1,8-Naphthalimide-Cu(ІІ) ensemble based turn-on fluorescent probe for the detection of thiols in organic aqueous media

Bioorg Med Chem Lett. 2013 May 1;23(9):2538-42. doi: 10.1016/j.bmcl.2013.03.004. Epub 2013 Mar 14.

Abstract

A 1,8-naphthalimide-Cu(II) ensemble was rationally designed and synthesized as a new turn-on fluorescent probe utilizing the 'chemosensing ensemble' method for detections of thiols (Cys, Hcy and GSH) with high selectivity over other α-amino acids at pH 7.4 in organic aqueous media (EtOH/HEPES, v/v=9:1). The recognition mechanism was attributed to the remove Cu(II) from the 1,8-naphthalimide-Cu(II) ensemble by thiols and the release of flurescence of ligand 1. Remarkable fluorescence enhancements were therefore observed in the sensing process of thiols by the 1,8-naphthalimide-Cu(II) ensemble. Furthermore, the 1,8-naphthalimide-Cu(II) ensemble was successfully applied to the fluorescence imaging of thiols in CHO cells with high sensitivity and selectivity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • CHO Cells
  • Catalysis
  • Copper / chemistry*
  • Cricetinae
  • Cricetulus
  • Crystallography, X-Ray
  • Fluorescent Dyes / chemical synthesis
  • Fluorescent Dyes / chemistry*
  • Microscopy, Fluorescence
  • Molecular Conformation
  • Naphthalimides / chemistry*
  • Sulfhydryl Compounds / chemistry*

Substances

  • Fluorescent Dyes
  • Naphthalimides
  • Sulfhydryl Compounds
  • Copper