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Synthetic Analogues of Aminoadamantane as Influenza Viral Inhibitors-In Vitro, In Silico and QSAR Studies

R. Chayrov, NA. Parisis, MV. Chatziathanasiadou, E. Vrontaki, K. Moschovou, G. Melagraki, H. Sbirkova-Dimitrova, B. Shivachev, M. Schmidtke, Y. Mitrev, M. Sticha, T. Mavromoustakos, AG. Tzakos, I. Stankova

. 2020 ; 25 (17) : . [pub] 20200901

Language English Country Switzerland

Document type Journal Article

Persistent link   https://www.medvik.cz/link/bmc21012221

A series of nineteen amino acid analogues of amantadine (Amt) and rimantadine (Rim) were synthesized and their antiviral activity was evaluated against influenza virus A (H3N2). Among these analogues, the conjugation of rimantadine with glycine illustrated high antiviral activity combined with low cytotoxicity. Moreover, this compound presented a profoundly high stability after in vitro incubation in human plasma for 24 h. Its thermal stability was established using differential and gravimetric thermal analysis. The crystal structure of glycyl-rimantadine revealed that it crystallizes in the orthorhombic Pbca space group. The structure-activity relationship for this class of compounds was established, with CoMFA (Comparative Molecular Field Analysis) 3D-Quantitative Structure Activity Relationships (3D-QSAR) studies predicting the activities of synthetic molecules. In addition, molecular docking studies were conducted, revealing the structural requirements for the activity of the synthetic molecules.

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$a Chayrov, Radoslav $u Department of Chemistry, South-West University "Neofit Rilski", 2700 Blagoevgrad, Bulgaria
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$a A series of nineteen amino acid analogues of amantadine (Amt) and rimantadine (Rim) were synthesized and their antiviral activity was evaluated against influenza virus A (H3N2). Among these analogues, the conjugation of rimantadine with glycine illustrated high antiviral activity combined with low cytotoxicity. Moreover, this compound presented a profoundly high stability after in vitro incubation in human plasma for 24 h. Its thermal stability was established using differential and gravimetric thermal analysis. The crystal structure of glycyl-rimantadine revealed that it crystallizes in the orthorhombic Pbca space group. The structure-activity relationship for this class of compounds was established, with CoMFA (Comparative Molecular Field Analysis) 3D-Quantitative Structure Activity Relationships (3D-QSAR) studies predicting the activities of synthetic molecules. In addition, molecular docking studies were conducted, revealing the structural requirements for the activity of the synthetic molecules.
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$a Parisis, Nikolaos A $u Section of Organic Chemistry and Biochemistry, Department of Chemistry, University of Ioannina, 45110 Ioannina, Greece
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$a Chatziathanasiadou, Maria V $u Section of Organic Chemistry and Biochemistry, Department of Chemistry, University of Ioannina, 45110 Ioannina, Greece
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$a Vrontaki, Eleni $u Division of Organic Chemistry, Department of Chemistry, National and Kapodistri`an University of Athens, 15771 Zografou, Greece $u Division of Pharmaceutical Chemistry, Department of Pharmacy, National and Kapodistrian University of Athens, 15771 Zografou, Greece
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$a Moschovou, Kalliopi $u Division of Organic Chemistry, Department of Chemistry, National and Kapodistri`an University of Athens, 15771 Zografou, Greece
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$a Melagraki, Georgia $u Division of Physical Sciences and Applications, Department of Military Sciences, Hellenic Military Academy, Vari-Koropi Avenue, 16672 Vári, Greece
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$a Sbirkova-Dimitrova, Hristina $u Institute of Mineralogy and Crystallography "Acad. Ivan Kostov", Bulgarian Academy of Sciences, 1113 Sofia, Bulgaria
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$a Shivachev, Boris $u Institute of Mineralogy and Crystallography "Acad. Ivan Kostov", Bulgarian Academy of Sciences, 1113 Sofia, Bulgaria
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$a Schmidtke, Michaela $u Department of Virology and Antiviral Therapy, Friedrich Schiller University, 207745 Jena, Germany
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$a Mitrev, Yavor $u Institute of Organic Chemistry with Centre of Phytochemistry, Bulgarian Academy of Science, 1113 Sofia, Bulgaria
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$a Sticha, Martin $u Department of Analytical Chemistry, Charles University, 11636 Prague 1, Czech Republic
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$a Mavromoustakos, Thomas $u Division of Organic Chemistry, Department of Chemistry, National and Kapodistri`an University of Athens, 15771 Zografou, Greece
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$a Tzakos, Andreas G $u Section of Organic Chemistry and Biochemistry, Department of Chemistry, University of Ioannina, 45110 Ioannina, Greece
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$a Stankova, Ivanka $u Department of Chemistry, South-West University "Neofit Rilski", 2700 Blagoevgrad, Bulgaria
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