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Molecules 2014, 19(10), 15900-15917; doi:10.3390/molecules191015900

New Water-Soluble Carbamate Ester Derivatives of Resveratrol

1
Department of Chemical Sciences, University of Padova, Via F. Marzolo 1, 35131 Padova, Italy
2
Department of Chemistry and Pharmacy, University of Sassari, Viale Vienna 2, 07100 Sassari, Italy
3
Department of Biomedical Sciences, University of Padova, Viale G. Colombo 3, 35121 Padova, Italy
4
CNR Neuroscience Institute, Viale G. Colombo 3, 35121 Padova, Italy
*
Author to whom correspondence should be addressed.
Received: 27 August 2014 / Revised: 22 September 2014 / Accepted: 24 September 2014 / Published: 1 October 2014
(This article belongs to the Special Issue Resveratrol)
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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. View Full-Text
Keywords: resveratrol; prodrugs; carbamate esters; solubility; poly(ethylene glycol); glucose resveratrol; prodrugs; carbamate esters; solubility; poly(ethylene glycol); glucose
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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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MDPI and ACS Style

Mattarei, A.; Carraro, M.; Azzolini, M.; Paradisi, C.; Zoratti, M.; Biasutto, L. New Water-Soluble Carbamate Ester Derivatives of Resveratrol. Molecules 2014, 19, 15900-15917.

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