Antifungal activity of bis-azasqualenes, inhibitors of oxidosqualene cyclase

Mycoses

Volumn 53, Issue 6, 2010, Pages 481-487

  Voyron, Samuele ^a   Rocco, Flavio ^a   Ceruti, Maurizio ^a   Forni, Paolo ^a   Pla, Alessandra Fiorio ^a   Sarpietro, Maria Grazia ^b   Varese, Giovanna Cristina ^a   Marchisio, Valeria Filipello ^a  

^a UNIVERSITY OF TURIN   (Italy)

^b UNIVERSITY OF CATANIA   (Italy)

Author keywords

Antifungals; Antimycotic Drugs; Aspergillus Spp.; Bis Azasqualenes; Dermatophytes; Mycoses; Oxidosqualene Cyclase Inhibitors

Indexed keywords

ANTIFUNGAL AGENT; LANOSTEROL SYNTHASE; SQUALENE BIS DIETHYLAMINE; SQUALENE BIS DIETHYLMETHYLAMMONIUM IODIDE; SQUALENE DERIVATIVE; UNCLASSIFIED DRUG;

ANIMAL CELL; ANTIFUNGAL ACTIVITY; ARTICLE; CELL STRAIN; CONTROLLED STUDY; DERMATOPHYTE; DRUG CYTOTOXICITY; DRUG STRUCTURE; ENDOTHELIUM CELL; FUNGAL STRAIN; HUMAN; HUMAN CELL; IN VITRO STUDY; MICROSPORUM CANIS; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; PRIORITY JOURNAL; SCOPULARIOPSIS BREVICAULIS; TRICHOPHYTON MENTAGROPHYTES; VASCULAR ENDOTHELIUM;

ANIMALS; ANTIFUNGAL AGENTS; CELL SURVIVAL; CELLS, CULTURED; DOGS; FUNGI; HUMANS; INTRAMOLECULAR TRANSFERASES; MICROBIAL SENSITIVITY TESTS; SQUALENE;

ANIMALIA; ARTHRODERMA BENHAMIAE; ARTHRODERMATACEAE; ASPERGILLUS; FUNGI; MICROSPORUM CANIS; SCOPULARIOPSIS BREVICAULIS;

EID: 77958091601     PISSN: 09337407     EISSN: 14390507     Source Type: Journal    
DOI: 10.1111/j.1439-0507.2009.01742.x     Document Type: Article

References (37)

1. De Hoog GS, Guarro J, Gené J et al. Atlas of Clinical fungi, 2nd edn. Utrecth, The Netherlands: Centraalburaeu voor Schimmelcultures, 2000.
2. John W, Baddley MD, Stephen A, Moser PhD. Emerging fungal resistance. Clin Lab Med 2004; 24: 721-35.
3. Fernandez-Torres B, Carrillo AJ, Martin E et al. In vitro activities of 10 antifungal drugs against 508 dermatophyte strains. Antimicrob Agents Chemother 2001; 45: 2524-8.
4. Niewiadomy A, Matysiak J, Ma̧cik-Niewiadomy G. In vitro evaluation of 2,4-dihydroxythiobenzanilides against various moulds. Eur J Pharm Sci 2001; 13: 243-8.
5. Benveniste P. Biosynthesis and accumulation of sterols. Annu Rev Plant Biol 2004; 55: 429-57.
6. Abe I, Rohmer M, Prestwich GD. Enzymatic cyclization of squalene and oxidosqualene to sterols and triterpenes. Chem Rev 1993; 93: 2189-06.
7. Corey EJ, Virgil SC, Cheng H et al. New insights regarding the cyclization pathway for sterol biosynthesis from (S)-2,3-oxidosqualene. J Am Chem Soc 1995; 117: 11819-20.
8. Wendt KU, Schulz GE, Corey EJ, Liu DR. Enzyme mechanisms for polycyclic triterpene formation. Angew Chem Int Ed Engl 2000; 39: 2812-33.
9. Xiong Q, Rocco F, Wilson WK, Xu R, Ceruti M, Matsuda SPT. Structure and reactivity of the dammarenyl cation: configurational transmission in triterpene synthesis. J Org Chem 2005; 70: 5362-75.
10. Milla P, Athenstaed K, Viola F et al. Yeast Oxidosqualene cyclase (Erg7p) is a major component of lipid particles. J Biol Chem 2002; 277: 2406-12.
11. 13C NMR, crystallographic observations, and molecular mechanics calculations. J Am Chem Soc 1998; 120: 5970-80.
12. Moreau RA, Nes WD, Bach TJ, Parish EJ, Zawistowski J. Recent advances in sterol research presented at the 99th AOCS annual meeting & expo in Seattle Washington, May 2008. Lipids 2008; 43: 1091-3.
13. Vanden Bossche H, Marichal P, Coene M-C et al. Target for antifungal agents and herbicides. In: Nes W.D., Parish E.J., Trzaskos J.M. (eds), Regulation of Isopentenoid Metabolism. Washington D.C: American Chemical Society, 1992: 219-30.
14. Ryder NS, Stuetz A, Nussbaumer P. Squalene epoxidase inhibitors: structural determinants for activity and selectivity of allylamines and related compounds. In: Nes W.D., Parish E.J., Trzaskos J.M. (eds), Regulation of Isopentenoid Metabolism. Washington D.C: American Chemical Society, 1992: 192-204.
15. Ceruti M, Balliano G, Viola F, Cattel L, Gerst N, Schuber F. Synthesis and biological activity of azasqualenes, bis-azasqualenes and derivatives. Eur J Med Chem 1987; 22: 199-08.
16. Ceruti M, Balliano G, Viola F, Grosa G, Rocco F, Cattel L. 2,3-Epoxy-10-aza-10,11-dihydrosqualene, a high-energy intermediate analogue inhibitor of 2,3-oxidosqualene cyclase. J Med Chem 1992; 35: 3050-8.
17. Cattel L, Ceruti M. Inhibitors of 2,3-oxidosqualene cyclase as tools for studying the mechanism and function of the enzyme. Crit Rev Biochem Mol Biol 1998; 33: 353-73.
18. National Committee for Clinical Laboratory Standards. Reference Method for Broth Dilution Antifungal Susceptibility Testing of Yeasts; Approved Standards. Wayne, PA: NCCLS, 2002 (NCCLS document M27-A2).
19. National Committee for Clinical Laboratory Standards. Reference Method for Broth Dilution Antifungal Susceptibility Testing of Filamentous Fungi: Approved Standard. Wayne, PA: NCCLS, 2002 (NCCLS Document M-38A).
20. Airaudi D, Ceruti M, Giannetta A, Filipello Marchisio V. Preliminary screening of some squalenoid derivates for toxicity test towards dermatophytes. Mycoses 1995; 38: 311-5.
21. Airaudi D, Ceruti M, Bianco C, Filipello Marchisio V. In vitro susceptibility of fungi to acylic inhibitors of 2,3-oxidosqualene cyclases. Mycoses 1996; 39: 51-6.
22. Alio AB, Mendoza M, Zambrano EA, Diaz E, Cavallera E. Dermatophytes growth curve and in vitro susceptibility test: a broth micro-titration method. Med Mycol 2005; 43: 319-25.
23. Cetinkaya Z, Kiraz N, Karaca S et al. antifungal susceptibilities of dermatophytic agents isolated from clinical specimens. Eur J Dermatol 2005; 15: 258-61.
24. Brilhante RSN, Cordeiro RA, Medrano DJA, Monteiro AJ, Sidrim JJC, Rocha MFG. antifungal susceptibility and genotypical pattern of Microsporum canis strains. Can J Microbiol 2005; 51: 507-10.
25. Esteban A, Abarca ML, Cabañes FJ. Comparison of disk diffusion method and broth microdilution method for antifungal susceptibility testing of dermatophytes. Med Mycol 2005; 43: 61-6.
26. Fernandez-Torres B, Izna I, Guarro J. Comparison of in vitro antifungal susceptibilities of conidia and hyphae of dermatophytes with thick-wall macroconidia. Antimicrob Agents Chemother 2003; 47: 3371-2.
27. Santos DA, Hamdan JS. Evaluation of broth microdilution antifungal susceptibility testing conditions for Trichophyton rubrum. J Clin Microbiol 2005; 4: 1917-20.
28. Carrillo-Muñoz AJ, Giusiano G, Guarro J et al. In vitro activity of voriconazole against dermatophytes, Scopulariopsis brevicaulis and other opportunistic fungi as agents of onychomycosis. Int J Antimicrob Agents 2007; 30: 157-61.
29. Fernandez-Torres B, Izna I, Guarro J. In vitro activities of the new antifungal drug Eberconazole and three other topical agents against 200 strains of dermatophytes. J Clin Microbiol 2003; 41: 5209-11.
30. Li RY, Wan Z, Wang AP et al. In vitro susceptibility testing of amorolfine in pathogenic fungi isolated from dermatomycosis patients in China. Mycoses 2003; 47: 402-6.
31. Mallie M, Bastide JM, Blancard A et al. In vitro susceptibility testing of Candida and Aspergillus spp. to voriconazole and other antifungal agents using Etest (R): results of a french multicentre study. Int J Antimicrob Agents 2005; 25: 321-8.
32. Meletiadis J, Mouton JW, Meis JFGM et al. Comparison of the Etest and the sensititre colorimetric methods with the NCCLS proposed standard for antifungal susceptibility testing of Aspergillus species. J Clin Microbiol 2002; 40: 2876-85.
33. Shimokawa O, Niimi M, Kikuchi K, Saito M, Kajiawara H, Yoshida S. Relationship between MIC and minimum sterol 14α-demethylation-inhibitory concentration as a factor in evaluating activities of azoles against various fungal species. J Clin Microbiol 2005; 43: 5547-9.
34. Espinel-Ingroff A, Johnson E, Hockey H, Toke P. Activities of voriconazole, itraconazole and amphotericin B in vitro against 590 moulds from 323 patients in the voriconazole Phase III clinical studies. J Antimicrob Chemother 2008; 61: 616-20.
35. Cuenca-Estrella M, Gomez-Lopez A, Mellado E, Buitrago MJ, Monzon A, Rodriguez-Tudela JL. Scopulariopsis brevicaulis, a fungal pathogen resistant to broad-spectrum antifungal agents. Antimicrob Agents Chemother 2003; 47: 2339-41.
36. Perkins A, Gomez-Lopez A, Mellado E, Rodriguez-Tudela JL, Cuenca Estrella M. Rates of antifungal resistance among spanish clinical isolates of Cryptococcus neoformans var. neoformans. J Antimicrob Chemother 2005; 56: 1144-7.
37. Cuenca-Estrella M, Gomez-Lopez A, Buitrago MJ, Mellado E, Garcia-Effron G, Rodriguez-Tudela JL. In vitro activities of 10 combinations of antifungal agents against the multiresistant pathogen Scopulariopsis brevicaulis. Antimicrob Agents Chemother 2006; 50: 2248-50.