Dual Inhibition of Mycobacterial Fatty Acid Biosynthesis and Degradation by 2-Alkynoic Acids

Chemistry & Biology - Tập 13 - Trang 297-307 - 2006
Hector R. Morbidoni1, Catherine Vilchèze1, Laurent Kremer2, Robert Bittman3, James C. Sacchettini4, William R. Jacobs1
1Department of Microbiology and Immunology, Howard Hughes Medical Institute, Albert Einstein College of Medicine, 1300 Morris Park Avenue, Bronx, New York 10461
2Laboratoire de Dynamique Moléculaire des Interactions Membranaires, CNRS UMR 5539, Université de Montpellier II, case 107, Place Eugène Bataillon, 34095 Montpellier Cedex 05, France
3Department of Chemistry and Biochemistry, Queens College of the City University of New York, Flushing, New York 11367
4Department of Biochemistry and Biophysics, Texas A&M University, College Station, Texas 77843

Tài liệu tham khảo

Corbett, 2003, The growing burden of tuberculosis: global trends and interactions with the HIV epidemic, Arch. Intern. Med., 163, 1009, 10.1001/archinte.163.9.1009 Espinal, 2003, The global situation of MDR-TB, Tuberculosis (Edinb.), 83, 44, 10.1016/S1472-9792(02)00058-6 Park, 1996, Outcome of MDR-TB patients, 1983–1993. Prolonged survival with appropriate therapy, Am. J. Respir. Crit. Care Med., 153, 317, 10.1164/ajrccm.153.1.8542137 Kent, 1993, The epidemiology of multidrug-resistant tuberculosis in the United States, Med. Clin. North Am., 77, 1391, 10.1016/S0025-7125(16)30200-0 Fox, 1952, The chemical approach to the control of tuberculosis, Science, 116, 129, 10.1126/science.116.3006.129 Bernstein, 1952, Chemotherapy of experimental tuberculosis, Am. Rev. Tuberc., 65, 357 Takayama, 1972, Effect of isoniazid on the in vivo mycolic acid synthesis, cell growth, and viability of Mycobacterium tuberculosis, Antimicrob. Agents Chemother., 2, 29, 10.1128/AAC.2.1.29 Banerjee, 1994, inhA, a gene encoding a target for isoniazid and ethionamide in Mycobacterium tuberculosis, Science, 263, 227, 10.1126/science.8284673 Quemard, 1995, Enzymatic characterization of the target for isoniazid in Mycobacterium tuberculosis, Biochemistry, 34, 8235, 10.1021/bi00026a004 Vilcheze, 2000, Inactivation of the inhA-encoded fatty acid synthase II (FASII) enoyl-acyl carrier protein reductase induces accumulation of the FASI end products and cell lysis of Mycobacterium smegmatis, J. Bacteriol., 182, 4059, 10.1128/JB.182.14.4059-4067.2000 Rozwarski, 1999, Crystal structure of the Mycobacterium tuberculosis enoyl-ACP reductase, InhA, in complex with NAD+ and a C16 fatty acyl substrate, J. Biol. Chem., 274, 15582, 10.1074/jbc.274.22.15582 Marrakchi, 2000, InhA, a target of the antituberculous drug isoniazid, is involved in a mycobacterial fatty acid elongation system, FAS-II, Microbiol., 146, 289, 10.1099/00221287-146-2-289 Bhatt, 2005, Conditional depletion of KasA, a key enzyme of mycolic acid biosynthesis, leads to mycobacterial cell lysis, J. Bacteriol., 187, 7596, 10.1128/JB.187.22.7596-7606.2005 Kremer, 2003, Inhibition of InhA activity, but not KasA activity, induces formation of a KasA-containing complex in mycobacteria, J. Biol. Chem., 278, 20547, 10.1074/jbc.M302435200 Larsen, 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, 10.1046/j.1365-2958.2002.03162.x Bloch, 1977, Control mechanisms for fatty acid synthesis in Mycobacterium smegmatis, Adv. Enzymol. Relat. Areas Mol. Biol., 45, 1 Barry, 1998, Mycolic acids: structure, biosynthesis and physiological functions, Prog. Lipid Res., 37, 143, 10.1016/S0163-7827(98)00008-3 Konthikamee, 1982, Effect of 2-alkynoic acids on in vitro growth of bacterial and mammalian cells, Antimicrob. Agents Chemother., 22, 805, 10.1128/AAC.22.5.805 Kremer, 2000, Thiolactomycin and related analogues as novel anti-mycobacterial agents targeting KasA and KasB condensing enzymes in Mycobacterium tuberculosis, J. Biol. Chem., 275, 16857, 10.1074/jbc.M000569200 Parrish, 1999, Antimycobacterial activity of cerulenin and its effects on lipid biosynthesis, J. Antimicrob. Chemother., 43, 219, 10.1093/jac/43.2.219 Boshoff, 2002, Effects of pyrazinamide on fatty acid synthesis by whole mycobacterial cells and purified fatty acid synthase I, J. Bacteriol., 184, 2167, 10.1128/JB.184.8.2167-2172.2002 Zimhony, 2000, Pyrazinamide inhibits the eukaryotic-like fatty acid synthetase I (FASI) of Mycobacterium tuberculosis, Nat. Med., 6, 1043, 10.1038/79558 CaJacob, 1986, Mechanism-based in vivo inactivation of lauric acid hydroxylases, Biochemistry, 25, 4705, 10.1021/bi00364a038 Powell, 1988, 2-octynoyl coenzyme A is a mechanism-based inhibitor of pig kidney medium-chain acyl coenzyme A dehydrogenase: isolation of the target peptide, Biochemistry, 27, 8022, 10.1021/bi00421a008 Kunau, 1995, β-oxidation of fatty acids in mitochondria, peroxisomes, and bacteria: a century of continued progress, Prog. Lipid Res., 34, 267, 10.1016/0163-7827(95)00011-9 Wood, 1981, Metabolism of 2-hexadecynoate and inhibition of fatty acid elongation, J. Biol. Chem., 256, 12379, 10.1016/S0021-9258(18)43283-8 Miesowicz, 1979, Purification of hog liver isomerase. Mechanism of isomerization of 3-alkenyl and 3-alkynyl thioesters, J. Biol. Chem., 254, 5868, 10.1016/S0021-9258(18)50494-4 Branchini, 1977, Allenic thioester hydration activity of beef liver crotonase, Bioorg. Chem., 6, 49, 10.1016/0045-2068(77)90007-4 Alipui, 2002, Direct hydration of 3-octynoyl-CoA by crotonase: a missing link in Bloch's enzymatic studies with 3-alkynoyl thioesters, Biochem. Biophys. Res. Commun., 292, 1171, 10.1006/bbrc.2001.2024 Holland, 1972, Mechanisms of inhibition of fatty acid oxidation by pent-4-enoic acid: evidence against the coenzyme A-depletion hypothesis, Biochem. J., 127, 79P, 10.1042/bj1270079Pb Cole, 1998, Deciphering the biology of Mycobacterium tuberculosis from the complete genome sequence, Nature, 393, 537, 10.1038/31159 Bloch, 1956, Biochemical differentiation of Mycobacterium tuberculosis grown in vivo and in vitro, J. Bacteriol., 72, 132, 10.1128/JB.72.2.132-141.1956 Munoz-Elias, 2005, Mycobacterium tuberculosis isocitrate lyases 1 and 2 are jointly required for in vivo growth and virulence, Nat. Med., 11, 638, 10.1038/nm1252 Wood, 1980, Effect of methyl 2-hexadecynoate on hepatic fatty acid metabolism, Lipids, 15, 141, 10.1007/BF02540960 Sampath Kumar, 1999, SiO2 catalysed expedient synthesis of [E]-3-alkenoic acids in dry media, Tetrahedron Lett., 40, 2401, 10.1016/S0040-4039(99)00113-6 Barnick, 1979, A convenient direct method for the preparation of β-keto-acids, Synthesis (Mass.), 787, 10.1055/s-1979-28830 Hartmans, 1992 Camps, 1992, Synthesis of biosynthetic inhibitors of the sex pheromone of Spodoptera littoralis. Part II: Acetylenic and cyclopropane fatty acids, Chem. Phys. Lipids, 61, 157, 10.1016/0009-3084(92)90008-D Valicenti, 1985, Synthesis of octadecynoic acids and [1-14C] labeled isomers of octadecenoic acids, Lipids, 20, 234, 10.1007/BF02534194 Swenson, 1982, Rapidly growing mycobacteria: testing of susceptibility to 34 antimicrobial agents by broth microdilution, Antimicrob. Agents Chemother., 22, 186, 10.1128/AAC.22.2.186 Okuyama, 1967, Positional distribution of fatty acids in phospholipids from Mycobacteria, J. Biochem. (Tokyo), 61, 732, 10.1093/oxfordjournals.jbchem.a128607