Methoxyquinoline-diethylenetriamine conjugate as a fluorescent zinc sensor

Dalton Trans. 2011 May 14;40(18):4976-81. doi: 10.1039/c0dt00791a. Epub 2011 Mar 15.

Abstract

A 6-methoxyquinoline conjugated diethylenetriamine derivative, N,N''-bis(6-methoxy-2-quinolylmethyl)diethylenetriamine (6-MeOBQDIEN) has been synthesized and its fluorescent response toward zinc ion was investigated. In the presence of zinc ion, 6-MeOBQDIEN exhibits fluorescence (λ(ex) = 329 nm, λ(em) = 418 nm, φ = 0.039). The fluorescent intensity of the zinc complex of the compound is two times higher than the parent BQDIEN (φ = 0.021) under the same conditions. The crystal structure of 6-MeOBQDIEN-Zn complex shows that all five nitrogen atoms participate to the metal coordination in a distorted square-pyramidal geometry (τ = 0.145) with the aliphatic nitrogen in an apical position. Fluorescent microscopic analysis using 6-MeOBQDIEN reveals the zinc ion concentration change in living cells.

MeSH terms

  • Animals
  • Cell Line, Tumor
  • Crystallography, X-Ray
  • Hydrogen-Ion Concentration
  • Molecular Conformation
  • Polyamines / chemical synthesis
  • Polyamines / chemistry*
  • Polyamines / pharmacology
  • Quinolines / chemical synthesis
  • Quinolines / chemistry*
  • Quinolines / pharmacology
  • Rats
  • Spectrophotometry, Ultraviolet
  • Zinc / chemistry*

Substances

  • N,N''-bis(6-methoxy-2-quinolylmethyl)diethylenetriamine
  • Polyamines
  • Quinolines
  • diethylenetriamine
  • 6-methoxyquinoline
  • Zinc