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Synthesis, H2S releasing properties, antiviral and antioxidant activities and acute cardiac effects of nucleoside 5'-dithioacetates
M. Bege, M. Lovas, D. Priksz, B. Bernát, I. Bereczki, RG. Kattoub, R. Kajtár, S. Eskeif, L. Novák, J. Hodek, J. Weber, P. Herczegh, I. Lekli, A. Borbás
Language English Country England, Great Britain
Document type Journal Article, Research Support, Non-U.S. Gov't
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- MeSH
- Adenosine analogs & derivatives MeSH
- Antioxidants * pharmacology chemistry MeSH
- Antiviral Agents * pharmacology chemical synthesis chemistry MeSH
- Cell Line MeSH
- COVID-19 Drug Treatment MeSH
- Humans MeSH
- Nucleosides pharmacology chemistry metabolism MeSH
- SARS-CoV-2 drug effects metabolism MeSH
- Hydrogen Sulfide * metabolism MeSH
- Animals MeSH
- Check Tag
- Humans MeSH
- Animals MeSH
- Publication type
- Journal Article MeSH
- Research Support, Non-U.S. Gov't MeSH
Hydrogen sulfide (H2S) is an endogenous gasotransmitter with cardioprotective and antiviral effects. In this work, new cysteine-selective nucleoside-H2S-donor hybrid molecules were prepared by conjugating nucleoside biomolecules with a thiol-activatable dithioacetyl group. 5'-Dithioacetate derivatives were synthesized from the canonical nucleosides (uridine, adenosine, cytidine, guanosine and thymidine), and the putative 5'-thio metabolites were also produced from uridine and adenosine. According to our measurements made with an H2S-specific sensor, nucleoside dithioacetates are moderately fast H2S donors, the guanosine derivative showed the fastest kinetics and the adenosine derivative the slowest. The antioxidant activity of 5'-thionucleosides is significantly higher than that of trolox, but lower than that of ascorbic acid, while intact dithioacetates have no remarkable antioxidant effect. In human Calu cells, the guanosine derivative showed a moderate anti-SARS-CoV-2 effect which was also confirmed by virus yield reduction assay. Dithioacetyl-adenosine and its metabolite showed similar acute cardiac effects as adenosine, however, it is noteworthy that both 5'-thio modified adenosines increased left ventricular ejection fraction or stroke volume, which was not observed with native adenosine.
HUN REN UD Pharmamodul Research Group University of Debrecen Nagyerdei krt 98 Debrecen 4032 Hungary
Institute of Healthcare Industry University of Debrecen Nagyerdei krt 98 Debrecen 4032 Hungary
National Laboratory of Virology University of Pécs Ifjúság útja 20 Pécs 7624 Hungary
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