Synthesis and discovery of asiatic acid based 1,2,3-triazole derivatives as antitumor agents blocking NF-κB activation and cell migration

MedChemComm
2019.0

Abstract

A series of asiatic acid (AA) based 1,2,3-triazole derivatives were designed, synthesized and subjected to a cell-based NF-κB inhibition screening assay. Among the tested compounds, compound <b>6k</b> displayed impressive NF-κB inhibitory activity with an IC<sub>50</sub> value in the low micromolar range. A molecular docking study was performed to reveal key interactions between <b>6k</b> and NF-κB in which the 1,2,3-triazole moiety and the hydroxyl groups of the AA skeleton were important for improving the inhibitory activity. Subsequently, surface plasmon resonance analysis validated the high affinity between compound <b>6k</b> and NF-κB protein with an equilibrium dissociation constant (KD) value of 0.36 μM. Further studies showed that compound <b>6k</b> observably inhibited the NF-κB DNA binding, nuclear translocation and IκBα phosphorylation. Moreover, <i>in vitro</i> antitumor activity screening showed that compound <b>6k</b> (IC<sub>50</sub> = 2.67 ± 0.06 μM) exhibited the best anticancer activity against A549 cells, at least partly, by inhibition of the activity of NF-κB. Additionally, the treatment of A549 cells with compound <b>6k</b> resulted in apoptosis induction potency and <i>in vitro</i> cell migration inhibition. Thus, we conclude that AA based 1,2,3-triazole derivatives may be potential NF-κB inhibitors with the ability to induce apoptosis and suppress cell migration.

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