The conformation-dependent lipophilicity of morphine glucuronides as calculated from their molecular lipophilicity potential

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Abstract

A whole range of conformers of morphine-6-O-glucuronide and morphine 3-O-glucuronide were examined for their theoretical log P values using the molecular lipophilicity potential method. The results substantiate the “chameleonic” behavior of morphine glucuronides to exist in water as hydrophilic, extended conformers, and in lipidic media as folded, more lipophilic conformers.

The lipophilicity of conformers of morphine-3-O-glucuronide (M3G) and morphine-6-O-glucuronide (M6G) was calculated by the molecular lipophilicity potential method (MLP) in order to quantify the “chameleonic” behavior (hydrophilic in water, lipophilic in lipidic media) of these compounds.

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