Synthesis and cytogenetic effects of aminoquinone derivatives with a di- and a tripeptide

Anticancer Drugs. 2002 Apr;13(4):367-72. doi: 10.1097/00001813-200204000-00005.

Abstract

Quinones are of significant interest due to their important role in specific cellular functions. Quinoproteins are a big class of oxyreductive agents occurring in bacteria and other organisms. In this investigation derivatives of 2-amino-1,4-benzoquinone, 2-amino-1,4-naphthoquinone and 2-amino-5,8-dihydroxy-1,4-naphthoquinone with a di- and a tripeptide were prepared for first time. The effect of the synthesized compounds on sister chomatid exchange (SCE) rates and human lymphocyte proliferation kinetics on a molar basis was studied. Among these coupled products the most effective in inducing SCEs and depressing proliferation rate indices is the coupling product of 2-amino-1,4-naphthoquinone with the tripeptide GHK (10). Next in order of magnitude in inducing cytogenetic effects is 2-amino-1,4-naphthoquinone (2) and its coupling products with glycine and serine (4 and 5), while the rest displayed marginal activity.

MeSH terms

  • Benzoquinones / chemical synthesis*
  • Benzoquinones / pharmacology*
  • DNA Damage
  • DNA Repair
  • Humans
  • Lymphocytes / ultrastructure
  • Metaphase / drug effects
  • Naphthoquinones / chemical synthesis*
  • Naphthoquinones / pharmacology*
  • Oligopeptides / chemistry*
  • Sister Chromatid Exchange / drug effects*

Substances

  • Benzoquinones
  • Naphthoquinones
  • Oligopeptides