Synthesis, Antitubercular Activity and Mechanism of Resistance of Highly Effective Thiacetazone Analogues

PLoS ONE

Volumn 8, Issue 1, 2013, Pages

  Coxon, Geoffrey D ^a   Craig, Derek ^a   Corrales, Rosa Milagros ^b   Vialla, Emilie ^b   Gannoun Zaki, Laila ^b   Kremer, Laurent ^b  

^a UNIVERSITY OF STRATHCLYDE   (United Kingdom)

^b UNIVERSITÉ DE MONTPELLIER   (France)

Author keywords

[No Author keywords available]

Indexed keywords

2 METHOXYBENZYLIDENEHYDRAZINECARBOTHIAMIDE; 3 METHOXYBENZYLIDENEHYDRAZINECARBOTHIAMIDE; 4 BUTOXYBENZYLTHIOSEMICARBAMIDE; 4 ETHOXYBENZYLIDENEHYDRAZINECARBOTHIAMIDE; 4 ETHOXYBENZYLTHIOSEMICARBAMIDE; 4 ETHYLBENZYLIDENE N PHENYL HYDRAZINECARBOTHIAMIDE; 4 ETHYLBENZYLIDENEHYDRAZINECARBOTHIAMIDE; 4 ISOPROPYLBENZYLIDENEHYDRAZINECARBOTHIAMIDE; 4 METHOXYBENZYLIDENE N METHYLHYDRAZINECARBOTHIAMIDE; 4 METHOXYBENZYLIDENE N PHENYLHYDRAZINECARBOTHIAMIDE; 4 METHOXYBENZYLIDENEHYDRAZINECARBOTHIAMIDE; 4 METHYLBENZYLIDENE N METHYL HYDRAZINECARBOTHIAMIDE; 4 METHYLBENZYLIDENE N PHENYL HYDRAZINECARBOTHIAMIDE; 4 METHYLBENZYLIDENEHYDRAZINECARBOTHIAMIDE; 4 PROPYLBENZYLIDENEHYDRAZINECARBOTHIAMIDE; BACTERIAL PROTEIN; BENZYLIDIENEHYDRAZINECARBOTHIAMIDE; BETA HYDROXYACYL ACP DEHYDRATASE; HADA PROTEIN; HADAB PROTEIN; HADABC PROTEIN; HADAC PROTEIN; HADC PROTEIN; HYDROLYASE; METHYLTRANSFERASE; MYCOLIC ACID; N METHYL 2 (4 ETHYLBENZYLIDENE)HYDRAZINECARBOTHIAMIDE; THIOACETAZONE; TUBERCULOSTATIC AGENT; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANTIBIOTIC RESISTANCE; ANTITUBERCULAR ACTIVITY; ARTICLE; BACTERIAL STRAIN; BACTERIUM ISOLATION; BIOSYNTHESIS; CONCENTRATION RESPONSE; DRUG ACTIVITY; DRUG EFFECT; DRUG EFFICACY; DRUG SCREENING; DRUG STRUCTURE; GENETIC MARKER; GENOTYPE; MINIMUM INHIBITORY CONCENTRATION; MISSENSE MUTATION; MUTATIONAL ANALYSIS; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN; PROTEIN EXPRESSION; STRUCTURE ACTIVITY RELATION; UPREGULATION;

ANTITUBERCULAR AGENTS; BACTERIAL PROTEINS; DOSE-RESPONSE RELATIONSHIP, DRUG; DRUG DESIGN; DRUG RESISTANCE, BACTERIAL; HUMANS; MICROBIAL SENSITIVITY TESTS; MUTATION; MYCOBACTERIUM TUBERCULOSIS; MYCOLIC ACIDS; OLIGONUCLEOTIDES; SEQUENCE ANALYSIS, DNA; THIOACETAZONE;

MYCOBACTERIUM TUBERCULOSIS;

EID: 84871905006     PISSN: None     EISSN: 19326203     Source Type: Journal    
DOI: 10.1371/journal.pone.0053162     Document Type: Article

References (40)

1. Mondal R, Jain A, (2007) Extensively drug-resistant Mycobacterium tuberculosis, India. Emerg Infect Dis 13: 1429-1431.
2. Espinal MA, (2003) The global situation of MDR-TB. Tuberculosis (Edinb) 83: 44-51.
3. Caminero JA, Sotgiu G, Zumla A, Migliori GB, (2010) Best drug treatment for multidrug-resistant and extensively drug-resistant tuberculosis. Lancet Infect Dis 10: 621-629.
4. Wei JR, Krishnamoorthy V, Murphy K, Kim JH, Schnappinger D, et al. (2011) Depletion of antibiotic targets has widely varying effects on growth. Proc Natl Acad Sci U S A 108: 4176-4181.
5. Vilcheze C, Wang F, Arai M, Hazbon MH, Colangeli R, et al. (2006) Transfer of a point mutation in Mycobacterium tuberculosis inhA resolves the target of isoniazid. Nat Med 12: 1027-1029.
6. Kremer LS, Besra GS, (2002) Current status and future development of antitubercular chemotherapy. Expert Opin Investig Drugs 11: 1033-1049.
7. Bugg TD, Braddick D, Dowson CG, Roper DI, (2011) Bacterial cell wall assembly: still an attractive antibacterial target. Trends Biotechnol 29: 167-173.
8. Banerjee A, Dubnau E, Quemard A, Balasubramanian V, Um KS, et al. (1994) inhA, a gene encoding a target for isoniazid and ethionamide in Mycobacterium tuberculosis. Science 263: 227-230.
9. Wang F, Langley R, Gulten G, Dover LG, Besra GS, et al. (2007) Mechanism of thioamide drug action against tuberculosis and leprosy. J Exp Med 204: 73-78.
10. Kremer L, Baulard AR, Besra GS (2000) Genetics of mycolic acid biosynthesis. In Molecular Genetics of Mycobacteria (ed Hatfull, GF, Jacobs, Jr, WR) 173-190, ASM Press.
11. Takayama K, Wang C, Besra GS, (2005) Pathway to synthesis and processing of mycolic acids in Mycobacterium tuberculosis. Clin Microbiol Rev 18: 81-101.
12. Ojha AK, Trivelli X, Guerardel Y, Kremer L, Hatfull GF, (2010) Enzymatic hydrolysis of trehalose dimycolate releases free mycolic acids during mycobacterial growth in biofilms. J Biol Chem 285: 17380-17389.
13. Glickman MS, Cox JS, Jacobs WR Jr, (2000) A novel mycolic acid cyclopropane synthetase is required for cording, persistence, and virulence of Mycobacterium tuberculosis. Mol Cell 5: 717-727.
14. Bhatt A, Fujiwara N, Bhatt K, Gurcha SS, Kremer L, et al. (2007) Deletion of kasB in Mycobacterium tuberculosis causes loss of acid-fastness and subclinical latent tuberculosis in immunocompetent mice. Proc Natl Acad Sci U S A 104: 5157-5162.
15. Dubnau E, Chan J, Raynaud C, Mohan VP, Laneelle MA, et al. (2000) Oxygenated mycolic acids are necessary for virulence of Mycobacterium tuberculosis in mice. Mol Microbiol 36: 630-637.
16. 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.
17. Dover LG, Alahari A, Gratraud P, Gomes JM, Bhowruth V, et al. (2007) EthA, a common activator of thiocarbamide-containing drugs acting on different mycobacterial targets. Antimicrob Agents Chemother 51: 1055-1063.
18. Baulard AR, Betts JC, Engohang-Ndong J, Quan S, McAdam RA, et al. (2000) Activation of the pro-drug ethionamide is regulated in mycobacteria. J Biol Chem 275: 28326-28331.
19. DeBarber AE, Mdluli K, Bosman M, Bekker LG, Barry CE 3rd (2000) Ethionamide activation and sensitivity in multidrug-resistant Mycobacterium tuberculosis. Proc Natl Acad Sci U S A 97: 9677-9682.
20. Alahari A, Trivelli X, Guerardel Y, Dover LG, Besra GS, et al. (2007) Thiacetazone, an antitubercular drug that inhibits cyclopropanation of cell wall mycolic acids in mycobacteria. PLoS ONE 2: e1343.
21. Rao V, Fujiwara N, Porcelli SA, Glickman MS, (2005) Mycobacterium tuberculosis controls host innate immune activation through cyclopropane modification of a glycolipid effector molecule. J Exp Med 201: 535-543.
22. Corrales RM, Molle V, Leiba J, Mourey L, de Chastellier C, et al. (2012) Phosphorylation of mycobacterial PcaA inhibits mycolic acid cyclopropanation: consequences for intracellular survival and for phagosome maturation block. J Biol Chem 287: 26187-26199.
23. Alahari A, Alibaud L, Trivelli X, Gupta R, Lamichhane G, et al. (2009) Mycolic acid methyltransferase, MmaA4, is necessary for thiacetazone susceptibility in Mycobacterium tuberculosis. Mol Microbiol 71: 1263-1277.
24. Belardinelli JM, Morbidoni HR, (2012) Mutations in the essential FAS II beta-hydroxyacyl ACP dehydratase complex confer resistance to thiacetazone in Mycobacterium tuberculosis and Mycobacterium kansasii. Mol Microbiol 86: 568-579.
25. Grzegorzewicz AE, Kordulakova J, Jones V, Born SE, Belardinelli JM, et al. (2012) A common mechanism of inhibition of the Mycobacterium tuberculosis mycolic acid biosynthetic pathway by isoxyl and thiacetazone. J Biol Chem 287: 38434-38441.
26. Sambandamurthy VK, Derrick SC, Hsu T, Chen B, Larsen MH, et al. (2006) Mycobacterium tuberculosis DeltaRD1 DeltapanCD: a safe and limited replicating mutant strain that protects immunocompetent and immunocompromised mice against experimental tuberculosis. Vaccine 24: 6309-6320.
27. Stover CK, de la Cruz VF, Fuerst TR, Burlein JE, Benson LA, et al. (1991) New use of BCG for recombinant vaccines. Nature 351: 456-460.
28. Slama N, Leiba J, Eynard N, Daffe M, Kremer L, et al. (2011) Negative regulation by Ser/Thr phosphorylation of HadAB and HadBC dehydratases from Mycobacterium tuberculosis type II fatty acid synthase system. Biochem Biophys Res Commun 412: 401-406.
29. Lutfalla G, Uze G, (2006) Performing quantitative reverse-transcribed polymerase chain reaction experiments. Methods Enzymol 410: 386-400.
30. Bermudez LE, Reynolds R, Kolonoski P, Aralar P, Inderlied CB, et al. (2003) Thiosemicarbazole (thiacetazone-like) compound with activity against Mycobacterium avium in mice. Antimicrob Agents Chemother 47: 2685-2687.
31. Davidson PT, Le HQ, (1992) Drug treatment of tuberculosis-1992. Drugs 43: 651-673.
32. Nunn P, Porter J, Winstanley P, (1993) Thiacetazone-avoid like poison or use with care? Trans R Soc Trop Med Hyg 87: 578-582.
33. Fegan D, (1994) Thiacetazone-use with care. Trans R Soc Trop Med Hyg 88: 714.
34. Fegan D, (1995) Use of thiacetazone. Lancet 345: 63.
35. Shahab FM, Kobarfard F, Shafaghi B, Dadashzadeh S, (2009) Preclinical pharmacokinetics of KBF611, a new antituberculosis agent in mice and rabbits, and comparison with thiacetazone. Xenobiotica 40: 225-234.
36. Rombouts Y, Brust B, Ojha AK, Maes E, Coddeville B, et al. (2012) Exposure of mycobacteria to cell wall-inhibitory drugs decreases production of arabinoglycerolipid related to mycolyl-arabinogalactan-peptidoglycan metabolism. J Biol Chem 287: 11060-11069.
37. Sacco E, Covarrubias AS, O'Hare HM, Carroll P, Eynard N, et al. (2007) The missing piece of the type II fatty acid synthase system from Mycobacterium tuberculosis. Proc Natl Acad Sci U S A 104: 14628-14633.
38. Veyron-Churlet R, Guerrini O, Mourey L, Daffe M, Zerbib D, (2004) Protein-protein interactions within the Fatty Acid Synthase-II system of Mycobacterium tuberculosis are essential for mycobacterial viability. Mol Microbiol 54: 1161-1172.
39. Veyron-Churlet R, Bigot S, Guerrini O, Verdoux S, Malaga W, et al. (2005) The biosynthesis of mycolic acids in Mycobacterium tuberculosis relies on multiple specialized elongation complexes interconnected by specific protein-protein interactions. J Mol Biol 353: 847-858.
40. Cantaloube S, Veyron-Churlet R, Haddache N, Daffe M, Zerbib D, (2011) The Mycobacterium tuberculosis FAS-II dehydratases and methyltransferases define the specificity of the mycolic acid elongation complexes. PLoS One 6: e29564.