Nucleotide derivatives of 2,7-diaminomitosene

Bhashyam S. Iyengar, Robert T Dorr, William A. Remers, Charles D. Kowal

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

Treatment of mitomycin C with pyrimidine nucleotides in acidic media produced derivatives of 2,7-diaminomitosene in which C-1 was covalentiy bound to the phosphate group of the nucleotides. On reduction, these derivatives liberated the nucleotides and a mitomycin intermediate that alkylated DNA. Their reduction in the presence of 2′-deoxyguanosine produced some bifunctional alkylation as did mitomycin C. They were readily taken up by L1210 leukemia cells, in which they showed potent cytotoxicity. These properties suggest that they are acting as prodrugs capable of conversion into two active species. The uridylate derivative showed activity comparable to that of mitomycin C against P-388 leukemia in mice.

Original languageEnglish (US)
Pages (from-to)1579-1585
Number of pages7
JournalJournal of Medicinal Chemistry
Volume31
Issue number8
StatePublished - 1988

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Mitomycin
Nucleotides
Derivatives
Pyrimidine Nucleotides
Leukemia L1210
Deoxyguanosine
Alkylation
Prodrugs
Cytotoxicity
Leukemia
Phosphates
2,7-diaminomitosene
DNA

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Iyengar, B. S., Dorr, R. T., Remers, W. A., & Kowal, C. D. (1988). Nucleotide derivatives of 2,7-diaminomitosene. Journal of Medicinal Chemistry, 31(8), 1579-1585.

Nucleotide derivatives of 2,7-diaminomitosene. / Iyengar, Bhashyam S.; Dorr, Robert T; Remers, William A.; Kowal, Charles D.

In: Journal of Medicinal Chemistry, Vol. 31, No. 8, 1988, p. 1579-1585.

Research output: Contribution to journalArticle

Iyengar, BS, Dorr, RT, Remers, WA & Kowal, CD 1988, 'Nucleotide derivatives of 2,7-diaminomitosene', Journal of Medicinal Chemistry, vol. 31, no. 8, pp. 1579-1585.
Iyengar BS, Dorr RT, Remers WA, Kowal CD. Nucleotide derivatives of 2,7-diaminomitosene. Journal of Medicinal Chemistry. 1988;31(8):1579-1585.
Iyengar, Bhashyam S. ; Dorr, Robert T ; Remers, William A. ; Kowal, Charles D. / Nucleotide derivatives of 2,7-diaminomitosene. In: Journal of Medicinal Chemistry. 1988 ; Vol. 31, No. 8. pp. 1579-1585.
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