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Molecules 2015, 20(9), 16085-16102; doi:10.3390/molecules200916085

N-Monosubstituted Methoxy-oligo(ethylene glycol) Carbamate Ester Prodrugs of Resveratrol

1
Department of Chemical Sciences, University of Padova, Via F. Marzolo, Padova 135131, Italy
2
Department of Biomedical Sciences, University of Padova, Viale G. Colombo, Padova 335121, Italy
3
CNR Neuroscience Institute, Viale G. Colombo, Padova 335121, Italy
4
OS srl, Via Campello sul Clitunno, Roma 3400181, Italy
These authors contributed equally to this work.
*
Author to whom correspondence should be addressed.
Academic Editors: Emilie Combet and Maria Rosário Bronze
Received: 28 July 2015 / Revised: 27 August 2015 / Accepted: 28 August 2015 / Published: 3 September 2015
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Abstract

Resveratrol is a natural polyphenol with many interesting biological activities. Its pharmacological exploitation in vivo is, however, hindered by its rapid elimination via phase II conjugative metabolism at the intestinal and, most importantly, hepatic levels. One approach to bypass this problem relies on prodrugs. We report here the synthesis, characterization, hydrolysis, and in vivo pharmacokinetic behavior of resveratrol prodrugs in which the OH groups are engaged in an N-monosubstituted carbamate ester linkage. As promoiety, methoxy-oligo(ethylene glycol) groups (m-OEG) (CH3–[OCH2CH2]n–) of defined chain length (n = 3, 4, 6) were used. These are expected to modulate the chemico-physical properties of the resulting derivatives, much like longer poly(ethylene glycol) (PEG) chains, while retaining a relatively low MW and, thus, a favorable drug loading capacity. Intragastric administration to rats resulted in the appearance in the bloodstream of the prodrug and of the products of its partial hydrolysis, confirming protection from first-pass metabolism during absorption. View Full-Text
Keywords: resveratrol; prodrugs; methoxy-oligo(ethylene glycol); poly(ethylene glycol); polyphenols; bioavailability; carbamate ester resveratrol; prodrugs; methoxy-oligo(ethylene glycol); poly(ethylene glycol); polyphenols; bioavailability; carbamate ester
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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.; Azzolini, M.; Zoratti, M.; Biasutto, L.; Paradisi, C. N-Monosubstituted Methoxy-oligo(ethylene glycol) Carbamate Ester Prodrugs of Resveratrol. Molecules 2015, 20, 16085-16102.

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