Slow-tight-binding inhibition of enoyl-acyl carrier protein reductase from Plasmodium falciparum by triclosan

Biochemical Journal

Volumn 381, Issue 3, 2004, Pages 719-724

  Kapoor, Mili ^a   Chandramouli Reddy, C ^a   Krishnasastry, M V ^b   Surolia, Namita ^c   Surolia, Avadhesha ^a  

^a INDIAN INSTITUTE OF SCIENCE   (India)

^b NATIONAL CENTRE FOR CELL SCIENCE   (India)

^c JAWAHARLAL NEHRU CENTRE FOR ADVANCED SCIENTIFIC RESEARCH   (India)

Author keywords

Crotonoyl CoA; Enoyl acyl carrier protein (enoyl ACP) reductase; Fatty acid biosynthesis; Plasmodium falciparum; Slow tight binding inhibitor; Triclosan

Indexed keywords

BIOSYNTHESIS; FLUORESCENCE; ISOMERIZATION; PROTEINS;

ACYL CARRIER PROTEINS; FLUORESCENCE ANALYSIS;

BIOCHEMISTRY;

ACYL CARRIER PROTEIN; ANTIMALARIAL AGENT; ENOYL-ACYL CARRIER PROTEIN REDUCTASE; FATTY ACID; FATTY ACID SYNTHASE; NICOTINAMIDE ADENINE DINUCLEOTIDE; OXIDOREDUCTASE; TRICLOSAN; UNCLASSIFIED DRUG;

ARTICLE; BINDING AFFINITY; CATALYSIS; DISSOCIATION; DRUG PROTEIN BINDING; ENZYME INHIBITION; ENZYME INHIBITOR COMPLEX; ENZYME KINETICS; FATTY ACID SYNTHESIS; FLUORESCENCE ANALYSIS; ISOMERIZATION; NONHUMAN; PLASMODIUM FALCIPARUM; PRIORITY JOURNAL; SURFACE PLASMON RESONANCE; TIMED DRUG RELEASE;

ANIMALS; ENOYL-(ACYL-CARRIER-PROTEIN) REDUCTASE (NADH); OXIDOREDUCTASES; PLASMODIUM FALCIPARUM; SPECTROMETRY, FLUORESCENCE; TRICLOSAN;

PLASMODIUM FALCIPARUM; PROTOZOA;

EID: 4344702214     PISSN: 02646021     EISSN: None     Source Type: Journal    
DOI: 10.1042/BJ20031821     Document Type: Article

References (36)

1. WHO (1999) The World Health Report, pp. 49-63
2. Rock, C. O. and Cronan, J. E. (1996) Escherichia coli as a model for the regulation of dissociable (type II) fatty acid biosynthesis. Biochim. Biophys. Acta 1302, 1-16
3. Heath, R. J. and Rock, C. O. (1995) Enoyl-acyl carrier protein reductase (FabI) plays a determinant role in completing cycles of fatty acid elongation in Bcherichia coli. J. Biol. Chem. 270, 26538-26542
4. Marrakchi, H., Zhang, Y.-M. and Rock, C. O. (2002) Mechanistic diversity and regulation of Type II fatty acid synthesis. Biochem. Soc. Trans. 30, 1050-1055
5. Parikh, S. L., Xiao, G. and Tonge, P. J. (2000) Roles of tyrosine 158 and lysine 165 in the catalytic mechanism of InhA, the enoyl-ACP reductase from Mycobacterium tuberculosis. Biochemistry 39, 7645-7650
6. Roujeinikova, A., Sedelnikova, S., de Boer, G. J., Stuitje, A. R., Slabas, A. R., Rafferty, J. B. and Rice, D. W. (1999) Inhibitor binding studies on enoyl reductase reveal conformational changes related to substrate recognition. J. Biol. Chem. 274, 30811-30817
7. Heath, R. J., Yu, Y. T., Shapiro, M. A., Olson, E. and Rock, C. O. (1998) Broad spectrum antimicrobial biocides target the FabI component of fatty acid synthesis. J. Biol. Chem. 273, 30316-30320
8. Levy, C. W., Roujeinikova, A., Sedelnikova, S., Baker, P. J., Stuitje, A. R., Slabas, A. R., Rice, D. W. and Rafferty, J. B. (1999) Molecular basis of triclosan activity. Nature (London) 398, 383-384
9. Tsay, J. T., Rock, C. O. and Jackowski, S. (1992) Overproduction of β-ketoacyl-acyl carrier protein synthase I imparts thiolactomycin resistance to Escherichia coli K-12. J. Bacteriol. 174, 508-513
10. Surolia, N. and Surolia, A. (2001) Triclosan offers protection against blood stages of malaria by inhibiting enoyl-ACP reductase of Plasmodium falciparum. Nat. Med. (N.Y.) 7, 167-173
11. McLeod, R., Muench, S. P., Rafferty, J. B., Kyle, D. E., Mui, E. J., Kirisits, M. J., Mack, D. G., Roberts, C. W., Samuel, B. U., Lyons, R. E. et al. (2001) Triclosan inhibits the growth of Plasmodium falciparum and Toxoplasma gondii by inhibition of apicomplexan Fab I. Int. J. Parasitol. 31, 109-113
12. Ward, W. H. J., Holdgate, G. A., Rowsell, S., McLean, E. G., Pauptit, R. A., Clayton, E., Nichols, W. W., Colls, J. G., Minshull, C. A., Jude, D. A. et al. (1999) Kinetic and structural characteristics of the inhibition of enoyl (acyl carrier protein) reductase by triclosan. Biochemistry 38, 12514-12525
13. Fawcett, T., Copse, C. L., Simon, J. W. and Slabas, A. R. (2000) Kinetic mechanism of NADH-enoyl-ACP reductase from Brassica napus. FEBS Lett. 484, 65-68
14. Parikh, S., Moynihan, D. P., Xiao, G. and Tonge, P. J. (1999) Roles of tyrosine 158 and lysine 165 in the catalytic mechanism of InhA, the enoyl-ACP reductase from Mycobacterium tuberculosis. Biochemistry 38, 13623-13634
15. Heath, R. J., Su, N., Murphy, C. K. and Rock, C. O. (2000) The enoyl-[acyl-carrier-protein] reductases FabI and FabL from Bacillus subtilis. J. Biol. Chem. 275, 40128-40133
16. Kapoor, M., Dar, M. J., Surolia, A. and Surolia, N. (2001) Kinetic determinants of the interaction of enoyl-ACP reductase from Plasmodium falciparum with its substrates and inhibitors. Biochem. Biophys. Res. Commun. 289, 832-837
17. Morrison, J. F. (1982) The slow-binding and slow, tight-binding inhibition of enzyme catalyzed reactions. Trends Biochem. Sci. 7, 102-105
18. Williams, J. W. and Morrison, J. F. (1979) The kinetics of reversible tight-binding inhibition. Methods Enzymol. 63, 437-467
19. Greco, W. R. and Hakala, M. T. (1979) Evaluation of methods for estimating the dissociation constant of tight binding enzyme inhibitors. J. Biol. Chem. 254, 12104-12109
20. Morrison, J. F. and Walsh, C. T. (1988) The behavior and significance of slow-binding enzyme inhibitors. Adv. Enzymol. Relat. Areas Mol. Biol. 61, 201-301
21. Hurtado-Guerrero, R., Pena-Diaz, J., Montalvetti, A., Ruiz-Perez, L. M. and Gonzalez-Pacanowska, O. (2002) Kinetic properties and inhibition of Trypanosoma cruzi 3-hydroxy-3-methylglutaryl CoA reductase. FEBS Lett. 510, 141-144
22. Kicska, G. A., Tyler, P. C., Evans, G. B., Furneaux, R. H., Kim, K. and Schramm, V. L. (2001) Transition state analogue inhibitors of purine nucleoside phosphorylase from Plasmodium falciparum. J. Biol. Chem. 277, 3219-3225
23. Sculley, M. J. and Morrison, J. F. (1986) The determination of kinetic constants governing the slow, tight-binding inhibition of enzyme-catalysed reactions. Biochim. Biophys. Acta 874, 44-53
24. Sculley, M. J., Morrison, J. F. and Cleland, W. W. (1996) Slow-binding inhibition: the general case. Biochim. Biophys. Acta 1298, 78-86
25. Mulvey, R. S., Gualtieri, R. J. and Beychok, S. (1974) Composition, fluorescence, and circular dichroism of rat lysozyme. Biochemistry 13, 782-787
26. Cha, S. (1976) Tight-binding inhibitors - III. A new approach for the determination of competition between tight-binding inhibitors and substrates-inhibition of adenosine deaminase by coformycin. Biochem. Pharmacol. 25, 2695-2702
27. Dash, C., Vathipadiekal, V., George, S. P. and Rao, M. (2002) Slow-tight binding inhibition of xylanase by an aspartic protease inhibitor: kinetic parameters and conformational changes that determine the affinity and selectivity of the bifunctional nature of the inhibitor. J. Biol. Chem. 277, 17978-17986
28. Lakowicz, J. R. (1983) Principles of Fluorescence Spectroscopy, Plenum Press, New York
29. Schloss, J. V. (1988) Significance of slow-binding enzyme inhibition and its relationship to reaction-intermediate analogs. Acc. Chem. Res. 21, 348-353
30. Heath, R. J., Li, J., Roland, G. E. and Rock, C. O. (2000) Inhibition of the Staphylococcus auteus NADPH-dependent enoyl-acyl carrier protein reductase by triclosan and hexachlorophene. J. Biol. Chem. 275, 4654-4659
31. Roujeinikova, A., Levy, C. W., Rowsell, S., Sedelnikova, S., Baker, P. J., Minshull, C. A., Mistry, A., Colls, J. G., Camble, R., Stuitje, A. R. et al. (1999) Crystallographic analysis of triclosan bound to enoyl reductase. J. Mol. Biol. 294, 527-535
32. Baldock, C., Rafferty, J. B., Sedelnikova, S. E., Baker, P. J., Stuitje, A. R., Slabas, A. R., Hawkes, T. R. and Rice, D. W. (1996) A mechanism of drug action revealed by structural studies of enoyl reductase. Science 274, 2107-2110
33. Levy, C. W., Baldock, C., Wallace, A. J., Sedelnikova, S., Viner, R. C., Clough, J. M., Stuitje, A. R., Slabas, A. R., Rice, D. W. and Rafferty, J. B. (2001) A study of the structure-activity relationship for diazaborine inhibition of Escherichia coli enoyl-ACP reductase. J. Mol. Biol. 309, 171-180
34. Perozzo, R., Kuo, M., Sidhu, A. S., Valiyaveettil, J. T., Bittman, R., Jacobs, Jr, W. R., Fidock, D. A. and Sacchettini, J. C. (2002) Targeting tuberculosis and malaria through inhibition of enoyl reductase: compound activity and structural data. J. Biol. Chem. 277, 13106-13114
35. +. Biochem. J. 381, 725-733
36. Kapoor, M., Gopalakrishnapai, J., Surolia, N. and Surolia, A. (2004) Mutational analysis of the triclosan-binding region of enoyl-ACP (acyl-carrier protein) reductase from Plasmodium falciparum. Biochem. J. 381, 735-741