Introducing Lipophilicity to (Polyhydroxyalkyl)thiazolidine Carboxylic Acids Via Acylation

Abstract

The therapeutic efficacy of bioactive compounds is related to their bioavailability. In turn, the bioavailability depends on the equilibrium between the hydrophilicity and the lipophilicity. 2(R,S)-(Polyhydroxyalkyl)thiazolidine-4(R) carboxylic acids (TCAs), obtained from the condensation of l-cysteine and an aldose, have been recognized as nontoxic precursors of glutathione with important preventive and therapeutic effects. The bioavailability of these compounds can be improved by enhancing their lipophilicity. This can be achieved by the introduction of some acyl groups derived from fatty acids via esterification of the aldose hydroxyl groups. With this purpose four new compounds were synthesized through a selective palmitoyl acylation of d-(-)-ribose and d-(+)-glucose and subsequent condensation with l-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.