Reverse type i inhibitor of Mycobacterium tuberculosis CYP125A1

Bioorganic and Medicinal Chemistry Letters

Volumn 21, Issue 1, 2011, Pages 332-337

  Ouellet, Hugues ^a   Kells, Petrea M ^a   Ortiz De Montellano, Paul R ^a   Podust, Larissa M ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Cholesterol degradation; CYP125; CYP125 inhibitor complex; Mycobacterium tuberculosis; P450; X ray structure

Indexed keywords

ALPHA [(4 METHYLCYCLOHEXYL)CARBONYLAMINO] N 4 PYRIDINYL 1H INDOLE 3 PROPANAMIDE; CYTOCHROME P450; CYTOCHROME P450 125A1; ENZYME INHIBITOR; LP 10; UNCLASSIFIED DRUG;

AMINO ACID SUBSTITUTION; ARTICLE; BINDING AFFINITY; COMPLEX FORMATION; CRYSTAL STRUCTURE; DRUG PROTEIN BINDING; DRUG STRUCTURE; GENE EXPRESSION; LIPOPHILICITY; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN; TRYPANOSOMA CRUZI; ULTRAVIOLET SPECTROSCOPY;

ANTITUBERCULAR AGENTS; BINDING SITES; CATALYTIC DOMAIN; COMPUTER SIMULATION; CRYSTALLOGRAPHY, X-RAY; CYTOCHROME P-450 ENZYME SYSTEM; ENZYME INHIBITORS; MYCOBACTERIUM TUBERCULOSIS; PROTEIN BINDING; SPECTROPHOTOMETRY, ULTRAVIOLET;

MYCOBACTERIUM TUBERCULOSIS; TRYPANOSOMA CRUZI;

EID: 78650516871     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2010.11.007     Document Type: Article

References (47)

1. A. Bellamine, A.T. Mangla, W.D. Nes, and M.R. Waterman Proc. Natl. Acad. Sci. U.S.A. 96 1999 8937
2. J. Johnston, P.M. Kells, L.M. Podust, and P.R. Ortiz de Montellano Proc. Natl. Acad. Sci. U.S.A. 106 2009 20687
3. P. Belin, M.H. Le Du, A. Fielding, O. Lequin, M. Jacquet, J.-B. Charbonnier, A. Lecoq, R. Thai, M. Courcon, C. Masson, C. Dugave, R. Genet, J.-L. Pernodet, and M. Gondry Proc. Natl. Acad. Sci. U.S.A. 106 2009 7426
4. J.K. Capyk, R. Kalscheuer, G.R. Stewart, J. Liu, H. Kwon, R. Zhao, S. Okamoto, W.R. Jacobs Jr., L.D. Eltis, and W.W. Mohn J. Biol. Chem. 284 2009 35534
5. K.J. McLean, P. Lafite, C. Levy, M.R. Cheesman, N. Mast, I.A. Pikuleva, D. Leys, and A.W. Munro J. Biol. Chem. 284 2009 35524
6. H. Ouellet, S. Guan, J.B. Johnston, E.D. Chow, P.M. Kells, A.L. Burlingame, J.S. Cox, L.M. Podust, and P.R. Ortiz de Montellano Mol. Microbiol. 77 2010 730
7. J.C. Chang, N.S. Harik, R.P. Liao, and D.R. Sherman J. Infect. Dis. 196 2007 788
8. A.K. Pandey, and C.M. Sassetti Proc. Natl. Acad. Sci. U.S.A. 105 2008 4376
9. J.C. Chang, M.D. Miner, A.K. Pandey, W.P. Gill, N.S. Harik, C.M. Sassetti, and D.R. Sherman J. Bacteriol. 191 2009 5232
10. K.C. Yam, I. D'Angelo, R. Kalscheuer, H. Zhu, J.X. Wang, V. Snieckus, L.H. Ly, P.J. Converse, W.R. Jacobs Jr., N. Strynadka, and L.D. Eltis PLoS Pathog. 5 2009 e1000344
11. Y. Hu, R. van der Geize, G.S. Besra, S.S. Gurcha, A. Liu, M. Rohde, M. Singh, and A. Coates Mol. Microbiol. 75 2010 107
12. K.Z. Rosloniec, M.H. Wilbrink, J.K. Capyk, W.W. Mohn, M. Ostendorf, R. van der Geize, L. Dijkhuizen, and L.D. Eltis Mol. Microbiol. 74 2009 1031
13. Johnston, J. B.; Ouellet, H.; Podust, L. M.; Ortiz de Montellano, P. R. Arch. Biochem. Biophys., in press, doi:10.1016/j.abb.2010.08.011.
14. J.B. Schenkman, H. Remmer, and R.W. Estabrook Mol. Pharmacol. 3 1967 113
15. L.M. Podust, J.P. von Kries, A. Nasser Eddine, Y. Kim, L.V. Yermalitskaya, R. Kuehne, H. Ouellet, T. Warrier, M. Altekoster, J.-S. Lee, J. Rademann, H. Oschkinat, S.H.E. Kaufmann, and M.R. Waterman Antimicrob. Agents Chemother. 51 2007 3915
16. J.P. von Kries, T. Warrier, and L.M. Podust Curr. Protocol Microbiol. 2010 16 Chapter 17: Unit 17.4
17. J.B. Schenkman, D.L. Cinti, S. Orrenius, P. Moldeus, and R. Kraschnitz Biochemistry 11 1972 4243
18. B.J. Wilson, and S. Orrenius Biochim. Biophys. Acta 261 1972 94
19. A.D. Vaz, M.J. Coon, H. Peegel, and K.M. Menon Drug Metab. Dispos. 20 1992 108
20. T. Shimada, K. Tanaka, S. Takenaka, M.K. Foroozesh, N. Murayama, H. Yamazaki, F.P. Guengerich, and M. Komori Chem. Res. Toxicol. 22 2009 1325
21. Y. Yoshida, and H. Kumaoka J. Biochem. 78 1975 55
22. K. Kumaki, M. Sato, H. Kon, and D.W. Nebert J. Biol. Chem. 253 1978 1048
23. T.L. Poulos, and A.J. Howard Biochemistry 26 1987 8165
24. H.E. Seward, A. Roujeinikova, K.J. McLean, A.W. Munro, and D. Leys J. Biol. Chem. 281 2006 39437
25. K.J. McLean, K.R. Marshall, A. Richmond, I.S. Hunter, K. Fowler, T. Kieser, S.S. Gurcha, G.S. Besra, and A.W. Munro Microbiology 148 2002 2937
26. Z. Ahmad, S. Sharma, and G.K. Khuller FEMS Microbiol. Lett. 251 2005 19
27. Z. Ahmad, S. Sharma, G.K. Khuller, P. Singh, J. Faujdar, and V.M. Katoch Int. J. Antimicrob. Agents 28 2006 543
28. Z. Ahmad, S. Sharma, and G.K. Khuller FEMS Microbiol. Lett. 258 2006 200
29. E. Banfi, G. Scialino, D. Zampieri, M.G. Mamolo, L. Vio, M. Ferrone, M. Fermeglia, M.S. Paneni, and S. Pricl J. Antimicrob. Chemother. 58 2006 76
30. S.T. Byrne, S.M. Denkin, P. Gu, E. Nuermberger, and Y. Zhang J. Med. Microbiol. 56 2007 1047
31. Z. Ahmad, S. Sharma, and G.K. Khuller FEMS Microbiol. Lett. 261 2006 181
32. K.J. McLean, and A.W. Munro Drug Metab. Rev. 40 2008 427
33. H. Ouellet, J.B. Johnston, and P.R. Ortiz de Montellano Arch. Biochem. Biophys. 493 2010 82
34. H. Ouellet, J. Lang, M. Couture, and P.R. Ortiz de Montellano Biochemistry 48 2009 863
35. C.-K. Chen, P.S. Doyle, L.V. Yermalitskaya, Z.B. Mackey, K.K.H. Ang, J.H. McKerrow, and L.M. Podust PLoS Negl. Trop. Dis. 3 2009 e372
36. P.S. Doyle, C.-K. Chen, J.B. Johnston, S.D. Hopkins, S.S.F. Leung, M.P. Jacobson, J.C. Engel, J.H. McKerrow, and L.M. Podust Antimicrob. Agents Chemother. 54 2010 2480
37. H.J. Barnes, M.P. Arlotto, and M.R. Waterman Proc. Natl. Acad. Sci. U.S.A. 88 1991 5597
38. H. Ouellet, L.M. Podust, and P.R. Ortiz de Montellano J. Biol. Chem. 283 2008 5069
39. T. Omura, and R. Sato J. Biol. Chem. 239 1964 2379
40. C.A. Appleby Methods Enzymol. 52 1978 157
41. J. Holton, and T. Alber Proc. Natl. Acad. Sci. U.S.A. 101 2004 1537
42. G. Langer, S.X. Cohen, V.S. Lamzin, and A. Perrakis Nat. Protocol 3 2008 1171
43. P. Emsley, and K. Cowtan Acta Crystallogr., Sect, D Biol. Crystallogr. 60 2004 2126
44. G.N. Murshudov, A.A. Vagin, and E.J. Dodson Acta Crystallogr., Sect. D Biol. Crystallogr. 53 1997 240
45. L.M. Podust, L.V. Yermalitskaya, G.I. Lepesheva, V.N. Podust, E.A. Dalmasso, and M.R. Waterman Structure 12 2004 1937
46. L.M. Podust, H. Ouellet, J.P. von Kries, and P.R. Ortiz de Montellano J. Biol. Chem. 284 2009 25211
47. A.L. Hopkins, C.R. Groom, and A. Alex Drug Discovery Today 9 2004 430