Development of an Si-rhodamine-based far-red to near-infrared fluorescence probe selective for hypochlorous acid and its applications for biological imaging

J Am Chem Soc. 2011 Apr 20;133(15):5680-2. doi: 10.1021/ja111470n. Epub 2011 Mar 28.

Abstract

A far-red to near-infrared (NIR) fluorescence probe, MMSiR, based on Si-rhodamine, was designed and synthesized for sensitive and selective detection of HOCl in real time. MMSiR and its oxidized product SMSiR have excellent properties, including pH-independence of fluorescence, high resistance to autoxidation and photobleaching, and good tissue penetration of far-red to NIR fluorescence emission. The value of MMSiR was confirmed by real-time imaging of phagocytosis using a fluorescence microscope. wsMMSiR, a more hydrophilic derivative of MMSiR, permitted effective in vivo imaging of HOCl generation in a mouse peritonitis model. This probe is expected to be a useful tool for investigating the wide range of biological functions of HOCl.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Fluorescence
  • Fluorescent Dyes / chemistry*
  • Hypochlorous Acid / analysis*
  • Mice
  • Mice, Inbred C57BL
  • Microscopy, Fluorescence / methods
  • Neutrophils / cytology
  • Phagocytosis
  • Rhodamines / chemistry*
  • Silicon Compounds / chemistry*
  • Swine

Substances

  • Fluorescent Dyes
  • Rhodamines
  • Silicon Compounds
  • Hypochlorous Acid