The antifungal activity of 2,2'-diamino-4,4'-dithiazole derivatives is due to the possible inhibition of lanosterol-14-α-demethylase

Journal of Enzyme Inhibition

Volumn 14, Issue 1, 1998, Pages 49-68

  Scozzafava, Andrea ^a   Nicolae, Anca ^b   Maior, Ovidiu ^b   Briganti, Fabrizio ^a   Supuran, Claudiu T ^a  

^a UNIVERSITY OF FLORENCE   (Italy)

^b UNIVERSITY OF BUCHAREST   (Romania)

Author keywords

(Thio)ureas; 2,2' Diamino 4,4' dithiazole; Antifungal compounds; Ergosterol biosynthesis inhibitors; Lanosterol 14 demethylase; Sulfonamides

Indexed keywords

2 (2 CARBOXYPHENYLSULFONYLAMIDO) 2' AMINO 4,4' DITHIAZOLE; 2 (2 CARBOXYTETRABROMOPHENYLSULFONYLAMIDO) 2' AMINO 4,4' DITHIAZOLE; 2 (2 NITROPHENYLSULFONYLAMIDO) 2' AMINO 4,4' DITHIAZOLE; 2 (2,4,6 TRIMETHYLPHENYLSULFONYLAMIDO) 2' AMINO 4,4' DITHIAZOLE; 2 (3 AMINOPHENYLSULFONYLAMDIO) 2' AMINO 4,4' DITHIAZOLE; 2 (3 CHLORO 4 NITROPHENYLSULFONYLAMIDO) 2' AMINO 4,4' DITHIAZOLE; 2 (3 NITROPHENYLSULFONYLAMIDO) 2' AMINO 4,4' DITHIAZOLE; 2 (4 ACETYLAMINOPHENYLSULFONYLAMIDO) 2' AMINO 4,4' DITHIAZOLE; 2 (4 AMINOPHENYLSULFONYLAMIDO) 2' AMINO 4,4' DITHIAZOLE; 2 (4 BROMOPHENYLSULFONYLAMIDO) 2' AMINO 4,4' DITHIAZOLE; 2 (4 CHLOROPHENYLSULFONYLAMIDO) 2' AMINO 4,4' DITHIAZOLE; 2 (4 FLUOROPHENYLSULFONYLAMIDO) 2' AMINO 4,4' DITHIAZOLE; 2 (4 IODOPHENYLSULFONYLAMIDO) 2' AMINO 4,4' DITHIAZOLE; 2 (4 METHOXYPHENYLSULFONYLAMIDO) 2' AMINO 4,4' DITHIAZOLE; 2 (4 NITROPHENYLSULFONYLAMIDO) 2' AMINO 4,4' DITHIAZOLE; 2 (ISONICOTINYLAMIDO) 2' AMINO 4,4' DITHIAZOLE; 2 (N,N DIMETHYLSULFAMOYLAMIDO) 2' AMINO 4,4' DITHIAZOLE; 2 (N,N DIPHENYLCARBAMOYLAMIDO) 2' AMINO 4,4' DITHIAZOLE; 2 P TOSYLAMIDO 2' AMINO 4,4' DITHIAZOLE; 2 PENTAFLUOROPHENYLSULFONYLAMIDO 2' AMINO 4,4' DITHIAZOLE; 2 PHENYLMETHYLSULFONYLAMIDO 2' AMINO 4,4' DITHIAZOLE; 2 TRIFLUOROMETHYLSULFONYLAMIDO 2' AMINO 4,4' DITHIAZOLE; 2,2' DIAMINO 4,4' DITHIAZOLE; 2,2' DIAMINO 4,4' DITHIAZOLE DIHYDROBROMIDE; ANTIFUNGAL AGENT; ERGOSTEROL; FUNGAL PROTEIN; ITRACONAZOLE; THIAZOLE DERIVATIVE; UNCLASSIFIED DRUG; UNINDEXED DRUG;

ANTIFUNGAL ACTIVITY; ARTICLE; ASPERGILLUS; CANDIDA; CONTROLLED STUDY; DRUG MECHANISM; DRUG PROTEIN BINDING; DRUG SYNTHESIS; ENZYME INHIBITION; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN; PRIORITY JOURNAL;

ASPERGILLUS NIGER; CANDIDA ALBICANS;

ANTIFUNGAL AGENTS; ASPERGILLUS NIGER; CANDIDA ALBICANS; CYTOCHROME P-450 ENZYME SYSTEM; ENZYME INHIBITORS; ERGOSTEROL; MOLECULAR STRUCTURE; OXIDOREDUCTASES; THIAZOLES;

EID: 0032414320     PISSN: 87555093     EISSN: None     Source Type: Journal    
DOI: 10.3109/14756369809036545     Document Type: Article

References (38)

1. (a) Mallie, M. and Bastide, J.M (1996) Drugs Exp. Clin. Res., 22, 301-307
2. (b) Yoshida, Y. (1988) Curr. Top. Med. Mycol., 2, 388-418.
3. Crameri, R (1998) Int. Arch. Allergy Immunol., 115, 99-114.
4. (a) Denning, D.W., Radford, S.A , Oakley, K.L , Hall, L., Johnson, E.M and Warnock, D.W. (1997) J. Antimicrob. Chemother , 40, 401-414
5. (b) Joseph-Horne, T., Hollomon, D., Loeffler, R.S. and Kelly, S.L. (1995) FEBS Lett., 374, 174-178.
6. (a) Khan, Z.U., Sanyal, S.C., Mokaddas, E., Vislocky, I., Anim, J.T., Salama, A.L. and Shuhaiber, H. (1997) Mycoses, 40, 213-217
7. (b) Kelly, S L., Lamb, D.C., Corran, A.J., Baldwin, B C. and Kelly, D.E. (1995) Biochem. Biophys. Res Commun., 207, 910-915.
8. Weishaar, P.D., Flynn. H.W., Murray, T.G., Davis, J.L., Barr, C.C., Gross, J.G., Mein, C.E., McLean, W.C. and Killian, J.H. (1998) Ophthalmology, 105, 57-65.
9. Vanden Bossche, H. (1986) Drug Dev. Res , 8, 287-298.
10. (a) Marichal, P. and Vanden Bossche, H. (1995) Acta Biochim. Pol., 42, 509-516
11. (b) Odds, F.C. (1993), J Antimicrob. Chemother., 31, 463-471.
12. Joseph-Thorne, T. and Hollomon, D.W. (1997) FEMS Microbiol. Lett., 149, 141-149.
13. White, T.C. (1997) Antimicrob. Agents Chemother., 41, 1488-1494.
14. Koymans, L.M., Moereels, H. and Vanden Bossche, H. (1995) J. Steroid. Biochem. Mol. Biol., 53, 191-197.
15. Rozman, D., Stromstedt, M., Tsui, L C., Scherer, S.W. and Waterman, M R. (1996) Genomics, 15, 371-381.
16. Sanglard, D., Ischer, F., Koymans, L. and Bille, J. (1998) Antimicrob Agents Chemother., 42, 241-253.
17. Hitchcock, C.A., Brown, S.B., Evans, E G. and Adams, D J. (1989) Biochem. J., 260, 549-556.
18. Fischer, R.T., Stam, S.H., Johnson, P.R., Ko, S.S., Magolda, R.L., Gaylor, J.L. and Trzaskos, J.M. (1989) J. Lipid Res., 30, 1621-1632.
19. Bak, S., Kahn, R.A , Olsen, C.E. and Halkier, B.A. (1997) Plant. J., 11, 191-201.
20. Nicolae, A., Cristea, T. and Supuran, C.T. (1997) Rev. Roum. Chim., 42, 301-306.
21. Supuran, C.T , Scozzafava, A., Briganti, F., Loloiu, G. and Maior, O., (1998) Eur. J. Med. Chem., 33, in press.
22. Supuran, C.T., Scozzafava, A., Briganti, F , Loloiu, G and Maior, O., (1998) J. Enz Inhib., 13, in press.
23. Briganti, F., Scozzafava, A and Supuran, C.T. (1997) Eur J. Med. Chem., 32, 901-910.
24. Beyer, H. and Kreutzberger, A. (1951) Chem. Ber., 84, 518-521.
25. (a) Kuhn, R. and Dury, K. (1951) Ann. Chem. 44, 571-578
26. (b) Plouvier, B. and Houssin, R. (1989). J. Het. Chem., 26, 1643-1647.
27. Ruggli, P., Herzog, M., Wegmann, J. and Dahn, H. (1946) Helv. Chim. Acta, 29, 95-99
28. (a) Barboru, M., Cimpoesu, M., Guran, C. and Supuran, C.T (1996) Metal Based Drugs, 3, 227-232
29. (b) Barboiu, M., Guran, C., Jitaru, I., Cimpoesu, M. and Supuran, C.T. (1996) Metal based Drugs, 3, 233-240.
30. Kinsman, O.S., Livermore, D.G. and Smith, C. (1993) Antimicrob. Agents Chemother., 37, 1242-1246.
31. (a) Hansbury, E. and Scallen, T.J. (1978) J. Lipid Res., 19, 742-746
32. (b) Ruan, B., Gerst, N., Emmons, G.T., Shey, J. and Schroepfer, G.J. (1997), J. Lipid Res., 38, 2615-2626.
33. (a) Aoyama, Y., Yoshida, Y., Sonoda, Y. and Sato, Y. (1991) Biochim Biophys. Acta, 1081, 262-266
34. (b) Aoyama, Y., Yoshida, Y., Sonoda, Y. and Sato, Y. (1992) Biochim. Biophys. Acta, 1122, 251-255.
35. (a) Aoyama, Y. and Yoshida, Y. (1992) Biochem. Biophys. Res. Commun., 183, 1266-1272
36. (b) Trzaskos, J.M., Ko, S.S., Magolda, R.L., Favata, M.F., Fischer, R.T., Stam, S.H., Johnson, P.R. and Gaylor, J.L (1995) Biochemistry, 34, 9670-9676.
37. Northey, E.H. (1948) The Sulfonamides and Allied Compounds, pp. 3-339. Reinhold: New York.
38. Mandell, G.L. and Sande, M.A. (1990), "Antimicrobial agents": In Goodman and Gilman's The Pharmacological Basis of Therapeutics A.G. Gilman et al. Eds , 8th Edition, pp. 1047-1057, Pergamon: New York.