Bicyclic peptidomimetics targeting secreted aspartic protease 2 (SAP2) from Candida albicans reveal a constrained inhibitory chemotype

Bioorganic and Medicinal Chemistry

Volumn 20, Issue 24, 2012, Pages 7206-7213

  Calugi, Chiara ^a   Trabocchi, Andrea ^a   De Bernardis, Flavia ^b   Arancia, Silvia ^b   Navarra, Pierluigi ^c   Cauda, Roberto ^c   Cassone, Antonio ^b   Guarna, Antonio ^a  

^a UNIVERSITY OF FLORENCE   (Italy)

^b ISTITUTO SUPERIORE DI SANITÀ   (Italy)

^c CATHOLIC UNIVERSITY   (Italy)

Author keywords

Infectious disease; Inhibitor; Molecular docking; Peptidomimetic; Protease

Indexed keywords

ASPARTIC PROTEINASE; ASPARTIC PROTEINASE INHIBITOR; METHYL 2 (2,2 DIMETHOXYETHYLAMINO) 4 METHYLPENTANOIC ACID; METHYL 4 METHYL 2 (2 OXO 7 (PIPERIDINE 1 CARBONYL) 6,8 DIOXA 3 AZABICYCLO [3.2.1] OCTAN 3 YL)PENTANOIC ACID; METHYL 4 METHYL 2 [2 OXO 7 (PIPERIDINE 1 CARBONYL) 6,8 DIOXA 3 AZABICYCLO [3.2.1] OCTAN 3 YL]PENTANOIC ACID; PEPTIDOMIMETIC AGENT; SECRETED ASPARTIC PROTEINASE 2; UNCLASSIFIED DRUG;

ARTICLE; CANDIDA ALBICANS; CATALYSIS; DRUG CONFORMATION; DRUG SCREENING; DRUG STRUCTURE; DRUG SYNTHESIS; ENZYME ASSAY; ENZYME INHIBITION; HYDROGEN BOND; HYDROPHOBICITY; MOLECULAR DOCKING; MOLECULAR MODEL; NONHUMAN; PEPTIDOMICS; PROTEIN SECRETION; PROTEIN TARGETING; STEREOCHEMISTRY;

ANTIFUNGAL AGENTS; ASPARTIC ACID ENDOPEPTIDASES; CANDIDA ALBICANS; FUNGAL PROTEINS; MOLECULAR DOCKING SIMULATION; PEPTIDES, CYCLIC; PEPTIDOMIMETICS; STEREOISOMERISM;

CANDIDA ALBICANS;

EID: 84870054638     PISSN: 09680896     EISSN: 14643391     Source Type: Journal    
DOI: 10.1016/j.bmc.2012.09.031     Document Type: Article

References (38)

1. K.A. Marr Curr. Opin. Oncol. 22 2009 138
2. M.A. Pfaller, and D.J. Diekema Clin. Microbiol. Rev. 20 2007 133
3. H. Wisplinghoff, T. Bischoff, S.M. Tallent, H. Seifert, R.P. Wenzel, and M.B. Edmond Clin. Infect. Dis. 39 2004 309
4. C.R. Sims, L. Ostrosky-Zeichner, and J.H. Rex Arch. Med. Res. 36 2005 660
5. N.N. Mishra, T. Prasad, N. Sharma, A. Payasi, R. Prasad, D.K. Gupta, and R. Singh Acta Microbiol. Immunol. Hung. 54 2007 201
6. B. Hube Curr. Opin. Microbiol. 7 2004 336
7. R.A. Calderone, and W.A. Fonzi Trends microbiol. 9 2001 327
8. R.A. Akins Med. Mycol. 43 2005 285
9. K. Gauwerky, C. Borelli, and H.C. Korting Drug Discovery Today 14 2009 214
10. L.E. Alksne, and S.J. Projan Curr. Opin. Biotechnol. 11 2000 625
11. M.N. Alekshun, and S.B. Levy Drug. Discovery Today: Ther. Strateg. 1 2004 483
12. J.R. Naglik, S.J. Challacombe, and B. Hube Microbiol. Mol. Biol. Rev. 67 2003 400
13. M.W. Ollert, C. Wende, M. Görlich, C.G. McMullan-Vogel, M. Borg-von Zepelin, C.W. Vogel, and H.C. Korting J. Clin. Microbiol. 33 1995 2543
14. T. Wu, K. Wright, S.F. Hurst, and C.J. Morrison Antimicrob. Agents Chemother. 44 2000 1200
15. D.H. Navarathna, J.M. Hornby, N. Hoerrmann, A.M. Parkhurst, G.E. Duhamel, and K.W. Nickerson J. Antimicrob. Chemother. 56 2005 1156
16. A. Cassone, F. De Bernardis, F. Mondello, T. Ceddia, and L. Agatensi J. Infect. Dis. 156 1987 777
17. S.K. Pranav Kumar, and V.M. Kulkarni Bioorg. Med. Chem. 10 2002 1153
18. B. Degel, P. Staib, S. Rohrer, J. Scheiber, E. Martina, C. Büchold, K. Baumann, J. Morschhäuser, and T. Schirmeister ChemMedChem 3 2008 302
19. C. Büchold, Y. Hemberger, C. Heindl, A. Welker, B. Degel, T. Pfeuffer, P. Staib, S. Schneider, P.J. Rosenthal, J. Gut, J. Morschhäuser, G. Bringmann, and T. Schirmeister ChemMedChem 6 2011 141
20. H.C. Korting, M. Schaller, G. Eder, G. Hamm, U. Böhmer, and B. Hube Antimicrob. Agents Chemother. 43 1999 2038
21. C. Abad-Zapatero, R. Goldman, S.W. Muchmore, C. Hutchins, K. Stewart, J. Navaza, C.D. Payne, and T.L. Ray Protein Sci. 5 1996 640
22. I. Pichova, L. Pavlickova, J. Dostal, E. Dolejsi, O. Hruskova- Heidingsfeldova, J. Weber, T. Ruml, and M. Soucek Eur. J. Biochem. 268 2001 2669
23. D. Backman, and U.H. Danielson Biochim. Biophys. Acta, Proteins Proteomics 1646 2003 184
24. A. Tossi, F. Benedetti, S. Norbedo, D. Skrbec, F. Berti, and D. Romeo Bioorg. Med. Chem. 11 2003 4719
25. C. Abad-Zapatero, R. Goldman, S.W. Muchmore, C. Hutchins, T. Oie, K. Stewart, S.M. Cutfield, J.F. Cutfield, S.I. Foundling, and T.L. Ray Adv. Exp. Med. Biol. 436 1998 297
26. D. Sanglard, and F.C. Odds Lancet Infect. Dis. 2 2002 73
27. D. Peres-Bota, H. Rodriguez-Villalobos, G. Dimopoulos, C. Melot, and J.L. Vincent Clin. Microbiol. Infect. 10 2004 550
28. A. Trabocchi, C. Mannino, F. Machetti, F. De Bernardis, S. Arancia, R. Cauda, A. Cassone, and A. Guarna J. Med. Chem. 53 2010 2502
29. G.M. Morris, D.S. Goodsell, R.S. Halliday, R. Huey, W.E. Hart, R.K. Belew, and A.J. Olson J. Comput. Chem. 19 1998 1639
30. F. Mohamadi, N.G.J. Richards, W.C. Guida, R. Liskamp, M. Lipton, C. Caufield, G. Chang, T. Hendrickson, and W.C. Still J. Comput. Chem. 11 1990 440
31. W.B. Jennings, B.M. Farrell, and J.F. Malone Acc. Chem. Res. 34 2001 885
32. S.M. Cutfield, E.J. Dodson, B.F. Anderson, P.C. Moody, C.J. Marshall, P.A. Sullivan, and J.F. Cutfield Structure 3 1995 1261
33. F. De Bernardis, P.A. Sullivan, and A. Cassone Med. Mycol. 39 2001 303
34. F. De Bernardis, S. Arancia, L. Morelli, B. Hube, D. Sanglard, W. Schäfer, and A. Cassone J. Infect. Dis. 179 1999 201
35. A. Gillet, M. Sanner, D. Stoffler, and A. Olson Structure 13 2005 483
36. DeLano, W. L. 'The PyMOL Molecular Graphics System.' DeLano Scientific LLC, San Carlos, CA, USA. [http://www.pymol.org.]
37. W.L. Jorgensen, and J. Tirado-Rives J. Am. Chem. Soc. 110 1988 1657
38. W.C. Still, A. Tempczyk, R.C. Hawley, and T. Hendrickson J. Am. Chem. Soc. 112 1990 6127