A novel chromo- and fluorogenic dual sensor for Mg(2+) and Zn(2+) with cell imaging possibilities and DFT studies

Analyst. 2014 Aug 21;139(16):4022-30. doi: 10.1039/c3an02347h.

Abstract

A diformyl-p-cresol (DFC)-8-aminoquinoline based dual signaling probe was found to exhibit colorimetric and fluorogenic properties on selective binding towards Mg(2+) and Zn(2+). Turn-on fluorescent enhancements (FE) as high as 40 fold and 53 fold in 9 : 1 MeCN/water (v/v) at pH 7.2 in HEPES buffer for Mg(2+) and Zn(2+), respectively, were observed. The binding constants determined from the fluorescence titration data are: K = (1.52 ± 0.21) × 10(5) M(-1) and (9.34 ± 4.0) × 10(3) M(-2) at n = 1 and 0.5, for Mg(2+) and Zn(2+), respectively. The L : M binding ratios were also determined by Job's method, which support the above findings. This is further substantiated by HRMS analysis. Due to solubility in mixed organo-aqueous solvents as well as cell permeability it could be used for the in vitro/in vivo cell imaging of Mg(2+) and Zn(2+) ions with no or negligible cytotoxicity. This probe could be made selective towards Mg(2+) over Zn(2+) in the presence of TPEN, both under intra- and extracellular conditions and is superior to other Mg(2+) probes which suffer from selectivity of Mg(2+) over Ca(2+) or Zn(2+). Furthermore the dissociation constant (Kd = 6.60 μM) of the Mg(2+)-() complex is far lower than the so far reported Mg(2+) probes which fall in the mM range.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aminoquinolines / chemistry*
  • Cations, Divalent / analysis
  • Colorimetry
  • Cresols / chemistry*
  • Fluorescent Dyes / chemistry*
  • Hep G2 Cells
  • Humans
  • Magnesium / analysis
  • Microscopy, Fluorescence
  • Models, Molecular
  • Optical Imaging*
  • Spectrometry, Fluorescence
  • Zinc / analysis*

Substances

  • Aminoquinolines
  • Cations, Divalent
  • Cresols
  • Fluorescent Dyes
  • 4-cresol
  • Magnesium
  • Zinc
  • 8-aminoquinoline