Amphiphilic Sialic Acid Derivatives as Potential Dual-Specific Inhibitors of Influenza Hemagglutinin and Neuraminidase

LÖRINCZ, Eszter Boglárka, Mihály HERCZEG, Josef HOUSER, Martina RIEVAJOVÁ, Ákos KUKI, Lenka MALINOVSKÁ, Lieve NAESENS, Michaela WIMMEROVÁ, Anikó BORBÁS, Pál HERCZEGH and Ilona BERECZKI. Amphiphilic Sialic Acid Derivatives as Potential Dual-Specific Inhibitors of Influenza Hemagglutinin and Neuraminidase. International Journal of Molecular Sciences. MDPI, 2023, vol. 24, No 24, p. 1-23. ISSN 1661-6596. Available from: https://dx.doi.org/10.3390/ijms242417268.

Basic information

• Original name: Amphiphilic Sialic Acid Derivatives as Potential Dual-Specific Inhibitors of Influenza Hemagglutinin and Neuraminidase
• Authors: LÖRINCZ, Eszter Boglárka (348 Hungary), Mihály HERCZEG (348 Hungary), Josef HOUSER (203 Czech Republic, belonging to the institution), Martina RIEVAJOVÁ (703 Slovakia, belonging to the institution), Ákos KUKI, Lenka MALINOVSKÁ (203 Czech Republic, belonging to the institution), Lieve NAESENS, Michaela WIMMEROVÁ (203 Czech Republic, guarantor, belonging to the institution), Anikó BORBÁS (348 Hungary), Pál HERCZEGH (348 Hungary) and Ilona BERECZKI (348 Hungary).
• Edition: International Journal of Molecular Sciences, MDPI, 2023, 1661-6596.

Other information

• Original language: English
• Type of outcome: Article in a journal
• Field of Study: 10600 1.6 Biological sciences
• Country of publisher: Switzerland
• Confidentiality degree: is not subject to a state or trade secret
• WWW: URL
• Impact factor: Impact factor: 5.600 in 2022
• RIV identification code: RIV/00216224:14310/23:00132714
• Organization unit: Faculty of Science
• Doi: http://dx.doi.org/10.3390/ijms242417268
• UT WoS: 001130681500001
• Keywords in English: influenza; sialic acid; neuraminidase; hemagglutinin; aggregates
• Tags: CF BIC, rivok
• Tags: International impact, Reviewed

Abstract

Blocking viral hemagglutinin with multivalent N-acetylneuraminic acid derivatives is a promising approach to prevent influenza infection. Moreover, dual inhibition of both hemagglutinin and neuraminidase may result in a more powerful effect. Since both viral glycoproteins can bind to neuraminic acid, we have prepared three series of amphiphilic self-assembling 2-thio-neuraminic acid derivatives constituting aggregates in aqueous medium to take advantage of their multivalent effect. One of the series was prepared by the azide-alkyne click reaction, and the other two by the thio-click reaction to yield neuraminic acid derivatives containing lipophilic tails of different sizes and an enzymatically stable thioglycosidic bond. Two of the three bis-octyl derivatives produced proved to be active against influenza viruses, while all three octyl derivatives bound to hemagglutinin and neuraminidase from H1N1 and H3N2 influenza types.

Links

• EF18_046/0015974, research and development project: Name: Modernizace České infrastruktury pro integrativní strukturní biologii
• LM2023042, research and development project: Name: Česká infrastruktura pro integrativní strukturní biologii

Investor: Ministry of Education, Youth and Sports of the CR, CIISB - Czech Infrastructure for Integrative Structural Biology

• MUNI/A/1313/2022, interní kód MU: Name: Podpora biochemického výzkumu v roce 2023

Investor: Masaryk University

• 90242, large research infrastructures: Name: CIISB III