Synthesis, electrochemical and spectral properties of some ω-N-quinonyl amino acids

S. Bittner, S. Gorohovsky, O. Paz-Tal Levi, J. Y. Becker

Research output: Contribution to journalArticlepeer-review

33 Scopus citations

Abstract

Four series of ω-N-quinonyl amino acids were synthesized by Michael-like additions. The quinones include 2-phenylthio-1,4-benzoquinone, 1,4-naphthoquinone, 2-methyl-1,4-naphthoquinone and 2,3-dichloro-1,4-naphthoquinone. These modified amino acids can be used for post chain assembly modifications of biologically active peptides, which target the quinonic drug to a cancer damaged area. The electron-transfer capabilities of the modified amino acids were probed by cyclic voltammetry measurements. The results described in this paper show that the novel N-quinonyl amino acids are effective in producing semiquinone radicals similarly to the unconjugated quinones themselves. A direct relation was found between the first reduction potentials of the quinones and their reactivity towards the ω-amino acids. The successful generation of stable semiquinone radicals by the novel quinone derivatives is a prerequisite for the manifestation of site-directed antitumor activity of corresponding quinone-peptide conjugates.

Original languageEnglish
Pages (from-to)71-93
Number of pages23
JournalAmino Acids
Volume22
Issue number1
DOIs
StatePublished - 28 Feb 2002

Keywords

  • Amino acids
  • Cyclic voltammetry
  • Quinones
  • Redox potentials

ASJC Scopus subject areas

  • Biochemistry
  • Clinical Biochemistry
  • Organic Chemistry

Fingerprint

Dive into the research topics of 'Synthesis, electrochemical and spectral properties of some ω-N-quinonyl amino acids'. Together they form a unique fingerprint.

Cite this