Chemical evaluation of fatty acid desaturases as drug targets in Trypanosoma cruzi

International Journal for Parasitology

Volumn 39, Issue 9, 2009, Pages 985-993

  Alloatti, Andrés ^a   Testero, Sebastián A ^a   Uttaro, Antonio D ^a  

^a Departamento de Microbiología ^*  (Argentina)

Author keywords

Chagas' disease; Desaturase; Drug target; Fatty acids; Isoxyl; Thia fatty acid; Thiastearate; Trypanosoma cruzi

Indexed keywords

ACYL COENZYME A DESATURASE; FATTY ACID; LINOLEIC ACID; OLEIC ACID; PALMITIC ACID; PALMITOLEIC ACID; STEARIC ACID; STEARIC ACID DERIVATIVE; THIASTEARIC ACID; TIOCARLIDE; UNCLASSIFIED DRUG;

CELL ORGANELLE; CHEMICAL ANALYSIS; DRUG; ENZYME ACTIVITY; FATTY ACID; PARASITE;

ARTICLE; CELL MEMBRANE; CONCENTRATION (PARAMETERS); CONTROLLED STUDY; CULTURE MEDIUM; DRUG STRUCTURE; DRUG TARGETING; ENZYME ACTIVITY; ENZYME INHIBITION; ENZYME STRUCTURE; EPIMASTIGOTE; FATTY ACID SYNTHESIS; GROWTH INHIBITION; LIPID COMPOSITION; MAMMAL CELL; MYCOBACTERIUM; NONHUMAN; SPECIES DIFFERENCE; TRYPANOSOMA CRUZI;

ANIMALS; CELL MEMBRANE; CELLS, CULTURED; DRUG DELIVERY SYSTEMS; STEAROYL-COA DESATURASE; TRYPANOSOMA CRUZI;

CORYNEBACTERINEAE; MAMMALIA; THIA; TRYPANOSOMA CRUZI;

EID: 67349191914     PISSN: 00207519     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ijpara.2009.01.011     Document Type: Article

References (30)

1. Almeida I.C., and Gazzinelli R.T. Proinflammatory activity of glycosylphosphatidylinositol anchors derived from Trypanosoma cruzi: structural and functional analyses. J. Leukoc. Biol. 70 (2001) 467-477
2. Barrett M.P., Burchmore R.J.S., Stich A., Lazzari J.O., Frasch A.C., Cazzulo J.J., and Krishna S. The trypanosomiases. Lancet 362 (2003) 1469-1480
3. Beach D.H., Pascal Jr. R.A., and Holz Jr. G.G. Effects of thiastearic acids on growth and on dihydrosterculic acid and other phospholipid fatty acyl groups of Leishmania promastigotes. Mol. Biochem. Parasitol. 35 (1989) 57-66
4. Berge R.K., Skorve J., Tronstad K.J., Berge K., Gudbrandsen O.A., and Grav H. Metabolic effects of thia fatty acids. Curr. Opin. Lipidol. 13 (2002) 295-304
5. Bligh E.G., and Dyer W.J. A rapid method of total lipid extraction and purification. Can. J. Biochem. Physiol. 37 (1959) 911-917
6. Buist P.H., Dallmann G.H., Rymerson R.R., Siegel P.M., and Skala P. Use of sulfur as an oxidant detector. Tetrahedron Lett. 29 (1988) 435-438
7. Campos M.A., Almeida I.C., Takeuchi O., Akira S., Valente E.P., Procópio D.O., Travassos L.R., Smith J.A., Golenbock D.T., and Gazzinelli R.T. Activation of Toll-like receptor-2 by glycosylphosphatidylinositol anchors from a protozoan parasite. J. Immunol. 167 (2001) 416-423
8. Cazzulo J.J., Franke de Cazzulo B.M., Engel J.C., and Cannata J.J. End products and enzyme levels of aerobic fermentation in trypanosomatids. Mol. Biochem. Parasitol. 16 (1985) 329-343
9. Dover L.G., Alahari A., Gratraud P., Gomes J.M., Bhowruth V., Reynolds R.C., Besra G.S., and Kremer L. EthA, a common activator of thiocarbamide-containing drugs acting on different mycobacterial targets. Antimicrob. Agents Chemother. 51 (2007) 1055-1063
10. Florin-Christensen M., Florin-Christensen J., de Isola E.D., Lammel E., Meinardi E., Brenner R.R., and Rasmussen L. Temperature acclimation of Trypanosoma cruzi epimastigote and metacyclic trypomastigote lipids. Mol. Biochem. Parasitol. 88 (1997) 25-33
11. Gazzinelli R.T., and Denkers E.Y. Protozoan encounters with Toll-like receptor signalling pathways: implications for host parasitism. Nat. Rev. Immunol. 6 (2006) 895-906
12. Haughan P.A., and Goad L.J. Lipid biochemistry of trypanosomatids. In: Coombs G.H., and North M.J. (Eds). Biochemical Protozoology (1991), Taylor and Frances, London, Washington, DC 312-328
13. Høvik K.E., Spydevold O.S., and Bremer J. Thia fatty acids as substrates and inhibitors of stearoyl-CoA desaturase. Biochim. Biophys. Acta 1349 (1997) 251-256
14. Korduláková J., Janin Y.L., Liav A., Barilone N., Dos Vultos T., Rauzier J., Brennan P.J., Gicquel B., and Jackson M. Isoxyl activation is required for bacteriostatic activity against Mycobacterium tuberculosis. Antimicrob. Agents Chemother. 51 (2007) 3824-3829
15. Lambelin G. Pharmacology and toxicology of Isoxyl. Antibiot. Chemother. 16 (1970) 84-95
16. Livore V.I., Tripodi K.E.J., and Uttaro A.D. Elongation of polyunsaturated fatty acids in trypanosomatids. FEBS J. 274 (2007) 264-274
17. Maldonado R.A., Kuniyoshi R.K., Linss J.G., and Almeida I.C. Trypanosoma cruzi oleate desaturase: molecular characterization and comparative analysis in other trypanosomatids. J. Parasitol. 92 (2006) 1064-1074
18. Mellors A., and Samad S.A. The acquisition of lipids by African trypanosomes. Parasitol. Today 5 (1989) 239-244
19. 5-like domain is linked to the carboxyl terminus of the Saccharomyces cerevisiae Δ-9 fatty acid desaturase. J. Biol. Chem. 270 (1995) 29766-29772
20. Morris L.J. Separations of lipids by silver ion chromatography. J. Lipid Res. 7 (1966) 717-732
21. Oliveira A.C., Peixoto J.R., de Arruba L.B., Campos M.A., Gazzinelli R.T., Golenbock D.T., Akira S., Previato J.O., Mendonça-Previato L., Nobrega A., and Bellio M. Expression of functional TLR4 confers proinflammatory responsiveness to Trypanosoma cruzi glycoinositolphospholipids and higher resistance to infection with T. cruzi. J. Immunol. 173 (2004) 5688-5696
22. Pascal Jr. R.A., and Ziering D.L. Synthesis of heteroatom-substituted analogues of stearic acid. J. Lipid Res. 27 (1986) 221-224
23. Petrini G.A., Altabe S.G., and Uttaro A.D. Trypanosoma brucei oleate desaturase may use a cytochrome b5-like domain in another desaturase as an electron donor. Eur. J. Biochem. 271 (2004) 1079-1086
24. Pettersen R.J., Salem M., Skorve J., Ulvik R.J., Berge R.K., and Nordrehaug J.E. Pharmacology and safety of tetradecylthioacetic acid (TTA): phase-1 study. J. Cardiovasc. Pharmacol. 51 (2008) 410-417
25. Phetsuksiri B., Jackson M., Scherman H., McNeil M., Besra G.S., Baulard A.R., Slayden R.A., DeBarber A.E., Barry III C.E., Baird M.S., Crick D.C., and Brennan P.J. Unique mechanism of action of the thiourea drug Isoxyl on Mycobacterium tuberculosis. J. Biol. Chem. 278 (2003) 53123-53130
26. Rahman M.D., Ziering D.L., Mannarelli S.J., Swartz K.L., Huang D.S., and Pascal Jr. R.A. Effects of sulfur-containing analogues of stearic acid on growth and fatty acid biosynthesis in the protozoan Crithidia fasciculata. J. Med. Chem. 31 (1988) 1656-1659
27. Tripodi K.E.J., Buttigliero L.V., Altabe S.G., and Uttaro A.D. Functional characterization of front-end desaturases from trypanosomatids depicts the first polyunsaturated fatty acid biosynthetic pathway from a parasitic protozoan. FEBS J. 273 (2006) 271-280
28. Tyler K.M., and Engman D.M. The life cycle of Trypanosoma cruzi revisited. Int. J. Parasitol. 31 (2001) 472-481
29. Urbancik B. Clinical experience with thiocarlide (Isoxyl). Antibiot. Chemother. 16 (1970) 117-123
30. Uttaro A.D. Biosynthesis of polyunsaturated fatty acids in lower eukaryotes. IUBMB Life 58 (2006) 563-571