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Discovery of lysosome-targeted covalent anticancer agents based on isosteviol skeleton.

Abstract：

:Covalent drugs play corresponding bioactivities by forming covalent bonds with the target, which possess many significant pharmacological advantages including high potency, ligand efficiency, and long-lasting effects. However, development of covalent inhibitors is a challenge due to their presumed indiscriminate reactivity. Here, we report the discovery of series of lysosome-targeting covalent anticancer agents by introducing nitrogenous bases to the modified isosteviol skeleton in order to minimize the toxicity and increase the selectivity. By introducing the electrophilic α, β-unsaturated ketones into the A- and D-rings of isosteviol, the cytotoxicity of the obtained compounds were greatly increased. Further nitrogen-containing modifications to the D-ring led to the discovery of novel molecules that targeted lysosomes, and of which, compound 30 was the most potent and selective antiproliferative one to kill A549 cells in vitro and in vivo. Mechanism investigation revealed that compound 30 was trapped into lysosomes and damaged lysosomes to cause cell death.

journal_name

Eur J Med Chem

journal_title

European journal of medicinal chemistry

authors

Liu J,Li L,Li X,Wang X,Zhao X,Qiao Y,Xu Y,Sun Y,Qian L,Liu Z,Ji A,Lou H

doi

10.1016/j.ejmech.2020.112896

subject

Has Abstract

pub_date

2021-01-01 00:00:00

pages

112896

eissn

0223-5234

issn

1768-3254

pii

S0223-5234(20)30868-0

journal_volume

209

pub_type

杂志文章

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