Design, Synthesis, and Evaluation of New Sugar-Substituted Imidazole Derivatives as Selective c-MYC Transcription Repressors Targeting the Promoter G-Quadruplex

Journal of Medicinal Chemistry
2022.0

Abstract

<i>c-MYC</i> is a key driver of tumorigenesis. Repressing the transcription of <i>c-MYC</i> by stabilizing the G-quadruplex (G4) structure with small molecules is a potential strategy for cancer therapy. Herein, we designed and synthesized 49 new derivatives by introducing carbohydrates to our previously developed <i>c-MYC</i> G4 ligand <b>1</b>. Among these compounds, <b>19a</b> coupled with a d-glucose 1,2-orthoester displayed better <i>c-MYC</i> G4 binding, stabilization, and protein binding disruption abilities than <b>1</b>. Our further evaluation indicated that <b>19a</b> blocked <i>c-MYC</i> transcription by targeting the promoter G4, leading to <i>c-MYC</i>-dependent cancer cell death in triple-negative breast cancer cell MDA-MB-231. Also, <b>19a</b> significantly inhibited tumor growth in the MDA-MB-231 mouse xenograft model accompanied by <i>c-MYC</i> downregulation. Notably, the safety of <b>19a</b> was dramatically improved compared to <b>1</b>. Our findings indicated that <b>19a</b> could become a promising anticancer candidate, which suggested that introducing carbohydrates to improve the G4-targeting and antitumor activity is a feasible option.

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