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Biophys J, July 2000, p. 406-415, Vol. 79, No. 1

Specific Binding of Ethanol to Cholesterol in Organic Solvents

Vladimir A. Daragan,* Alexei M. Voloshin,* Svetlana V. Chochina,dagger Teodor N. Khazanovich,Dagger W. Gibson Wood,dagger Nicolai A. Avdulov,dagger and Kevin H. Mayo*

 *Department of Biochemistry, Molecular Biology and Biophysics, University of Minnesota Health Sciences Center, Minneapolis, 55455, and  dagger VA Medical Center, GRECC, and Department of Pharmacology, University of Minnesota, Minneapolis, Minnesota 55417, and  Dagger Institute of Chemical Physics, Russian Academy of Science, Moscow 117977, Russia

Although ethanol has been reported to affect cholesterol homeostasis in biological membranes, the molecular mechanism of action is unknown. Here, nuclear magnetic resonance (NMR) spectroscopic techniques have been used to investigate possible direct interactions between ethanol and cholesterol in various low dielectric solvents (acetone, methanol, isopropanol, DMF, DMSO, chloroform, and CCl4). Measurement of 13C chemical shifts, spin-lattice and multiplet relaxation times, as well as self-diffusion coefficients, indicates that ethanol interacts weakly, yet specifically, with the HC-OH moiety and the two flanking methylenes in the cyclohexanol ring of cholesterol. This interaction is most strong in the least polar-solvent carbon tetrachloride where the ethanol-cholesterol equilibrium dissociation constant is estimated to be 2 × 10-3 M. 13C-NMR spin-lattice relaxation studies allow insight into the geometry of this complex, which is best modeled with the methyl group of ethanol sandwiched between the two methylenes in the cyclohexanol ring and the hydroxyl group of ethanol hydrogen bonded to the hydroxyl group of cholesterol.

Biophys J, July 2000, p. 406-415, Vol. 79, No. 1
© 2000 by the Biophysical Society   0006-3495/00/07/406/10  $2.00


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