Synthesis and evaluation of 9-O-substituted berberine derivatives containing aza-aromatic terminal group as highly selective telomeric G-quadruplex stabilizing ligands

被引：77

作者：

Ma, Yan ^{[1
]}

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 510275, Guangdong, Peoples R China

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2009年 / 19卷 / 13期

关键词：

G-Quadruplex; Berberine derivatives; Selectivity; Telomerase inhibitors; ANTITUMOR POLYCYCLIC ACRIDINES; ANTIMICROBIAL ACTIVITY; CATIONIC PORPHYRINS; CELL-PROLIFERATION; BINDING; DNA; TELOMESTATIN; INHIBITORS; AGENTS;

D O I：

10.1016/j.bmcl.2009.05.030

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

A series of new 9-O-substituted berberine derivatives (4a-j) as telomeric quadruplex ligands was synthesized and evaluated. The results from biophysical and biochemical assay indicated that introducing of positive charged aza-aromatic terminal group into the side chain of 9-position of berberine significantly improved the binding ability with G-quadruplex, and exhibited the inhibitory effect on the hybridization and on telomerase activity. These derivatives showed excellent selectivity for telomeric G-quadruplex DNA over duplex. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：3414 / 3417

页数：4

共 11 条

[1] Isaindigotone Derivatives: A New Class of Highly Selective Ligands for Telomeric G-Quadruplex DNA
Tan, Jia-Heng
Ou, Tian-Miao
Hou, Jin-Qiang
Lu, Yu-Jing
Huang, Shi-Liang
Luo, Hai-Bin
Wu, Jian-Tong
Huang, Zhi-Shu
Wong, Kwok-Yin
Gu, Lian-Quan
JOURNAL OF MEDICINAL CHEMISTRY, 2009, 52 (09) : 2825 - 2835
[2] Design and Synthesis of Xanthone Analogues Conjugated with Aza-aromatic Substituents as Promising G-Quadruplex Stabilizing Ligands and their Selective Cancer Cell Cytotoxic Action
Roy, Soma
Chakraborty, Nirmal
Maiti, Bappa
Muniyappa, Kalappa
Bhattacharya, Santanu
CHEMBIOCHEM, 2023, 24 (04)
[3] Synthesis and evaluation of 10-(3,5-dimethoxy)benzyl-9(10H)-acridone derivatives as selective telomeric G-quadruplex DNA ligands
Gao, Chunmei
Li, Shangfu
Lang, Xuliang
Liu, Hongxia
Liu, Feng
Tan, Chunyan
Jiang, Yuyang
TETRAHEDRON, 2012, 68 (38) : 7920 - 7925
[4] Disubstituted quinazoline derivatives as a new type of highly selective ligands for telomeric G-quadruplex DNA
Li, Zeng
Tan, Jia-Heng
He, Jin-Hui
Long, Yi
Ou, Tian-Miao
Li, Ding
Gu, Lian-Quan
Huang, Zhi-Shu
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2012, 47 : 299 - 311
[5] Disubstituted 2-phenyl-benzopyranopyrimidine derivatives as a new type of highly selective ligands for telomeric G-quadruplex DNA
Wu, Wei-Bin
Chen, Shu-Han
Hou, Jin-Qiang
Tan, Jia-Heng
Ou, Tian-Miao
Huang, Shi-Liang
Li, Ding
Gu, Lian-Quan
Huang, Zhi-Shu
ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (08) : 2975 - 2986
[6] Synthesis and biological evaluation of novel 4,5-bis(dialkylaminoalkyl)-substituted acridines as potent telomeric G-quadruplex ligands
Laronze-Cochard, Marie
Kim, Young-Min
Brassart, Bertrand
Riou, Jean-Francois
Laronze, Jean Yves
Sapi, Janos
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2009, 44 (10) : 3880 - 3888
[7] Design, Synthesis, and Evaluation of New Sugar-Substituted Imidazole Derivatives as Selective c-MYC Transcription Repressors Targeting the Promoter G-Quadruplex
Li, Mao-Lin
Yuan, Jing-Mei
Yuan, Hao
Wu, Bi-Han
Huang, Shi-Liang
Li, Qing-Jiang
Ou, Tian-Miao
Wang, Hong-Gen
Tan, Jia-Heng
Li, Ding
Chen, Shuo-Bin
Huang, Zhi-Shu
JOURNAL OF MEDICINAL CHEMISTRY, 2022, 65 (19) : 12675 - 12700
[8] Design, Synthesis, and Evaluation of Novel p-(Methylthio)styryl Substituted Quindoline Derivatives as Neuroblastoma RAS (NRAS) Repressors via Specific Stabilizing the RNA G-Quadruplex
Peng, Wang
Sun, Zhi-Yin
Zhang, Qi
Cheng, Sui-Qi
Wang, Shi-Ke
Wang, Xiao-Na
Kuang, Guo-Tao
Su, Xiao-Xuan
Tan, Jia-Heng
Huang, Zhi-Shu
Ou, Tian-Miao
JOURNAL OF MEDICINAL CHEMISTRY, 2018, 61 (15) : 6629 - 6646
[9] Design, Synthesis, and Evaluation of 2,9-Bis[(substituted-aminomethyl)phenyl]-1,10-phenanthroline Derivatives as G-Quadruplex Ligands
Gueddouda, Nassima Meriem
Hurtado, Miyanou Rosales
Moreau, Stephane
Ronga, Luisa
Das, Rabindra Nath
Savrimoutou, Solene
Rubio, Sandra
Marchand, Adrien
Mendoza, Oscar
Marchivie, Mathieu
Elmi, Lilian
Chansavang, Albain
Desplat, Vanessa
Gabelica, Valerie
Bourdoncle, Anne
Mergny, Jean-Louis
Guillon, Jean
CHEMMEDCHEM, 2017, 12 (02) : 146 - 160
[10] Synthesis and evaluation of 7-substituted-5,6-dihydrobenzo[c] acridine derivatives as new c-KIT promoter G-quadruplex binding ligands
Guo, Qian-Liang
Su, Hua-Fei
Wang, Ning
Liao, Sheng-Rong
Lu, Yu-Ting
Ou, Tian-Miao
Tan, Jia-Heng
Li, Ding
Huang, Zhi-Shu
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2017, 130 : 458 - 471

← 1 2 →