Identification of 2-aminothiazole-4-carboxylate derivatives active against Mycobacterium tuberculosis H37Rv and the β-ketoacyl-ACP synthase mtFabH

PLoS ONE

Volumn 4, Issue 5, 2009, Pages

  Al Balas, Qosay ^a   Anthony, Nahoum G ^a   Al Jaidi, Bilal ^a   Alnimr, Amani ^b   Abbott, Grainne ^a   Brown, Alistair K ^c   Taylor, Rebecca C ^c   Besra, Gurdyal S ^c   McHugh, Timothy D ^b   Gillespie, Stephen H ^b   Johnston, Blair F ^a   Mackay, Simon P ^a   Coxon, Geoffrey D ^a  

^a UNIVERSITY OF STRATHCLYDE   (United Kingdom)

^b UNIVERSITY COLLEGE LONDON   (United Kingdom)

^c UNIVERSITY OF BIRMINGHAM   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

2 (2 BROMOACETAMIDO) 5 (3 CHLOROPHENYL)THIAZOLE 4 CARBOXYLIC ACID; 2 (2 BROMOACETAMIDO) 5 (3 CHLOROPHENYL)THIAZOLE 4 CARBOXYLIC ACID METHYL ESTER; 2 (2 BROMOACETAMIDO) 5 METHYLTHIAZOLE 4 CARBOXYLIC ACID; 2 (2 BROMOACETAMIDO) 5 METHYLTHIAZOLE 4 CARBOXYLIC ACID METHYL ESTER; 2 (2 BROMOACETAMIDO) 5 PHENYLTHIAZOLE 4 CARBOXYLIC ACID; 2 (2 BROMOACETAMIDO) 5 PHENYLTHIAZOLE 4 CARBOXYLIC ACID METHYL ESTER; 2 AMINO 5 (3 CHLOROPHENYL)THIAZOLE 4 CARBOXYLIAC ACID; 2 AMINO 5 (3 CHLOROPHENYL)THIAZOLE 4 CARBOXYLIC ACID METHYL ESTER; 2 AMINO 5 BENZYLTHIAZOLE 4 CARBOXYLIAC ACID; 2 AMINO 5 BENZYLTHIAZOLE 4 CARBOXYLIC ACID METHYL ESTER; 2 AMINO 5 METHYLTHIAZOLE 4 CARBOXYLIAC ACID; 2 AMINO 5 METHYLTHIAZOLE 4 CARBOXYLIC ACID METHYL ESTER; 2 AMINO 5 PHENYLTHIAZOLE 4 CARBOXYLIAC ACID; 2 AMINO 5 PHENYLTHIAZOLE 4 CARBOXYLIC ACID METHYL ESTER; 2 AMINOTHIAZOLE 4 CARBOXYLIC ACID DERIVATIVE; 3 OXOACYL ACYL CARRIER PROTEIN SYNTHASE; 5 BENZYL 2 (2 BROMOACETAMIDO)THIAZOLE 4 CARBOXYLIC ACID METHYL ESTER; THIOLACTOMYCIN; TUBERCULOSTATIC AGENT; UNCLASSIFIED DRUG; THIAZOLE DERIVATIVE;

ANTIBACTERIAL ACTIVITY; ARTICLE; BACTERIAL STRAIN; CHEMICAL MODIFICATION; CONTROLLED STUDY; DRUG CYTOTOXICITY; DRUG STRUCTURE; DRUG SYNTHESIS; DRUG TARGETING; ENZYME INHIBITION; FIBROBLAST CULTURE; HUMAN; HUMAN CELL; IC 50; IN VITRO STUDY; MINIMUM INHIBITORY CONCENTRATION; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN; STRUCTURE ACTIVITY RELATION; TUBERCULOSIS; CHEMICAL STRUCTURE; CHEMISTRY; DRUG ANTAGONISM; DRUG EFFECT; ENZYMOLOGY; MICROBIOLOGICAL EXAMINATION; SYNTHESIS;

MYCOBACTERIUM TUBERCULOSIS;

3-OXOACYL-(ACYL-CARRIER-PROTEIN) SYNTHASE; ANTITUBERCULAR AGENTS; MICROBIAL SENSITIVITY TESTS; MOLECULAR STRUCTURE; MYCOBACTERIUM TUBERCULOSIS; THIAZOLES;

EID: 66149086944     PISSN: None     EISSN: 19326203     Source Type: Journal    
DOI: 10.1371/journal.pone.0005617     Document Type: Article

References (29)

1. Dye C, Scheele S, Dolin P, Pathania V, Raviglione MC (1999) Global burden of tuberculosis estimated incidence, prevalence, and mortality by country. JAMA 282: 677-686.
2. Bloom BR, Small PM (1998) The evolving relation between humans and mycobacterium tuberculosis. N Engl J Med 338: 677-678.
3. Mitchison DA (2004) The search for new sterilizing anti-tuberculosis drugs. Front Biosci 9: 1059-1072.
4. Selwyn PA, Sckell BM, Alcabes P, Friedland GH, Klein RS, et al. (1992) High risk of active tuberculosis in HIV-infected drug users with cutaneous anergy. JAMA 268: 504-509.
5. Migliori GB, Ortmann J, Giradi E, Besozzi G, Lange C, et al. (2007) Extensively drug-resistant tuberculosis, Italy and Germany. Emerg Infect Dis 13: 780-782.
6. Cole ST, Brosch R, Parkhill J, Garnier T, Churcher C, et al. (1998) Deciphering the biology of Mycobacterium tuberculosis from the complete genome sequence. Nature 393: 537-544.
7. Takayama K, Wang C, Besra GS (2005) Pathway to synthesis and processing of mycolic acids in Mycobacterium tuberculosis. Clin Microbiol Rev 18: 81-101.
8. Portevin D, De Sousa-D'Auria C, Houssin C, Grimaldi C, Chami M, et al. (2004) A polyketide synthase catalyzes the last condensation step of mycolic acid biosynthesis in mycobacteria and related organisms. Proc Natl Acad Sci USA 101: 314-319.
9. Kremer L, Baulard AR, Besra GS (2000) Genetics of mycolic acid biosynthesis. Molecular Genetics of Mycobacteria. ASM Press. 173 p.
10. Yuan Y, Lee RE, Besra GS, Belisle JT, Barry CE (1995) Identification of a gene involved in the biosynthesis of cyclopropanated mycolic acids in Mycobacterium tuberculosis. Proc Natl Acad Sci USA 92: 6630-6634.
11. Oishi N, Noto T, Sasaki H, Suzuki K, Hayashi T, et al. (1982) Thiolactomycin, a new antibiotic. Taxonomy of the producing organism, fermentation and biological properties. Antibiot 35: 391-395.
12. Noto T, Miyakawa S, Oishi H, Endo H, Okazaki H (1982) Thiolactomycin, a new antibiotic. In vitro antibacterial activity. J Antibiot 35: 401-410.
13. Slayden RA, Lee R, Armour JW, Cooper AM, Orme IM, et al. (1996) Antimycobacterial action of thiolactomycin: an inhibitor of fatty acid and mycolic acid synthesis. Antimicro Agents Chemother 40: 2813-2819.
14. Choi KH, Kremer L, Besra GS, Rock CO (2000) Identification and substrate specificity of beta -ketoacyl (acyl carrier protein) synthase III (mtFabH) from Mycobacterium tuberculosis. J Biol Chem 275: 28201-28207.
15. Kremer L, Douglas JD, Baulard AR, Morehouse C, Guy MR, et al. (2000) Thiolactomycin and related analogues as novel anti-mycobacterial agents targeting KasA and KasB condensing enzymes in Mycobacterium tuberculosis. J Biol Chem 275: 16857-16864.
16. Schaeffer ML, Agnihotri J, Volker C, Kallender H, Brennan PJ, et al. (2001) Purification and biochemical characterization of the Mycobacterium tuberculosis beta-ketoacyl-acyl carrier protein synthases KasA and KasB. J Biol chem 276: 47029-47037.
17. Kremer L, Dover LG, Carrere S, Nampoothiri KM, Lesjean S, et al. (2002) Mycolic acid biosynthesis and enzymic characterization of the beta-ketoacyl-ACP synthase A-condensing enzyme from Mycobacterium tuberculosis. Biochem J 364: 423-430.
18. Kim P, Zhang Y-M, Shenoy G, Hguyen Q-A, Boshoff HI, et al. (2006) structure-activity relationships at the 5-position of thiolactomycin: An intact (5R)-isoprene unit is required for activity against the condensing enzymes from Mycobacterium tuberculosis and Escherichia coli. J Med Chem 49: 159-171.
19. Kamal A, Shaik A, Sinha R, Yadav JS, Arora SK (2005) Antitubercular agents Part 2: new thiolactomycin analogues active against Mycobacterium tuberculosis. Bioorg Med Chem Lett 15: 1927-1929.
20. Senior SJ, Illarionov PA, Gurcha SS, Campbell IB, Schaeffer ML, Minnikin DE, Besra GS (2003) Biphenyl-based analogues of thiolactomycin, active against Mycobacterium tuberculosis mtFabH fatty acid condensing enzyme. Bioorg Med Chem Letts 13: 3685-3688.
21. Senior SJ, Illarionov PA, Gurcha SS, Campbell IB, Schaeffer ML, Minnikin DE, Besra GS (2003) Acetylene-based analogues of thiolactomycin, active against Mycobacterium tuberculosis mtFabH fatty acid condensing enzyme. Bioorg Med Chem Letts 14: 373-376.
22. Bhowruth V, Brown AK, Senior SJ, Snaith JS, Besra GS (2007) Acetylene-based analogues of thiolactomycin, active against Mycobacterium tuberculosis mtFabH fatty acid condensing enzyme. Bioorg Med Chem Letts 17: 5643-5646.
23. Brown AK, Sridharan S, Kremer L, Lindenberg S, Dover LG, et al. (2005) Probing the mechanism of the Mycobacterium tuberculosis beta-ketoacyl-acyl carrier protein synthase III mtFabH: factors influencing catalysis and substrate specificity. J Biol Chem 280: 32539-32547.
24. Sachdeva S, Musayev F, Alhamadsheh M, Scarsdale NJ, Wright TH, et al. (2008) Separate entrance and exit portals for ligand traffic in Mycobacterium tuberculosis FabH. Chem Biol 15: 402-12.
25. Price AC, Choi K-H, Heath RJ, Li Z, White SW, et al. (2001) Inhibition of beta -Ketoacyl-Acyl Carrier Protein Synthases by Thiolactomycin and Cerulenin, structure and mechanism. J Biol Chem 276: 6551-6559.
26. Ashek A, Cho SJ (2006) A combined approach of docking and 3D QSAR study of [beta]-ketoacyl-acyl carrier protein synthase III (FabH) inhibitors. Bio Med Chem 14: 1474-1482.
27. Barton A, Breukelman SP, Kaye PT, Meakins DG, Morgan DJ (1982) The preparation of thiazole-4- and -5-carboxylates, and an infrared study of their rotational isomers. J Chem Soc, Perkin Trans 1: 159-164.
28. Jones G, Willett P, Glen RC (1995) Molecular Recognition of Receptor Sites using a Genetic Algorithm with a Description of Desolvation. J Mol Biol 245: 43-53.
29. Palomino JC, Martin A, Camacho M, Guerra H, Swings J, et al. (2002) Resazurin microtiter assay plate: simple and inexpensive method for detection of drug resistance in Mycobacterium tuberculosis. Antimicrob Agents Chemother 46: 2720-2722.