Over the years, our lab has been working on some rhein-derived anthraquinone-based anti-cancer agents. A systematic approach was made to improve their aqueous solubility. BW-AQ-238, an analog of the lead compound was synthesized by introducing two hydroxylethyl groups. In vitro studies confirmed its comparable activity and mechanism of action with the lead compound. Prodrugs of BW-AQ-238 were made by esterification of the hydroxyl group with various natural amino acids. Solubility and enzyme-catalyzed release kinetics of the parent drug as well as cytotoxicity in Hela and EU-1 cells were studied. The results suggested that the amino acid prodrugs significantly improved the solubility while maintaining the potency of the parent drug, therefore, could be considered as candidates for overcoming solubility problems.

Design, synthesis, and biological evaluation of water-soluble amino acid prodrugs of a rhein-derived anti-cancer agent

2019 Spring National Meeting

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