Synthesis of 7- and 10-spermine conjugates of paclitaxel and 10-deacetyl-paclitaxel as potential prodrugs

Arturo Battaglia, Andrea Guerrini, Eleonora Baldelli, Gabriele Fontana, Greta Varchi, Cristian Samorì, Ezio Bombardelli

Research output: Contribution to journalArticle

15 Scopus citations

Abstract

Efficient syntheses of two taxol analogs bearing the linear polyamine spermine at 7- and 10-positions of paclitaxel and 10-deacetyl-paclitaxel have been developed. These polyamine-taxol-conjugates were isolated as water soluble difluoride salts. The aim of the present work was to introduce a chemical modification into taxol skeleton in order to increase drug selectivity toward tumor cells. The cytotoxic activity of these conjugates was evaluated in MCF7 and MCF7-R cell lines. The observed low cytotoxicity suggests that these conjugates could act as potential prodrugs.

Original languageEnglish (US)
Pages (from-to)2667-2670
Number of pages4
JournalTetrahedron Letters
Volume47
Issue number16
DOIs
StatePublished - Apr 17 2006

Keywords

  • Antitumor
  • Paclitaxel
  • Prodrug conjugates
  • Spermine

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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