Reductively activated disulfide prodrugs of paclitaxel

Bioorganic and Medicinal Chemistry Letters

Volumn 12, Issue 24, 2002, Pages 3591-3594

  Vrudhula, Vivekananda M ^a   MacMaster, John F ^a   Li, Zhengong ^a   Kerr, David E ^a   Senter, Peter D ^a  

^a BRISTOL MYERS SQUIBB   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CAPTOPRIL; DISULFIDE; PACLITAXEL; PRODRUG; DITHIOTHREITOL;

ANIMAL EXPERIMENT; ANIMAL MODEL; ANTINEOPLASTIC ACTIVITY; ARTICLE; CARCINOMA CELL; CONTROLLED STUDY; DRUG ACTIVITY; DRUG SYNTHESIS; IN VIVO STUDY; NONHUMAN; ANIMAL; CELL CULTURE; CELL DIVISION; DRUG EFFECT; EXPERIMENTAL NEOPLASM; HALF LIFE TIME; HUMAN; IC 50; METABOLISM; MOUSE; NUDE MOUSE; OXIDATION REDUCTION REACTION; SYNTHESIS; TREATMENT OUTCOME;

ANIMALS; CELL DIVISION; DISULFIDES; DITHIOTHREITOL; HALF-LIFE; HUMANS; INHIBITORY CONCENTRATION 50; MICE; MICE, NUDE; NEOPLASMS, EXPERIMENTAL; OXIDATION-REDUCTION; PACLITAXEL; PRODRUGS; TREATMENT OUTCOME; TUMOR CELLS, CULTURED;

EID: 0036889637     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(02)00784-9     Document Type: Article

References (17)

1. Wouters B.G., Weppler S.A., Koritzinsky M., Landuyt W., Nuyts S., Theys J., Chiu R.K., Lambin P. Eur. J. Cancer. 38:2002;240.
2. (a) Iyer V.N., Szybalski W. Science. 145:1964;55.
3. (b) Tomasz M. Curr. Biol. 9:1995;575.
4. Brown J.M. Br. J. Cancer. 67:1993;1163.
5. (a) Hay M.P., Sykes B.M., Denny W.A., Wilson W.R. Bioorg. Med. Chem. Lett. 9:1999;2237.
6. (b) Denny W.A. Curr. Pharm. Des. 8:2002;1349.
7. Damen E.W.P., Nevalainen T.J., van den Bergh T.J.M., de Groot F.M.H., Scheeren H.W. Bioorg. Med. Chem. 10:2002;71.
8. (a) Vyas, D. M.; Chang, Y.; Benigni, D.; Rose, W. C.; Bradner, W. T.; Doyle, T. W. In Recent Advances in Chemotherapy, Anticancer Section 1; Ishigami, J. Ed.; University of Tokyo: Tokyo, 1985; pp 485-486.
9. (b) Senter, P. D.; Langley, D. R.; Manger, W. E.; Vyas, D. M. J. Antibiot. 1988, 41, 199.
10. Taxane Anticancer Agents Basic Science and Current Status; Georg, G. I., Chen, T. T., Ojima, I., Vyas, D. M., Eds. ACS Symposium Series 583, American Chemical Society: Washington D.C., 1995.
11. Senter P.D., Marquardt H., Thomas B.A., Hammock B.D., Frank I.S., Svensson H.P. Cancer Res. 56:1996;1471.
12. Zhao Z., Kingston D.G.I. J. Nat. Prod. 54:1991;1607.
13. Eliel, E. L. In Stereochemistry of Carbon Compounds: McGraw Hill: New York, 1962: pp 197-202.
14. Volpert O.V., Ward W.F., Lingen M.W., Chesler L., Solt D.B., Johnson M.D., Molteni A., Polverini P.J., Bouck N.P. J: Clin. Invest. 98:1996;671.
15. Singh G., Sharma P.D. Indian J. Pharm. Sci. 56:1994;69.
16. Baas J.L., Davies-Fidder A., Huisman H.O. Tetrahedron. 22:1966;285.
17. 2O (3:2). Fractions containing required compound were analyzed on 5 μ Brownlee reversed-phase column with MeCN: Sod.phosphate buffer (50 mM, pH 3.5, 2:3) at λ 230 nm. Fractions containing pure compound were combined and lyophilized to give 3 (63 mg, 53% yield).