Hydrophilic molecular rotor derivatives-synthesis and characterization

Bioorg Chem. 2004 Aug;32(4):274-89. doi: 10.1016/j.bioorg.2004.04.002.

Abstract

Recent research shows high potential for some p-N,N-dialkylaminobenzylidenecyanoacetates, part of a group known as fluorescent molecular rotors, to serve as fluorescent, non-mechanical viscosity sensors. Of particular interest are molecules compatible with aqueous environments. In this study, we present the synthesis and physical characterization of derivatives from 9-(2-carboxy-2-cyanovinyl)-julolidine and related molecules. All compounds show a power-law relationship of fluorescence emission with the viscosity of the solvent, different mixtures of ethylene glycol and glycerol to modulate viscosity. Compounds with high water solubility exhibit the same behavior in aqueous solutions of dextran, where the dextran concentration was varied to modulate viscosity. In addition, some compounds have been found to have low sensitivity towards changes in the pH in the physiological range. The compounds presented show promise to be used in biofluids, such as blood plasma or lymphatic fluid, to rapidly and non-mechanically determine viscosity.

Publication types

  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Acetates / chemical synthesis
  • Acetates / chemistry
  • Fluorescent Dyes / chemical synthesis*
  • Fluorescent Dyes / chemistry
  • Hydrophobic and Hydrophilic Interactions
  • Methods
  • Molecular Probes / chemical synthesis*
  • Molecular Probes / chemistry
  • Nitriles / chemical synthesis
  • Nitriles / chemistry
  • Solvents
  • Static Electricity
  • Viscosity*
  • Water

Substances

  • Acetates
  • Fluorescent Dyes
  • Molecular Probes
  • Nitriles
  • Solvents
  • Water