Novel isopentenyladenosine analogues: Synthesis, characterization, and evaluation of antiproliferative activity on bladder carcinoma cells

Roberta Ottria, Silvana Casati, J. A M Maier, Massimo Mariotti, Pierangela Ciuffreda

Research output: Contribution to journalArticle

Abstract

Isopentenyladenosine (iPA), a member of the cytokinin family of plant hormones, exerts a marked antiproliferative activity on some leukemic and epithelial cancer cell lines. To characterize the molecular moieties required for the in vitro antitumor activity of the molecule and to obtain cytostatic iPA derivatives potentially useful as chemotherapeutic agents, N9-acyclic analogues have been synthesized using regioselective Mitsunobu reaction and characterized by elemental analyses, 1H and 13C NMR. These compounds were analyzed for their activity on human bladder cancer cell lines. In this study, we report that iPA inhibited the proliferation but not the migration of human bladder cancer cells, while the newly synthesized analogues revealed no significant cytostatic activity apart from the compound with a saturated double bond of the isopentenyl chain. These results indicate that the integrity of the ribose ring is required for the cytostatic activity of iPA.

Original languageEnglish
Pages (from-to)736-751
Number of pages16
JournalNucleosides, Nucleotides and Nucleic Acids
Volume28
Issue number8
DOIs
Publication statusPublished - Aug 2009

Keywords

  • Acyclic nucleosides
  • Antitumor agents
  • Bladder carcinoma cells
  • Isopentenyladenosine

ASJC Scopus subject areas

  • Biochemistry
  • Genetics
  • Molecular Medicine

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