A two-photon fluorescent probe for intracellular detection of tyrosinase activity

Chem Asian J. 2012 Dec;7(12):2782-5. doi: 10.1002/asia.201200762. Epub 2012 Sep 28.

Abstract

AAN effective sensor: The two-photon turn-on fluorescent probe NHU was synthesized to optically detect tyrosinase activity in vitro and in melanoma cells. NHU is composed of a 4-aminophenol moiety and a naphthylamine unit, both of which are connected through a urea linkage. Upon exposure to tyrosinase, the 4-aminophenol site is gradually oxidized to the corresponding orthoquinone, ultimately releasing the highly fluorescent product 6-acyl-N-methyl-2-naphthylamine (AAN).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • 2-Naphthylamine / chemistry
  • 2-Naphthylamine / metabolism
  • Aminophenols / chemistry
  • Aminophenols / metabolism*
  • Cell Line, Tumor
  • Enzyme Activation
  • Enzyme Assays / methods
  • Fluorescent Dyes / chemistry
  • Fluorescent Dyes / metabolism*
  • Humans
  • Melanoma / enzymology
  • Microscopy, Confocal / methods
  • Monophenol Monooxygenase / analysis
  • Monophenol Monooxygenase / metabolism*
  • Oxidation-Reduction

Substances

  • Aminophenols
  • Fluorescent Dyes
  • 2-Naphthylamine
  • Monophenol Monooxygenase
  • 4-aminophenol