Discovery of novel InhA reductase inhibitors: Application of pharmacophore- and shape-based screening approach

Future Medicinal Chemistry

Volumn 5, Issue 3, 2013, Pages 249-259

  Kumar, Uday Chandra ^a,b   Bvs, Suneel Kumar ^a   Mahmood, Shaik ^b   Sriram, D ^c   Kumar Sahu, Prashanta ^a,d   Pulakanam, Sridevi ^b   Ballell, Lluís ^e   Alvarez Gomez, Daniel ^e   Malik, Siddharth ^a   Jarp, Sarma ^a  

^a GVK BIOSCIENCES PVT LTD   (India)

^b OSMANIA UNIVERSITY   (India)

^c BIRLA INSTITUTE OF TECHNOLOGY AND SCIENCE   (India)

^d RAYALASEEMA UNIVERSITY   (India)

^e GLAXOSMITHKLINE   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ENZYME INHIBITOR; INHA REDUCTASE INHIBITOR; TUBERCULOSTATIC AGENT; UNCLASSIFIED DRUG;

ARTICLE; CRYSTAL STRUCTURE; DRUG SCREENING; DRUG STRUCTURE; ENZYME INHIBITION; HYDROGEN BOND; HYDROPHOBICITY; MOLECULAR DOCKING; MOLECULAR INTERACTION; PHARMACOPHORE; PRIORITY JOURNAL;

ANTITUBERCULAR AGENTS; BACTERIAL PROTEINS; DRUG DESIGN; ENZYME INHIBITORS; HUMANS; MOLECULAR DOCKING SIMULATION; MYCOBACTERIUM TUBERCULOSIS; OXIDOREDUCTASES; TUBERCULOSIS;

EID: 84874744999     PISSN: 17568919     EISSN: 17568927     Source Type: Journal    
DOI: 10.4155/fmc.12.211     Document Type: Article

References (35)

1. Aziz MA, Wright A, Laszlo A et al. Epidemiology of antituberculosis drug resistance (the global project on anti-tuberculosis drug resistance surveillance): an updated analysis. Lancet 368(9553), 2142-2154 (2006).
2. Raviglione MC, Smith IMN. XDR tuberculosis - implications for global public health. N. Engl. J. Med. 356(7), 656-659 (2007).
3. Pasqualoto KF, Ferreira EI, Santos-Filho OA, Hopfinger AJ. Rational design of new antituberculosis agents: receptor-independent four-dimensional quantitative structure- activity relationship analysis of a set of isoniazid derivatives. J. Med. Chem. 47(15), 3755-3764 (2004).
4. Wei CJ, Lei B, Musser JM, Tu SC. Isoniazid activation defects in recombinant Mycobacterium tuberculosis catalase-peroxidase (KatG) mutants evident in InhA inhibitor production. Antimicrob. Agents Chemother. 47(2), 670-675 (2003).
5. Morlock GP, Metchock B, Sikes D, Crawford JT, Cooksey RC. EthA, InhA, and katG loci of ethionamide-resistant clinical Mycobacterium tuberculosis isolates. Antimicrob. Agents Chemother. 47(12), 3799-3805 (2003).
6. Ormerod LP. Multidrug-resistant tuberculosis (MDR-TB): epidemiology, prevention and treatment. Br. Med. Bull. 73(1), 17-24 (2005).
7. Zhao X, Yu S, Magliozzo RS. Characterization of the binding of isoniazid and analogues to Mycobacterium tuberculosis catalase-peroxidase. Biochemistry 46(11), 3161-3170 (2007).
8. Scior T, Morales IM, Solon JGE, Domeyer D, Laufer S. Antitubercular isoniazid and drug resistance of Mycobacterium tuberculosis - a review. Arch. Pharm. (Weinheim) 335(11-12), 511-525 (2003).
9. Schaeffer ML, Agnihotri G, Volker C, Kallender H, Brennan PJ, Lonsdale JT. Purification and biochemical characterization of the Mycobacterium tuberculosis beta -ketoacyl-acyl carrier protein synthases KasA and KasB. J. Biol. Chem. 276(50), 47029-47037 (2001).
10. Kuo MR, Morbidoni HR, Alland D et al. Targeting tuberculosis and malaria through inhibition of enoyl reductase: compound activity and structural data. J. Biol. Chem. 278(23), 20851-20859 (2003).
11. Choi KH, Kremer L, Besra GS, Rock CO. Identification and substrate specificity of beta-ketoacyl (acyl carrier protein) synthase III (mtFabH) from Mycobacterium tuberculosis. J. Biol. Chem. 275(2000), 28201-28207 (2000).
12. Kremer L, Douglas JD, Baulard AR, Guy MR et al. Thiolactomycin and related analogues as novel anti-mycobacterial agents targeting KasA and KasB condensing enzymes in Mycobacterium tuberculosis. J. Biol. Chem. 275(22), 16857-16864 (2000).
13. Ducasse-Cabanot S, Cohen-Gonsaud M, Marrakchi H et al. In vitro inhibition of the Mycobacterium tuberculosis beta-ketoacyl-acyl carrier protein reductase MabA by isoniazid. Antimicrob. Agents Chemother. 48(1), 242-249 (2004).
14. Vilcheze C, Weisbrod TR. Altered NADH/ NAD+ ratio mediates coresistance to isoniazid and ethionamide in mycobacteria. Antimicrob. Agents Chemother. 49(2), 708-720 (2005).
15. Brennan PJ, Rooney SA, Winder FG. The lipids of Mycobacterium tuberculosis BCG: fractionation, composition, turnover and the effects of isoniazid. Ir. J. Med. Sci. 3(8), 371-390 (1970).
16. Johnsson K, King DS, Schultz PG. Studies on the mechanism of isoniazid and ethionamide in the chemotherapy of tuberculosis. J. Am. Chem. Soc. 117(17), 5009-5010 (1995).
17. Marcinkeviciene JA, Magliozzo RS, Blanchard JS. Purification and characterization of the Mycobacterium smegmatis catalase-peroxidase involved in isoniazid activation. J. Biol. Chem. 270(38), 22290-22295 (1995).
18. Basso LA, Zheng RJ, Blanchard JS. Kinetics of inactivation of WT and C243S mutant of Mycobacterium tuberculosis enoyl reductase by activated isoniazid. J. Am. Chem. Soc. 118, 11301-11302 (1996).
19. Quemard A, Dessen A, Sugantino M, Jacobs WR Jr, Sacchettini JC, Blanchard JS. Binding of catalase-peroxidase-activated isoniazid to wild-type and mutant Mycobacterium tuberculosis enoyl reductases. J. Am. Chem. Soc. 118, 1561-1562 (1996).
20. Rawat R, Whitty A, Tonge P. The isoniazid- NAD adduct is a slow, tight-binding inhibitor of InhA, the Mycobacterium tuberculosis enoyl reductase: adduct affinity and drug resistance. Proc. Natl Acad. Sci. USA 100(24), 13881-13886 (2003).
21. Zhang Y, HeymB, Allen B, Young D, Cole, S. The catalase-peroxidase gene and isoniazid resistance of Mycobacterium tuberculosis. Nature 358(6387), 591-593 (1992).
22. Stoeckle MY, Guan L, Riegler N et al. Catalase-peroxidase gene sequences in isoniazid-sensitive and -resistant strains of Mycobacterium tuberculosis from New York City. J. Infect. Dis. 168(4), 1063-1065 (1993).
23. Musser JM, Kapur V, Williams DL, Kreiswirth BN, van Soolingen D, van Embden JD. Characterization of the catalase-peroxidase gene (katG) and inhA locus in isoniazid-resistant and -susceptible strains of Mycobacterium tuberculosis by automated DNA sequencing: restricted array of mutations associated with drug resistance. J. Infect. Dis. 173(1), 196-202 (1996).
24. Ramaswamy SV, Reich R, Dou SJ et al. Single nucleotide polymorphisms in genes associated with isoniazid resistance in Mycobacterium tuberculosis. Antimicrob. Agents Chemother. 47(4), 1241-1250 (2003).
25. He X, Alian A, Ortiz de Montellano PR. Inhibition of the Mycobacterium tuberculosis enoyl acyl carrier protein reductase InhA by arylamides. Bioorg. Med. Chem. 15(21), 6649-6658 (2007).
26. Kuo MR, Morbidoni HR, Alland D et al. Targeting tuberculosis and malaria through inhibition of enoyl reductase: compound activity and structural data. J. Biol. Chem. 278(23), 20851-20859 (2003).
27. He X, Alian A, Stroud R, Ortiz de Montellano PR. Pyrrolidine carboxamides as a novel class of inhibitors of enoyl acyl carrier protein reductase from Mycobacterium tuberculosis. J. Med. Chem. 49(21), 6308-6323 (2006).
28. Cao S, Lee AS, Huang Y et al. Agonodepsides A and B: two new depsides from a filamentous fungus F7524. J. Nat. Prod. 65, 1037-1038 (2002).
29. Sutter J, Guner O, Hoffman R, Li H, Waldman M. Effect of variable weights and tolerances on predictive model generation. In: Pharmacophore, Perception, Development, and use in Drug Design. International University Line, CA, USA, 501-511 (2000).
30. Smellie A, Teig SL, Towbin P. Poling: promoting conformational variation. J. Comput. Chem. 16(2), 171-187 (1995).
31. Smellie A, Kahn SD, Teig SL. Analysis of conformational coverage. 1. Validation and estimation of coverage. J. Chem. Inf. Comput. Sci. 35(2), 285-294 (1995).
32. Smellie A, Kahn SD, Teig SL. Analysis of conformational coverage. 2. Validation and estimation of coverage. J. Chem. Inf. Comput. Sci. 35(2), 295-304 (1995).
33. Kaminski GA, Friesner RA, Tirado-Rives J, Jorgensen WL. Evaluation and reparametrization of the OPLS-AA force field for proteins via comparison with accurate quantum chemical calculations on peptides. J. Phys. Chem. B 105(28), 6474-6487 (2001).
34. Staveski MM, Sneddon Scott F, Yee C, Janjigian A: W001/56974 A2.
35. WHO Report. Global tuberculosis control - surveillance, planning, financing. www.who.int/tb/publications/global- report/2007/pdf/full.pdf