Inhibition of isolated Mycobacterium tuberculosis fatty acid synthase I by pyrazinamide analogs

Antimicrobial Agents and Chemotherapy

Volumn 51, Issue 7, 2007, Pages 2430-2435

  Ngo, Silvana C ^a   Zimhony, Oren ^b   Woo, Jin Chung ^a   Sayahi, Halimah ^a   Jacobs Jr , William R ^c   Welch, John T ^a  

^a STATE UNIVERSITY OF NEW YORK   (United States)

^b HEBREW UNIVERSITY OF JERUSALEM   (Israel)

^c ALBERT EINSTEIN COLLEGE OF MEDICINE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

5 CHLOROPYRAZINAMIDE; BENZAMIDE; CERULENIN; ETHAMBUTOL; FATTY ACID SYNTHASE; FATTY ACID SYNTHASE INHIBITOR; PYRAZINAMIDE; PYRAZINOIC ACID; REDUCED NICOTINAMIDE ADENINE DINUCLEOTIDE PHOSPHATE; UNCLASSIFIED DRUG;

ARTICLE; COMPETITIVE INHIBITION; ENZYME ACTIVITY; ENZYME INHIBITION; ENZYME METABOLISM; ENZYME PURIFICATION; ENZYME SUBSTRATE; MYCOBACTERIUM SMEGMATIS; MYCOBACTERIUM TUBERCULOSIS; NONHUMAN; PRIORITY JOURNAL; SPECTROPHOTOMETRY;

BACTERIAL PROTEINS; CELL-FREE SYSTEM; FATTY ACID SYNTHETASE COMPLEX; HUMANS; INHIBITORY CONCENTRATION 50; KINETICS; MASS SPECTROMETRY; MOLECULAR STRUCTURE; MYCOBACTERIUM TUBERCULOSIS; NADP; OXIDATION-REDUCTION; PYRAZINAMIDE; REPRODUCIBILITY OF RESULTS; SUBSTRATE SPECIFICITY;

EID: 34447258829     PISSN: 00664804     EISSN: None     Source Type: Journal    
DOI: 10.1128/AAC.01458-06     Document Type: Article

References (34)

1. Bass, J. B., Jr., L. S. Farer, P. C. Hopewell, R. O'Brien, R. F. Jacobs, F. Ruben, D. E. Snider, Jr., and G. Thornton. 1994. Treatment of tuberculosis and tuberculosis infection in adults and children. Am. J. Respir. Crit. Care Med. 149:1359-1374.
2. Belanger, A. E., G. S. Besra, M. E. Ford, K. Mikusova, J. T. Belisle, P. J. Brennan, and J. M. Inamine. 1996. The embAB genes of Mycobacterium avium encode an arabinosyl transferase involved in cell wall arabinan biosynthesis that is the target for the antimycobacterial drug ethambutol. Proc. Natl. Acad. Sci. USA 93:11919-11924.
3. Bloch, K. 1975. Fatty acid synthases from Mycobacterium phlei. Methods Enzymol. 35:84-90.
4. Boshoff, H. I., V. Mizrahi, and C. E. Barry III. 2002. Effects of pyrazinamide on fatty acid synthesis by whole mycobacterial cells and purified fatty acid synthase I. J. Bacteriol. 184:2167-2172.
5. Boshoff, H. I. M., and V. Mizrahi. 2000. Expression of Mycobacterium smegmatis pyrazinamidase in Mycobacterium tuberculosis confers hypersensitivity to pyrazinamide and related amides. J. Bacteriol. 182:5479-5485.
6. Brindley, D. N., S. Matsumura, and K. Bloch. 1969. Mycobacterium phlei fatty acid synthetase; a bacterial multienzyme complex. Nature 224:666-669.
7. 50: a more general use of the Dixon plot. J. Chem. Educ. 80:214-218.
8. Cynamon, M. H., R. Gimi, F. Gyenes, C. A. Sharpe, K. E. Bergmann, H. J. Han, L. B. Gregor, R. Rapolu, G. Luciano, and J. T. Welch. 1995. Pyrazine-carboxylate esters with broad spectrum in vitro antimycobacterial activity. J. Med. Chem. 38:3902-3907.
9. Cynamon, M. H., S. P. Klemens, T. S. Chou, R. H. Gimi, and J. T. Welch. 1992. Antimycobacterial activity of a series of pyrazinoic acid esters. J. Med. Chem. 35:1212-1215.
10. Cynamon, M. H., R. J. Speirs, and J. T. Welch. 1998. In vitro antimycobacterial activity of 5-chloropyrazinamide. Antimicrob. Agents Chemother. 42:462-463.
11. Dick, J. D., and F. P. Kuhajda. January 1995. Inhibitors of fatty acid synthesis as antimicrobial agents. U.S. patent 9,519,706.
12. Heath, R. J., S. W. White, and C. O. Rock. 2001. Lipid biosynthesis as a target for antibacterial agents. Prog. Lipid Res. 40:467-497.
13. Kawaguchi, A., and S. Okuda. 1977. Fatty acid synthetase from Brevibacterium ammoniagenes: formation of monounsaturated fatty acids by a multienzyme complex. Proc. Natl. Acad. Sci. USA 74:3180-3183.
14. Linn, T. C. 1981. Purification and crystallization of rat liver fatty acid synthetase. Arch. Biochem. Biophys. 209:613-619.
15. Lynen, F. 1969. Yeast fatty acid synthase. Methods Enzymol. 14:17-33.
16. Marrakchi, H., G. Laneelle, and A. Quemard. 2000. InhA, a target of the antituberculous drug isoniazid, is involved in a mycobacterial fatty acid elongation system, FAS-II. Microbiology 146:289-296.
17. Nelson, D. L., and M. M. Cox. 2000. Lehninger principles of biochemistry. Worth Publishers, New York, NY.
18. Prescott, D. J., and P. R. Vagelos. 1972. Acyl carrier protein. Adv. Enzymol. 36:269-311.
19. Steele, M. A., and R. M. Des Prez. 1988. The role of pyrazinamide in tuberculosis chemotherapy. Chest 94:845-850.
20. Stoops, J. K., M. J. Arslanian, Y. H. Oh, K. C. Aune, T. C. Vanaman, and S. J. Wakil. 1975. Presence of two polypeptide chains comprising fatty acid synthetase. Proc. Natl. Acad. Sci. USA 72:1940-1944.
21. Sun, Z., A. Scorpio, and Y. Zhang. 1997. The pncA gene from naturally pyrazinamide-resistant Mycobacterium avium encodes pyrazinamidase and confers pyrazinamide susceptibility to resistant M. tuberculosis complex organisms. Microbiology 143:3367-3373.
22. Sun, Z., and Y. Zhang. 1999. Reduced pyrazinamidase activity and the natural resistance of Mycobacterium kansasii to the antituberculosis drug pyrazinamide. Antimicrob. Agents Chemother. 43:537-542.
23. Volpe, J. J., and P. R. Vagelos. 1973. Saturated fatty acid biosynthesis and its regulation. Annu. Rev. Biochem. 42:21-60.
24. Wheeler, P. R., K. Bulmer, and C. Ratledge. 1990. Enzymes for biosynthesis de novo and elongation of fatty acids in mycobacteria grown in host cells: is Mycobacterium leprae competent in fatty acid biosynthesis? J. Gen. Microbiol. 136:211-217.
25. Wood, W. I., D. O. Peterson, and K. Bloch. 1978. Subunit structure of Mycobacterium smegmatis fatty acid synthetase. Evidence for identical multifunctional polypeptide chains. J. Biol. Chem. 253:2650-2656.
26. Wood, W. I., D. O. Peterson, and K. Bloch. 1977. Mycobacterium smegmatis fatty acid synthetase. A mechanism based on steady state rates and product distributions. J. Biol. Chem. 252:5745-5749.
27. World Health Organization. 2004. Tuberculosis. Fact sheet no. 104. World Health Organization, Geneva, Switzerland. http://www.who.int/mediacentre/ factsheets/fs104/en/.
28. Zhang, Y., and D. Mitchison. 2003. The curious characteristics of pyrazinamide: a review. Int. J. Tuberc. Lung Dis. 7:6-21.
29. Zhang, Y., S. Permar, and Z. Sun. 2002. Conditions that may affect the results of susceptibility testing of Mycobacterium tuberculosis to pyrazinamide. J. Med. Microbiol. 51:42-49.
30. Zhang, Y., A. Scorpio, H. Nikaido, and Z. Sun. 1999. Role of acid pH and deficient efflux of pyrazinoic acid in unique susceptibility of Mycobacterium tuberculosis to pyrazinamide. J. Bacteriol. 181:2044-2049.
31. Zhang, Y., M. M. Wade, A. Scorpio, H. Zhang, and Z. Sun. 2003. Mode of action of pyrazinamide: disruption of Mycobacterium tuberculosis membrane transport and energetics by pyrazinoic acid. J. Antimicrob. Chemother. 52:790-795.
32. Zimhony, O., J. S. Cox, J. T. Welch, C. Vilcheze, and W. R. Jacobs, Jr. 2000. Pyrazinamide inhibits the eukaryotic-like fatty acid synthetase I (FASI) of Mycobacterium tuberculosis. Nat. Med. 6:1043-1047.
33. Zimhony, O., C. Vilcheze, and W. R. Jacobs, Jr. 2004. Characterization of Mycobacterium smegmatis expressing the Mycobacterium tuberculosis fatty acid synthase I (fas1) gene. J. Bacteriol. 186:4051-4055.
34. Zimhony, O., C. Vilcheze, M. Arai, J. T. Welch and W. R. Jacobs, Jr. 2007. Pyrazinoic acid and its n-propyl ester inhibit fatty acid synthase type I in replicating tubercle bacilli. Antimicrob. Agents Chemother. 51:752-754.