Dihydropyridine-derived BODIPY probe for detecting exogenous and endogenous nitric oxide in mitochondria

Talanta. 2018 Jan 1:176:382-388. doi: 10.1016/j.talanta.2017.08.044. Epub 2017 Aug 14.

Abstract

A mitochondria-targetable probe Mito-DHP for nitric oxide (NO) was designed and synthesized by introducing dihydropyridine and triphenylphosphonium (TPP) moieties into boron dipyrromethene (BODIPY) dye. Mito-DHP was able to effectively detect nitric oxide through the aromatization of dihydropyridine to fluorescent pyridine product under oxygen-free conditions. The probe Mito-DHP showed high selectivity to NO over a number of reactive oxygen/nitrogen species (ROS/RNS) as well as high sensitivity (detection limit at 25nM), pH stability and bio-compatibility. Furthermore, Mito-DHP proved to target mitochondria specifically and to visualize both exogenous and endogenous NO in real time.

Keywords: BODIPY; Dihydropyridine; Fluorescent sensor; Mitochondria; Nitric oxide.

MeSH terms

  • Animals
  • Boron Compounds / chemistry*
  • Boron Compounds / pharmacology
  • Cell Survival / drug effects
  • Dihydropyridines / chemistry*
  • Dihydropyridines / pharmacology
  • Fluorescent Dyes / chemistry*
  • Fluorescent Dyes / pharmacology
  • Hep G2 Cells
  • Humans
  • Mice
  • Mitochondria / chemistry*
  • Mitochondria / drug effects
  • Mitochondria / metabolism
  • Nitric Oxide / analysis*
  • Nitric Oxide / chemistry
  • Nitric Oxide / metabolism
  • Organophosphorus Compounds / chemistry
  • Organophosphorus Compounds / pharmacology
  • RAW 264.7 Cells

Substances

  • 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene
  • Boron Compounds
  • Dihydropyridines
  • Fluorescent Dyes
  • Organophosphorus Compounds
  • triphenylphosphine
  • Nitric Oxide
  • 1,4-dihydropyridine