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Molecules 2018, 23(1), 49; doi:10.3390/molecules23010049

Discrimination of Stereoisomers by Their Enantioselective Interactions with Chiral Cholesterol-Containing Membranes

Department of Dental Basic Education, Asahi University School of Dentistry, Mizuho, Gifu 501-0296, Japan
Department of Anesthesiology and Reanimatology, University of Fukui Faculty of Medical Sciences, Eiheiji-cho, Fukui 910-1193, Japan
Author to whom correspondence should be addressed.
Received: 30 November 2017 / Revised: 22 December 2017 / Accepted: 22 December 2017 / Published: 25 December 2017
(This article belongs to the Special Issue Chirality in Health and Environment: Recent developments)
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Discrimination between enantiomers is an important subject in medicinal and biological chemistry because they exhibit markedly different bioactivity and toxicity. Although stereoisomers should vary in the mechanistic interactions with chiral targets, their discrimination associated with the mode of action on membrane lipids is scarce. The aim of this study is to reveal whether enantiomers selectively act on chiral lipid membranes. Different classes of stereoisomers were subjected at 5–200 μM to reactions with biomimetic phospholipid membranes containing ~40 mol % cholesterol to endow the lipid bilayers with chirality and their membrane interactions were comparatively evaluated by measuring fluorescence polarization. All of the tested compounds interacted with cholesterol-containing membranes to modify their physicochemical property with different potencies between enantiomers, correlating to those of their experimental and clinical effects. The rank order of membrane interactivity was reversed by changing cholesterol to C3-epimeric α-cholesterol. The same selectivity was also obtained from membranes prepared with 5α-cholestan-3β-ol and 5β-cholestan-3α-ol diastereomers. The opposite configuration allows molecules to interact with chiral sterol-containing membranes enantioselectively, and the specific β configuration of cholesterol’s 3-hydroxyl group is responsible for such selectivity. The enantioselective membrane interaction has medicinal implications for the characterization of the stereostructures with higher bioactivity and lower toxicity. View Full-Text
Keywords: stereoisomer; discrimination; enantioselective membrane interaction; chiral membrane; cholesterol stereoisomer; discrimination; enantioselective membrane interaction; chiral membrane; cholesterol

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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Tsuchiya, H.; Mizogami, M. Discrimination of Stereoisomers by Their Enantioselective Interactions with Chiral Cholesterol-Containing Membranes. Molecules 2018, 23, 49.

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