Synthesis and evaluation of p-nitrophenyl β-D-glucopyranosiduronic analogues as new triggers for β-glucuronidase mediated prodrug mono-therapy

Letters in Drug Design and Discovery

Volumn 2, Issue 8, 2005, Pages 631-637

  Combaud, Damien ^a   Thomas, Mickaël ^a   Papot, Śbastien ^a   Gesson, Jean Pierre ^a  

^a UNIVERSITÉ DE POITIERS   (France)

Author keywords

D glucuronide; glucuronidase; A.D.E.P.T.; Cancer; Chemotherapy; P.M.T.; Prodrug; Trigger

Indexed keywords

4 NITROPHENYL 3 DEOXY 3 BETA DEXTRO GLUCOPYRANOSYLURONIC ACID; 4 NITROPHENYL 3 DEOXY 3 FLUORO BETA DEXTRO GLUCOPYRANOSYLURONIC ACID; 4 NITROPHENYL 3 O METHYL BETA DEXTRO GLUCOPYRANOSYLURONIC ACID; 4 NITROPHENYL 4 DEOXY BETA DEXTRO GLUCOPYRANOSYLURONIC ACID; BETA GLUCURONIDASE; GLUCOPYRANOSIDE; GLUCURONIDE; LIVER ENZYME; PRODRUG; UNCLASSIFIED DRUG;

ARTICLE; CONTROLLED STUDY; COW; DRUG HYDROLYSIS; DRUG SCREENING; DRUG SYNTHESIS; ENZYME SUBSTRATE COMPLEX; ESCHERICHIA COLI; MONOTHERAPY; NONHUMAN; PRIORITY JOURNAL;

EID: 29044437267     PISSN: 15701808     EISSN: None     Source Type: Journal    
DOI: 10.2174/157018005774717271     Document Type: Article

References (30)

1. Andersen, J.H., Warrens, H.W. and McAndle, C.S. Clin. Pharmacokinet., 1994, 27, 1994.
2. Thorpe, P.E. and Burrows, F.J. Breast Cancer Res. Treat., 1995, 36, 237-251.
3. Gabizon, A. In Drug Carriers Systems. Roerdinck, F.H and Kroon, A.M. Eds, 1989, 185, Wiley.
4. Reisfeld, R.A. and Schrappe, M. In Therapeutic Monoclonal Antibodies, Borrebaeck, C.A.K. and Larrick, J.W. Eds, 1990, 57, Stockton Press.
5. Lappi, D.A. and Baird, A. Prog. Growth Factor Res., 1991, 2, 223.
6. Rooseboom, M., Commandeur, J.N.M. and Vermeulen, N.P.E. Pharmacol. Rev., 2004, 56, 53.
7. Denny, W.A. Aust. J. Chem., 2004, 57, 821.
8. Papot, S., Tranoy, I., Tillequin, F., Florent, J.-C. and Gesson, J.-P. Curr. Med. Chem.- Anticancer agents, 2002, 2, 155.
9. Bagshawe, K.D. Drug Dev. Res., 1995, 34, 220.
10. Springer, C. and Niculescu-Duvaz, I. J. Clin, Inv., 2000, 105, 1161.
11. Naylor, M.A. and Thomson, P. Mini Rev. Med. Chem.,2001, 1, 17.
12. Florent, J.-C., Dong, X., Gaudel, G., Mitaku, S., Monneret, C., Gesson, J.-P., Jacquesy, J.-C., Mondon, M., Renoux, B., Andrianomenjanahary, S., Koch, M., Michel, S., Tillequin, F., Gerken, M., Czech, J., Straub, R., Bosslet, K. J. Med. Chem. 1998, 41, 3572.
13. A.D.E.P.T.: Antibody Directed Enzyme Prodrug Therapy. Bosslet, K., Czech, J., Lorenz, P., Sedlacek, H.H., Schuermann, M. and Seeman, G. Br. J. Cancer, 1992, 65, 234.
14. P.M.T.: Prodrug Mono-Therapy. Bosslet, K., Czech, J. and Hoffman, D. Tumor Targeting, 1995, 1, 45.
15. Azoulay, M., Ivastehenko, N., Florent, J.-C. and Monneret, C. Bioorg. Med. Chem. Lett., 1997, 7, 1307.
16. Namchuk, M.N. and Withers, S.G. Biochemistry, 1995, 34, 16194.
17. Zeller, S.G., D'Ambra, A.J., Rice, M.J. and Gray, G.R. Carbohydr. Res., 1988, 182, 53.
18. Adiyaman, M., Lawson, J.A., Hwang, S.-W., Khanapure, S.P., FitzGerald, G.A. and Rokach, J. Tetrahedron Lett., 1996, 37, 4849.
19. Argentini, M., Weinreich, R., Oberti, R., Ungaretti, L. J. Fluorine Chem., 1986, 32, 239.
20. Sen, A.S., Sarkar, K.K., Banerji, N. J. Carbohydr. Chem., 1988, 7, 645.
21. Withers, S.G., Percival, M.D., Street, I.P. Carbohydr. Res., 1989, 187, 43.
22. Withers, S.G., MacLennan, D.J. and Street, I.P. Carbohydr. Res., 1986, 154, 127.
23. Bordas, A., Liptak, A. Carbohydr. Res., 1993, 241, 99.
24. Goebel, W.F., Babers, F.H. J. Biol. Chem., 1933, 100, 744.
25. Glanzer, B., Gyorgydeàk, Z., Bernet, B., Vasella, A. Helv. Chem. Acta, 1991, 74, 343.
26. Bazin, H.G., Kerns, R.J., Linhart, R.J. Tetrahedron Lett., 1997, 38, 923.
27. de Graaf, M., Nevalainen, T.J., Scheeren, H.W., Pinedo, H.M., Haisma, H.J. and Boven, E. Biochem. Pharmacol., 2004, 68, 2273.
28. Jain, S., Drendel, W.B., Chen, Z.-N., Mathews, F.S., Sly, W.S., Grubb, J.H. Nat. Struct. Biol., 1996, 3, 375.
29. Himino, M., Hashiguchi, Y., Kato, K.J. J. Biochem., 1974, 76, 1243.
30. Brot, F.E., Bell, C. Jr., Sly, W.S. Biochemistry, 1978, 17, 385.