Recognition and sensing of nucleoside monophosphates by a dicopper(II) cryptate

J Am Chem Soc. 2010 Jan 13;132(1):147-56. doi: 10.1021/ja9046262.

Abstract

The dimetallic cryptate [Cu(2)(II)(1)](4+) selectively recognizes guanosine monophosphate with respect to other nucleoside monophosphates (NMPs) in a MeOH/water solution at pH 7. Recognition is efficiently signaled through the displacement of the indicator 6-carboxyfluorescein bound to the receptor, monitoring its yellow fluorescent emission. Titration experiments evidenced the occurrence of several simultaneous equilibria involving 1:1 and 2:1 receptor/NMP and receptor/indicator complexes. It was demonstrated that the added NMP displaces the indicator from the 2:1 receptor/indicator complex, forming the 1:1 receptor/analyte inclusion complex. Recognition selectivity is thus ascribed to the nature of nucleotide donor atoms involved in the coordination and their ability to encompass the Cu(II)-Cu(II) distance within the cryptate.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Copper / chemistry*
  • Crown Ethers / chemistry*
  • Fluorescent Dyes / chemistry
  • Fluorescent Dyes / metabolism
  • Hydrogen-Ion Concentration
  • Methanol / chemistry
  • Models, Molecular
  • Molecular Conformation
  • Nitrogen / chemistry
  • Nucleotides / metabolism*
  • Organometallic Compounds / chemistry*
  • Organometallic Compounds / metabolism*
  • Oxygen / chemistry
  • Substrate Specificity
  • Water / chemistry

Substances

  • Crown Ethers
  • Fluorescent Dyes
  • Nucleotides
  • Organometallic Compounds
  • Water
  • Copper
  • Nitrogen
  • Oxygen
  • Methanol