Статья

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

A. Sokolova, O. Yarovaya, A. Shernyukov, M. Pokrovsky, A. Pokrovsky, V. Lavrinenko, V. Zarubaev, T. Tretiak, P. Anfimov, O. Kiselev, A. Beklemishev, N. Salakhutdinov,
2021

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 C9H18 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. © 2013 Elsevier Ltd. All rights reserved.

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  • 1. Version of Record от 2021-04-27

Метаданные

Об авторах
  • A. Sokolova
    N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, Lavrentjev Avenue 9, 630090 Novosibirsk, Russian Federation
  • O. Yarovaya
    Novosibirsk State University, Pirogova St. 2, 630090 Novosibirsk, Russian Federation
  • A. Shernyukov
    Department of Chemotherapy, Influenza Research Institute, 15/17 Prof. Popova St., 197376 St.-Petersburg, Russian Federation
  • M. Pokrovsky
    Research Institute for Biochemistry, Siberian Branch, Russian Academy of Medical Sciences, Timakova St. 2, 630117 Novosibirsk, Russian Federation
  • A. Pokrovsky
  • V. Lavrinenko
  • V. Zarubaev
  • T. Tretiak
  • P. Anfimov
  • O. Kiselev
  • A. Beklemishev
  • N. Salakhutdinov
Название журнала
  • Bioorganic and Medicinal Chemistry
Том
  • 21
Выпуск
  • 21
Страницы
  • 6690-6698
Ключевые слова
  • aliphatic compound; amantadine; camphor derivative; carbon; deitiphorin; green fluorescent protein; n,n diethyl n methyl 2 [(1,7,7 trimethylbicyclo[2.2.1]heptan 2 ylidene)amino]ethanaminium iodide; n,n' [1,4 phenylenebis(methylene)]bis[n,n diethyl 2 [(1,7,7 trimethylbicyclo[2.2.1]heptan 2ylidene)amino]ethanaminium]bromide; n,n,n triethyl 2 [(1,7,7 trimethylbicyclo[2.2.1]heptan 2 ylidene)amino]ethanaminium bromide; n1,n1,n10,n10 tetraethyl n1,n10 bis[2 [(1,7,7 trimethylbicyclo[2.2.1]heptan 2ylidene)amino]ethyl]decane 1,10 diaminium bromide; n1,n1,n12,n12 tetraethyl n1,n10 bis[2 [(1,7,7 trimethylbicyclo[2.2.1]heptan 2ylidene)amino]ethyl]dodecane 1,12 diaminium bromide; n1,n1,n5,n5 tetraethyl n1,n5 bis[2 [(1,7,7 trimethylbicyclo[2.2.1]heptan 2ylidene)amino]ethyl]pentane 1,5 diaminium bromide; n1,n1,n6,n6 tetraethyl n1,n6 bis[2 [(1,7,7 trimethylbicyclo[2.2.1]heptan 2ylidene)amino]ethyl]hexane 1,6 diaminium bromide; n1,n1,n9,n9 tetraethyl n1,n9 bis[2 [(1,7,7 trimethylbicyclo[2.2.1]heptan 2ylidene)amino]ethyl]nonane 1,9 diaminium bromide; nalidixic acid; nitrogen; quaternary ammonium derivative; rimantadine; unclassified drug; water; animal cell; antiviral activity; article; biosensor; cancer cell culture; carbon nuclear magnetic resonance; computer model; controlled study; drug cytotoxicity; drug screening; drug structure; drug synthesis; Escherichia coli; Fourier transformation; genotoxicity; human; human cell; Influenza virus A H1N1; molecular docking; nonhuman; nuclear Overhauser effect; virus inhibition; Dryobalanops; Influenzavirus A; Antivirals; Camphor; Cytotoxicity; Genotoxicity; Imine derivatives; Influenza; Animals; Antiviral Agents; Bicyclo Compounds; Binding Sites; Camphor; Cell Line, Tumor; Cell Survival; Dogs; Escherichia coli; Humans; Influenza A Virus, H1N1 Subtype; Madin Darby Canine Kidney Cells; Molecular Docking Simulation; Mutagenicity Tests; Protein Structure, Tertiary; Quaternary Ammonium Compounds; Viral Matrix Proteins
Тип документа
  • journal article
Тип лицензии Creative Commons
  • CC
Правовой статус документа
  • Свободная лицензия
Источник
  • scopus