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New water-soluble carbamate ester derivatives of resveratrol

Mattarei, Andrea and Carraro, Massimo and Azzolini, Michele and Paradisi, Cristina and Zoratti, Mario and Biasutto, Lucia (2014) New water-soluble carbamate ester derivatives of resveratrol. Molecules, Vol. 2014 (19), p. 15900-15917. eISSN 1420-3049. Article.

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DOI: 10.3390/molecules191015900

Abstract

Low bioavailability severely hinders exploitation of the biomedical potential of resveratrol. Extensive phase-II metabolism and poor water solubility contribute to lowering the concentrations of resveratrol in the bloodstream after oral administration. Prodrugs may provide a solution—protection of the phenolic functions hinders conjugative metabolism and can be exploited to modulate the physicochemical properties of the compound. We report here the synthesis and characterization of carbamate ester derivatives of resveratrol bearing on each nitrogen atom a methyl group and either a methoxy-poly(ethylene glycol)-350 (mPEG-350) or a butyl-glucosyl promoiety conferring high water solubility. Ex vivo absorption studies revealed that the butyl-glucosyl conjugate, unlike the mPEG-350 one, is able to permeate the intestinal wall. In vivo pharmacokinetics confirmed absorption after oral administration and showed that no hydrolysis of the carbamate groups takes place. Thus, sugar groups can be attached to resveratrol to obtain soluble derivatives maintaining to some degree the ability to permeate biomembranes, perhaps by facilitated or active transport.

Item Type:Article
ID Code:10158
Status:Published
Refereed:Yes
Uncontrolled Keywords:Resveratrol, prodrugs, carbamate esters, solubility, poly(ethylene glycol), glucose
Subjects:Area 03 - Scienze chimiche > CHIM/06 Chimica organica
Divisions:001 Università di Sassari > 01-a Nuovi Dipartimenti dal 2012 > Chimica e Farmacia
Publisher:Molecular Diversity Preservation International
eISSN:1420-3049
Copyright Holders:© 2014 by the authors; licensee MDPI, Basel, Switzerland
Deposited On:08 Oct 2014 11:36

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