Hydrophilic molecular rotor derivatives - Synthesis and characterization

Mark A. Haidekker, Thomas P. Brady, Sevag H. Chalian, Walter Akers, Darcy Lichlyter, Emmanuel A. Theodorakis

Research output: Contribution to journalArticlepeer-review

51 Scopus citations


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.

Original languageEnglish (US)
Pages (from-to)274-289
Number of pages16
JournalBioorganic Chemistry
Issue number4
StatePublished - Aug 2004
Externally publishedYes

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Biology
  • Drug Discovery
  • Organic Chemistry


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