New azole antifungal agents with novel modes of action: Synthesis and biological studies of new tridentate ligands based on pyrazole and triazole

European Journal of Medicinal Chemistry

Volumn 46, Issue 9, 2011, Pages 4117-4124

  Bendaha, Hasnae ^a   Yu, Lisa ^b   Touzani, Rachid ^a   Souane, Rachid ^c   Giaever, Guri ^b,d   Nislow, Corey ^b,d   Boone, Charles ^b,d   El Kadiri, Sghir ^a   Brown, Grant W ^b   Bellaoui, Mohammed ^a  

^a FACULTÉ DES SCIENCES   (Morocco)

^b UNIVERSITY OF TORONTO   (Canada)

^c UNIVERSITÉ DE STRASBOURG   (France)

^d UNIVERSITY OF TORONTO   (Canada)

Author keywords

Azole antifungal; DNA damage; Functional genomics; Pyrazole; Triazole; Tridentate ligands

Indexed keywords

ANTIFUNGAL AGENT; N,N [10 BIS[(1,2,4 TRIAZOL 1 YL)METHYL]]DIETHYLAMINO 3' PROPANAMINE; N,N [10 BIS[(3,5 DIMETHYL PYRAZOL 1 YL)METHYL]]DIETHYLAMINO 3' PROPANAMINE; PYRAZOLE; TRIAZOLE; UNCLASSIFIED DRUG;

ANTIFUNGAL ACTIVITY; ARTICLE; CELL CYCLE; CELL DIVISION; DNA DAMAGE; DNA REPAIR; DRUG SYNTHESIS; GENE DELETION; GENOMICS; NONHUMAN; SACCHAROMYCES CEREVISIAE; YEAST CELL;

ANTIFUNGAL AGENTS; CELL CYCLE; DNA REPAIR; LIGANDS; MAGNETIC RESONANCE SPECTROSCOPY; PROTEIN KINASE C; PYRAZOLES; SACCHAROMYCES CEREVISIAE; SPECTROPHOTOMETRY, INFRARED; TRIAZOLES;

EID: 80052932426     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2011.06.012     Document Type: Article

References (66)

1. J. Wendland Fungal Genet. Biol. 34 2001 63 82
2. S.D. Harris, and M. Momany Fungal Genet. Biol. 41 2004 391 400
3. S.J. Lin, J. Schranz, and S.M. Teutsch Clin. Infect. Dis. 32 2001 358 366
4. B. Spellberg, J. Edwards Jr., and A. Ibrahim Clin. Microbiol. Rev. 18 2005 556 569
5. M.M. Roden, T.E. Zaoutis, W.L. Buchanan, T.A. Knudsen, T.A. Sarkisova, R.L. Schaufele, M. Sein, T. Sein, C.C. Chiou, J.H. Chu, D.P. Kontoyiannis, and T.J. Walsh Clin. Infect. Dis. 41 2005 634 653
6. D.P. Kontoyiannis, M.S. Lionakis, R.E. Lewis, G. Chamilos, M. Healy, C. Perego, A. Safdar, H. Kantarjian, R. Champlin, T.J. Walsh, and I.I. Raad J. Infect. Dis. 191 2005 1350 1360
7. T.E. Zaoutis, E. Roilides, C.C. Chiou, W.L. Buchanan, T.A. Knudsen, T.A. Sarkisova, R.L. Schaufele, M. Sein, T. Sein, P.A. Prasad, J.H. Chu, and T.J. Walsh Pediatr. Infect. Dis. J. 26 2007 723 727
8. P.A. Prasad, S.E. Coffin, K.H. Leckerman, T.J. Walsh, and T.E. Zaoutis Pediatr. Infect. Dis. J. 27 2008 1083 1088
9. K. Suzuki, Y. Sugawara, T. Sekine, K. Nakase, and N. Katayama J. Infect. Chemother. 15 2009 42 45
10. D. Neofytos, D. Horn, E. Anaissie, W. Steinbach, A. Olyaei, J. Fishman, M. Pfaller, C. Chang, K. Webster, and K. Marr Clin. Infect. Dis. 48 2009 265 273
11. G. Sanjay, S.G. Revankar, and D.A. Sutton Clin. Microbiol. Rev. 23 2010 884 928
12. P.G. Pappas Am. J. Med. Sci. 340 2010 253 257
13. M.A. Pfaller, and D.J. Diekema Crit. Rev. Microbiol. 36 2010 1 53
14. K. Leventakos, R.E. Lewis, and D.P. Kontoyiannis Clin. Infect. Dis. 50 2010 405 415
15. M. Baginski, H. Resat, and E. Borowski Biochim. Biophys. Acta 1567 2002 63 78
16. B. Spellberg, T.J. Walsh, D.P. Kontoyiannis, J. Edwards Jr., and A.S. Ibrahim Clin. Infect. Dis. 48 2009 1743 1751
17. J.R. Wingard, P. Kubilis, L. Lee, G. Yee, M. White, L. Walshe, R. Bowden, E. Anaissie, J. Hiemenz, and J. Lister Clin. Infect. Dis. 29 1999 1402 1407
18. M. Baginski, J. Czub, and K. Sternal Chem. Rec. 6 2006 320 332
19. K.E. Estes, S.R. Penzak, K.A. Calis, and T.J. Walsh Pharmacotherapy 29 2009 17 30
20. D.W. Denning J. Microb. Chemother. 40 1997 611 614
21. M.A. Pfaller, S.A. Messer, R.J. Hollis, R.N. Jones the SENTRY Participants Group Antimicrob. Agents Chemother. 46 2002 1032 1037
22. E. Spreghini, C.M. Maida, S. Tomassetti, F. Orlando, D. Giannini, M.E. Milici, G. Scalise, and F. Barchiesi Antimicrob. Agents Chemother. 52 2008 1929 1933
23. V. Nagappan, and S. Deresinski Clin. Infect. Dis. 45 2007 1610 1717
24. J.H. Rex, M.G. Rinaldi, and M.A. Pfaller Agents Chemother. 39 1995 1 8
25. J.R. Maenza, W.G. Merz, M.J. Romagnoli, J.C. Keruly, R.D. Moore, and J.E. Gallant Clin. Infect. Dis. 24 1997 28 34
26. T.C. White, K.A. Marr, and R.A. Bowden Microbiol. Rev. 11 1998 382 402
27. M.A. Ghannoum, and L.B. Rice Clin. Microbiol. Rev. 12 1999 501 517
28. D. Sanglard, and F.C. Odds Lancet Infect. Dis. 2 2002 73 85
29. A.S. Chau, C.A. Mendrick, F.J. Sabatelli, D. Loebenberg, and P.M. McNicholas Antimicrob. Agents Chemother. 48 2004 2124 2131
30. L.E. Cowen, and S. Lindquist Science 309 2005 2185 2189
31. A.A. Panackal, J.L. Gribskov, J.F. Staab, K.A. Kirby, M. Rinaldi, and K.A. Marr J. Clin. Microbiol. 44 2006 1740 1743
32. G. Giaever, D.D. Shoemarker, T.W. Jones, H. Liang, E.A. Winzeler, A. Astromoff, and R.W. Davis Nat. Genet. 21 1999 278 283
33. G. Giaever, P. Flaherty, J. Kumm, M. Proctor, C. Nislow, D.F. Jaramillo, A.M. Chu, M.I. Jordan, A.P. Arkin, and R.W. Davis Proc. Natl. Acad. Sci. USA 101 2004 793 798
34. P.Y. Lum, C.D. Armour, S.B. Stepaniants, G. Cavet, M.K. Wolf, J.S. Butler, J.C. Hinshaw, P. Garnier, G.D. Prestwich, A. Leonardson, P. Garrett-Engele, C. Rush, M.M. Bard, G. Schimmack, J.W. Phillips, C.J. Roberts, and D.D. Shoemaker Cell 116 2004 121 137
35. A.B. Parsons, A. Lopez, I.E. Givoni, D.E. Williams, C.A. Gray, J. Porter, G. Chua, R. Sopko, R.L. Brost, C.H. Ho, J. Wang, T. Ketela, C. Brenner, J.A. Brill, G.E. Fernandez, T.C. Lorenz, G.S. Payne, S. Ishihara, Y. Ohya, B. Andrews, T.R. Hughes, B.J. Frey, T.R. Graham, R.J. Andersen, and C. Boone Cell 126 2006 611 625
36. L. Yu, A. Lopez, A. Anaflous, B. El Bali, A. Hamal, E. Ericsson, L.E. Heisler, A. McQuibban, G. Giaever, C. Nislow, C. Boone, G.W. Brown, and M. Bellaoui PLoS Genet. 4 2008 e1000284
37. B. Qaddouri, A. Guaadaoui, A. Bellirou, A. Hamal, A. Melhaoui, G.B. Brown, and M. Bellaoui Evid. Based Complement. Alternat. Med. 2009 nep069
38. H. Al Bay, B. Quaddouri, A. Guaadaoui, R. Touzani, N. Benchat, A. Hamal, M. Taleb, M. Bellaoui, and S. El Kadiri Lett. Drug Des. Discov. 7 2010 41 45
39. I. Dvoretzky, and G.H. Richter J. Org. Chem. 15 1950 1285 1288
40. R. Touzani, A. Ramdani, S. El Kadiri, and F. Gourand Molecules 4 1999 M116
41. R. Touzani, A. Ramdani, and S. El Kadiri Molecules 5 2000 M139
42. D.B. Grotjahn, D. Combs, S. Van, G. Aguirre, and F. Ortega Inorg. Chem. 39 2000 2080 2086
43. A. Togni, and L.M. Venanzi Chem. Int. Ed. Engl. 33 1994 497 526
44. R. Touzani, A. Ramdani, T. Ben-Hadda, S. El Kadiri, O. Maury, H.L. Bozec, and P.H. Dixneuf Synth. Comm. 31 2001 1315 1321
45. R. Touzani, S. Garbacia, O. Lavastre, V.K. Yadav, B. Carboni, and J. Comb Chem 5 2003 375 378
46. S.A. Synowsky, and A.J. Heck Protein Sci. 17 2007 119 125
47. T.I. Orban, and E. Izaurralde RNA 11 2005 459 469
48. B.O. Krogh, and L.S. Symington Annu. Rev. Genet. 38 2004 233 271
49. C. Arora, K. Kee, S. Maleki, and S. Keeney Mol. Cell 13 2004 549 559
50. J. Li, G.W. Hooker, and G.S. Roeder Genetics 173 2006 1969 1981
51. D.K. Nag, J.D. Pata, and M. Sironi Mol. Gen. Genomics 276 2006 313 321
52. S. Maleki, M.J. Neale, C. Arora, K.A. Henderson, and S. Keeney Chromosoma 116 2007 471 486
53. D.R. Koehn, S.J. Haring, J.M. Williams, and R.E. Malone Genetics 182 2009 447 458
54. M. Lisby, R. Rothstein, and U.H. Mortensen Proc. Natl. Acad. Sci. USA 98 2001 8276 8282
55. M. Lisby, U.H. Mortensen, and R. Rothstein Nat. Cell. Biol. 5 2003 572 577
56. M. Lisby, J.H. Barlow, R.C. Burgess, and R. Rothstein Cell 118 2004 699 713
57. D.E. Levin Microbial. Mol. Biol. Rev. 69 2005 262 291
58. K.N. Huang, and L.S. Symington Mol. Cell. Biol. 14 1994 6039 6045
59. N.A. Mouchel, and J.R. Jenkins FEBS Lett. 580 2006 51 57
60. A. Sussman, K. Huss, L.C. Chio, S. Heidler, M. Shaw, D. Ma, G. Zhu, R.M. Campbell, T.S. Park, P. Kulanthaivel, J.E. Scott, J.W. Carpenter, M.A. Strege, M.D. Belvo, J.R. Swartling, A. Fischl, W.K. Yeh, C. Shih, and X.S. Ye Eukaryot. Cell 3 2004 932 943
61. J.J. Heinisch Biochim. Biophys. Acta 1754 2005 171 182
62. C.B. Brachmann, A. Davies, G.J. Cost, E. Caputo, J. Li, P. Hieter, and J.D. Boeke Yeast 14 1998 115 132
63. E.A. Winzeler, D.D. Shoemaker, A. Astromoff, H. Liang, K. Anderson, B. Andre, R. Bangham, R. Benito, J.D. Boeke, H. Bussey, A.M. Chu, C. Connelly, K. Davis, F. Dietrich, S.W. Dow, M. El Bakkoury, F. Foury, S.H. Friend, E. Gentalen, G. Giaever, J.H. Hegemann, T. Jones, M. Laub, H. Liao, N. Liebundguth, D.J. Laekhart, A. Lucau-Danila, M. Lussier, N. M'Rabet, P. Menard, M. Mittman, C. Pai, C. Rebischung, J.L. Revuelta, J. Riles, C.J. Roberts, P. Ross-MacDonald, B. Scherens, M. Snyder, S. Sookhai-Mahadeo, R.K. Storms, S. Veronneau, M. Voet, G. Volekaert, T.R. Ward, R. Wysocki, G.S. Yen, K. Yu, K. Zimmerman, P. Philippsen, M. Johnston, and R.W. Davis Science 285 1999 901 906
64. F. Sherman Methods Enzymol. 350 2002 3 41
65. M. Chang, M. Bellaoui, C. Boone, and G.W. Brown Proc. Natl. Acad. Sci. USA 99 2002 16934 16939
66. S.E. Pierce, R.W. Davis, C. Nislow, and G. Giaever Nat. Protoc. 2 2007 2958 2974