Antifungal activities of novel non-azole molecules against S. cerevisiae and C. albicans

European Journal of Medicinal Chemistry

Volumn 47, Issue 1, 2012, Pages 270-277

  Tani, Niina ^a   Rahnasto Rilla, Minna ^a   Wittekindt, Carsten ^a,b   Salminen, Kaisa A ^a   Ritvanen, Anniina ^a   Ollakka, Riina ^a   Koskiranta, Jenna ^a   Raunio, Hannu ^a   Juvonen, Risto O ^a  

^a UNIVERSITY OF EASTERN FINLAND   (Finland)

^b COSMOlogic GmbH and Co KG ^*  (Germany)

Author keywords

Antifungal; C. albicans; CYP enzyme; CYP51; Reactive group; S. cerevisiae

Indexed keywords

2 [[(1,1' BIPHENYL) 4 YLMETHYLENE]AMINO]] 5 (3,4 DIMETHOXYPHENYL) 4 METHYLTHIOPHENE 3 CARBONITRILE; 2 [[(3,5 DICHLORO 2 HYDROXYPHENYL)METHYLENE]AMINO] 4 METHYL 5 PHENYL 3 THIOPHENECARBONITRILE; 2 [[4 [(2 CYANOETHYL)(METHYL)AMINO]BENZYLIDENE]AMINO] 5 (3,4 DIMETHOXYPHENYL) 4 METHYLTHIOPHENE 3 CARBONITRILE; 4,6 DIMETHYL 3 [2 (3 THIENYL)VINYL] 6,7 DIHYDROISOXAZOLO[3,4 D]PYRIDAZIN 7 ONE; AFLATOXIN B1; ANTIFUNGAL AGENT; CYTOCHROME P450; LIVER ENZYME; N ALLYL 5,6,7,8 TETRAHYDRO[1]BENZOTHIENO[2,3 D]PYRIMIDIN 4 AMINE; STEROL 14ALPHA DEMETHYLASE; UNCLASSIFIED DRUG;

ANTIFUNGAL ACTIVITY; ARTICLE; BIOASSAY; CANDIDA ALBICANS; MOLECULAR DOCKING; MOLECULAR MODEL; PHARMACOPHORE; REFERENCE DATABASE; REGULATORY MECHANISM; SACCHAROMYCES CEREVISIAE; VIRTUAL REALITY; YEAST CELL;

ANTIFUNGAL AGENTS; CANDIDA ALBICANS; DRUG DESIGN; DRUG EVALUATION, PRECLINICAL; ENZYME INHIBITORS; HUMANS; LIVER; MODELS, MOLECULAR; NITRILES; PROTEIN CONFORMATION; SACCHAROMYCES CEREVISIAE; STEROL 14-DEMETHYLASE; USER-COMPUTER INTERFACE;

EID: 84855781147     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2011.10.053     Document Type: Article

References (42)

1. N.N. Mishra, T. Prasad, N. Sharma, A. Payasi, R. Prasad, D.K. Gupta, and R. Singh Pathogenicity and drug resistance in Candida albicans and other yeast species. A review Acta Microbiol. Immunol. Hung. 54 2007 201 235
2. L. Ostrosky-Zeichner, A. Casadevall, J.N. Galgiani, F.C. Odds, and J.H. Rex An insight into the antifungal pipeline: selected new molecules and beyond Nat. Rev. Drug Discov. 9 2010 719 727
3. C.C. Lai, C.K. Tan, Y.T. Huang, P.L. Shao, and P.R. Hsueh Current challenges in the management of invasive fungal infections J. Infect. Chemother. 14 2008 77 85
4. R.P. Rapp Changing strategies for the management of invasive fungal infections Pharmacotherapy 24 2004 4 28
5. M. Klepser The value of amphotericin B in the treatment of invasive fungal infections J. Crit. Care 26 2011 1 10
6. T.D. Edlind, and S.K. Katiyar Mutational analysis of flucytosine resistance in Candida glabrata Antimicrob. Agents Chemother. 54 2010 4733 4738
7. T.P. Ko, J.J. Lin, C.Y. Hu, Y.H. Hsu, A.H. Wang, and S.H. Liaw Crystal structure of yeast cytosine deaminase. Insights into enzyme mechanism and evolution J. Biol. Chem. 278 2003 19111 19117
8. E. Giavini, and E. Menegola Are azole fungicides a teratogenic risk for human conceptus? Toxicol. Lett. 198 2010 106 111
9. H. Ji, W. Zhang, M. Zhang, M. Kudo, Y. Aoyama, Y. Yoshida, C. Sheng, Y. Song, S. Yang, Y. Zhou, J. Lu, and J. Zhu Structure-based de novo design, synthesis, and biological evaluation of non-azole inhibitors specific for lanosterol 14alpha-demethylase of fungi J. Med. Chem. 46 2003 474 485
10. J. Xu, Y. Cao, J. Zhang, S. Yu, Y. Zou, X. Chai, Q. Wu, D. Zhang, Y. Jiang, and Q. Sun Design, synthesis and antifungal activities of novel 1,2,4-triazole derivatives Eur. J. Med. Chem. 46 2011 3142 3148
11. C. Sheng, X. Che, W. Wang, S. Wang, Y. Cao, J. Yao, Z. Miao, and W. Zhang Structure-based design, synthesis, and antifungal activity of new triazole derivatives Chem. Biol. Drug Des. 78 2011 309 313
12. X. Chai, J. Zhang, Y. Cao, Y. Zou, Q. Wu, D. Zhang, Y. Jiang, and Q. Sun Design, synthesis and molecular docking studies of novel triazole as antifungal agent Eur. J. Med. Chem. 46 2011 3167 3176
13. G.I. Lepesheva, and M.R. Waterman CYP51 - the omnipotent P450 Mol. Cell. Endocrinol. 215 2004 165 170
14. Y. Aoyama, Y. Yoshida, and R. Sato Yeast cytochrome P-450 catalyzing lanosterol 14 alpha-demethylation. II. Lanosterol metabolism by purified P-450(14)DM and by intact microsomes J. Biol. Chem. 259 1984 1661 1666
15. S.L. Kelly, S. Kenna, A. Arnoldi, and D.E. Kelly Studies on azole-induced cell death in Saccharomyces cerevisiae FEMS Microbiol. Lett. 115 1994 219 222
16. C.J. Jackson, D.C. Lamb, N.J. Manning, D.E. Kelly, and S.L. Kelly Mutations in Saccharomyces cerevisiae sterol C5-desaturase conferring resistance to the CYP51 inhibitor fluconazole Biochem. Biophys. Res. Commun. 309 2003 999 1004
17. K.S. Barker, M.M. Pearson, and P.D. Rogers Identification of genes differentially expressed in association with reduced azole susceptibility in Saccharomyces cerevisiae J. Antimicrob. Chemother. 51 2003 1131 1140
18. M.M. Balkis, S.D. Leidich, P.K. Mukherjee, and M.A. Ghannoum Mechanisms of fungal resistance: an overview Drugs 62 2002 1025 1040
19. M.A. Ghannoum, and L.B. Rice Antifungal agents: mode of action, mechanisms of resistance, and correlation of these mechanisms with bacterial resistance Clin. Microbiol. Rev. 12 1999 501 517
20. A.S. Kalgutkar, I. Gardner, R.S. Obach, C.L. Shaffer, E. Callegari, K.R. Henne, A.E. Mutlib, D.K. Dalvie, J.S. Lee, Y. Nakai, J.P. O'Donnell, J. Boer, and S.P. Harriman A comprehensive listing of bioactivation pathways of organic functional groups Curr. Drug Metab. 6 2005 161 225
21. E. Fontana, P.M. Dansette, and S.M. Poli Cytochrome p450 enzymes mechanism based inhibitors: common sub-structures and reactivity Curr. Drug Metab. 6 2005 413 454
22. Y.F. Ueng, T. Shimada, H. Yamazaki, and F.P. Guengerich Oxidation of aflatoxin B1 by bacterial recombinant human cytochrome P450 enzymes Chem. Res. Toxicol. 8 1995 218 225
23. S. Rawal, S.S. Yip, and R.A. Coulombe Jr. Cloning, expression and functional characterization of cytochrome P450 3A37 from turkey liver with high aflatoxin B1 epoxidation activity Chem. Res. Toxicol. 23 2010 1322 1329
24. P. Pelkonen, M.A. Lang, M. Negishi, C.P. Wild, and R.O. Juvonen Interaction of aflatoxin B1 with cytochrome P450 2A5 and its mutants: correlation with metabolic activation and toxicity Chem. Res. Toxicol. 10 1997 85 90
25. B. Rupp, S. Raub, C. Marian, and H.D. Holtje Molecular design of two sterol 14alpha-demethylase homology models and their interactions with the azole antifungals ketoconazole and bifonazole J. Comput. Aided Mol. Des. 19 2005 149 163
26. S. Hawser, and K. Islam Comparisons of the effects of fungicidal and fungistatic antifungal agents on the morphogenetic transformation of Candida albicans J. Antimicrob. Chemother. 43 1999 411 413
27. C. Brass, J.Z. Shainhouse, and D.A. Stevens Variability of agar dilution-replicator method of yeast susceptibility testing Antimicrob. Agents Chemother. 15 1979 763 768
28. D.R. Hospenthal, C.K. Murray, and M.G. Rinaldi The role of antifungal susceptibility testing in the therapy of candidiasis Diagn. Microbiol. Infect. Dis. 48 2004 153 160
29. EUCAST Definitive Document E.DEF 3.1, June 2000: Determination of minimum inhibitory concentrations (MICs) of antibacterial agents by agar dilution Clin. Microbiol. Infect. 6 2000 509 515
30. B. Yao, H. Ji, Y. Cao, Y. Zhou, J. Zhu, J. Lu, Y. Li, J. Chen, C. Zheng, Y. Jiang, R. Liang, and H. Tang Synthesis and antifungal activities of novel 2-aminotetralin derivatives J. Med. Chem. 50 2007 5293 5300
31. Z. Lv, C. Sheng, Y. Zhang, T. Wang, J. Feng, H. Sun, H. Zhong, M. Zhang, H. Chen, and K. Li Synthesis and in vitro antifungal activities of new 3-substituted benzopyrone derivatives Bioorg. Med. Chem. Lett. 20 2010 7106 7109
32. G.I. Lepesheva, and M.R. Waterman Sterol 14alpha-demethylase cytochrome P450 (CYP51), a P450 in all biological kingdoms Biochim. Biophys. Acta 1770 2007 467 477
33. O. Pelkonen, M. Turpeinen, J. Hakkola, P. Honkakoski, J. Hukkanen, and H. Raunio Inhibition and induction of human cytochrome P450 enzymes: current status Arch. Toxicol. 82 2008 667 715
34. C. Sheng, X. Che, W. Wang, S. Wang, Y. Cao, J. Yao, Z. Miao, and W. Zhang Design and synthesis of antifungal benzoheterocyclic derivatives by scaffold hopping Eur. J. Med. Chem. 46 2011 1706 1712
35. P.S. Fogue, P.K. Lunga, E.S. Fondjo, J. De Dieu Tamokou, B. Thaddee, J. Tsemeugne, A.T. Tchapi, and J.R. Kuiate Substituted 2-aminothiophenes: antifungal activities and effect on Microsporum gypseum protein profile Mycoses 2011
36. N. Fokialakis, C.L. Cantrell, S.O. Duke, A.L. Skaltsounis, and D.E. Wedge Antifungal activity of thiophenes from Echinops ritro J. Agric. Food Chem. 54 2006 1651 1655
37. G. Stefancich, M. Artico, G. Ortar, R. Silvestri, G. Simonetti, and G. Apuzzo Antibacterial and antifungal agents. XV. Synthesis and antifungal activity of structural analogues of bifonazole and ketoconazole Arch. Pharm. (Weinheim) 325 1992 687 694
38. I. Okoli, J.J. Coleman, E. Tampakakis, W.F. An, E. Holson, F. Wagner, A.L. Conery, J. Larkins-Ford, G. Wu, A. Stern, F.M. Ausubel, and E. Mylonakis Identification of antifungal compounds active against Candida albicans using an improved high-throughput Caenorhabditis elegans assay PLoS ONE 4 2009 e7025
39. N. Strushkevich, S.A. Usanov, and H.W. Park Structural basis of human CYP51 inhibition by antifungal azoles J. Mol. Biol. 397 2010 1067 1078
40. C.A. Lipinski, F. Lombardo, B.W. Dominy, and P.J. Feeney Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings Adv. Drug Deliv. Rev. 46 2001 3 26
41. T. Patton, J. Barrett, J. Brennan, and N. Moran Use of a spectrophotometric bioassay for determination of microbial sensitivity to manuka honey J. Microbiol. Methods 64 2006 84 95
42. K.A. Salminen, A. Meyer, L. Jerabkova, L.E. Korhonen, M. Rahnasto, R.O. Juvonen, P. Imming, and H. Raunio Inhibition of human drug metabolizing cytochrome P450 enzymes by plant isoquinoline alkaloids Phytomedicine 18 2011 533 538