Evaluation of toxicity on epithelial and tumor cells of biaryl dipeptide tyrosines

Eur J Med Chem. 2016 May 23:114:1-7. doi: 10.1016/j.ejmech.2016.02.062. Epub 2016 Mar 2.

Abstract

We report a method to obtain biaryl dipeptide tyrosine via Suzuki-Miyaura and alkynyl dipeptide tyrosine by Sonogashira cross-coupling reactions. Analysis of the biological action of biaryl dipeptide tyrosine 4d compound showed its ability to impair the metabolism and proliferation of SK-Mel-28 human melanoma lineage cells, independently of mitochondrial membrane depolarization, apoptosis and necrosis. Moreover, 4d compound did not cause toxicity to human umbilical vein endothelial cells (HUVEC), suggesting its toxic specificity to cancer cells.

Keywords: Alkyne; Dipeptide; Melanoma; Tumor; Tyrosine.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cell Death / drug effects
  • Cell Proliferation / drug effects
  • Cells, Cultured
  • Dipeptides / chemical synthesis
  • Dipeptides / chemistry
  • Dipeptides / toxicity*
  • Dose-Response Relationship, Drug
  • Human Umbilical Vein Endothelial Cells / cytology*
  • Human Umbilical Vein Endothelial Cells / metabolism
  • Humans
  • Molecular Structure
  • Neoplasms / metabolism
  • Neoplasms / pathology*
  • Structure-Activity Relationship
  • Tyrosine / chemical synthesis
  • Tyrosine / chemistry
  • Tyrosine / toxicity*

Substances

  • Dipeptides
  • Tyrosine