Introducing Lipophilicity to (Polyhydroxyalkyl) thiazolidine Carboxylic Acids Via Acylation
Novo Fernández, Olalla
Méndez Arteaga, Jonh J.
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he therapeutic efficacy of bioactive compounds isrelated to their bioavailability. In turn, the bioavailability dependson the equilibrium between the hydrophilicity and the lipophilicity.2(R,S)-(Polyhydroxyalkyl)thiazolidine-4(R)carboxylicacids(TCAs), obtained from the condensation ofL-cysteine and analdose, have been recognized as nontoxic precursors of glutathionewith important preventive and therapeutic effects. The bioavail-ability of these compounds can be improved by enhancing theirlipophilicity. This can be achieved by the introduction of some acylgroups derived from fatty acids via esterification of the aldosehydroxyl groups. With this purpose four new compounds weresynthesized through a selective palmitoyl acylation ofD-(−)-ribose andD-(+)-glucose and subsequent condensation withL-cysteine.In addition, the log P of the new compounds was calculated as a measure of the lipophilicity, and in vitro 2,2′-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) tests were performed as a measure of the antioxidant capability.
Is part ofACS Omega, 2022, vol. 7, núm. 13, p. 11075–11081
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