Design and multi-step synthesis of chalcone-polyamine conjugates as potent antiproliferative agents

被引：16

作者：

Rioux, Benjamin ^{[1
]}

Pouget, Christelle ^{[1
]}

Fidanzi-Dugas, Chloe ^{[1
]}

Gamond, Aurelie ^{[1
]}

Laurent, Aurelie ^{[1
]}

Semaan, Josiane ^{[1
]}

Pinon, Aline ^{[1
]}

Champavier, Yves ^{[2
]}

Leger, David Y. ^{[1
]}

Liagre, Bertrand ^{[1
]}

Duroux, Jean-Luc ^{[1
]}

Fagnere, Catherine ^{[1
]}

Sol, Vincent ^{[1
]}

机构：

[1] Univ Limoges, Lab Chim Subst Nat, EA 1069, F-87000 Limoges, France

[2] Univ Limoges, BISCEm, F-87000 Limoges, France

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2017年 / 27卷 / 18期

关键词：

Chalcones; Polyamines; Organic synthesis; Antiproliferative activity; Prostate and colorectal cancer cell lines; TARGETING TOPOISOMERASE-II; PROSTATE-CANCER CELLS; BIOLOGICAL EVALUATION; INDUCED APOPTOSIS; TRANSPORT-SYSTEM; DERIVATIVES; PATHWAY; CYTOTOXICITY; RESISTANCE; INHIBITORS;

D O I：

10.1016/j.bmcl.2017.08.024

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

The aim of this study is to synthesize chalcone-polyamine conjugates in order to enhance bioavailability and selectivity of chalcone core towards cancer cells, using polyamine-based vectors. 3-hydroxy-3',4,4',5'-tetramethoxychalcone (1) and 3',4,4',5'-tetramethoxychalcone (2) were selected as parent chalcones since they were found to be efficient anti-proliferative agents on various cancer cells. A series of ten chalcone-polyamine conjugates was obtained by reacting carboxychalcones with different polyamine tails. Chalcones 1 and 2 showed a strong cytotoxic activity against two prostatic cancer (PC-3 and DU-145) and two colorectal cancer (HT-29 and HCT-116) cell lines. Then, chalcone-spermine conjugates 7d and 8d were shown to be the most active of the series and could be considered as promising compounds for colon and prostatic cancer adjuvant therapy. (C) 2017 Elsevier Ltd. All rights reserved.

引用

页码：4354 / 4357

页数：4

共 35 条

[31] Polyamine conjugates of meso-tritolyiporphyrin and protoporphyrin IX:: Potential agents for photodynamic therapy of cancers [J].

Sol, V ;

Lamarche, F ;

Enache, M ;

Garcia, G ;

Granet, R ;

Guilloton, M ;

Blais, JC ;

Krausz, P .

BIOORGANIC & MEDICINAL CHEMISTRY, 2006, 14 (05) :1364-1377

[32] Synthesis, cytotoxicity and apoptosis of naphthalimide polyamine conjugates as antitumor agents [J].

Tian, Zhi-yong ;

Xie, Song-qiang ;

Du, Yao-wu ;

Ma, Yuan-fang ;

Zhao, Jin ;

Gao, Wen-yuan ;

Wang, Chao-jie .

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2009, 44 (01) :393-399

[33] Molecular requirements for targeting the polyamine transport system. Synthesis and biological evaluation of polyamine-anthracene conjugates [J].

Wang, CJ ;

Delcros, JG ;

Biggerstaff, J ;

Phanstiel, O .

JOURNAL OF MEDICINAL CHEMISTRY, 2003, 46 (13) :2672-2682

[34] A novel quinazolinone chalcone derivative induces mitochondrial dependent apoptosis and inhibits PI3K/Akt/mTOR signaling pathway in human colon cancer HCT-116 cells [J].

Wani, Zahoor Ahmad ;

Guru, Santosh Kumar ;

Rao, A. V. Subba ;

Sharma, Sonia ;

Mahajan, Girish ;

Behl, Akanksha ;

Kumar, Ashok ;

Sharma, P. R. ;

Kamal, Ahmed ;

Bhushan, Shashi ;

Mondhe, Dilip M. .

FOOD AND CHEMICAL TOXICOLOGY, 2016, 87 :1-11

[35] Synthesis, Evaluation, and Mechanism Study of Novel Indole-Chalcone Derivatives Exerting Effective Antitumor Activity Through Microtubule Destabilization in Vitro and in Vivo [J].

Yan, Jun ;

Chen, Jie ;

Zhang, Shun ;

Hu, Jinhui ;

Huang, Ling ;

Li, Xingshu .

JOURNAL OF MEDICINAL CHEMISTRY, 2016, 59 (11) :5264-5283

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