Nucleosides and nucleotides. 155. Synthesis, antitumor effects, and possible enzymatic activation mechanism of 5'-phosphatidyl-2'-deoxy-2'-methylenecytidine (DMDC)

Bioorganic and Medicinal Chemistry Letters

Volumn 6, Issue 18, 1996, Pages 2177-2182

  Shuto, Satoshi ^a   Awano, Hirokazu ^a   Fujii, Akihiro ^b   Yamagami, Keiji ^b   Matsuda, Akira ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

^b Yoshitomi Pharmaceutical Industries Ltd   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ANTINEOPLASTIC AGENT; NUCLEOSIDE DERIVATIVE; PHOSPHOLIPID;

ANIMAL MODEL; ANIMAL TISSUE; ANTINEOPLASTIC ACTIVITY; ARTICLE; BACILLUS CEREUS; CATTLE; CONTROLLED STUDY; DRUG SYNTHESIS; ENZYME ACTIVATION; INTRAPERITONEAL DRUG ADMINISTRATION; LEUKEMIA; MOUSE; NONHUMAN; ORAL DRUG ADMINISTRATION; PANCREAS; SARCOMA; STREPTOMYCES;

ANIMALIA; BACILLUS CEREUS; BOS TAURUS; BOVINAE; STREPTOMYCES;

EID: 0030591703     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/0960-894X(96)00389-7     Document Type: Article

References (30)

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19. + form) to give 3 or 4 as a sodium salt.
20. 11PNa·2/3H2O: C, 58.80; H, 8.99; N, 4.57. Found: C, 58.82; H, 8.94; N, 4.59.
21. 2O: C, 58.81; H, 8.66; N, 4.57. Found: C, 58.72; H, 8.64; N, 4.40.
22. 8. Langdon, S. P.; Gescher, A.; Hickman, J. A.; Stevens, M. F. G. Eur. J. Cancer Clin. Oncol. 1984, 20, 699-705.
23. 9. PLC and PLD from mammalian sources were unavailable.
24. 2 was purchased from Sigma.
25. 2O (400 μL).
26. 2O: C, 52.92; H, 7.58; N, 6.38. Found: C, 52.84; H, 7.53; N, 6.16.
27. 2O (500 μL).
28. 14. In a preliminary experiment, 3 was inactive against DMDC-resistant P388 leukemia, which is deficient in deoxycytidine kinase activity, in mice (Yamagami, K. et al. unpublished results). This result suggests the inefficient intracellular release of DMDC 5′-phosphate by PLC.
29. 2O (500 μL).
30. 16. A time-dependent increase in DMDC was detected by HPLC.