New lipophilic phthalimido- and 3-phenoxybenzyl sulfonates: Inhibition of antigen 85C mycolyltransferase activity and cytotoxicity

Journal of Enzyme Inhibition and Medicinal Chemistry

Volumn 21, Issue 4, 2006, Pages 391-397

  Kovač, Andreja ^a   Wilson, Rosalind A ^b   Besra, Gurdyal S ^b   Filipič, Metka ^c   Kikelj, Danijel ^a   Gobec, Stanislav ^a  

^a UNIVERSITY OF LJUBLJANA   (Slovenia)

^b UNIVERSITY OF BIRMINGHAM   (United Kingdom)

^c NATIONAL INSTITUTE OF BIOLOGY   (Slovenia)

Author keywords

Anticancer agents; Antigen 85C; Antituberculosis agents; Cytotoxicity; Mycolyltransferase; Sulfonate inhibitors

Indexed keywords

1 (3 PHENOXY)BENZYL 1 BUTANESULFONATE; 1 (3 PHENOXY)BENZYL 1 OCTANESULFONATE; 2 (1,3 DIOXO 1,3 DIHYDRO 2H ISOINDOL 2 YL)ETHYL 1 BUTANESULFONATE; 2 (1,3 DIOXO 1,3 DIHYDRO 2H ISOINDOL 2 YL)ETHYL 1 OCTANESULFONATE; ALKYL GROUP; ANTIGEN 85C; ANTINEOPLASTIC AGENT; MYCOLIC ACID; MYCOLYLTRANSFERASE; PHTHALIMIDE DERIVATIVE; SULFONIC ACID DERIVATIVE; TRANSFERASE; TREHALOSE; TUBERCULOSTATIC AGENT; UNCLASSIFIED DRUG;

ALPHA CHAIN; ANTINEOPLASTIC ACTIVITY; ARTICLE; BACTERIAL CELL WALL; BETA CHAIN; BREAST CANCER; CANCER CELL CULTURE; CATALYSIS; CONTROLLED STUDY; CRYSTAL STRUCTURE; CYTOTOXICITY; DRUG DESIGN; DRUG SELECTIVITY; DRUG STRUCTURE; ENZYME INHIBITION; HUMAN; HUMAN CELL; IC 50; IN VITRO STUDY; LIPOPHILICITY; MYCOBACTERIUM; NONHUMAN; PRIORITY JOURNAL;

ACYLTRANSFERASES; ANTIGENS; ANTIGENS, BACTERIAL; ANTITUBERCULAR AGENTS; BINDING SITES; CATALYSIS; CRYSTALLOGRAPHY, X-RAY; DRUG DESIGN; ENZYME INHIBITORS; INHIBITORY CONCENTRATION 50; MODELS, CHEMICAL; MODELS, MOLECULAR; MYCOLIC ACIDS; SULFONIC ACIDS;

EID: 33748486937     PISSN: 14756366     EISSN: 14756374     Source Type: Journal    
DOI: 10.1080/14756360600703214     Document Type: Article

References (24)

1. World Health Organisation [internet]., Tuberculosis: Fact Sheet No. 104; 2005-[cited 2005 Apr]; Available from: http://www.who.int/mediacentre/ factsheets/fs104/en
2. Zhang, Y and Amzel, LM. (2002) Tuberculosis drug targets Curr. Drug Targ., 3, pp. 131-154.
3. Kremer, L and Besra, GS. (2002) Current status and future development of antitubercular chemotherapy Exp. Opin. Invest. Drugs, 11, pp. 1033-1049.
4. Brennan, PJ and Nikaido, H. (1995) The envelope of mycobacteria Ann Rev. in Biochem., 64, pp. 29-63.
5. Barry, CE and Lee, RE and Mdluli, K and Sampson, AE and Schroeder, BG and Slayden, RA and Yuan, Y. (1998) Mycolic acids: Structure biosynthesis and physiological functions Progr Lipid Res., 37, pp. 143-179.
6. Besra, GS and Khoo, K-H and McNeil, MR and Dell, A and Morris, HR and Brennan, PJ. (1995) A new interpretation of the structure of the mycolyl arabinogalactan complex of mycobacterium tuberculosis as revealed through characterization of oligoglycosylalditol fragments by fast-atom-bombardment mass-spectrometry and H-1 nuclear-magnetic-resonance spectroskopy Biochemistry, 34, pp. 4257-4266.
7. McNeil, MR and Daffe, M and Brennan, PJ. (1991) Location of the Mycolyl Ester Substituents in the Cell walls of mycobacteria J. Biol. Chem., 266, pp. 13217-13223.
8. Belisle, JT and Vissa, VD and Sievert, T and Takayama, K and Brennan, PJ and Besra, GS. (1997) Role of mayor antigen of Mycobacterium tuberculosis in Cell Wall Biogenesis Science, 276, pp. 1420-1422.
9. Jackson, M and Raynaud, C and Laneelle, MA and Guilhot, C and Laurent-Winter, C and Ensergueix, D and Gicquel, B and Daffe, M. (1999) Inactivation of the antigen 85C gene profoundly affects the mycolate content and alters the permeability of the Mycobacterium tuberculosis cell envelope Molec. Microbiol., 31, pp. 1573-1578.
10. Ronning, DR and Klabunde, T and Besra, GS and Vissa, VD and Belisle, JT and Sacchettini, JC. (2000) Crystal structure of the secreted form of antigen 85C reveals potential target for mycobacterial drugs and vaccines Nature Struct. Biol., 7, pp. 141-146.
11. Gobec, S and Plantan, I and Mravljak, J and Wilson, RA and Besra, GS and Kikelj, D. (2004) Phosphonate inhibitors of antigen 85C, a crucial enzyme involved in the biosynthesis of the Mycobacterium tuberculosis cell wall Bioorgan. Med. Chem. Lett., 14, pp. 3559-3562.
12. Yang, K-W and Golich, FC and Sigdel, TK and Crowder, MW. (2005) Phosphinate, sulfonate, and sulfonamidate dipeptides as potential inhibitors of Escherichia coli aminopeptidase N Bioorgan. Med. Chem. Lett., 15, pp. 5150-5153.
13. Hall, IH and Wong, OT and Scovill, JP. (1995) The citotoxicity of N-pyridinyl and N-quinolinyl substituted derivatives of phthalimide and succinimide Biomed. Pharmacother., 5, pp. 251-258.
14. Hall, IH and Wong, OT and Chapman, JM. (1995) Citotoxicity of imides-N-alkyl semicarbazones, thiosemicarbazones, acetylhydrazones and related derivatives Anti-Cancer Drugs, 6, pp. 147-153.
15. Ronning, DR and Vissa, V and Besra, GS and Belisle, JT and Sacchettini, JC. (2004) Mycobacterium tuberculosis antigen 85A and 85C structures confirm binding orientation and conserved substrate specificity J. Biol. Chem., 279, pp. 36771-36777.
16. Peuckmann, V and Fisch, M and Bruera, E. (2000) Potential novel uses of thalidomide Drugs, 60, pp. 273-292.
17. Hashimoto, A. (1998) Novel biological response modifiers derivated from thalidomide Curr. Med. Chem., 5, pp. 163-178.
18. Calabrese, L and Fleischer, AB. (2000) Thalidomide: Current and potential clinical application Amer. J. Med., 108, pp. 487-495.
19. Fanelli, M and Sarmiento, R and Gattuso, D and Carillio, G and Capaccetti, B and Vacca, A and Roccaro, AM and Gasparini, G. (2003) Thalidomide: A new anticancer drug? Exp. Opin. Investig. Drugs, 12, pp. 1211-1225.
20. Mosmann, T. (1983) Rapid colorimetric assay for cellular growth and survival - application to proliferation and cyto-toxicity assays J. Immunol. Meth., 65, pp. 55-63.
21. Morris, GM and Goodsell, DS and Halliday, RS and Huey, R and Hart, WE and Belew, RK and Olson, AJ. (1998) Automated docking using a Lamarckian genetic algorithm and an empirical binding free energy function J. Comput. Chem., 19, pp. 1693-1662.
22. Weiner, SJ and Kollman, PA and Case, DA and Singh, UC and Ghio, C and Alagona, G and Profeta, S and Weiner, P. (1984) A new force-field for molecular mechanical simulation of nucleic acids and proteins J. Amer. Chem. Soc., 106, pp. 765-784.
23. Gasteiger, J and Marsili, M. (1980) Iterative partial equalization of orbital electronegativity - a rapid access to atomic charges Tetrahedron, 36, pp. 3219-3228.
24. Mehler, EL and Solmajer, T. (1991) Electrostatic effects in proteins-comparison of dielectric and charge models Prot. Eng., 4, pp. 903-910.