Synthesis and cytotoxic activity of 4-N-carboxybutyl-5-fluorocytosyl-Arg- Gln-Trp-Arg-Arg-Trp-Trp-Gln-Arg-NH 2

Csaba Somlai, Estela Correche, Monica Olivella, Laia Tolosa, Maria José Gomez Lechon, György Dombi, Gábor K. Tóth, Botond Penke, Ricardo D. Enriz

Research output: Contribution to journalArticle

2 Citations (Scopus)

Abstract

The chemical synthesis of 4-N-carboxybutyl-5-fluorocytosine (II) in solution phase starting from 5-fluorocytosine and the solid phase synthesis of Arg-Gln-Trp-Arg-Arg-Trp-Trp-Gln-Arg-NH 2 attached to the 4-N-carboxybutyl-5-fluorocytosine residue at the N-terminus of the peptide (III) via peptide bond formation is reported. The target compound exhibited a significant cytotoxic activity against a culture of HepG2 cells. In addition our results demonstrated that this new compound affect cell viability, produce mitochondrial dysfunction as well as interfere with intracellular calcium homeostasis control; leading to cell malfunction and death.

Original languageEnglish
Pages (from-to)4233-4237
Number of pages5
JournalBioorganic and Medicinal Chemistry Letters
Volume22
Issue number13
DOIs
Publication statusPublished - Jul 1 2012

Keywords

  • 5-Fluorocytosine adduct
  • Cytotoxic activity
  • Mitochondrial dysfunction
  • Nonapeptide attached to 4-N-carboxybutyl-5- fluorocytosine

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

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