New quaternary ammonium camphor derivatives and their antiviral activity, genotoxic effects and cytotoxicity

The synthesis and biological evaluation of a novel series of dimeric camphor derivatives are described. The resulting compounds were studied for their antiviral activity, cyto- and genotoxicity. Compounds 3a and 3d in which the quaternary nitrogen atoms are separated by the C5H10 and С9H18 aliphatic...

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Veröffentlicht in:	Bioorganic & medicinal chemistry 2013-11, Vol.21 (21), p.6690-6698
Hauptverfasser:	Sokolova, Anastasiya S., Yarovaya, Оlga I., Shernyukov, Аndrey V., Pokrovsky, Мichail A., Pokrovsky, Аndrey G., Lavrinenko, Valentina A., Zarubaev, Vladimir V., Tretiak, Tatiana S., Anfimov, Pavel M., Kiselev, Oleg I., Beklemishev, Anatoly B., Salakhutdinov, Nariman F.
Format:	Artikel
Sprache:	eng
Schlagworte:	Animals Antiviral Agents - chemical synthesis Antiviral Agents - chemistry Antiviral Agents - toxicity Antivirals Binding Sites Bridged Bicyclo Compounds - chemical synthesis Bridged Bicyclo Compounds - chemistry Bridged Bicyclo Compounds - toxicity Camphor Camphor - analogs & derivatives Camphor - chemical synthesis Camphor - toxicity Cell Line, Tumor Cell Survival - drug effects Cytotoxicity Dogs Escherichia coli - drug effects Escherichia coli - genetics Genotoxicity Humans Imine derivatives Influenza Influenza A Virus, H1N1 Subtype - drug effects Influenza A Virus, H1N1 Subtype - metabolism Influenza virus Madin Darby Canine Kidney Cells Molecular Docking Simulation Mutagenicity Tests Protein Structure, Tertiary Quaternary Ammonium Compounds - chemical synthesis Quaternary Ammonium Compounds - chemistry Quaternary Ammonium Compounds - toxicity Viral Matrix Proteins - chemistry Viral Matrix Proteins - metabolism
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Beschreibung
Zusammenfassung:	The synthesis and biological evaluation of a novel series of dimeric camphor derivatives are described. The resulting compounds were studied for their antiviral activity, cyto- and genotoxicity. Compounds 3a and 3d in which the quaternary nitrogen atoms are separated by the C5H10 and С9H18 aliphatic chain, exhibited the highest efficiency as an agent inhibiting the reproduction of the influenza virus A(H1N1)pdm09. The cytotoxicity data of compounds 3 and 4 revealed their moderate activity against malignant cell lines; compound 3f had the highest activity for the CEM-13 cells. These results show close agreement with the data of independent studies on toxicity of these compounds, in particular that the toxicity of compounds strongly depends on spacer length.
ISSN:	0968-0896 1464-3391
DOI:	10.1016/j.bmc.2013.08.014