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

[Display omitted] 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...

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Published in:Bioorganic & medicinal chemistry letters 2017-09, Vol.27 (18), p.4354-4357
Main Authors: Rioux, Benjamin, Pouget, Christelle, Fidanzi-Dugas, Chloë, Gamond, Aurélie, Laurent, Aurélie, Semaan, Josiane, Pinon, Aline, Champavier, Yves, Léger, David Y., Liagre, Bertrand, Duroux, Jean-Luc, Fagnère, Catherine, Sol, Vincent
Format: Article
Language:English
Subjects:
Antineoplastic Agents - chemical synthesis
Antineoplastic Agents - chemistry
Antineoplastic Agents - pharmacology
Antiproliferative activity
Cancer
Cell Line, Tumor
Cell Proliferation - drug effects
Chalcone - chemistry
Chalcone - pharmacology
Chalcones
Chemical Sciences
Dose-Response Relationship, Drug
Drug Design
Drug Screening Assays, Antitumor
Humans
Life Sciences
Molecular Structure
Organic chemistry
Organic synthesis
Polyamines
Polyamines - chemistry
Polyamines - pharmacology
Prostate and colorectal cancer cell lines
Structure-Activity Relationship
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Summary:[Display omitted] 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.
ISSN:0960-894X
1464-3405
DOI:10.1016/j.bmcl.2017.08.024