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

C. Somlai, Estela Correche, Monica Olivella, Laia Tolosa, Maria José Gomez Lechon, G. Dombi, G. Tóth, B. 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

Fingerprint

Flucytosine
Peptides
Solid-Phase Synthesis Techniques
Hep G2 Cells
Cell Survival
Homeostasis
Cell Death
Cells
Calcium

Keywords

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

ASJC Scopus subject areas

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

Cite this

Synthesis and cytotoxic activity of 4-N-carboxybutyl-5-fluorocytosyl-Arg- Gln-Trp-Arg-Arg-Trp-Trp-Gln-Arg-NH 2 . / Somlai, C.; Correche, Estela; Olivella, Monica; Tolosa, Laia; Lechon, Maria José Gomez; Dombi, G.; Tóth, G.; Penke, B.; Enriz, Ricardo D.

In: Bioorganic and Medicinal Chemistry Letters, Vol. 22, No. 13, 01.07.2012, p. 4233-4237.

Research output: Contribution to journalArticle

Somlai, C. ; Correche, Estela ; Olivella, Monica ; Tolosa, Laia ; Lechon, Maria José Gomez ; Dombi, G. ; Tóth, G. ; Penke, B. ; Enriz, Ricardo D. / Synthesis and cytotoxic activity of 4-N-carboxybutyl-5-fluorocytosyl-Arg- Gln-Trp-Arg-Arg-Trp-Trp-Gln-Arg-NH 2 In: Bioorganic and Medicinal Chemistry Letters. 2012 ; Vol. 22, No. 13. pp. 4233-4237.
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AU - Tolosa, Laia

AU - Lechon, Maria José Gomez

AU - Dombi, G.

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AU - Penke, B.

AU - Enriz, Ricardo D.

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