title: New quaternary ammonium camphor derivatives and their antiviral activity, genotoxic effects and cytotoxicity.
abstract: 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.
authors.affiliation: N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, Lavrentjev Avenue 9, 630090 Novosibirsk, Russia; Novosibirsk State University, Pirogova St. 2, 630090 Novosibirsk, Russia.
authors.forename: Anastasiya S
authors.initials: AS
authors.lastname: Sokolova
authors.forename: Capital O Cyrilliclga I
authors.initials: CO
authors.lastname: Yarovaya
authors.forename: Capital A Cyrillicndrey V
authors.initials: CA
authors.lastname: Shernyukov
authors.forename: Capital Em Cyrillicichail A
authors.initials: CE
authors.lastname: Pokrovsky
authors.forename: Capital A Cyrillicndrey G
authors.initials: CA
authors.lastname: Pokrovsky
authors.forename: Valentina A
authors.initials: VA
authors.lastname: Lavrinenko
authors.forename: Vladimir V
authors.initials: VV
authors.lastname: Zarubaev
authors.forename: Tatiana S
authors.initials: TS
authors.lastname: Tretiak
authors.forename: Pavel M
authors.initials: PM
authors.lastname: Anfimov
authors.forename: Oleg I
authors.initials: OI
authors.lastname: Kiselev
authors.forename: Anatoly B
authors.initials: AB
authors.lastname: Beklemishev
authors.forename: Nariman F
authors.initials: NF
authors.lastname: Salakhutdinov
mesh_terms: D000818:Animals; D000998:Antiviral Agents / Q000138:chemical synthesis / Q000737:chemistry* / Q000633:toxicity; D001665:Binding Sites; D001643:Bridged Bicyclo Compounds / Q000138:chemical synthesis / Q000737:chemistry* / Q000633:toxicity; D002164:Camphor / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000633:toxicity; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D004285:Dogs; D004926:Escherichia coli / Q000187:drug effects / Q000235:genetics; D006801:Humans; D053118:Influenza A Virus, H1N1 Subtype / Q000187:drug effects / Q000378:metabolism; D061985:Madin Darby Canine Kidney Cells; D062105:Molecular Docking Simulation; D009152:Mutagenicity Tests; D017434:Protein Structure, Tertiary; D000644:Quaternary Ammonium Compounds / Q000138:chemical synthesis / Q000737:chemistry* / Q000633:toxicity; D014763:Viral Matrix Proteins / Q000737:chemistry / Q000378:metabolism; D000086082:Viroporin Proteins
chemical_list: D000998:Antiviral Agents; D001643:Bridged Bicyclo Compounds; D002164:Camphor; D000644:Quaternary Ammonium Compounds; D014763:Viral Matrix Proteins; C488937:M2 protein, Influenza A virus; D000086082:Viroporin Proteins; C000588462:N1,N1,N12,N12-tetraethyl-N1,N12-bis(2-((1,7,7-trimethylbicyclo(2.2.1)heptan-2-ylidene)amino)ethyl)dodecane-1,12-diaminium
keywords: Antivirals; Camphor; Cytotoxicity; Genotoxicity; Imine derivatives; Influenza