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Synthesis and Anticancer Research of <i>N</i> ‐(2‐aminophenyl)benzamide Acridine Derivatives as Dual Topoisomerase I and Isoform‐Selective HDAC Inhibitors

Bin Zhang, Qiting Zhang, Zedong Liu, Ning Wang, Haixiao Jin, Feng Liu, Cunlong Zhang, Shan He

2020ChemistrySelect13 citationsDOI

Abstract

Abstract Topoisomerase (Topo) and histone deacetylase (HDAC) are considered to be effective targets for the treatment of cancer. In this study, 16 new N ‐(2‐aminophenyl)benzamide acridine analogues ( 8 a‐8 p ) were designed and synthesized as Topo I and subtype‐selective HDAC inhibitors. Most of the compounds displayed good antiproliferative activity against CCRF‐CEM, K562 and U937 cells. Among them, 8 a demonstrated the highest anti‐proliferative activity (IC 50 =0.12‐0.35 μM). Further studies showed that 8 a and some analogues displayed Topo I inhibitory activity and exhibited selective inhibition for HDAC1 (class I HDAC). Additionally, 8 a can significantly induce DNA damage and histone H3 acetylation in these tested cancer cells. Moreover, 8 a triggered dose‐dependent G0/G1 cell cycle arrest and induced cellular apoptosis. This study provides new perspectives for the further structural optimization of N ‐(2‐aminophenyl)benzamide acridine analogues for use in cancer research.

Topics & Concepts

BenzamideHistone deacetylaseTopoisomeraseChemistryAcetylationHDAC1Acridine orangeAcridineGene isoformDNA damageCell cycleCancer cellApoptosisHistoneBiochemistryBiologyDNAStereochemistryCancerGeneticsGeneOrganic chemistryHistone Deacetylase Inhibitors ResearchProtein Degradation and InhibitorsCancer therapeutics and mechanisms
Synthesis and Anticancer Research of <i>N</i> ‐(2‐aminophenyl)benzamide Acridine Derivatives as Dual Topoisomerase I and Isoform‐Selective HDAC Inhibitors | Litcius