Pyrrole-coupled salicylimine-based fluorescence "turn on" probe for highly selective recognition of Zn²⁺ ions in mixed aqueous media: Application in living cell imaging

J Mol Recognit. 2015 Jun;28(6):369-75. doi: 10.1002/jmr.2451. Epub 2015 Feb 24.

Abstract

Cation sensing behaviour of a pyrrole-based derivative (2-hydroxyl 3 methyl 6 isopropyl benzaldehyde}-3,4-dimethyl-1H-pyrrole-2-carbohydrazide (receptor 3) has been explored and is found to be selective towards Zn(2+) over a variety of tested cations. The receptor 3 has shown high selectivity and sensitivity towards Zn(2+) over the other alkali, alkaline earth and transition metal ions. In the presence of Zn(2+), absorption band of receptor 3 has shown the red shift. The sensing behaviour has been suggested to continue via enhancement process which has further been supported by UV-vis absorption and theoretical density functional theory (DFT) calculations indicating the formation of a 1:1 complex between the pyrrole based receptor 3 and Zn(2+). The present work is presenting a highly selective dual channel colorimetric sensor for zinc with great sensitivity. The developed sensor was successfully applied to image intracellular Zn(2+) in living cells.

Keywords: (2-hydroxyl 3 methyl 6 isopropyl benzaldehyde}-3,4-dimethyl-1H-pyrrole-2-carbohydrazide (receptor 3); UV-vis absorption; Zn2+; cell image; density functional theory (DFT).

MeSH terms

  • Fluorescent Dyes / chemistry*
  • HeLa Cells
  • Humans
  • Hydrazines / chemistry*
  • Pyrroles / chemistry*
  • Spectrometry, Fluorescence
  • Zinc / analysis*
  • Zinc / chemistry

Substances

  • Fluorescent Dyes
  • Hydrazines
  • Pyrroles
  • Zinc