Analogs of squalene and oxidosqualene inhibit oxidosqualene cyclase of Trypanosoma cruzi expressed in Saccharomyces cerevisiae

Lipids

Volumn 40, Issue 12, 2005, Pages 1257-1262

  Oliaro Bosso, Simonetta ^a   Ceruti, Maurizio ^a   Balliano, Gianni ^a   Milla, Paola ^a   Rocco, Flavio ^a   Viola, Franca ^a  

^a UNIVERSITY OF TURIN   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

BIOSYNTHESIS; CELLS; DISEASES; GENES; YEAST;

CHAGAS' DISEASE; PARASITE AGENTS; SQUALENE; TRYPANOSOMA CRUZI;

ENZYME INHIBITION;

CHOLESTEROL; ERGOSTEROL; LIVER EXTRACT; OXIDOSQUALENE CYCLASE; PHENYLTHIOVINYL DERIVATIVE; SQUALENE; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ARTICLE; CHAGAS DISEASE; ENZYME INHIBITION; GENE EXPRESSION; IC 50; MOLECULAR CLONING; NONHUMAN; SACCHAROMYCES CEREVISIAE; STEROL SYNTHESIS; SWINE; TRYPANOSOMA CRUZI;

ANIMALS; ENZYME INHIBITORS; GENES, PROTOZOAN; INTRAMOLECULAR TRANSFERASES; PROTOZOAN PROTEINS; RECOMBINANT PROTEINS; SACCHAROMYCES CEREVISIAE; SQUALENE; STRUCTURE-ACTIVITY RELATIONSHIP; TRYPANOSOMA CRUZI;

MAMMALIA; SACCHAROMYCES CEREVISIAE; SUS SCROFA; TRYPANOSOMA CRUZI;

EID: 30944457581     PISSN: 00244201     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11745-005-1493-y     Document Type: Article

References (37)

1. Mercer, E.I. (1991) Sterol Synthesis Inhibitors: Their Current Status and Modes of Action, Lipids 26, 584-597.
2. Abe, I., and Prestwich, G.D. (1999) Squalene Epoxidase and Oxidosqualene Lanosterol Cyclase - Key Enzymes in Cholesterol Biosynthesis, in Comprehensive Natural Products Chemistry, Isoprenoid Including Carotenoids and Steroids (Cane, D., ed.), Vol. 2, pp. 267-298, Elsevier, Oxford, United Kingdom.
3. Urbina, J.A. (1997) Lipid Biosynthesis Pathways as Chemotherapeutic Targets in Kinetoplastid Parasites, Parasitology 114, S91-S99.
4. Coppens, I., and Courtoy, P.J. (1995) Exogenous and Endogenous Sources of Sterols in the Culture-Adapted Procyclic Trypomastigotes of Trypanosoma brucei, Mol. Biochem. Parasitol. 73, 179-188.
5. Contreras, L.M., Vivas, J., and Urbina, J.A. (1997) Altered Lipid Composition and Enzyme Activities of Plasma Membranes from Trypanosoma (Schizotrypanum) cruzi Epimastigotes Grown in the Presence of Sterol Biosynthesis Inhibitors, Biochem. Pharmacol. 53, 697-704.
6. Ryder, N.S., Stuetz, A., and Nussbaumer, P. (1992) Squalene Epoxidase Inhibitors: Structural Determinants for Activity and Selectivity of Allylamines and Related Compounds, in Regulation of Isopentenoid Metabolism (Nes, W.D., Parish, E.J., and Trzaskos, J.M., eds.), pp. 192-204, American Chemical Society, Washington, DC.
7. Vanden Bossche, H., Marichal, P., Coene, M.-C., Willemsens, G., Le Jeune, L., Cools, W., and Verhoeven, H. (1992) Cytochrome P450-dependent 14α-Demethylase: Target for Antifungal Agents and Herbicides, in Regulation of Isopentenoid Metabolism (Nes, W.D., Parish, E.J., and Trzaskos, J.M., eds.), pp. 219-230, American Chemical Society, Washington, DC.
8. Docampo, R., and Schmuñis, G.A. (1997) Sterol Biosynthesis Inhibitors: Potential Chemotherapeutics Against Chagas Disease, Parasitol. Today 13, 129-130.
9. Urbina, J.A., Concepcion, J.L., Rangel, S., Visbal, G., and Lira, R. (2002) Squalene Synthase as Chemotherapeutic Target in Trypanosoma cruzi and Leishmania mexicana, Mol. Biochem. Parasitol. 125, 15-45.
10. Orene Lorentes, S., Gomez, R., Jimenez, C., Cammerer, S., Yardley, V., de Luca-Fradley, K., Croft, S.L., Ruiz-Perez, L.M., Urbina, J., Gonzalez Pacanowska, D., et al. (2005) Biphenylquinuclidines as Inhibitors of Squalene Synthase and Growth of Parasitic Protozoa, Bioorg. Med. Chem. 13, 3519-3529.
11. Buckner, F.S., Griffin, J.H., Wilson, A.J., and Van Voorhis, W.C. (2001) Potent Anti-Trypanosoma cruzi Activities of Oxidosqualene Cyclase Inhibitors, Antimicrob. Agents Chemother. 45, 1210-1215.
12. Oliaro-Bosso, S., Viola, F., Matsuda, S., Cravotto, G., Tagliapietra, S., and Balliano, G. (2004) Umbelliferone Aminoalkyl Derivative as Inhibitors of Oxidosqualene Cyclase from Saccharomyces cerevisiae, Trypanosoma cruzi, and Pneumocystis carinii, Lipids 39, 1007-1012.
13. Abe, I., Rohmer, M., and Prestwich, G.D. (1993) Enzymatic Cyclization of Squalene and Oxidosqualene to Sterol and Triterpenes, Chem. Rev. 93, 2189-2206.
14. Thoma, R., Schulz-Gasch, T., D'Arcy, B., Benz, J., Aebi, J., Dehmlow, H., Hennig, M., Stihle, M., and Ruf, A. (2004) Insight into Steroid Scaffold Formation from the Structure of Human Oxidosqualene Cyclase. Nature 432, 118-122.
15. Viola, F., Brusa, P., Balliano, G., Ceruti, M., Boutaud, O., Schuber, F., and Cattel, L. (1995) Inhibition of 2.3-Oxidosqualene Cyclase and Sterol Biosynthesis by 10- and 19-Azasqualene Derivatives, Biochem. Pharmacol. 50, 787-796.
16. Ceruti, M., Rocco, F., Viola, F., Balliano, G., Milla, P., Arpicco, S., and Cattel, L. (1998) 29-Methylidene-2.3-oxidosquitlene Derivatives as Stereospecific Mechanism-Based Inhibitors of Liver and Yeast Oxidosqualene Cyclase, J. Med. Chem. 41, 540-554.
17. Viola, F., Balliano, G., Milla, P., Cattel, L., Rocco, F., and Ceruti, M. (2000) Stereospecific Synthesis of trans-Vinyldioxidosqualene and β-Hydroxysulfide Derivatives, as Potent and Time-Dependent 2,3-Oxidosqualene Cyclase Inhibitors. Bioorg. Med. Chem. 8, 223-232.
18. Viola, F., Ceruti, M., Cattel, L., Milla, P., Poralla, K., and Balliano, G. (2000) Rationally Designed Inhibitors as Tools for Comparing the Mechanism of Squalene-Hopene Cyclase with Oxidosqualene Cyclase. Lipids 35, 297-303.
19. Ceruti, M., Balliano, G., Rocco, F., Milla, P., Arpicco, S., Cattel, L., and Viola, F. (2001) Vinyl Sulfide Derivatives of Truncated Oxidosqualene as Selective Inhibitors of Oxidosqualene and Squalene Hopene Cyclases, Lipids 36, 629-636.
20. Rocco, F., Oliaro-Bosso, S., Viola, F., Milla, P., Roma, G., Grossi, G., and Ceruti, M. (2003) Conjugated Methyl Sulfide and Phenyl Sulfide Derivatives of Oxidosqualene as Inhibitors of Oxidosqualene and Squalene-Hopene Cyclases, Lipids. 38, 201-207.
21. Joubert, B.M., Buckner, F.S., and Matsuda, S.P.T. (2001) Trypanosome and Animal Lanosterol Synthases Use Different Catalytic Motifs, Org. Lett. 3, 1957-1960.
22. Xiao, X., and Prestwich, G.D. (1991) 29-Methylidene-2.3-oxidosqualene: A Potent Mechanism-Based Inactivator of Oxidosqualene Cyclase, J. Am. Chem. Soc. 113, 9673-9678.
23. Ceruti, M., Balliano, G., Viola, F., Cattel, L., Gerst, N., and Schuber, F. (1987) Synthesis and Biological Activity of Azasqualenes, bis-Azasqualenes and Derivatives. Eur. J. Med. Chem. 22, 199-208.
24. Field, R.B., Holmund, C.E., and Whittaker, N.F. (1979) The Effects of the Hypocholesteremic Compound 3 β-(β-dimethylaminoethoxy)-androst-5-en- 17-one on the Sterol and Steryl Ester Composition of Saccharomyces cerevisiae, Lipids 14, 741-747.
25. Duriaiti, A., Bouvier-Navé. P., Benveniste, P., Schuber, F., Delprino, L., Balliano, G., and Cattel, L. (1985) In vitro Inhibition of Animal and Higher Plants 2.3-Oxidosqualene-Sterol Cyclases by 2-Aza-2,3-dihydrosqualene and Derivatives, and by Other Ammonium-Containing Molecules. Biochem. Pharmacol. 34, 2765-2777.
26. Ceruti, M., Rocco, F., Viola, F., Balliano, G., Grosa, G., Dosio, F., and Cattel, L. (1993) Synthesis and Biological Activity of 19-Azasqualene 2,3-Epoxide as Inhibitor of 2,3-Oxidosqualene Cyclase. Eur. J. Med. Chem. 28, 675-682.
27. Corey, E.J., Matsuda, S.P.T., Baker, C.H., Ting, A.Y., and Cheng, H. (1996) Molecular Cloning of a Schizosaccharomyces pombe cDNA Encoding Lanosterol Synthase and Investigation of Conserved Tryptophan Residues. Biochem. Biophys. Res. Commun. 219, 327-331.
28. Hart, E.A., Hua, L., Darr, L.B., Wilson, W.K., Pang, J., and Matsuda, S.P.T. (1999) Directed Evolution to Investigate Steric Control of Enzymatic Oxidosqualene Cyclization. An Isoleucine-to-Valine Mutation in Cycloartenol Synthase Allows Lanosterol and Parkeol Biosynthesis. J. Am. Chem. Soc. 121, 9887-9888.
29. Peterson, G.L. (1977) A Simplification of the Protein Assay Method of Lowry et al. Which Is More Generally Applicable, Anal. Biochem. 83, 346-356.
30. Duggleby, R.G. (1981) A Nonlinear Regression Program for Small Computers. Anal. Biochem. 110. 9-18.
31. Milla, P., Viola, F., Oliaro-Bosso, S., Rocco, F., Cattel, L., Joubert, B.M., LeClair, R.J., Matsuda, S.P.T., and Balliano, G. (2002) Subcellular Localization of Oxidosqualene Cyclases from Arabidopsis thaliana. Trypanosoma cruzi, and Pneumocyctis carinii Expressed in Yeast. Lipids 37, 1171-1176.
32. Milla, P., Athenstaedt, K., Viola, F., Oliaro-Bosso, S., Kohlwein, S.D., Damn, G., and Balliano, G. (2002) Yeast Oxidosqualene Cyclase (Erg7p) Is a Major Component of Lipid Particles, J. Biol. Chem. 277, 2406-2412.
33. Balliano, G., Viola, F., Ceruti, M., and Cattel, L. (1988) Inhibition of Sterol Biosynthesis in Saccharomyces cerevisiae by N,N-Diethylazasqualene and Derivatives. Biochim. Biophys. Acta 959, 9-19.
34. Talon, M., Benveniste, P., and Rahier, A. (1992) Inhibition of 2.3-Oxidosqualene Cyclases, Biochemistry 31, 7892-7898.
35. Meyer, M.M., Segura, M.J.R., Wilson, W.K., and Matsuda. S.P.T. (2000) Oxidosqualene Cyclase Residues That Promote Formation of Cycloartenol, Lanosterol, and Parkeol. Angew. Chem. Int. 39, 4090-4092.
36. Herrera, J.B.R., Wilson, W.K., and Malsuda, S.P.T. (2000) A Tyrosine-to-Threonine Mutation Converts Cycloartenol Synthase to an Oxidosqualene Cyclase That Forms Lanosterol as Its Major Product. J. Am. Chem. Soc. 122, 6765-6766.
37. Segura, M.J.R., Lodeiro, S., Meyer, M.M., Patel, A.K., and Matsuda, S.P.T. (2002) Directed Evolution Experiments Reveal Mutation at Cycloarlenol Synthase Residue His477 That Dramatically Alter Catalysis. Org. Lett. 4, 4459-4462.