Highly selective and sensitive 1-amino BODIPY-based red fluorescent probe for thiophenols with high off-to-on contrast ratio

Anal Chem. 2015 Jan 6;87(1):399-405. doi: 10.1021/ac5028947. Epub 2014 Dec 9.

Abstract

A highly selective and sensitive turn-on red fluorescent 1-amino BODIPY-based probe (where BODIPY denotes indole-based boron-dipyrromethene) with high off-to-on contrast ratio has been developed. The probe displayed selective response to thiophenols over aliphatic thiols. Probe 1 is promising for the quantitative detection of thiophenol with a linear response from 6 × 10(-6) M to 1 × 10(-4) M, and the detection limit for thiophenol (PhSH) reaches 4 × 10(-6) M measured in acetonitrile/PBS buffer. The detection limit could be improved to 37 nM (detection limit to 4 ppb) in water when 1% Tween 20 was used to assist the dissolvation of probe 1 in water. Probe 1 is also a useful fluorescent probe for detecting thiophenols in living cells in red emission, which may greatly improve the detectable sensitivity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Boron Compounds* / chemistry
  • Carcinoma, Hepatocellular
  • Contrast Media* / chemistry
  • Crystallography, X-Ray
  • Fluorescent Dyes* / chemistry
  • Humans
  • Hydrogen-Ion Concentration
  • Image Processing, Computer-Assisted
  • Limit of Detection
  • Liver Neoplasms
  • Microscopy, Fluorescence
  • Phenols / analysis*
  • Sensitivity and Specificity
  • Sulfhydryl Compounds / analysis*
  • Tumor Cells, Cultured

Substances

  • 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene
  • Boron Compounds
  • Contrast Media
  • Fluorescent Dyes
  • Phenols
  • Sulfhydryl Compounds
  • thiophenol