Article Dans Une Revue Bioorganic Chemistry Année : 2020

Correlation study on methoxylation pattern of flavonoids and their heme-targeted antiplasmodial activity

Résumé

A library of 33 polymethoxylated flavones (PMF) was evaluated for heme-binding affinity by biomimetic MS assay and in vitro antiplasmodial activity on two strains of P. falciparum. Stability of heme adducts was discussed using the dissociation voltage at 50% (DV 50). No correlation was observed between the methoxylation pattern and the antiparasitic activity, either for the 3D7 chloroquine-sensitive or for the W2 chloroquine-resistant P. falciparum strains. However, in each PMF family an increased DV 50 was observed for the derivatives meth-oxylated in position 5. Measurement of intra-erythrocytic hemozoin formation of selected derivatives was performed and hemozoin concentration was inversely correlated with heme-binding affinity. Kaempferol showed no influence on hemozoin formation, reinforcing the hypothesis that this compound may exert in vitro antiplasmodial activity mostly through other pathways. Pentamethoxyquercetin has simultaneously demonstrated a significant biological activity and a strong interaction with heme, suggesting that inhibition of he-mozoin formation is totally or partially responsible for its antiparasitic effect.

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hal-02990750 , version 1 (17-11-2020)

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Sergio Ortiz, Pedro G Vásquez-Ocmín, Sandrine Cojean, Chouaha Bouzidi, Sylvie Michel, et al.. Correlation study on methoxylation pattern of flavonoids and their heme-targeted antiplasmodial activity. Bioorganic Chemistry, 2020, 104, ⟨10.1016/j.bioorg.2020.104243⟩. ⟨hal-02990750⟩
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