Synthesis of a new water-soluble oligo(phenylenevinylene) containing a tyrosine moiety for tyrosinase activity detection

Org Lett. 2008 Dec 4;10(23):5369-72. doi: 10.1021/ol802210s.

Abstract

A new water-soluble oligo(phenylenevinylene) containing a tyrosine unit (OPV-Tyr) was synthesized as a fluorescent probe to optically detect tyrosinase activity. Upon the addition of tyrosinase, the tyrosine moiety was oxidized to quinone, which quenched the fluorescence of OPV-Tyr via intramolecular electron transfer from the phenylenevinylene unit to the quinone site. OPV-Tyr was elaborated to detect tyrosinase activity both in aqueous buffer solution and in agarose gel.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Enzyme Assays / methods*
  • Fluorescent Dyes / chemical synthesis
  • Fluorescent Dyes / chemistry
  • Monophenol Monooxygenase / metabolism*
  • Polyethylene Glycols / chemistry
  • Polyvinyls / chemical synthesis*
  • Polyvinyls / chemistry*
  • Solubility
  • Spectrometry, Fluorescence
  • Tyrosine / chemistry*
  • Water / chemistry*

Substances

  • Fluorescent Dyes
  • Polyvinyls
  • oligo(p-phenylene vinylene)
  • Water
  • Polyethylene Glycols
  • Tyrosine
  • Monophenol Monooxygenase