Allyl Fluorescein Ethers as Promising Fluorescent Probes for Carbon Monoxide Imaging in Living Cells

Anal Chem. 2017 Mar 21;89(6):3754-3760. doi: 10.1021/acs.analchem.7b00135. Epub 2017 Feb 28.

Abstract

Recently, the fluorescent detection of carbon monoxide (CO) in living cells has attracted great attention. However, due to the lack of effective ways to construct fluorescent CO probes, fluorescent detection of CO in living cells is still in its infancy. In this paper, we report for the first time the use of allyl ether as a reaction site for construction of fluorescent CO probes. By this way, two readily available allyl fluorescein ethers were prepared, which were found to be highly selective and sensitive probes for CO in the presence of PdCl2. These probes have the merits of good stability, good water-solubility, and rapid and distinct colorimetric and remarkable fluorescent turn-on signal changes. Moreover, a very low dose of these two probes can be used to detect and track CO in living cells, indicating that these two probes could be very promising biological tools for CO detection in living systems. Overall, this work provided not only two new promising fluorescent CO probes but also a new way to devise fluorescent CO probes.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Allyl Compounds / chemistry*
  • Allyl Compounds / pharmacology
  • Carbon Monoxide / analysis*
  • Cell Survival / drug effects
  • Dose-Response Relationship, Drug
  • Ethers / chemistry*
  • Ethers / pharmacology
  • Fluorescein / chemistry*
  • Fluorescein / pharmacology
  • Fluorescent Dyes / chemical synthesis
  • Fluorescent Dyes / chemistry*
  • Fluorescent Dyes / pharmacology
  • HeLa Cells
  • Humans
  • Hydrogen-Ion Concentration
  • Molecular Structure
  • Optical Imaging*
  • Spectrometry, Fluorescence

Substances

  • Allyl Compounds
  • Ethers
  • Fluorescent Dyes
  • Carbon Monoxide
  • Fluorescein