TY - JOUR
T1 - Hydrophilic molecular rotor derivatives - Synthesis and characterization
AU - Haidekker, Mark A.
AU - Brady, Thomas P.
AU - Chalian, Sevag H.
AU - Akers, Walter
AU - Lichlyter, Darcy
AU - Theodorakis, Emmanuel A.
N1 - Funding Information:
We gratefully acknowledge financial support through NIH Grant 1R21-RR018399. We thank the reviewers for helpful comments, particularly the question of calibrating the intensity measurements, and the note on the additional use of the enantiomers of 10 .
PY - 2004/8
Y1 - 2004/8
N2 - 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.
AB - 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.
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U2 - 10.1016/j.bioorg.2004.04.002
DO - 10.1016/j.bioorg.2004.04.002
M3 - Article
C2 - 15210341
AN - SCOPUS:2942731411
SN - 0045-2068
VL - 32
SP - 274
EP - 289
JO - Bioorganic Chemistry
JF - Bioorganic Chemistry
IS - 4
ER -