Total synthesis and structure-activity relationships of new echinocandin-like antifungal cyclolipohexapeptides

European Journal of Medicinal Chemistry

Volumn 50, Issue , 2012, Pages 196-208

  Yao, Jianzhong ^a   Liu, Hongming ^a   Zhou, Ting ^a   Chen, Hai ^a   Miao, Zhenyuan ^a   Sheng, Chunquan ^a   Zhang, Wannian ^a  

^a SECOND MILITARY MEDICAL UNIVERSITY   (China)

Author keywords

Antifungal; Caspofungin; Cyclolipohexapeptide; Echinocandin; SAR; Total synthesis

Indexed keywords

ANTIFUNGAL AGENT; CASPOFUNGIN; CYCLOLIPOHEXAPEPTIDE AMINE 4 TOSYLATE; ECHINOCANDIN; HEXAPEPTIDE; UNCLASSIFIED DRUG;

ANTIFUNGAL ACTIVITY; ARTICLE; ASPERGILLUS FUMIGATUS; CANDIDA ALBICANS; CANDIDA KRUSEI; CANDIDA PARAPSILOSIS; CANDIDA TROPICALIS; CONTROLLED STUDY; CRYPTOCOCCUS NEOFORMANS; DRUG SYNTHESIS; IN VITRO STUDY; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; STRUCTURE ACTIVITY RELATION; TRICHOPHYTON RUBRUM;

ADULT; ANIMALS; ANTIFUNGAL AGENTS; ASPERGILLUS FUMIGATUS; CANDIDA ALBICANS; DRUG DESIGN; ECHINOCANDINS; HUMANS; LIPOPEPTIDES; MALE; MOLECULAR STRUCTURE; PEPTIDES, CYCLIC; QUANTITATIVE STRUCTURE-ACTIVITY RELATIONSHIP; RATS; RATS, SPRAGUE-DAWLEY;

EID: 84862802184     PISSN: 02235234     EISSN: 17683254     Source Type: Journal    
DOI: 10.1016/j.ejmech.2012.01.054     Document Type: Article

References (39)

1. J.J. Caston-Osorio, A. Rivero, and J. Torre-Cisneros Int. J. Antimicrob. Agents 32 Suppl 2 2008 S103 S109
2. M. Cuenca-Estrella, L. Bernal-Martinez, M.J. Buitrago, M.V. Castelli, A. Gomez-Lopez, O. Zaragoza, and J.L. Rodriguez-Tudela Int. J. Antimicrob. Agents 32 Suppl 2 2008 S143 S147
3. T.F. Patterson Lancet 366 2005 1013 1025
4. J.P. Latge Clin. Microbiol. Rev. 12 1999 310 350
5. J.N. Steenbergen, and A. Casadevall J. Clin. Microbiol. 38 2000 1974 1976
6. C. Sheng, and W. Zhang Curr. Med. Chem. 18 2011 733 766
7. H.A. Gallis, R.H. Drew, and W.W. Pickard Rev. Infect. Dis. 12 1990 308 329
8. V. Fanos, and L. Cataldi J. Chemother. 12 2000 463 470
9. L. Ostrosky-Zeichner, K.A. Marr, J.H. Rex, and S.H. Cohen Clin. Infect. Dis. 37 2003 415 425
10. D.J. Sheehan, C.A. Hitchcock, and C.M. Sibley Clin. Microbiol. Rev. 12 1999 40 79
11. Y. Aoyama, Y. Yoshida, and R. Sato J. Biol. Chem. 259 1984 1661 1666
12. I.A. Casalinuovo, P. Di Francesco, and E. Garaci Eur. Rev. Med. Pharmacol. Sci. 8 2004 69 77
13. D.W. Denning J. Antimicrob. Chemother. 49 2002 889 891
14. F. Benz, F. Knusel, J. Nuesch, H. Treichler, W. Voser, R. Nyfeler, and W. Keller-Schierlein Helv. Chim. Acta 57 1974 2459 2477
15. W.W. Hope, S. Shoham, and T.J. Walsh Expert Opin. Drug Metab. Toxicol. 3 2007 263 274
16. G. Keating, and D. Figgitt Drugs 63 2003 2235 2263
17. V.A. Morrison Curr. Opin. Investig. Drugs 3 2002 1432 1436
18. Z. Temesgen, J. Barreto, and S. Vento Drugs Today (Barc) 45 2009 469 478
19. P. de la Torre, D.K. Meyer, and A.C. Reboli Future Microbiol. 3 2008 593 601
20. D.M. Schmatz, G. Abruzzo, M.A. Powles, D.C. McFadden, J.M. Balkovec, R.M. Black, K. Nollstadt, and K. Bartizal J. Antibiot. (Tokyo) 45 1992 1886 1891
21. P.A. Warn, A. Sharp, G. Morrissey, and D.W. Denning Int. J. Antimicrob. Agents 35 2010 146 151
22. D.W. Denning Lancet 362 2003 1142 1151
23. C. Wagner, W. Graninger, E. Presterl, and C. Joukhadar Pharmacology 78 2006 161 177
24. A.K. Zaas, and B.D. Alexander Expert Opin. Pharmacother. 6 2005 1657 1668
25. A.J. Sucher, E.B. Chahine, and H.E. Balcer Ann. Pharmacother. 43 2009 1647 1657
26. M. Debono, B.J. Abbott, D.S. Fukuda, M. Barnhart, K.E. Willard, R.M. Molloy, K.H. Michel, J.R. Turner, T.F. Butler, and A.H. Hunt J. Antibiot. (Tokyo) 42 1989 389 397
27. M. Debono, W.W. Turner, L. LaGrandeur, F.J. Burkhardt, J.S. Nissen, K.K. Nichols, M.J. Rodriguez, M.J. Zweifel, D.J. Zeckner, and R.S. Gordee J. Med. Chem. 38 1995 3271 3281
28. B. Lal, V.G. Gund, N.B. Bhise, and A.K. Gangopadhyay Bioorg. Med. Chem. 12 2004 1751 1768
29. B. Lal, V.G. Gund, A.K. Gangopadhyay, S.R. Nadkarni, V. Dikshit, D.K. Chatterjee, and R. Shirvaikar Bioorg. Med. Chem. 11 2003 5189 5198
30. F.A. Bouffard, R.A. Zambias, J.F. Dropinski, J.M. Balkovec, M.L. Hammond, G.K. Abruzzo, K.F. Bartizal, J.A. Marrinan, M.B. Kurtz, and D.C. McFadden J. Med. Chem. 37 1994 222 225
31. R.M. Black, J.M. Balkovec, K.M. Nollstadt, S. Dreikorn, K.F. Bartizal, and G.K. Abruzzo Bioorg. Med. Chem. Lett. 7 1997 2879 2884
32. A. Fujie, T. Iwamoto, B. Sato, H. Muramatsu, C. Kasahara, T. Furuta, Y. Hori, M. Hino, and S. Hashimoto Bioorg. Med. Chem. Lett. 11 2001 399 402
33. K. Masubuchi, T. Okada, M. Kohchi, T. Murata, M. Tsukazaki, O. Kondoh, T. Yamazaki, Y. Satoh, Y. Ono, T. Tsukaguchi, K. Kobayashi, N. Ono, T. Inoue, I. Horii, and N. Shimma Bioorg. Med. Chem. Lett. 11 2001 1273 1276
34. K. Masubuchi, T. Okada, M. Kohchi, M. Sakaitani, E. Mizuguchi, H. Shirai, M. Aoki, T. Watanabe, O. Kondoh, T. Yamazaki, Y. Satoh, K. Kobayashi, T. Inoue, I. Horii, and N. Shimma Bioorg. Med. Chem. Lett. 11 2001 395 398
35. L.L. Klein, L. Li, H.J. Chen, C.B. Curty, D.A. DeGoey, D.J. Grampovnik, C.L. Leone, S.A. Thomas, C.M. Yeung, K.W. Funk, V. Kishore, E.O. Lundell, D. Wodka, J.A. Meulbroek, J.D. Alder, A.M. Nilius, P.A. Lartey, and J.J. Plattner Bioorg. Med. Chem. 8 2000 1677 1696
36. W. Wang, Q. Li, L. Hasvold, B. Steiner, D.A. Dickman, H. Ding, A. Clairborne, H.J. Chen, D. Frost, R.C. Goldman, K. Marsh, Y.H. Hui, B. Cox, A. Nilius, D. Balli, P. Lartey, J.J. Plattner, and Y.L. Bennani Bioorg. Med. Chem. Lett. 13 2003 489 493
37. A. Suzuki, N. Miyaura, and T. Yanagi Synth. Commun. 11 1981 513 519
38. R.A. Zambias, M.L. Hammond, J.V. Heck, K. Bartizal, C. Trainor, G. Abruzzo, D.M. Schmatz, and K.M. Nollstadt J. Med. Chem. 35 1992 2843 2855
39. See Supplementary Information.