Synthesis, biological evaluation and molecular docking studies of resveratrol derivatives possessing curcumin moiety as potent antitubulin agents

A series of resveratrol derivatives possessing curcumin moiety were synthesized and evaluated for their antiproliferative and antitubulin activity. Docking simulation was performed to position compound C5 into the colchicine binding site to determine the probable binding mode. A series of resveratro...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry 2012-01, Vol.20 (2), p.1113-1121
Main Authors: Ruan, Ban-Feng, Lu, Xiang, Li, Ting-Ting, Tang, Jian-Feng, Wei, Yao, Wang, Xiao-Liang, Zheng, Shi-Li, Yao, Ri-Sheng, Zhu, Hai-Liang
Format: Article
Language:English
Subjects:
Animals
Antineoplastic Agents - chemical synthesis
Antineoplastic Agents - chemistry
Antineoplastic Agents - pharmacology
Antiproliferative activity
Antitubulin polymerization activity
Binding Sites
Cell Cycle Checkpoints
Cell Line, Tumor
Cell Proliferation - drug effects
Computer Simulation
Curcumin
Curcumin - chemistry
Drug Screening Assays, Antitumor
hepatoma
Humans
inhibitory concentration 50
lung neoplasms
melanoma
Mice
Molecular docking
polymerization
Protein Structure, Tertiary
Resveratrol
Stilbenes - chemical synthesis
Stilbenes - chemistry
Stilbenes - pharmacology
Structure-Activity Relationship
tubulin
Tubulin - chemistry
Tubulin - metabolism
Tubulin Modulators - chemical synthesis
Tubulin Modulators - chemistry
Tubulin Modulators - pharmacology
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Summary:A series of resveratrol derivatives possessing curcumin moiety were synthesized and evaluated for their antiproliferative and antitubulin activity. Docking simulation was performed to position compound C5 into the colchicine binding site to determine the probable binding mode. A series of resveratrol derivatives possessing curcumin moiety were synthesized and evaluated for their antiproliferative activity against three cancer cell lines including murine melanoma B16-F10, human hepatoma HepG2 and human lung carcinoma A549. Among them, compound C5 displayed the most potent in vitro antiproliferative activity against B16-F10 with IC50 value of 0.71μg/mL. Compound C5 also exhibited good tubulin polymerization inhibitory activity with IC50 value of 1.45μg/mL. Furthermore, docking simulation was carried out to position C5 into the tubulin-colchicine binding site to determine the probable binding mode.
ISSN:0968-0896
1464-3391
DOI:10.1016/j.bmc.2011.11.017