Novel sulphur-rich BODIPY systems that enable stepwise fluorescent O-atom turn-on and H2O2 neuronal system probing

Chem Commun (Camb). 2012 Jul 25;48(58):7298-300. doi: 10.1039/c2cc33076h. Epub 2012 Jun 14.

Abstract

Bis-arylsulfide BODIPY systems were prepared and studied for multiple O-atom sensing (at 522 nm); 2- and 3-atom loading was optimal (50-fold, "turn on"). Neuronal studies showed greater H(2)O(2) sensitivity than 2',7'-dichlorofluorescein diacetate. The novel 1,3,6-trimethyl BODIPY formed as a biproduct under Lindsey conditions.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Boron Compounds / chemistry*
  • Cell Line, Tumor
  • Chlorobenzoates / chemistry
  • Copper / chemistry
  • Crystallography, X-Ray
  • Fluorescent Dyes / chemistry
  • Humans
  • Hydrogen Peroxide / analysis*
  • Magnetic Resonance Spectroscopy
  • Microscopy, Fluorescence*
  • Molecular Conformation
  • Neurons / metabolism
  • Oxidation-Reduction
  • Oxygen / chemistry*
  • Sulfur / chemistry*

Substances

  • 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene
  • Boron Compounds
  • Chlorobenzoates
  • Fluorescent Dyes
  • Sulfur
  • Copper
  • Hydrogen Peroxide
  • 3-chloroperbenzoic acid
  • Oxygen