First round of a focused library of cholera toxin inhibitors

Carbohydrate Research

Volumn 342, Issue 12-13, 2007, Pages 1651-1660

  Podlipnik, Črtomir ^a   Velter, Ingrid ^b   Ferla, Barbara La ^b   Marcou, Gilles ^a   Belvisi, Laura ^a   Nicotra, Francesco ^b   Bernardi, Anna ^a  

^a UNIVERSITY OF MILAN   (Italy)

^b UNIVERSITY OF MILANO BICOCCA   (Italy)

Author keywords

C Glycosides; Carbohydrate mimics; Cholera toxin; Glycomimetics; GM1 ganglioside

Indexed keywords

C-GLYCOSIDES; CHOLERA TOXIN; GLYCOMIMETICS; GM1 GANGLIOSIDE; MICROMOLAR AFFINITY;

CARBOHYDRATES; SCAFFOLDS; TOXIC MATERIALS;

ENZYME INHIBITION;

1 AZIDO 2 (2,3,4,6 TETRA O ACETYL ALPHA DEXTRO GALACTOPYRANOSYL)ETHANE; 2 (2,3,4,6 TETRA O ACETYL ALPHA DEXTRO GALACTOPYRANOSYL)ETHANOL; 2 (ALPHA DEXTRO GALACTOPYRANOSYL)ETHYLAMINE; 3 (2,3,4,6 TETRA O ACETYL ALPHA DEXTRO GALACTOPYRANOSYL)PROPENE; ANTITOXIN; ASIALOFETUIN; CHOLERA TOXIN; GALACTOSIDE; SCAFFOLD PROTEIN; UNCLASSIFIED DRUG;

ARTICLE; CARBOHYDRATE ANALYSIS; HYDROLYSIS; LIBRARY SCIENCE; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; PROTEIN BINDING; SCORING SYSTEM; TOXICITY TESTING; VALIDATION PROCESS; X RAY CRYSTALLOGRAPHY;

ANTITOXINS; CARBOHYDRATE CONFORMATION; CARBOHYDRATE SEQUENCE; CHOLERA TOXIN; GLYCOSIDES; MODELS, MOLECULAR; MOLECULAR SEQUENCE DATA; OLIGOSACCHARIDES;

EID: 34447296192     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carres.2007.06.006     Document Type: Article

References (47)

1. Cholera 1999, WHO Weekly Epidemiolog. Rev. Vol. 75, August 4, 2000; pp 249-256.
2. Lencer W.I., and Slaslwsky D. Biochim. Biophys. Acta 1746 (2005) 314-321
3. Fan E., O'Neil C.J., Mithchell D.D., Robien M.A., Zhang Z., Pickens J.C., Tan X.-J., Korotkov K., Roach C., Krumm B., Verlinde C.L.M.J., and Merritt E.A. Int. J. Med. Micr. 294 (2004) 217-223
4. Moss J., and Vaughan M. J. Biol. Chem. 252 (1977) 2455-2457
5. Cassel D., and Pfeuffer T. Proc. Natl. Acad. Sci. U.S.A. 75 (1978) 2669-2673
6. Fan E., Merritt E.A., Verlinde C.L.M.J., and Hol W.G.J. Curr. Opin. Chem. Biol. 10 (2000) 680-686
7. Velter I.A., Politi M., Podlipnik C., and Nicotra F. Minirev. Med. Chem. 7 (2007) 159-170
8. Merritt E.A., Kuhn P., Sarfaty S., Erbe J.L., Holmes R.K., and Hol W.G.J. J. Mol. Biol. 282 (1998) 1043-1059
9. Merritt E.A., Sarfaty S., van den Akker F., L'Hoir C., Martial J.A., and Hol W.G.J. Protein Sci. 3 (1994) 166-175
10. Turnbull W.B., Precious B.L., and Homans S.W. J. Am. Chem. Soc. 126 (2004) 1047-1054
11. Bernardi A., Checchia A., Brocca P., Sonnino S., and Zuccotto F. J. Am. Chem. Soc. 121 (1999) 2032-2036
12. Acquotti D., Poppe L., Dabrowski J., van der Lieth C.-W., Sonnino S., and Tettamanti G. J. Am. Chem. Soc. 112 (1990) 7772-7778
13. Bernardi A., Podlipnik C., and Jiménez-Barbero J. GM1 Glycomimetics and Bacterial Enterotoxins. Protein-Carbohydrate Interactions in Infectious Diseases (2006), RSC, Bewley, CA 73-91
14. Bernardi A., Arosio D., Potenza D., Sanchez-Medina I., Mari S., Cañada F.J., and Jiménez-Barbero J. Chem. Eur. J. 10 (2004) 4395-4406
15. Arosio D., Baretti S., Cattaldo S., Potenza D., and Bernardi A. Bioorg. Med. Chem. Lett. (2003) 3831-3834
16. Bernardi A., Carrettoni V., Grosso Ciponte V., Monti D., and Sonnino S. Bioorg. Med. Chem. Lett. 13 (2000) 2197-2200
17. Bernardi A., Potenza D., Capelli A.M., Garcìa-Herrero A., Cañada F.J., and Jiménez-Barbero J. Chem. Eur. J. 8 (2002) 4598-4612
18. Bernardi A., Arosio D., and Sonnino S. Neurochem. Res. 27 (2002) 539-545
19. Bernardi A., Arosio D., Manzoni L., Monti D., Posteri H., Potenza D., Mari S., and Jiménez-Barbero J. Org. Biomol. Chem. 1 (2003) 1-9
20. Minke W.E., Roach C., Hol W.G., and Verlinde C.L. Biochem. 38 (1999) 5684-5692
21. Minke W.E., Hong F., Verlinde C.L., Hol W.G., and Fan E. J. Biol. Chem. 274 (1999) 33469-33473
22. Pickens J.C., Merritt E.A., Ahn M., Verlinde C.L.M.J., Hol W.G.J., and Fan E. Chem. Biol. 9 (2002) 215-224
23. Mitchell D.D., Pickens J.C., Korotkov K., Fan E., and Hol W.G.J. Bioorg. Med. Chem. 12 (2004) 907-920
24. Postema M.H.D. C-Glycoside Synthesis (1995), CRC Press, Boca Raton
25. Levy D.E., and Tang C. The Chemistry of C-Glycosides. Tetrahedron Organic Chemistry Series Vol. 13 (1995), Pergamon, New York
26. Nicotra F. Synthesis of C-glycosides of Biological Interest. Topics in Current Chemistry Vol. 187 (1997), Springer, Berlin Heidelberg 56-83
27. Nicotra F. Modified Carbohydrates and Carbohydrate Analogs (1997), Chapman & Hall, Blackie Academic & Professional, London pp 384-429
28. Du Y., and Linhardt J.R. Tetrahedron 54 (1998) 9913-9959
29. Bililign T.G.B.R., and Thorson J.S. Nat. Prod. Rep. 22 (2005) 742-760
30. Yuan Y., and Linhardt J.R. Curr. Top. Med. Chem. 5 (2005) 1393-1430
31. La Ferla B., Cardona F., Perdigão I., and Nicotra F. Synlett 17 (2005) 2641-2642
32. Morris G.M., Goodsell D.S., Halliday R.S., Huey R., Hart W.E., Belew R.K., and Olson A.J. J. Comput. Chem. 19 (1998) 1639-1662
33. Minke W.E., Diller D.J., Hol W.G.J., and Verlinde C.L. J. Med. Chem. 42 (1999) 1778-1788
34. Friesner R.A., Banks J.L., Murphy R.B., Halgren T.A., Klicic J.J., Mainz D.T., Repasky M.P., Knoll E.H., Shaw D.E., Shelley M., Perry J.K., Francis P., and Shenkin P.S. J. Med. Chem. 47 (2004) 1739-1749
35. Halgren T.A., Murphy R.B., Friesner R.A., Beard H.S., Frye L.L., Pollard W.T., and Banks J.L. J. Med. Chem. 47 (2004) 1750-1759
36. Bennek J.A., and Gray G.A. J. Org. Chem. 52 (1987) 892-897
37. Broxterman H.J.G., Kooreman P.A., van der Elst H., Roelen H.C.P.F., van der Marel G.A., and van Boom J.H. Recl. Trav. Chim. Pays-Bas 109 (1990) 583
38. Arosio D., Vrasidas I., Valentini P., Liskamp R.M.J., Pieters R.J., and Bernardi A. Org. Biomol. Chem. 2 (2004) 2113-2124
39. de Mol N.J., Plomp E., Fischer M.J.E., and Ruijtenbeek R. Anal. Biochem. 279 (2000) 61-70
40. Schrodinger. FirstDiscovery 2.5, User Manual, March 2003.
41. Bernardi A., Raimondi L., and Zuccotto F. J. Med. Chem. 40 (1997) 1855-1862
42. Warren G.L., Andrews C.W., Capelli A.-M., Clarke B., LaLonde J., Lambert M.H., Lindvall M., Nevins N., Semus S.F., Senger S., Tedesco G., Wall I.D., Woolven J.M., Peishoff C.E., and Head M.S. J. Med. Chem. 49 (2006) 5912-5931
43. Senderowitz H., Parish C., and Still W.C. J. Am. Chem. Soc. 118 (1996) 2078-2086
44. Weininger D. J. Chem. Inf. Comput. Sci. 28 (1988) 31-36
45. Sadowski J., and Gasteiger J. Chem. Rev. 93 (1993) 2567-2581
46. Sadowski J., Gasteiger J., and Klebe G. J. Chem. Inf. Comput. Sci. 34 (1994) 1000-1008
47. Mertz J.A., McCann J.A., and Picking W.D. Biochem. Biophys. Res. Commun. 226 (1996) 140-144