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The 6-epimer of the plakortide H acid ( 1 ), along with the endoperoxides plakortide E ( 2 ), plakortin ( 3 ), and dihydroplakortin ( 4 ) have been isolated from a sample of the Caribbean sponge Plakortis halichondrioides . To perform a comparative study on the cytotoxicity towards the drug-sensitive leukemia CCRF-CEM cell line and its multi-drug resistant subline CEM/ADR5000, the acid of plakortin, namely plakortic acid ( 5 ), as well as the esters plakortide E methyl ester ( 6 ) and 6-epi-plakortide H ( 7 ) were synthesized by hydrolysis and Steglich esterification, respectively. The data obtained showed that the acids ( 1 , 2 , 5 ) exhibited potent cytotoxicity towards both cell lines, whereas the esters showed no activity ( 6 , 7 ) or weaker activity ( 3 , 4 ) compared to their corresponding acids. Plakortic acid ( 5 ) was the most promising derivative with half maximal inhibitory concentration (IC 50) values of ca. 0.20 µM for both cell lines.

marine drugs

Cytotoxicity of Endoperoxides from the Caribbean Sponge Plakortis halichondrioides towards Sensitive and Multidrug-Resistant Leukemia Cells: Acids vs. Esters Activity Evaluation