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Keto-enol-based Modification on Piperlongumine to Generate a Potent Cu(II) Ionophore That Triggers Redox Imbalance and Death of HepG2 Cells

Keto-enol-based Modification on Piperlongumine to Generate a Potent Cu(II) Ionophore That Triggers Redox Imbalance and Death of HepG2 Cells

Fang Dai, Cui-Hong Yuan, Yuan Ji, Yu-Ting Du, Xia-Zhen Bao, Ling-Xi Wu, Xiao-Ling Jin, Bo Zhou

Free Radic Biol Med. 2018 May 20;120:124-132.

PMID: 29555591

Abstract:

Altered redox status including higher levels of copper in cancer cells than in normal cells inspired many researchers to develop copper ionophores targeting this status. We have recently found that flavon-3-ol (3-HF) works as a potent Cu(II) ionophore by virtue of its keto-enol moiety. To further emphasize the significance of this moiety for developing Cu(II) ionophores, we herein designed a β-diketo analog of piperlongumine, PL-I, characterized by the presence of high proportion of the keto-enol form in dimethylsulfoxide and chloroform, and identified its keto-enol structure by NMR and theoretical calculations. Benefiting from deprotonation of its enolic hydroxyl group, this molecule is capable of facilitating the transport of Cu(II) through cellular membranes to disrupt redox homeostasis of human hepatoma HepG2 cells and trigger their death.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP125769677	Copper(II) ionophore I		125769-67-7	Price

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