Dithiocarbamates are strong inhibitors of the beta-class fungal carbonic anhydrases from Cryptococcus neoformans, Candida albicans and Candida glabrata

Bioorganic and Medicinal Chemistry Letters

Volumn 22, Issue 2, 2012, Pages 859-862

  Monti, Simona Maria ^a   Maresca, Alfonso ^b   Viparelli, Francesca ^a   Carta, Fabrizio ^b   Simone, Giuseppina De ^a   Mühlschlegel, Fritz A ^c   Scozzafava, Andrea ^b   Supuran, Claudiu T ^b  

^a CNR   (Italy)

^b UNIVERSITY OF FLORENCE   (Italy)

^c UNIVERSITY OF KENT   (United Kingdom)

Author keywords

Beta class enzyme; Candida albicans; Candida glabrata; Carbonic anhydrase; Cryptococcus neoformans; Dithiocarbamate; Inhibitor

Indexed keywords

ANTIFUNGAL AGENT; CARBONATE DEHYDRATASE; DITHIOCARBAMIC ACID DERIVATIVE; NITROGEN; ZINC BINDING PROTEIN;

ANTIFUNGAL RESISTANCE; ARTICLE; CANDIDA ALBICANS; CANDIDA GLABRATA; CRYPTOCOCCUS NEOFORMANS; CRYSTAL STRUCTURE; DRUG EFFICACY; DRUG MECHANISM; DRUG STRUCTURE; ENZYME INHIBITION; NONHUMAN; STRUCTURE ACTIVITY RELATION;

CANDIDA ALBICANS; CANDIDA GLABRATA; CARBONIC ANHYDRASE INHIBITORS; CRYPTOCOCCUS NEOFORMANS; DOSE-RESPONSE RELATIONSHIP, DRUG; MOLECULAR STRUCTURE; STRUCTURE-ACTIVITY RELATIONSHIP; THIOCARBAMATES;

CANDIDA ALBICANS; CANDIDA GLABRATA; FILOBASIDIELLA NEOFORMANS;

EID: 84855658697     PISSN: 0960894X     EISSN: 14643405     Source Type: Journal    
DOI: 10.1016/j.bmcl.2011.12.033     Document Type: Article

References (41)

1. C. Marzano, L. Ronconi, F. Chiara, M.C. Giron, I. Faustinelli, P. Cristofori, A. Trevisan, and D. Fregona Int. J. Cancer 129 2011 487
2. E. Amin, A.A. Saboury, H. Mansuri-Torshizi, and A.A. Moosavi-Movahedi J. Enzyme Inhib. Med. Chem. 25 2010 272
3. L. Morpurgo, A. Desideri, A. Rigo, P. Viglino, and G. Rotilio Biochim. Biophys. Acta. 746 1983 168
4. C.T. Supuran Nat. Rev. Drug Disc. 7 2008 168
5. C.T. Supuran Bioorg. Med. Chem. Lett. 20 2010 3467
6. D. Neri, and C.T. Supuran Nat. Rev. Drug Disc. 10 2011 767
7. S. Pastorekova, S. Parkkila, J. Pastorek, and C.T. Supuran J. Enzyme Inhib. Med. Chem. 19 2004 199
8. C.T. Supuran Future Med. Chem. 3 2011 1165
9. C.T. Supuran Mol. Divers. 15 2011 305
10. C.T. Supuran Front. Pharmacol. 2 2011 34
11. C.T. Supuran, A. Scozzafava, and A. Casini Med. Res. Rev. 23 2003 146
12. C. Schlicker, R.A. Hall, D. Vullo, S. Middelhaufe, M. Gertz, C.T. Supuran, F.A. Muhlschlegel, and C. Steegborn J. Mol. Biol. 385 2009 1207
13. A. Innocenti, D. Vullo, A. Scozzafava, J.R. Casey, and C.T. Supuran Bioorg. Med. Chem. Lett. 15 2005 573
14. A. Innocenti, R.A. Hall, C. Schlicker, F.A. Mühlschlegel, and C.T. Supuran Bioorg. Med. Chem. 17 2009 2654
15. A. Innocenti, W. Leewattanapasuk, F.A. Mühlschlegel, A. Mastrolorenzo, and C.T. Supuran Bioorg. Med. Chem. Lett. 19 2009 4802
16. R.A. Hall, and F.A. Mühlschlegel Fungal and nematode carbonic anhydrases: Their inhibition in drug design C.T. Supuran, J.Y. Winum, Drug Design of Zinc-Enzyme Inhibitors: Functional, Structural, and Disease Applications 2009 John Wiley & Sons Hoboken 301 322
17. U.M. Ohndorf, C. Schlicker, and C. Steegborn Crystallographic studies on carbonic anhydrases from fungal pathogens for structure-assisted drug development C.T. Supuran, J.Y. Winum, Drug Design of Zinc-Enzyme Inhibitors: Functional Structural, and Disease Applications 2009 John Wiley & Sons Hoboken 323 334
18. T. Klengel, W.J. Liang, J. Chaloupka, C. Ruoff, K. Schropel, J.R. Naglik, S.E. Eckert, E.G. Mogensen, K. Haynes, M.F. Tuite, L.R. Levin, J. Buck, and F.A. Mühlschlegel Curr. Biol. 15 2005 2021
19. Y.S. Bahn, G.M. Cox, J.R. Perfect, and J. Heitman Curr. Biol. 15 2005 2013
20. E.G. Mogensen, G. Janbon, J. Chaloupka, C. Steegborn, M.S. Fu, F. Moyrand, T. Klengel, D.S. Pearson, M.A. Geeves, J. Buck, L.R. Levin, and F.A. Mühlschlegel Eukaryot. Cell 5 2006 103
21. Y.S. Bahn, and F.A. Mühlschlegel Curr. Opin. Microbiol. 9 2006 572
22. A. Innocenti, A. Scozzafava, and C.T. Supuran Bioorg. Med. Chem. Lett. 19 2009 1855
23. A. Innocenti, A. Scozzafava, and C.T. Supuran Bioorg. Med. Chem. Lett. 20 2010 1548
24. C. Temperini, A. Scozzafava, and C.T. Supuran Bioorg. Med. Chem. Lett. 20 2010 474
25. S. Isik, F. Kockar, O. Arslan, O. Ozensoy Guler, A. Innocenti, and C.T. Supuran Bioorg. Med. Chem. Lett. 18 2008 6327
26. L. Syrjänen, M. Tolvanen, M. Hilvo, A. Olatubosun, A. Innocenti, A. Scozzafava, J. Leppiniemi, B. Niederhauser, V.P. Hytönen, T.A. Gorr, S. Parkkila, and C.T.B.M.C. Supuran Biochemistry 11 2010 28
27. Carta, F.; Aggarwal, M.; Maresca, A.; Scozzafava, A.; McKenna, R.; Supuran, C. T. Chem. Commun. in press, doi:10.1039/C2CC16395K.
28. S. Kolayli, F. Karahalil, H. Sahin, B. Dincer, and C.T. Supuran J. Enzyme Inhib. Med. Chem. 26 2011 895
29. A. Suarez Covarrubias, T.A. Larsson, M. Hogbom, J. Lindberg, T. Bergfors, C. Bjorkelid, S.L. Mowbry, T. Unge, and T.A. Jones J. Biol. Chem. 280 2005 18782
30. A. Suarez Covarrubias, T. Bergfors, T.A. Jones, and M. Hogbom J. Biol. Chem. 281 2006 4993
31. T. Minakuchi, I. Nishimori, D. Vullo, A. Scozzafava, and C.T. Supuran J. Med. Chem. 52 2009 2226
32. I. Nishimori, T. Minakuchi, D. Vullo, A. Scozzafava, A. Innocenti, and C.T. Supuran J. Med. Chem. 52 2009 3116
33. ,21 and represent the mean from at least three different determinations.
34. F. Pacchiano, F. Carta, D. Vullo, A. Scozzafava, and C.T. Supuran Bioorg. Med. Chem. Lett. 20 2010 102
35. International Programme of Chmical safety, available at: http://www.wpro.who.int/NR/rdonlyres/ED05F324-B487-4B7F-A240-16DBA39AD994/0/ Environmentalhealthcriteria78dithiocarbamatepesticidesethelynethioureaandpropyl enethioureaageneralintroduction.pdf.
36. H.F. Tsai, A.A. Krol, K.E. Sarti, and J.E. Bennett Antimicrob. Agents Chemother. 50 2006 1384
37. G. Ramage, B.L. Wickes, and J.L. Lopez-Ribot Am. Clin. Lab. 20 2001 42
38. M. Pai, R. Turpin, and K. Garey Antimicrob. Agents Chemother. 51 2007 35
39. R. Kaur, R. Domergue, M.L. Zupancic, and B.P. Cormack Curr. Opin. Microbiol. 8 2005 378
40. C.A. Hitchcock, G.W. Pye, P.F. Troke, E.M. Johnson, and D.W. Warnock Antimicrob. Agents Chemother. 37 1993 1962
41. P.L. Fidel Jr., J.A. Vazquez, and J.D. Sobel Clin. Microbiol. Rev. 12 1999 80