A near-infrared fluorescent probe based on a hemicyanine dye with an oxazolidine switch for mitochondrial pH detection

J Mater Chem B. 2021 Jan 28;9(3):857-863. doi: 10.1039/d0tb02181d.

Abstract

A near-infrared fluorescent probe (AH+) has been prepared by incorporating an oxazolidine switch into a near-infrared hemicyanine dye. The probe shows fast and sensitive responses to pH from an oxazolidine switch to the hemicyanine dye upon pH decreases from 10.0 to 5.0. The probe shows good photostability, low cytotoxicity, and reversible fluorescence responses to pH changes with a pKa value of 7.6. It has been successfully used to determine pH changes in mitochondria.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Carbocyanines / chemical synthesis
  • Carbocyanines / chemistry*
  • Carbocyanines / pharmacology
  • Cell Survival / drug effects
  • Density Functional Theory
  • Dose-Response Relationship, Drug
  • Fluorescent Dyes / chemical synthesis
  • Fluorescent Dyes / chemistry*
  • Fluorescent Dyes / pharmacology
  • HeLa Cells
  • Humans
  • Hydrogen-Ion Concentration
  • Mitochondria / drug effects
  • Molecular Structure
  • Oxazoles / chemistry*
  • Oxazoles / pharmacology
  • Particle Size
  • Spectrometry, Fluorescence
  • Surface Properties

Substances

  • Carbocyanines
  • Fluorescent Dyes
  • Oxazoles
  • tetramethylene hemicyanine
  • oxazolidine