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Synthesis of amphiphilic resveratrol lipoconjugates and evaluation of their anticancer activity towards neuroblastoma SH-SY5Y cell line.

European journal of medicinal chemistry (2015-05-02)
Rosa Chillemi, Nunzio Cardullo, Valentina Greco, Giuseppe Malfa, Barbara Tomasello, Sebastiano Sciuto
ABSTRACT

Resveratrol, a polyphenol present in grapes and other edible plants, possesses several important pharmacological activities, including anticancer activity. Nevertheless, its therapeutic use is still limited because of some unfavourable physicochemical and pharmacokinetic properties, mainly, poor cellular uptake and too rapid metabolism resulting in elimination from the body. To meet these drawbacks, some resveratrol conjugates would be useful, which would possess improved stability, uptake and bioavailability than the lead compound, and the ability to release it once it is internalized into the cell. In this paper we report a synthetic strategy which allowed us to obtain new amphiphilic resveratrol derivatives starting from different selectively protected resveratrol phosphoramidites or even from the resveratrol triphosphoramidite. Specifically, resveratrol was conjugated through phosphate bridge(s) to different lipophilic groups related to membrane lipids, such as cholesteryl or diacylglycero moieties. All the new lipoconjugates were tested towards human neuroblastoma SH-SY5Y cells and proved to be significantly more active than resveratrol, with a concentration-dependent activity.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
L-Glutamine, meets USP testing specifications, suitable for cell culture, 99.0-101.0%, from non-animal source
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L-Glutamine, ReagentPlus®, ≥99% (HPLC)
SAFC
L-Glutamine
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L-Glutamine, BioUltra, ≥99.5% (NT)
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L-Glutamine, γ-irradiated, BioXtra, suitable for cell culture
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1,2-Dipalmitoyl-sn-glycerol, ≥99%
Sigma-Aldrich
L-Glutamine