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

Shengyong Yan; Rong Huang; Changcheng Wang; Yimin Zhou; Jiaqi Wang; Boshi Fu; Xiaocheng Weng; Xiang Zhou

doi:10.1002/asia.201200762

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.

Authors

Shengyong Yan¹, Rong Huang, Changcheng Wang, Yimin Zhou, Jiaqi Wang, Boshi Fu, Xiaocheng Weng, Xiang Zhou

Affiliation

¹ College of Chemistry and Molecular Sciences, Key Laboratory of Biomedical Polymers of Ministry of Education, Wuhan University, Hubei, Wuhan, 430072, PR China.

PMID: 23023989
DOI: 10.1002/asia.201200762

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