A highly specific ferrocene-based fluorescent probe for hypochlorous acid and its application to cell imaging

Analyst. 2010 Mar;135(3):577-82. doi: 10.1039/b921187j. Epub 2010 Jan 18.

Abstract

A highly specific ferrocene-based fluorescent probe, (9-anthryl)ethenylferrocene, has been designed, synthesized and characterized for fluorescence imaging of hypochlorous acid (HOCl) in live cells. The design strategy for the probe is based on the strong quenching effect of electron-donor ferrocene on anthracene fluorescence via an intramolecular charge transfer process, and is accomplished through constructing the conjugated molecule by using a cleavable double bond as a linker. The double bond in the probe reacts selectively with HOCl rather than the other reactive oxygen species (e.g., *OH, *O(2)(-), (1)O(2), and H(2)O(2)) in pH 7.4, accompanied by more than 100-fold fluorescence enhancement. Moreover, the probe is cell membrane permeable, and its applicability has been successfully demonstrated for fluorescence imaging of HOCl in HeLa cells.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Ferrous Compounds / chemistry*
  • Fluorescent Dyes / chemistry*
  • HeLa Cells
  • Humans
  • Hypochlorous Acid / chemistry*
  • Metallocenes
  • Microscopy, Fluorescence / methods*
  • Reactive Oxygen Species / metabolism

Substances

  • Ferrous Compounds
  • Fluorescent Dyes
  • Metallocenes
  • Reactive Oxygen Species
  • Hypochlorous Acid
  • ferrocene