Synthesis and evaluation of 10-(3,5-dimethoxy)benzyl-9(10H)-acridone derivatives as selective telomeric G-quadruplex DNA ligands

被引：23
|
作者：
Gao, Chunmei [1 ,2 ]
Li, Shangfu [1 ,3 ]
Lang, Xuliang [2 ,4 ]
Liu, Hongxia [1 ,3 ]
Liu, Feng [1 ,2 ]
Tan, Chunyan [1 ,2 ]
Jiang, Yuyang [1 ,4 ,5 ]
机构：
[1] Tsinghua Univ, Grad Sch Shenzhen, Minist Prov Jointly Constructed Base, State Key Lab,Shenzhen Key Lab Chem Biol, Shenzhen 51855, Peoples R China
[2] Tsinghua Univ, Grad Sch Shenzhen, Shenzhen Antitumor Drug Dev Engn Lab, Shenzhen 518055, Peoples R China
[3] Key Lab Tumor Metabol Shenzhen City, Shenzhen 518055, Peoples R China
[4] Tsinghua Univ, Dept Chem, Beijing 100084, Peoples R China
[5] Tsinghua Univ, Sch Med, Dept Pharmacol & Pharmaceut Sci, Beijing 100084, Peoples R China
来源：
TETRAHEDRON | 2012年 / 68卷 / 38期
关键词：
Acridone derivatives; G-quadruplex; Mass spectrometry; Circular dichroism; ANTITUMOR POLYCYCLIC ACRIDINES; IONIZATION MASS-SPECTROMETRY; BINDING; RECOGNITION; INHIBITORS; DESIGN; AGENTS; CONVERSION; MOLECULE; AFFINITY;
D O I：
10.1016/j.tet.2012.07.016
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A class of 9(10H)-acridone derivatives with terminal ammonium substituents at C2 (and C7) position(s) on the acridone ring were successfully synthesized. The relative affinities of the acridone compounds to G-quadruplex DNA have been investigated and the results showed that these compounds had a binding specificity for G-quadruplex over duplex sequences. The acridones with two terminal ammonium substituents had much more effects on the human telomeric G-quadruplex DNA than the corresponding acridone derivatives with one terminal ammonium substituent, and more positive charges introduced to the side chains can improve the formation and stabilization of the G-quadruplex. (C) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码：7920 / 7925
页数：6
相关论文
共 5 条
  • [1] Synthesis and antiproliferative activity of 2,7-diamino l0-(3,5-dimethoxy)benzyl-9(10H)-acridone derivatives as potent telomeric G-quadruplex DNA ligands
    Gao, Chunmei
    Zhang, Wei
    He, Shengnan
    Li, Shangfu
    Liu, Feng
    Jiang, Yuyang
    BIOORGANIC CHEMISTRY, 2015, 60 : 30 - 36
  • [2] Novel synthetic 2-amino-10-(3,5-dimethoxy)benzyl-9(10H)-acridinone derivatives as potent DNA-binding antiproliferative agents
    Gao, Chunmei
    Liu, Feng
    Luan, Xudong
    Tan, Chunyan
    Liu, Hongxia
    Xie, Yonghua
    Jin, Yibao
    Jiang, Yuyang
    BIOORGANIC & MEDICINAL CHEMISTRY, 2010, 18 (21) : 7507 - 7514
  • [3] Synthesis and evaluation of 9-O-substituted berberine derivatives containing aza-aromatic terminal group as highly selective telomeric G-quadruplex stabilizing ligands
    Ma, Yan
    Ou, Tian-Miao
    Tan, Jia-Heng
    Hou, Jin-Qiang
    Huang, Shi-Liang
    Gu, Lian-Quan
    Huang, Zhi-Shu
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2009, 19 (13) : 3414 - 3417
  • [4] Synthesis and pharmacological evaluation of 9(10H)-acridone bearing 1,3,4-oxadiazole derivatives as antimicrobial agents
    Salimon, Jumat
    Salih, Nadia
    Yousif, Emad
    Hameed, Ayad
    Kreem, Ayad
    ARABIAN JOURNAL OF CHEMISTRY, 2010, 3 (04) : 205 - 210
  • [5] Microwave-assisted Synthesis of Imidazole 2 [4,5f][1,10] phenanthroline Derivatives as Apoptosis 3 Inducers in Chemotherapy by Stabilizing Bcl-2 4 G-quadruplex DNA
    Li, Li
    Li, Yu-Mei
    Qiong-Wu
    Wang, Cheng-Xi
    Zeng, Yong-Chang
    Zeng, Zhi-Ping
    Sun, Fen-Yong
    Mei, Wen-Jie
    20TH INTERNATIONAL ELECTRONIC CONFERENCE ON SYNTHETIC ORGANIC CHEMISTRY (ECSOC), 2016,
1