A highly fluorescent chemosensor for Zn(2+) and the recognition research on distinguishing Zn(2+) from Cd(2+)

Dalton Trans. 2014 Jan 14;43(2):706-13. doi: 10.1039/c3dt52165f.

Abstract

A new fluorescent sensor, 2-(2-oxo-2-(quinolin-8-ylamino)ethoxy)-N-(pyridine-2-ylmethyl) benzamide (L), composed of a quinoline group as the fluorogenic unit and a pyridin-2-ylmethanamine as the binding unit for metal ions has been synthesized. The sensor shows excellent selectivity and sensitivity with a fluorescence enhancement to Zn(2+) over other cations in acetonitrile aqueous solution. The X-ray crystal structure analysis reveals that sensor L coordinates to Zn(2+)via a 1 : 1 binding mode but to Cd(2+)via a 2 : 1 binding mode, which lead to a different spatial arrangement of the fluorogenic unit in these complexes. In addition, density functional theory calculations on L, and the Zn(2+)/L and Cd(2+)/L complexes also imply that the different structures of L significantly affect the molecular orbital energy levels and electron transition, which would result in the spectral changes to distinguish Zn(2+) from Cd(2+). The absorption study results may also suggest the Cd(2+) in the complex can be displaced by Zn(2+). Furthermore, the fluorescence imaging of Zn(2+) in living cells was obtained.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzamides / chemistry*
  • Binding, Competitive
  • Cadmium / chemistry*
  • Cell Survival
  • Chemistry Techniques, Analytical / instrumentation*
  • Crystallography, X-Ray
  • Fluorescent Dyes / chemistry*
  • Humans
  • Hydrogen-Ion Concentration
  • MCF-7 Cells
  • Models, Molecular
  • Molecular Conformation
  • Molecular Imaging
  • Quinolines / chemistry*
  • Zinc / analysis*
  • Zinc / chemistry*
  • Zinc / metabolism

Substances

  • 2-(2-oxo-2-(quinolin-8-ylamino)ethoxy)-N-(pyridine-2-ylmethyl)benzamide
  • Benzamides
  • Fluorescent Dyes
  • Quinolines
  • Cadmium
  • Zinc