Hydrophobic derivatives of 2-amino-2-deoxy-D-glucitol-6-phosphate: A new type of D-glucosamine-6-phosphate synthase inhibitors with antifungal action

Bioorganic and Medicinal Chemistry

Volumn 11, Issue 8, 2003, Pages 1653-1662

  Janiak, Agnieszka M ^a   Hoffmann, Maria ^a   Milewska, Maria J ^a   Milewski, Sławomir ^a  

^a GDANSK UNIVERSITY OF TECHNOLOGY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

2 (N ACETYLAMINO) 2 DEOXY DEXTRO GLUCITOL 6 PHOSPHATE DIETHYL ESTER; 2 (N ACETYLAMINO) 2 DEOXY DEXTRO GLUCITOL 6 PHOSPHATE ETHYL ESTER; 2 AMINO 2 DEOXY DEXTRO GLUCITOL 6 PHOSPHATE; 2 AMINO 2 DEOXY DEXTRO GLUCITOL 6 PHOSPHATE DIETHYL ESTER; 2 AMINO 2 DEOXY DEXTRO GLUCITOL 6 PHOSPHATE DIMETHYL ESTER; 2 N ACETYLAMINO 2 DEOXY DEXTRO GLUCITOL 6 PHOSPHATE DIMETHYL ESTER; 6 [2 DEOXY 2 (N ACETYLAMINO) DEXTRO GLUCOPYRANOSYL]DIETHYLPHOSPHATE; 6 [2 DEOXY 2 (N BENZYLOXYCARBONYLAMINO) DEXTRO GLUCOPYRANOSIDYL]DIETHYLPHOSPHATE; 6 [BENZYL 2 DEOXY 2 (N ACETYLAMINO) DEXTRO GLUCOPYRANOSIDYL]DIETHYLPHOSPHATE; 6 [METHYL 2 DEOXY 2 (N BENZYLOXYCARBONYLAMINO) DEXTRO GLUCOPYRANOSIDYL]DIETHYLPHOSPHATE; ANTIFUNGAL AGENT; BENZYL 2 DEOXY 2 (N ACETYLAMINO) DEXTRO GLUCOPYRANOSIDE; CHITIN; DEXTRO GLUCOSAMINE 6 PHOSPHATE SYNTHASE; ENZYME INHIBITOR; FUNGAL ENZYME; METHYL 2 DEOXY 2 (N BENZYLOXYCARBONYLAMINO) DEXTRO GLUCOPYRANOSIDE; N ACETYL 2 AMINO 2 DEOXY DEXTRO GLUCITOL 6 PHOSPHATE; N BUTANOYL 2 AMINO 2 DEOXY DEXTRO GLUCITOL 6 PHOSPHATE; N CHLOROACETYL 2 AMINO 2 DEOXY DEXTRO GLUCITOL 6 PHOSPHATE; N HEXANOYL 2 AMINO 2 DEOXY DEXTRO GLUCITOL 6 PHOSPHATE; N IODOACETYL 2 AMINO 2 DEOXY DEXTRO GLUCITOL 6 PHOSPHATE; PHOSPHORUS ACID DERIVATIVE; UNCLASSIFIED DRUG;

ANTIFUNGAL ACTIVITY; ARTICLE; CELL MEMBRANE; CELL TRANSPORT; CONTROLLED STUDY; DRUG BINDING; DRUG DIFFUSION; DRUG MECHANISM; DRUG SCREENING; DRUG SYNTHESIS; ENZYME ACTIVITY; ENZYME INHIBITION; FUNGAL CELL; FUNGAL STRAIN; HYDROPHOBICITY; MINIMUM INHIBITORY CONCENTRATION; NONHUMAN;

EID: 12244262320     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0968-0896(03)00049-X     Document Type: Article

References (31)

1. Neely M.N., Ghannoum M. Eur. J. Microbiol. Infect. Dis. 19:2000;897.
2. Georgopapadakou N.H. Curr. Opin. Microbiol. 1:1998;547.
3. Walsh T.J., Vivani M.A., Arathoon E., Chiou C., Ghannoum M., Groll A.H., Odds F.C. Med. Mycol. 38:2000;335.
4. Borowski E. Il Farmaco. 55:2000;206.
5. Milewski S., Chmara H., Andruszkiewicz R., Borowski E., Zaremba M., Borowski J. Drugs Exptl. Clin. Res. 14:1988;461.
6. Milewski S., Andruszkiewicz R., Borowski E. FEMS Microbiol. Lett. 50:1988;73.
7. Horak J. Biochim. Biophys. Acta. 1331:1997;41.
8. Badet-Denisot M.-A., Leriche C., Masserie F., Badet B. Bioorg. Med. Chem. Lett. 5:1995;815.
9. Le Camus C., Badet-Denisot M.-A., Badet B. Tetrahedron Lett. 39:1998;2571.
10. Le Camus C., Chassange A., Badet-Denisot M.-A., Badet B. Tetrahedron Lett. 39:1998;287.
11. Janiak A., Cybulska B., Szlinder-Richert J., Borowski E., Milewski S. Acta Biochim. Polon. 49:2002;77.
12. Bearne S.L. J. Biol. Chem. 271:1996;3052.
13. Ong S., Liu H., Pidgeon C. J. Chrom. A. 728:1996;113.
14. Bearne S.L., Blouin C. J. Biol. Chem. 275:2000;135.
15. Badet-Denisot, M.-A.; Leriche, C.; Badet, B. In Chitin Enzymology; Muzzarelli, R.A.A., Ed., European Chitin Society: Ancona, 1993, p 161.
16. Teplyakov A., Obmolova G., Badet-Denisot M.-A., Badet B. Protein Sci. 8:1999;596.
17. Leriche C., Badet-Denisot M.-A., Badet B. J. Am. Chem. Soc. 118:1996;1797.
18. Milewski S., Andruszkiewicz R., Kasprzak L., Mignini F., Mazerski J., Borowski E. Antimicrob. Agents Chemother. 35:1988;36.
19. Becker J.M., Covert N.L., Shenbagamurthi P., Steinfeld A.S., Naider F. Antimicrob. Agents Chemother. 23:1983;926.
20. Hector R.F., Brown P.C. Antimicrob. Agents Chemother. 29:1986;389.
21. Vespa M.N., Lebecq J.C. Mycoses. 39:1996;271.
22. Connors T.A. Xenobiotica. 16:1989;975.
23. Manoharan M., Johnson L.K., McGee G.P., Guinosso C.J., Ramasamy K., Springer R.H., Bennett C.F., Ecker D.J., Vickers T., Cowsert L. Ann. New York Acad. Sci. 660:1992;306.
24. Merck, E. In Anfärbereagenzien für Dünnschicht- und Papier-Chromatographie, Darmstadt, 1970, p 4-5.
25. Chargaff E., Bovarnick M. J. Biol. Chem. 118:1937;421.
26. Kenig M., Vandamme E., Abraham E.P. J. Gen. Microbiol. 94:1976;46.
27. Noltmann E.A. J. Biol. Chem. 239:1963;1545.
28. Chirgwin J.M., Noltmann E.A. J. Biol. Chem. 250:1975;7272.
29. Document M27-A. National Committee for Clinical Laboratory Standards: Wayne, PA, 1997.
30. Bartlett G. J. Biol. Chem. 234:1959;466.
31. Bollag, D. M.; Edelstein, J. S. In Protein Methods. Wiley-Liss: New York, 1991.