Facile synthesis of anthracene-appended amino acids as highly selective and sensitive fluorescent Fe3+ ion sensors

Bioorg Med Chem Lett. 2009 Nov 1;19(21):6069-73. doi: 10.1016/j.bmcl.2009.09.036. Epub 2009 Sep 17.

Abstract

We designed new fluorescent chemical sensors for Fe3+ ion detection, by conjugating amino acids as receptors into an anthracene fluorophore. The conjugates were synthesized in solid phase by Fmoc-chemistry. Fluorescence sensors containing Asp (1) and Glu (2) both had exclusive selectivity for Fe3+ in 100% aqueous solution and in a mixed organic-aqueous solvent system. Other metal ions did not interfere with the detection ability of the sensors for Fe3+. The sensors detect Fe3+ ions via a chelation-enhanced fluorescent quenching effect. The binding affinity, reversible monitoring, and pH sensitivity of the sensors were investigated. In addition, detection of fluoride ion among halide ions was done by a chemosensing ensemble method with 1-Fe3+ and 2-Fe3+ complexes.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amino Acids / chemistry*
  • Anthracenes / chemical synthesis*
  • Anthracenes / chemistry
  • Aspartic Acid / analogs & derivatives*
  • Aspartic Acid / chemical synthesis
  • Aspartic Acid / chemistry
  • Fluorescent Dyes / chemistry*
  • Glutamates / chemical synthesis*
  • Glutamates / chemistry
  • Hydrogen-Ion Concentration
  • Iron / analysis*
  • Spectrometry, Fluorescence

Substances

  • Amino Acids
  • Anthracenes
  • Fluorescent Dyes
  • Glutamates
  • Aspartic Acid
  • Iron
  • anthracene