.H. J. Am. Chem. Soc., 1952, 74, 3617.
18. Middlebrook, G. Am. Rev. Tuberc., 1952, 65, 765.
19. Mitchison, D.A. Tubercle, 1985, 66, 219.
20. World Health Organization. WHO document WHO/CDS/TB/2001.285, 2001, Geneva.
21. Pablos-Méndez, A.; Gowda, D.K.; Frieden, T.R. Bull. World Health Organ., 2002, 80, 489.
22. Takayama, K.; Wang, C.; Besra, G.S. Clin. Microb. Rev., 2005, 18(1), 81.
23. Brennan, P.J. Tuberulosis., 2003, 83, 91.
24. Brennan, P.J.; Nikaido, H. Annu. Rev. Biochem., 1995, 64, 29.
25. Barry III, C.E.; Boshoff, H.I. Drug.Disc. Today: Dis. Mech., 2006, 3(2), 237.
26. Schroeder, E.K.; de Souza, O.N.; Santos, D.S.; Basso, L.A. Curr. Pharm. Biotechnol., 2002, 3(3), 197.
27. Basso, L.A.; Santos, D.S. Med. Chem. Rev., 2005, 2, 393.
28. Watanabe, M.; Aoyagi, Y.; Mitome, H.; Fujita, T.; Naoki, H.; Ridell, M.; Minnikin, D.E. Microb., 2002, 148, 1881.
29. Boissier, F.; Bardou, F.; Guillet, V.; Uttenweiler-Joseph, S.; Daffé, M., Quémard, A., Mourev, L. J. Biol. Chem., 2006, 281(7), 4434.
30. Besra, G.S.; Kreme;, L. In Tuberculosis and the Tubercle Bacillus; Cole, S.T.; Eisenach, K.D.; McMurray, D.N.; Jacobs, W.L.Jr., Eds.; ASM Press: Washington, 2005, pp. 287-305.
31. Gronan, J.E.; Rock C.O. In Escherichia coli and Salmonella: Cellullar and Molecular Biology; Neidhardt, F.C., Ed.; ASM Press: Washington, 1996, pp. 612-636.
32. Brindley, DN; Matsumura, S.; Block, K. Nat., 1969, 224, 666.
33. Bloch, K. Methods Enzymol., 1975, 35, 84.
34. Slayden, R.A.; Barry III, C.E. Tuberculosis, 2002, 82, 149.
35. Veyron-Churlet, R.; Bigot, S.; Verdoux, O.G.S.; Malaga, W.; Daffé, M.; Zerbib, D. J. Mol. Biol., 2005, 353, 847.
36. Meyer, H.; Mally, J. Mont. für Chem., 1912, 33, 393.
37. Fox, H.H. Chem. Eng. News, 1951, 29, 3963.
38. Basso, L.A.; Blanchard, J.S. Adv. Exp. Med. Biol., 1998, 456, 115.
39. Banerjee, A.; Dubnau, E.; Quémard, A.; Balasubamanian, V.; Um, K.S.; Wilson, T.; Collins, D.; de lisle, G.; Jacobs, W.R.Jr. Science, 1994, 263, 227.
40. Quémard, A.; Sacchettini, J.C.; Dessen, A.; Vilchéze, C.; Bittman, R.; Jacobs, W.R.Jr.; Blanchard, J.S. Biochem., 1995, 34, 8235.
41. Vilchéze, C.; Morbidoni, H.R.; Weisbrod, T.R.; Iwamoto, H.; Kuo, M.; Sacchettini, J.C.; Jacobs, W.R.Jr. J. Bacteriol, 2000, 182, 4059.
42. Basso, L.A.; Zheng, R.; Musser, J.M.; Jacobs, W.R.Jr.; Blanchard, J.S. J. Infect. Dis., 1998, 178, 769.
43. Larsen, M.H.; Vilchéze, C.; Kremer, L.; Besra, G.S.; Parsons, L.; Salfinger, M.; Heifets, L.; Hazbon, M.H.; Alland, D.; Sacchettini, J.C.; Jacobs, W.R.Jr. Mol. Microb., 2002, 46, 453.
44. Vilchèze, C.; Wang, F.; Arai, M.; Hazbón, M.H.; Colangeli, R.; Kremer, L.; Weisbrod, T.R.; Alland, D.; Sacchettini, J.C.; Jacobs, W.RJr. Nat. Med., 2006, 12, 1027.
45. Kremer, L; Dover, L.G.; Morbidoni, H.R.; Vilchéze, C.; Maughan, W.N.; Baulard, A.; Tu, S.-C.; Honoré, N.; Deretic, V.; Sacchettini, J.C.; Locht, C.; Jacobs, W.R.Jr.; Besra, G.S. J. Biol. Chem., 2003, 278, 20547.
46. Rozwarski, D.A.; Grant, G.A.; Barton, D.H.R.; Jacobs, W.R.Jr.; Sacchettini, J.C. Sci., 1998, 279, 98.
47. Lei, B.; Wei, C.J.; Tu, S.C. J. Biol. Chem., 2000, 275, 2520.
48. Rawat, R.; Whitty, A.; Tonge, P.J. Proc. Nac. Acad. Scienc. USA., 2003, 100, 13881.
49. Ramaswamy, S.V.; Reich, R.; Dou, S.-J.; Jaspers, L.; Pan, X.; Wanger, A.; Quitugua, T.; Graviss, E.A. Antimicrob. Agents Chemother., 2003, 47, 1241.
50. Heym, B.; Alzari, P.M.; Honoré, N.; Cole, S.T. Mol. Microbiol., 1995, 15, 235.
51. Yu, S.;. Girotto, S.; Lee, C.; Magliozzo, R.S. J. Biol. Chem., 2003, 278, 14769.
52. Argyrou, A.; Vetting, M.W.; Aladegbami, B.; Blanchard, J.S. Nat. Struct. Mol Biol., 2006, 13, 408.
53. Gangadharam, P.R.; Harold, F.M.; Schaefer, W.B. Nature, 1963, 198, 712.
54. Oliveira, J.S.; Pereira, J.H.; Canduri, F.; Rodrigues, N.G.; Souza, O.N.; Azevedo, W.F.Jr.; Basso, L.A.; Santos, D.S. J. Mol. Biol., 2006, 359, 646.
55. Walsh, C. Nat. Rev. Microbiol., 2003; 1, 65.
56. Souza, E.H.S.; Pontes, D.L.; Diógenes, I.C.N; Lopes, L.G.F.; Oliveira, J.S.; Basso, L.A.; Santos, D.S.; Moreira, I.S. J. Inorg. Biochem., 2005, 99, 368.
57. DeBarber, A.E.; Mdluli, K.; Bosman, L.G.; Bekker, L.G.; Barry III, C.E. Proc. Natl. Acad. Sci. USA, 2000, 97, 9677.
58. Oliveira, J.S.; Sousa, E.H.S.; Basso, L.A.; Palaci, M.; Dietze, R.; Santos, D.S.; Moreira, I.S. Chem. Comm., 2004, 3, 312.
59. Oliveira, J.S.; Sousa, E.H.S.; Souza, O.N.; Moreira, I.S.; Santos, D.S.; Basso, L.A. Curr. Pharm. Des., 2006, 12, 2409.
60. Moreira, I.S.; Franco, D.W.; Inorg. Chem., 1994, 33, 1607.
61. Coelho, A.L.; Moreira, I.S.; Araújo, J.H.; Araújo, M.A.B. J. Radioanal. Nucl. Chem., 1989, 136, 299.
62. Dickson, D.P.E.; Berry, F.J. Mössbauer Spectroscopy, Cambridge University Press, London, 1986.
63. Moreira, I.S.; Lima, J.B.; Franco, D.W. Coord. Chem. Rev., 2000, 196, 197.
64. Morrison, J.F.; Walsh, C.T. Adv. Enzymol. Relat.Areas Mol. Biol., 1988, 61, 201.
65. Sculley, M.J.; Morrison, J.F.; Cleland, W.W. Biochim. et Biophys. Ac., 1996, 1298, 78.
66. Nakatani, H.; Hiromi, K. J. Biochem., 1980, 87, 1805.
67. Johnsson, K.; Schultz, P.G. J. Am. Chem. Soc., 1994, 116, 7425.
68. Robertson, J.G. Biochem., 2005, 44(15), 5561.
69. Copeland, R.A.; Pompliano, D.L.; Meek, T.D. Nat. Rev. Drug Discov., 2006, 5, 730.
70. Copeland, R.A. Evaluation of Enzyme Inhibitors in Drug Discovery: a Guide for Medicinal Chemists and Pharmacologists, Wiley: New York, 2005.
71. Williams, J.W.; Morrison, J.F.; Duggleby, R.G. Biochem., 1979, 18, 2567.
72. Copeland, R.A. Enzymes - A Practical Introduction to Structure, Mechanism, and Data Analysis, Wiley: New York, 2000.
73. Dagani, R. The bio side of organometallics. Chem. Eng. News, 2002, 80, 23.
74. Jiménez-Garrido, N.; Perelló, L.; Ortiz, R.; Alzuet, G.; González-Álvarez, M.; Cantón, E.; Liu-González, M., García-Granda, S.; Pérez-Priede, M. J. Inorg. Biochem., 2005, 99, 677.
75. Sandbhor, U.; Padhye, S.; Billington, D.; Rathbone, D.; Franzblau, S.; Anson, C.E.; Powell, A.K. J. Inorg. Biochem., 2002, 90, 127.
76. Razafimahefa, D.; Ralambomanana, D.A.; Hammouche, L.; Pélinski, L.; Lauvagie, S.; Bebear, C.; Brocard, J.; Maugein, J. Bioorg. Med. Chem. Lett., 2005, 15, 2301.