Phosphonate inhibitors of antigen 85C, a crucial enzyme involved in the biosynthesis of the Mycobacterium tuberculosis cell wall

Bioorganic and Medicinal Chemistry Letters

Volumn 14, Issue 13, 2004, Pages 3559-3562

  Gobec, Stanislav ^a   Plantan, Ivan ^a   Mravljak, Janez ^a   Wilson, Rosalind A ^b   Besra, Gurdyal S ^b   Kikelj, Danijel ^a  

^a UNIVERSITY OF LJUBLJANA   (Slovenia)

^b UNIVERSITY OF BIRMINGHAM   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

ANTIGEN 85C; BACTERIAL ANTIGEN; BACTERIAL ENZYME; ISOENZYME; MYCOLYLTRANSFERASE; PHOSPHONATE INHIBITOR OF ANTIGEN 85C; TUBERCULOSTATIC AGENT; UNCLASSIFIED DRUG;

ARTICLE; BACTERIAL CELL; CATALYSIS; CELL WALL; CONTROLLED STUDY; DRUG ACTIVITY; DRUG POTENCY; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ACTIVITY; ENZYME KINETICS; ENZYME MECHANISM; ENZYME STRUCTURE; ENZYME SUBUNIT; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN; PROTEIN FUNCTION;

ACYLTRANSFERASES; ANTIGENS, BACTERIAL; ANTITUBERCULAR AGENTS; BINDING SITES; CATALYSIS; CELL WALL; HYDROCARBONS, AROMATIC; HYDROPHOBICITY; INHIBITORY CONCENTRATION 50; MODELS, CHEMICAL; MOLECULAR MIMICRY; MYCOBACTERIUM TUBERCULOSIS; PHOSPHONIC ACIDS;

MYCOBACTERIUM; MYCOBACTERIUM TUBERCULOSIS;

EID: 2942626073     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2004.04.052     Document Type: Article

References (21)

1. Bloom B., Murray C. Science. 257:1992;1055
2. Murray C.J., Salomon J.A. Proc. Natl. Acad. Sci. U.S.A. 95:1998;13881
3. Zhang Y., Amzel L.M. Curr. Drug Targets. 3:2002;131
4. Kremer L., Besra G.S. Exp. Opin. Invest. Drugs. 11:2002;1033
5. Brennan P.J., Nikaido H. Ann. Rev. Biochem. 64:1995;29
6. Barry C.E. III, Lee R.E., Mdluli K., Sampson A.E., Schroeder B.G., Slayden R.A., Yuan Y. Prog. Lipid Res. 37:1998;143
7. Minkin D.E. Ratlage C., Stanford J. The Biology of Mycobacteria. Vol. 1:1992;95-184 Academic, London
8. Besra G.S., Khoo K.-H., McNeil M.R., Dell A., Morris H.R., Brennan P.J. Biochemistry. 34:1995;4257
9. McNeil M.R., Daffe M., Brennan P.J. J. Biol. Chem. 266:1991;6734
10. Belisle J.T., Vissa V.D., Sievert T., Takayama K., Brennan P.J., Besra G.S. Science. 276:1997;1420
11. Jackson M., Raynaud C., Laneelle M.-A., Guilhot C., Laurent-Winter C., Ensergueix D., Gicquel B., Daffé M. Mol. Microbiol. 31:1999;1573
12. Rose J.D., Maddry J.A., Comber R.N., Suling W.J., Wilson L.N., Reynolds R.C. Carbohydr. Res. 337:2002;105
13. Ronning D.R., Klabunde T., Besra G.S., Vissa V.D., Belisle J.T., Sacchettini J.C. Nat. Struct. Biol. 7:2000;141
14. Babine R.E., Bender S.L. Chem. Rev. 97:1997;1359-1472
15. Leung D., Abbenante G., Fairlie D.P. J. Med. Chem. 43:2000;305
16. Docking calculations were carried out using AutoDock 3.0 with the Lamarckian genetic algorithm as described previously: Morris G.M., Goodsell D.S., Huey R., Olson A.J. J. Comput.-Aid. Mol. Des. 10:1996;293
17. Morris G.M., Goodsell D.S., Halliday R.S., Huey R., Hart W.E., Belew R.K., Olson A.J. J. Comput. Chem. 19:1998;1639
18. Bhattacharya A.K., Thyagarajan G. Chem. Rev. 81:1981;415
19. Holy A. Synthesis. 1998;381
20. Campagne J.-M., Coste J., Jouin P. J. Org. Chem. 60:1995;5214
21. 5NP: C, 60.81; H, 7.60; N, 3.55. Found: C, 60.80; H, 7.73; N, 3.94