Inhibition of 2,3-oxidosqualene-lanosterol cyclase in Candida albicans by pyridinium ion-based inhibitors

Antimicrobial Agents and Chemotherapy

Volumn 40, Issue 4, 1996, Pages 1044-1047

  Goldman, Robert C ^a   Zakula, Dorothy ^a   Capobianco, John O ^a   Sharpe, Bradley A ^b   Griffin, John H ^b  

^a ABBOTT LABORATORIES   (United States)

^b STANFORD UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1 (5,9,13 TRIMETHYL 4,8,12 TETRADECATRIEN 1 YL)PICOLINIUM; 1 (5,9,13 TRIMETHYL 4,8,12 TETRADECATRIEN 1 YL)PYRIDINIUM; ANTIFUNGAL AGENT; LANOSTEROL SYNTHASE; PYRIDINIUM DERIVATIVE; UNCLASSIFIED DRUG;

ANTIFUNGAL ACTIVITY; CANDIDA ALBICANS; ENZYME INHIBITION; GENE SEQUENCE; MINIMUM INHIBITORY CONCENTRATION; MOLECULAR CLONING; NOTE; PRIORITY JOURNAL; SACCHAROMYCES CEREVISIAE; STEROL SYNTHESIS;

EID: 0029872330     PISSN: 00664804     EISSN: None     Source Type: Journal    
DOI: 10.1128/aac.40.4.1044     Document Type: Note

References (28)

1. Abe, I., M. Bai, X. Y. Xiao, and G. D. Prestwich. 1992 Affinity labeling of vertebrate oxidosqualene cyclases with a tritiated suicide substrate. Biochem. Biophys. Res Commun. 187:32-38.
2. Abe, I., and G. D. Preilwich. 1994. Active site mapping of affinity-labeled rat oxidosqualene cyclase. J. Biol. Chem. 269:802-804.
3. Abe, I., and G. D. Prestwich. 1995. Identification of the active site of vertebrate oxidosqualene cyclase. Lipids 30:231-234.
4. Balliano, G., G. Grosa, P. Milla, F. Viola, and L. Cattel. 1993, 3-Carboxy-4-nitrophenyl-dithio-1,1′.2-trisnorsqualene: a site-directed inactivator of yeast oxidosqualene cyclase. Lipids 28:903-906.
5. Balliano, G., P. Milla, M. Ceruti, L. Carrano, F. Viola, P. Brusa, and L. Cattel. 1994. Inhibition of sterol biosynthesis in Saccharomyces cerevisiae and Candida albicans by 22,23-epoxy-2-aza-2,3-dihydrosqualene and the corresponding N-oxide. Antimicrob. Agents Chemother. 38:1904-1908.
6. Balliano, G., P. Milla, M. Ceruti, F. Viola, L. Carrano, and L. Cattel. 1993. Differential inhibition of fungal oxidosqualene cyclase by 6E and 6Z isomers of 2,3-epoxy-10-aza-10,11-dihydrosqualene. FEES Lett. 320:203-206.
7. Balliano, G., F. Viola, and L. Cattel. 1989. Inhibitors of ergosterol biosynthesis as potential antifungal drugs Ital. J. Biochem. 38:299A-300A.
8. Balliano, G., F. Viola, M. Ceruti, and L. Cattel. 1988. Inhibition of sterol biosynthesis in Saccharomyces cerevisiae by N,N-diethylazasqualene and derivatives. Biochim. Biophys. Acta 959:9-19.
9. Buntel, C. J., and J. G. Griffin. 1992. Nucleotide sequence and deduced amino acid sequence of the oxidosqualene cyclase gene from Candida albicans. J. Am. Chem. Soc. 114:9711-9713.
10. Capobianco, J. O., C. C. Doran, R. C. Goldman, and B. De. 1992. A non-azole inhibitor of lanosterol 14α-methyl demethylase in Candida albicans. J. Antimicrob. Chemother. 30:781-790
11. Cattel, L., M. Ceruti, G. Balliano, and F. Viola. 1992. 2,3-Oxidosqualene cyclase and squalene epoxidase as target enzymes for the development of new sterol biosynthesis inhibitors, p. 174-191. In W. D. New, E J. Parish, and J. M. Trzaskos (ed.), Regulation of isopentenoid synthesis. ACS Symposium Series 97. American Cancer Society, Washington, D.C.
12. CatteL L., M. Ceruti, G. Balliano, F. Viola, G. Grosa, and F. Schuber. 1989. Drug design based on biosynthetic studies, synthesis, biological activity, and kinetics of new inhibitors of 2,3-oxidosqualene cvclase and squalene epoxidase. Steroids 53:363-391
13. Cattel, L., M. Ceruti, F. Viola, L. Delprino, G. Balliano, A. Duriatti, and P. Bouvier-Nave. 1986. The squalene-2,3-epoxide cyclase as a model for the development of new drugs. Lipids 21:31-38.
14. Ceruti, M., S. Amisano, P. Milla, F. Viola, F. Rocco, M. Jung, and L. Cattel. 1995 Stcreocontrolled synthesis of fluorosqualenes and fluoroepoxy-squalenes as inhibitors of squalene epoxidase and 2,3-oxidosqualene cyclase. J Chem. Soc. Perkin Trans. I 7:889-893.
15. Corey, E. J., S. P. Matsuda, and B. Bartel. 1994. Molecular cloning, characterization, and overexprcssion of ERG7, the Saccharomyces cerevisiae gene encoding lanosterol synthase Proc. Natl. Acad. Sci. USA 91:2211-2215.
16. Georgopapadakou, N. H., B. A. Dix, S. A. Smith, J. Freudenberger, and P. T. Funke. 1987. Effect of antifungal agents on lipid biosynthesis and membrane integrity in Candida albicans. Antimicrob. Agents Chemother. 31:46-51.
17. Jolidon, S., A. M. Polak, P. Guerry, and P. G. Hartman. 1990 Inhibitors of 2,3-oxidosqualene cyclase as potential antifungal agents. Biochem Soc. Trans. 18:47-48.
18. Jolidan, S., A. Polak-Wyss, P. G. Hartmen, and P. Guerry. 1993. 2,3-Oxidosqualene cyclase: an attractive target for antifungal drug design, p. 223-233. In P. H. Bentley and R Ponsford (ed.), Recent advances in the chemistry of anti-infective agents. Royal Society of Chemistry, Cambridge.
19. Kelly, R., S. M. Miller, M. H. Lai, and D. R. Kirsch. 1990. Cloning and characterization of the 2,3-oxidosqualene cyclase-coding gene of Candida albicans. Gene 87:177-183.
20. Lees, N. D., B. Skaggs, D. R, Kirsch, and M. Bard. 1995. Cloning of the late genes in the ergosterol biosynthetic pathway of Saccharomyces cererisiae - a review. Lipids 30:221-224.
21. National Committee for Clinical Laboratory Standards. 1992. Reference methods for broth dilution antifungal susceptibility testing for yeast. Proposed standard M27-P. National Committee for Clinical Laboratory Standards, Villanova, Pa.
22. Rose, I. C., B. A. Sharpe, R. C. Lee, J. H. Griffin, J. O. Capobianco, D. Zakula, and R. C. Goldman. Design synthesis and in vitro evaluation of pyridinium ion based cyclase inhibitors and antifungal agents. Bioorg Med. Chem., in press.
23. Ryder, N. S. 1991 Squalene epoxidase as a target for the allylaimnes. Biochem. Soc. Trans. 19:774-777.
24. Ryder, N. S. 1992 Terbinafine: mode of action and properties of the squalene epoxidase inhibition. Br J. Dermatol. 126:2-7.
25. Shi, Z., C. J. Buntel, and J. G. Griffin. 1994. Isolation and characterization of the gene encoding 2,3-oxidosqualene-lanosteroi cyclase from Saccharomyces cerevisiae Proc. Natl. Acad Sci. USA 91:7370-7374.
26. Vanden Bossche, H., P. Marichal, J. Gorrens, and M. C. Coene. 1990. Biochemical basis for the activity and selectivity of oral antifungal drugs Br. J. Clin. Pract. Symp. Suppl. 71 44:41-46.
27. Vanden Bossche, H., P. Marichal, J. Gorrens, M. C. Coene, G. Willemsens, D. Bellens, I. Roels, H. Moereels, and P. A. Janssen. 1989. Biochemical approaches to selective antifungal activity Focus on azolc antifungals. Mycoses 32:35-52.
28. Zheng, Y. F., D. S. Dodd, and A. C. Oehschlager. 1995 Synthesis of vinyl sulfide analogs of 2,3-oxidosqualene and their inhibition of 2,3-oxidosqualene lanosterol-cyclase. Tetrahedron 51:5255-5276.