Design, synthesis, molecular modeling, and biological evaluation of sulfanilamide-imines derivatives as potential anticancer agents

A series of sulfanilamide Schiff base derivatives (1 to 15) have been designed as potential antitubulin agents depending on the chemical structures of combretastatine A-4 and isoquinoline sulfamate (antimitotic agents under investigation). The designed compounds were synthesized by microwave chemica...

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Published in:Naunyn-Schmiedeberg's archives of pharmacology 2013-09, Vol.386 (9), p.813-822
Main Authors: Mohamed, Sofian S., Tamer, Abdalkarem R., Bensaber, Salah M., Jaeda, Mousa I., Ermeli, Nouri B., Allafi, Aemen Ali, Mrema, Ibrahim A., Erhuma, Mabrouk, Hermann, Anton, Gbaj, Abdul M.
Format: Article
Language:English
Subjects:
Antineoplastic Agents - pharmacology
Biomedical and Life Sciences
Biomedicine
Cell Line, Tumor
Cell Survival - drug effects
Drug Design
Humans
Imines - pharmacology
Ligands
MCF-7 Cells
Models, Molecular
Neurosciences
Original
Original Article
Pharmacology/Toxicology
Sulfanilamides - pharmacology
Tubulin - chemistry
Tubulin - metabolism
Tubulin Modulators - pharmacology
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Summary:A series of sulfanilamide Schiff base derivatives (1 to 15) have been designed as potential antitubulin agents depending on the chemical structures of combretastatine A-4 and isoquinoline sulfamate (antimitotic agents under investigation). The designed compounds were synthesized by microwave chemical synthesis, their purity was confirmed by melting point and HPLC and chemical structures were determined by FT-IR, UV, and 1 H and 13 C-NMR spectroscopic techniques. The synthesized compounds have been docked in the colchicine binding site of β-tubulin using molecular modeling programs and the antitumor activities were screened on human breast and lung cancer cells by cell counting assay. Some tested compounds showed potent and selective activity against breast cancer (MCF-7) with IC 50 range of 90 to 166 μM. With regarding broad-spectrum activity, compounds 4, 8, and 13 have shown potent antitumor activity against human breast and human lung cells with IC 50 range of 96 to 140 μM. The obtained results suggest that the sulfanilamide Schiff base derivatives might potentially constitute an interesting novel class of anticancer agents, which deserve further studies.
ISSN:0028-1298
1432-1912
DOI:10.1007/s00210-013-0883-y