Abstract
Herein, we report design and synthesis of series of adamantane derivatives containing modified peptides with thiazol moiety. New compounds were synthesized in solution using TBTU (2-(1H-Benzotriazole-1-yl)-1,1,3,3-tetramethylaminium tetrafluoroborate) as coupling agent. All derivatives were obtained with good yields. The antiviral activity of newly synthesized compounds against influenza virus H1N1 is studied. Cytotoxicity assay for determination of CC50 were done and IC50 values were calculated. The rimantadine analogue with thiazole ring Gly-Thz-rimantadine showed good activity against influenza virus A/Hongkong/68 with IC50 = 0.11 μg/mL and CC50 = 50 μg/mL. In addition, antimicrobial and antifungal activity against model strains of gram positive (Bacillus cereus), gram negative (Escherichia coli) microorganisms and fungi strain Yarrowia lipolytica 3344 were investigated. The compounds Gly-Thz-rimantadine with good antiviral activity also showed very good antifungal activity in two different concentrations.
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Acknowledgements
All strains of microorganisms, included in the Bulgarian National Collection, was kindly provided by the National Bank for Industrial Microorganisms and Cell Cultures (NBIMCC), Sofia, Bulgaria. We are grateful to South-West University “Neofit Rilski”, Blagoevgrad for financial support by Project RPY-A3/19.
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IS and DD contributed to the study conception and design of aimed compounds as well as in the writing, review and editing of the manuscript. Synthesis, isolation and characterization of newly synthesized compounds is realized by IS, KC and RC. Material preparation, data collection and interpretation of antiviral analysis is done by LM and AG. Material preparation, data collection and interpretation of antimicrobial analysis is realized by DM.
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Authors Ivanka Stankova, Kiril Chuchkov, Radoslav Chayrov, Luchia Mukova, Angel Galabov, Desislava Marinkova and Dancho Danalev declare that they have no conflict of interest. This work is not related to any experiments with human participants or animals.
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Stankova, I., Chuchkov, K., Chayrov, R. et al. Adamantane Derivatives Containing Thiazole Moiety: Synthesis, Antiviral and Antibacterial Activity. Int J Pept Res Ther 26, 1781–1787 (2020). https://doi.org/10.1007/s10989-019-09983-4
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DOI: https://doi.org/10.1007/s10989-019-09983-4