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Azevedo, Carlos M.G.; Afonso, Carlos M.M.; Sousa, Diana; Lima, Raquel T.; Helena Vasconcelos, M.; Pedro, Madalena; Barbosa, João; Corrêa, Arlene G.; Reis, Salette; Pinto, Madalena M.M.
Bioorganic & medicinal chemistry, 06/2013, Volume: 21, Issue: 11Journal Article
A promising antitumor xanthone derivative was optimized following a multidimensional approach that involved the synthesis of 17 analogues, the study of their lipophilicity and solubility, and the evaluation of their growth inhibitory activity on four human tumor cell lines. A new synthetic route for the hit xanthone derivative was also developed and applied for the synthesis of its analogues. Among the used cell lines, the HL-60 showed to be in general more sensitive to the compounds tested, with the most potent compound having a GI50 of 5.1μM, lower than the hit compound. Lipophilicity was evaluated by the partition coefficient (Kp) of a solute between buffer and two membrane models, namely liposomes and micelles. The compounds showed a logKp between 3 and 5 and the two membrane models showed a good correlation (r2=0.916) between each other. Studies concerning relationship between solubility and structure were developed for the hit compound and 5 of its analogues.
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