A daunorubicin β-galactoside prodrug for use in conjunction with gene- directed enzyme prodrug therapy

Ajit K. Ghosh, Saeed Khan, Frank Marini, J. Arly Nelson, David Farquhar

Research output: Contribution to journalArticle

Abstract

N-[4-(β-D-Galactopyranosyl)-3-nitrobenzyloxycarbonyl]daunomycin was synthesized as a neutral prodrug of daunomycin. Although stable in 0.05 M phosphate buffer, pH 7.4 at 37°C, it was rapidly converted to daunomycin and 3-nitro-4-hydroxybenzyl alcohol under the same conditions in the presence of E. coli β-galactosidase. (C) 2000 Elsevier Science Ltd.

Original languageEnglish (US)
Pages (from-to)4871-4874
Number of pages4
JournalTetrahedron Letters
Volume41
Issue number25
StatePublished - Jun 19 2000
Externally publishedYes

Keywords

  • β-Galactosidase
  • Anthracycline
  • Daunomycin
  • Gene therapy
  • Prodrug

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

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  • Cite this

    Ghosh, A. K., Khan, S., Marini, F., Nelson, J. A., & Farquhar, D. (2000). A daunorubicin β-galactoside prodrug for use in conjunction with gene- directed enzyme prodrug therapy. Tetrahedron Letters, 41(25), 4871-4874.