Thio-derived disulfides as potent inhibitors of botulinum neurotoxin type B: Implications for zinc interaction

Bioorganic and Medicinal Chemistry

Volumn 11, Issue 21, 2003, Pages 4655-4660

  Anne, Christine ^a   Blommaert, Armand ^a   Turcaud, Serge ^a   Martin, Anne Sophie ^a   Meudal, Hervé ^a   Roques, Bernard P ^a  

^a Laboratoire de Pharmacochimie   (France)

Author keywords

[No Author keywords available]

Indexed keywords

BENZOIC ACID DERIVATIVE; BOTULINUM TOXIN B; BOTULINUM TOXIN B INHIBITOR; DISULFIDE; TRIPEPTIDE DERIVATIVE; UNCLASSIFIED DRUG; ZINC ION;

ARTICLE; CHELATION; CHEMICAL MODIFICATION; DRUG PROTEIN BINDING; DRUG STRUCTURE; IC 50; STRUCTURE ANALYSIS;

EID: 0141504167     PISSN: 09680896     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0968-0896(03)00450-4     Document Type: Article

References (33)

1. Middlebrook, J. L. Cell surface receptors for protein toxins. In Botulinum Neurotoxin and Tetanus Toxin; Simpson L.L., Ed.; Academic: San Diego, CA, 1989; p 95.
2. Shapiro R.L., Hatheway C., Swerdlow D.L. Ann. Intern. Med. 129:1998;221.
3. Schiavo G., Santucci A., Dasgupta B.R., Mehta P.P., Jontes J., Benfenati F., Wilson M.C., Montecucco C. FEBS Lett. 335:1993;99.
4. Schiavo G., Benfenati F., Poulain B., Rossetto O., Polverino de Laureto P., DasGupta B.R., Montecucco C. Nature. 359:1992;832.
5. Yamasaki S., Baumeister A., Binz T., Blasi J., Link E., Cornille F., Roques B.P., Fykse E.M., Südhof T.C., Jahn R., Niemann H. J. Biol. Chem. 269:1994;12764.
6. Yamasaki S., Binz T., Hayashi T., Szabo E., Yamasaki N., Eklund M., Jahn R., Niemann H. Biochem. Biophys. Res. Commun. 200:1994;829.
7. Foran P., Lawrence G.W., Shone C.C., Foster K.A., Dolly J.O. Biochemistry. 35:1996;2630.
8. Simpson L.L. Pharmacol. Rev. 33:1981;155.
9. Montecucco C., Papini E., Schiavo G. FEBS Lett. 346:1994;92.
10. Schiavo G., Rossetto O., Santucci A., DasGupta B.R., Montecucco C. J. Biol. Chem. 267:1992;23479.
11. Leggiadro R.J. Infect. Control Hosp. Epidemiol. 21:2000;53.
12. Therre H. Eurosurveillance. 4:1999;2.
13. Shone C.C., Quinn C.P., Wait R., Hallis B., Fooks S.G., Hambleton P. Eur. J. Biochem. 217:1993;965.
14. Adler M., Nicholson J.D., Cornille F., Hackley B.E. Jr. FEBS Lett. 429:1998;234.
15. Adler M., Nicholson J.D., Starks D.F., Kane C.T., Cornille F., Hackley B.E. Jr. J. Appl. Toxicol. 19(Suppl. 1):1999;S5.
16. de Paiva A., Ashton A.C., Foran P., Schiavo G., Montecucco C., Dolly J.O. J. Neurochem. 61:1993;2338.
17. Foran P., Shone C.C., Dolly J.O. Biochemistry. 33:1994;15365.
18. Adler M., Dinterman R.E., Wannemacher R.W. Toxicon. 35:1997;1089.
19. Keller J.E., Nowakowski J.L., Filbert M.G., Adler M. J. Appl. Toxicol. 19(Suppl. 1):1999;S13.
20. Hanson M.A., Oost T.K., Sukonpan C., Rich D.H., Stevens R.C. J. Am. Chem. Soc. 122:2000;11268.
21. Garcia G.E., Moorad D.R., Gordon R.K. J. Appl. Toxicol. 19(Suppl. 1):1999;S19.
22. Satoh E., Ishii T., Shimizu Y., Sawamura S., Nishimura M. J. Pharmacol. 132:2001;797.
23. Anne, C., Turcaud, S., Quancard, J., Teffo, F., Meudal, H., Fournié-Zaluski, M.C., Roques, B.P. J. Med. Chem. in press.
24. Roques B.P., Noble F., Daugé V., Fournié-Zaluski M.C., Beaumont A. Pharmacol. Rev. 45:1993;87.
25. Fournié Zaluski M.C., Coric P., Turcaud S., Bruetschy L., Lucas E., Noble F., Roques B.P. J. Med. Chem. 35:1992;1259.
26. Jacobsen E.J., Mitchell M.A., Hendges S.K., Belonga K.L., Skaletzky L.L., Stelzer L.S., Lindberg T.J., Fritzen E.L., Schostarez H.J., O'Sullivan T.J., Maggiora L.L., Stuchly C.W., Laborde A.L., Kubicek M.F., Poorman R.A., Beck J.M., Miller H.R., Petzold G.L., Scott P.S., Truesdell S.E., Wallace T.L., Wilks J.W., Fisher C., Goodman L.V., Kaytes P.S., Ledbetter S.R., Powers C.A., Vogeli G., Mott J.E., Trepod C.M., Staples D.J., Baldwin E.T., Finzel B.C. J. Med. Chem. 42:1999;1525.
27. Anne C., Cornille F., Lenoir C., Roques B.P. Anal. Biochem. 291:2001;253.
28. Eswaramoorthy S., Kumaran D., Swaminathan S. Biochemistry. 41:2002;9795.
29. Hiskey R.G., Muthukumaraswamy N., Vunnam R.R. J. Org. Chem. 40:1975;950.
30. Ferris N.S., Woodruff W.H., Rorabacher D.B., Jones T.E., Ochymowycz L.A. J. Am. Chem. Soc. 100:1978;5939.
31. Yamauchi O., Seki H., Shoda T. Bull. Chem. Soc. Jpn. 56:1983;3258.
32. Mc Cormick, D. B., Griesser, R., Sigel, H. In Metal Ions in Biological Systems; Marcel Dekker: New York, 1974; p 213.
33. Harpp D.N., Granata A. J. Org. Chem. 45:1980;271.