Azulene-Derived Fluorescent Probe for Bioimaging: Detection of Reactive Oxygen and Nitrogen Species by Two-Photon Microscopy

J Am Chem Soc. 2019 Dec 11;141(49):19389-19396. doi: 10.1021/jacs.9b09813. Epub 2019 Nov 27.

Abstract

Two-photon fluorescence microscopy has become an indispensable technique for cellular imaging. Whereas most two-photon fluorescent probes rely on well-known fluorophores, here we report a new fluorophore for bioimaging, namely azulene. A chemodosimeter, comprising a boronate ester receptor motif conjugated to an appropriately substituted azulene, is shown to be an effective two-photon fluorescent probe for reactive oxygen species, showing good cell penetration, high selectivity for peroxynitrite, no cytotoxicity, and excellent photostability.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Azulenes / chemistry*
  • Azulenes / toxicity
  • Cell Survival / drug effects
  • Fluorescent Dyes / chemistry*
  • Fluorescent Dyes / toxicity
  • HeLa Cells
  • Humans
  • Limit of Detection
  • Microscopy, Fluorescence, Multiphoton / methods*
  • Reactive Nitrogen Species / analysis*
  • Reactive Oxygen Species / analysis*

Substances

  • Azulenes
  • Fluorescent Dyes
  • Reactive Nitrogen Species
  • Reactive Oxygen Species
  • azulene