Synthesis and biological evaluation of NAS-21 and NAS-91 analogues as potential inhibitors of the mycobacterial FAS-II dehydratase enzyme Rv0636

References

1. Banerjee A., Dubnau E., Quemard A., Balasubramanian V., Um K. S., Wilson T., Collins D., de Lisle G., Jacobs W. R. Jr 1994; inhA, a gene encoding a target for isoniazid and ethionamide in Mycobacterium tuberculosis. Science 263:227–230
   [Google Scholar]
2. Banerjee A., Sugantino M., Sacchettini J. C., Jacobs W. R. Jr 1998; The mabA gene from the inhA operon of Mycobacterium tuberculosis encodes a β-ketoacyl reductase that fails to confer isoniazid resistance. Microbiology 144:2697–2704
   [Google Scholar]
3. Brown A. K., Sridharan S., Kremer L., Lindenberg S., Dover L. G., Sacchettini J. C., Besra G. S. 2005; Probing the mechanism of the Mycobacterium tuberculosis β-ketoacyl-acyl carrier protein synthase III mtFabH: factors influencing catalysis and substrate specificity. J Biol Chem 280:32539–32547
   [Google Scholar]
4. Brown A. K., Bhatt A., Singh A., Saparia E., Evans A. F., Besra G. S. 2007a; Identification of the dehydratase component of the mycobacterial mycolic acid-synthesizing fatty acid synthase-II complex. Microbiology 153:4166–4173
   [Google Scholar]
5. Brown A. K., Papaemmanouil A., Bhowruth V., Bhatt A., Dover L. G., Besra G. S. 2007b; Flavonoid inhibitors as novel antimycobacterial agents targeting Rv0636, a putative dehydratase enzyme involved in Mycobacterium tuberculosis fatty acid synthase II. Microbiology 153:3314–3322
   [Google Scholar]
6. Burguiere A., Hitchen P. G., Dover L. G., Dell A., Besra G. S. 2005; Altered expression profile of mycobacterial surface glycopeptidolipids following treatment with the antifungal azole inhibitors econazole and clotrimazole. Microbiology 151:2087–2095
   [Google Scholar]
7. CDC 2006; Emergence of Mycobacterium tuberculosis with extensive resistance to second-line drugs – worldwide, 2000–2004. MMWR Morb Mortal Wkly Rep 55:301–305
   [Google Scholar]
8. Choi K. H., Kremer L., Besra G. S., Rock C. O. 2000; Identification and substrate specificity of β-ketoacyl (acyl carrier protein) synthase III ( mtFabH) from Mycobacterium tuberculosis. J Biol Chem 275:28201–28207
   [Google Scholar]
9. Dobson G., Minnikin D. E., Minnikin S. M., Parlett J. H., Goodfellow M., Ridell M., Magnusson M. 1985; Systematic analysis of complex mycobacterial lipids. In Chemical Methods in Bacterial Systematics pp 237–265 Edited by Goodfellow M., Minnikin D. E. London: Academic Press;
   [Google Scholar]
10. Franzblau S. G., Witzig R. S., McLaughlin J. C., Torres P., Madico G., Hernandez A., Degnan M. T., Cook M. B., Quenzer V. K. other authors 1998; Rapid, low-technology MIC determination with clinical Mycobacterium tuberculosis isolates by using the microplate Alamar Blue assay. J Clin Microbiol 36:362–366
    [Google Scholar]
11. Gande R., Gibson K. J., Brown A. K., Krumbach K., Dover L. G., Sahm H., Shioyama S., Oikawa T., Besra G. S., Eggeling L. 2004; Acyl-CoA carboxylases ( accD2 and accD3), together with a unique polyketide synthase (Cg- pks), are key to mycolic acid biosynthesis in Corynebacterianeae such as Corynebacterium glutamicum and Mycobacterium tuberculosis. J Biol Chem 279:44847–44857
    [Google Scholar]
12. Gratraud P., Surolia N., Besra G., Surolia A., Kremer L. 2008; Antimycobacterial activity and mechanism of action of NAS-91. Antimicrob Agents Chemother 52:1162–1166
    [Google Scholar]
13. Kass L. R., Bloch K. 1967; On the enzymatic synthesis of unsaturated fatty acids in Escherichia coli. Proc Natl Acad Sci U S A 58:1168–1173
    [Google Scholar]
14. Kass L. R., Brock D. J., Bloch K. 1967; β-hydroxydecanoyl thioester dehydrase. I. Purification and properties.. J Biol Chem 242:4418–4431
    [Google Scholar]
15. Kaye K., Frieden T. R. 1996; Tuberculosis control: the relevance of classic principles in an era of acquired immunodeficiency syndrome and multidrug resistance. Epidemiol Rev 18:52–63
    [Google Scholar]
16. Kikuchi S., Kusaka T. 1984; Purification of NADPH-dependent enoyl-CoA reductase involved in the malonyl-CoA dependent fatty acid elongation system of Mycobacterium smegmatis. J Biochem 96:841–848
    [Google Scholar]
17. Kremer L., Baulard A., Estaquier J., Content J., Capron A., Locht C. 1995; Analysis of the Mycobacterium tuberculosis 85A antigen promoter region. J Bacteriol 177:642–653
    [Google Scholar]
18. Kremer L., Douglas J. D., Baulard A. R., Morehouse C., Guy M. R., Alland D., Dover L. G., Lakey J. H., Jacobs W. R. Jr other authors 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
    [Google Scholar]
19. Kremer L., Dover L. G., Carrere S., Nampoothiri K. M., Lesjean S., Brown A. K., Brennan P. J., Minnikin D. E., Locht C., Besra G. S. 2002a; Mycolic acid biosynthesis and enzymic characterization of the β-ketoacyl-ACP synthase A-condensing enzyme from Mycobacterium tuberculosis. Biochem J 364:423–430
    [Google Scholar]
20. Kremer L., Dover L. G., Carrere S., Nampoothiri K. M., Lesjean S., Brown A. K., Brennan P. J., Minnikin D. E., Locht C., Besra G. S. 2002b; Mycolic acid biosynthesis and enzymic characterization of the β-ketoacyl-ACP synthase A-condensing enzyme from Mycobacterium tuberculosis. Biochem J 364:423–430
    [Google Scholar]
21. Larsen M. H., Vilcheze C., Kremer L., Besra G. S., Parsons L., Salfinger M., Heifets L., Hazbon M. H., Alland D. other authors 2002; Overexpression of inhA, but not kasA, confers resistance to isoniazid and ethionamide in Mycobacterium smegmatis, M. bovis BCG and M. tuberculosis. Mol Microbiol 46:453–466
    [Google Scholar]
22. Lea-Smith D. J., Pyke J. S., Tull D., McConville M. J., Coppel R. L., Crellin P. K. 2007; The reductase that catalyzes mycolic motif synthesis is required for efficient attachment of mycolic acids to arabinogalactan. J Biol Chem 282:11000–11008
    [Google Scholar]
23. Leesong M., Henderson B. S., Gillig J. R., Schwab J. M., Smith J. L. 1996; Structure of a dehydratase-isomerase from the bacterial pathway for biosynthesis of unsaturated fatty acids: two catalytic activities in one active site. Structure 4:253–264
    [Google Scholar]
24. Mdluli K., Slayden R. A., Zhu Y., Ramaswamy S., Pan X., Mead D., Crane D. D., Musser J. M., Barry C. E. III 1998; Inhibition of a Mycobacterium tuberculosis β-ketoacyl ACP synthase by isoniazid. Science 280:1607–1610
    [Google Scholar]
25. Portevin D., de Sousa-D'Auria C., Montrozier H., Houssin C., Stella A., Laneelle M. A., Bardou F., Guilhot C., Daffe M. 2005; The acyl-AMP ligase FadD32 and AccD4-containing acyl-CoA carboxylase are required for the synthesis of mycolic acids and essential for mycobacterial growth: identification of the carboxylation product and determination of the acyl-CoA carboxylase components. J Biol Chem 280:8862–8874
    [Google Scholar]
26. Sacco E., Covarrubias A. S., O'Hare H. M., Carroll P., Eynard N., Jones T. A., Parish T., Daffe M., Backbro K., Quemard A. 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
    [Google Scholar]
27. Schaeffer M. L., Agnihotri G., Volker C., Kallender H., Brennan P. J., Lonsdale J. T. 2001; Purification and biochemical characterization of the Mycobacterium tuberculosis β-ketoacyl-acyl carrier protein synthases KasA and KasB. J Biol Chem 276:47029–47037
    [Google Scholar]
28. Sharma S. K., Kapoor M., Ramya T. N., Kumar S., Kumar G., Modak R., Sharma S., Surolia N., Surolia A. 2003; Identification, characterization, and inhibition of Plasmodium falciparum β-hydroxyacyl-acyl carrier protein dehydratase (FabZ. J Biol Chem 278:45661–45671
    [Google Scholar]
29. Slayden R. A., Lee R. E., Armour J. W., Cooper A. M., Orme I. M., Brennan P. J., Besra G. S. 1996; Antimycobacterial action of thiolactomycin: an inhibitor of fatty acid and mycolic acid synthesis. Antimicrob Agents Chemother 40:2813–2819
    [Google Scholar]
30. Takayama K., Wang C., Besra G. S. 2005; Pathway to synthesis and processing of mycolic acids in Mycobacterium tuberculosis. Clin Microbiol Rev 18:81–101
    [Google Scholar]
31. Ullmann F., Sponagel P. 1905; Concerning the phenylisation of phenolene. Ber Dtsch Chem Ges 38:2211–2212
    [Google Scholar]
32. Vilcheze C., Weisbrod T. R., Chen B., Kremer L., Hazbon M. H., Wang F., Alland D., Sacchettini J. C., Jacobs W. R. Jr 2005; Altered NADH/NAD⁺ ratio mediates coresistance to isoniazid and ethionamide in mycobacteria. Antimicrob Agents Chemother 49:708–720
    [Google Scholar]
33. Waller R. F., Ralph S. A., Reed M. B., Su V., Douglas J. D., Minnikin D. E., Cowman A. F., Besra G. S., McFadden G. I. 2003; A type II pathway for fatty acid biosynthesis presents drug targets in Plasmodium falciparum. Antimicrob Agents Chemother 47:297–301
    [Google Scholar]