Quinolino-benzo-[5,6]-dihydroisoquindolium compounds derived from berberine: A new class of highly selective ligands for G-quadruplex DNA in c-myc oncogene

被引：49

作者：

Ma, Yan ^{[1
,2
]}

Ou, Tian-Miao ^{[1
]}

Tan, Jia-Heng ^{[1
]}

Hou, Jin-Qiang ^{[1
]}

Huang, Shi-Liang ^{[1
]}

Gu, Lian-Quan ^{[1
]}

Huang, Zhi-Shu ^{[1
]}

机构：

[1] Sun Yat Sen Univ, Sch Pharmaceut Sci, Guangzhou 510080, Guangdong, Peoples R China

[2] Shunde Polytech, Dept Med Sci, Foshan 528333, Guangdong, Peoples R China

来源：

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY | 2011年 / 46卷 / 05期

关键词：

Synthesis; Berberine; Quinolino-benzo-[5,6]-dihydroisoquindolium compounds; Biophysical and biochemical evaluation; C-myc G-quadruplex; STABILIZING LIGANDS; QUINDOLINE DERIVATIVES; DOWN-REGULATION; PROMOTER; TRANSCRIPTION; BINDING; DESIGN; TELOMERASE; INHIBITORS; ELEMENT;

D O I：

10.1016/j.ejmech.2011.02.020

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A series of quinolino-benzo-[5, 6]-dihydroisoquindolium compounds (3a, 3f, 3g, and 3j) derived from alkaloid berberine were designed and synthesized as novel G-quadruplex ligands. Subsequent biophysical and biochemical evaluation demonstrated that the addition of pyridine ring and amino group into berberine improved the binding ability and selectivity towards G-quadruplex DNA in comparison with the previously reported 9-N-substituted berberine derivatives. Furthermore, qRT-PCR assay showed compound 3j led the down-regulation of c-myc gene transcription in leukemia cell line HL60, while little effect on normal cell line ECV-304, which was consistent with the behavior of an effective G-quadruplex ligand targeting c-myc oncogene. (C) 2011 Elsevier Masson SAS. All rights reserved.

引用

页码：1906 / 1913

页数：8

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