A novel near-infrared fluorescent probe based on isophorone for the bioassay of endogenous cysteine

Org Biomol Chem. 2021 Jan 28;19(4):873-877. doi: 10.1039/d0ob02405h. Epub 2021 Jan 7.

Abstract

A dicyanoisophorone/acrylate-combined probe (DDP) was synthesized and designed as a near-infrared (NIR) fluorescent sensor for the rapid identification of Cys over Hcy and GSH in aqueous solution with a large Stokes shift (143 nm). The detection limit of Cys was 1.23 μM, which was lower than that of the intracellular Cys concentration. DDP was cell membrane-permeable and had been successfully applied to the detection of intracellular Cys in HeLa cells. The detection mechanism was determined by 1H NMR titration, MS and DFT calculations.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Biological Assay / methods*
  • Cyclohexanones / chemistry*
  • Cysteine / chemistry*
  • Cysteine / metabolism*
  • Density Functional Theory
  • Fluorescent Dyes / chemistry*
  • HeLa Cells
  • Humans
  • Infrared Rays*
  • Intracellular Space / metabolism
  • Limit of Detection
  • Models, Molecular
  • Molecular Conformation

Substances

  • Cyclohexanones
  • Fluorescent Dyes
  • isophorone
  • Cysteine