Arylphosphonate-Tethered Porphyrins: Fluorescence Silencing Speaks a Metal Language in Living Enterocytes*

Chembiochem. 2021 Jun 2;22(11):1925-1931. doi: 10.1002/cbic.202100031. Epub 2021 Mar 18.

Abstract

We report the application of a highly versatile and engineerable novel sensor platform to monitor biologically significant and toxic metal ions in live human Caco-2 enterocytes. The extended conjugation between the fluorescent porphyrin core and metal ions through aromatic phenylphosphonic acid tethers generates a unique turn off and turn on fluorescence and, in addition, shifts in absorption and emission spectra for zinc, cobalt, cadmium and mercury. The reported fluorescent probes p-H8 TPPA and m-H8 TPPA can monitor a wide range of metal ion concentrations via fluorescence titration and also via fluorescence decay curves. Cu- and Zn-induced turn off fluorescence can be differentially reversed by the addition of common chelators. Both p-H8 TPPA and m-H8 TPPA readily pass the mammalian cellular membrane due to their amphipathic character as confirmed by confocal microscopic imaging of living enterocytes.

Keywords: Caco-2; fluorescence sensors; homeostasis; metals; time-resolved fluorescence.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Caco-2 Cells
  • Coordination Complexes / chemistry*
  • Enterocytes / chemistry*
  • Fluorescence
  • Fluorescent Dyes / chemistry*
  • Humans
  • Metals, Heavy / analysis*
  • Organophosphonates / chemistry*
  • Porphyrins / chemistry*

Substances

  • Coordination Complexes
  • Fluorescent Dyes
  • Metals, Heavy
  • Organophosphonates
  • Porphyrins

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