Controllable selective synthesis of a polymerizable prodrug of cytarabine by enzymatic and chemical methods

Bioorganic and Medicinal Chemistry Letters

Volumn 15, Issue 18, 2005, Pages 4064-4067

  Wang, Na ^a   Zhi, Chun Chen ^a   De, Shui Lu ^a   Xian, Fu Lin ^a  

^a ZHEJIANG UNIVERSITY   (China)

Author keywords

Biocatalysis; Cytarabine; Enzymatic synthesis; Selectivity; Vinyl ester

Indexed keywords

ACETONE; ACRYLIC ACID RESIN; CYTARABINE DERIVATIVE; DICARBOXYLIC ACID; DIOXANE; PRODRUG; PYRIDINE; SUBTILISIN; TRIACYLGLYCEROL LIPASE;

ARTICLE; BACILLUS SUBTILIS; CANDIDA ANTARCTICA; CATALYSIS; DRUG SYNTHESIS; POLYMERIZATION; TRANSESTERIFICATION;

ACYLATION; ANTIMETABOLITES, ANTINEOPLASTIC; BACILLUS SUBTILIS; BACTERIAL PROTEINS; CYTARABINE; ENDOPEPTIDASES; ESTERS; LIPASE; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; POLYMERS; PRODRUGS;

BACILLUS SUBTILIS; CANDIDA ANTARCTICA;

EID: 23644442075     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.bmcl.2005.06.011     Document Type: Article

References (19)

1. T.S. Mansour, and R. Storer Curr. Pharm. Des. 3 1997 227
2. S. Czernecki, and J.M. Valery Z.J. Witczak K.A. Nieforth Carbohydrates in Drug Design 1997 Dekker New York 495
3. W. Plunkett, and V. Gandhi Cancer Chemother. Biol. Response Modif. Annu. 19 2001 21
4. R.L. Hanson, Z. Shi, D.B. Brozozowski, A. Banerjee, T.P. Kissick, J. Singh, A.J. Pullockaran, J.T. North, J. Fan, J. Howell, S.C. Durand, M.A. Montana, D.R. Kronenthal, R.H. Mueller, and R.N. Pater Bioorg. Med. Chem. 8 2000 2681
5. M. Ferrero, and V. Gotor Monatsh. Chem. 131 2000 585
6. M. Ferrero, and V. Gotor Chem. Rev. 100 2000 4319
7. M.G. Pallavicini Pharmacol. Ther. 25 1984 207
8. C.R. Wagner, V.V. Lyer, and E.J. Mclintee Cancer Res. 59 2000 2944
9. Q. Dang, B.S. Brown, P.D. Poelje, T.J. Colby, and M.D. Erion Bioorg. Med. Chem. Lett. 9 1999 1505
10. R.J. Jones, and N.M. Bischofberger Antiviral Res. 27 1995 1
11. S.C. Tobias, and R.F. Borch Mol. Pharmaceut. 1 2003 112
12. G. Cavallaro, G. Pitarresi, M. Licciardi, and G. Giammona Bioconjugate Chem. 12 2001 143
13. 2 corresponding exactly to 5′-O-vinlysebacate-cytarabine' molecular weight.
14. HPLC analysis: Samples were dissolved in methanol and analyzed by HPLC using a Kromasil 100 Å C-18 column (5 μm, 4.6 × 200 mm) in an Agilent 1100 system, eluted with acetonitrile/water (40/60, by vol.) at 1 ml/min and UV detection was carried out at 280 nm.
15. Q. Wu, N. Wang, Y.M. Xiao, and X.F. Lin Carbohydr. Res. 339 2004 2059
16. Y. Cai, S.P. Yao, Q. Wu, and X.F. Lin Biotechnol. Lett. 26 2004 525
17. N. Wang, Q. Wu, J.M. Xu, X.M. Jiang, and X.F. Lin Chin. Chem. Lett. 15 2004 547
18. D.L. Delinck, and A.L. Margolin Tetrahedron Lett. 31 1990 3093
19. K. Yoshimoto, Y. Itantani, and Y. Tsuda Chem. Pharm. Bull. 28 1980 2065