Zwitterionic N2O2-Type Protonated Dipyrrin Bearing a Phosphate Anionic Moiety as a pH-Responsive Fluorescence Indicator

Org Lett. 2015 Jun 19;17(12):3114-7. doi: 10.1021/acs.orglett.5b01414. Epub 2015 Jun 4.

Abstract

Zwitterionic protonated-dipyrrin 1 bearing a phosphate unit was synthesized from the N2O2-type tetradentate dipyrrin ligand. Compound 1 is in equilibrium with the deprotonated form 1' with a pKa value of 5.8. Compound 1 exhibited a pH-responsive fluorescence under physiological conditions; the fluorescence intensity increased in aqueous media as the pH increased. In living cells, 1 also exhibited emission responsive to pH. Thus, 1 should be applicable as a pH probe for detecting tumor cells.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Fluorescent Dyes / chemistry*
  • Hydrogen-Ion Concentration*
  • Ligands
  • Molecular Structure
  • Nitrous Oxide / chemistry*
  • Phosphates / chemistry*
  • Pyrroles / chemical synthesis*
  • Pyrroles / chemistry*
  • Spectrometry, Fluorescence

Substances

  • Fluorescent Dyes
  • Ligands
  • Phosphates
  • Pyrroles
  • Nitrous Oxide