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

J 2023

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 et. al.

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

Language

English

Type of outcome

Článek v odborném periodiku

Field of Study

10600 1.6 Biological sciences

Country of publisher

Switzerland

Confidentiality degree

není předmětem státního či obchodního tajemství

References:

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

Abstract

V originále

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

Citovat

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.

@article{2354958,
   author = {Lörincz, Eszter Boglárka and Herczeg, Mihály and Houser, Josef and Rievajová, Martina and Kuki, Ákos and Malinovská, Lenka and Naesens, Lieve and Wimmerová, Michaela and Borbás, Anikó and Herczegh, Pál and Bereczki, Ilona},
   article_number = {24},
   doi = {http://dx.doi.org/10.3390/ijms242417268},
   keywords = {influenza; sialic acid; neuraminidase; hemagglutinin; aggregates},
   language = {eng},
   issn = {1661-6596},
   journal = {International Journal of Molecular Sciences},
   title = {Amphiphilic Sialic Acid Derivatives as Potential Dual-Specific Inhibitors of Influenza Hemagglutinin and Neuraminidase},
   url = {https://www.mdpi.com/1422-0067/24/24/17268},
   volume = {24},
   year = {2023}
}

TY  - JOUR
ID  - 2354958
AU  - Lörincz, Eszter Boglárka - Herczeg, Mihály - Houser, Josef - Rievajová, Martina - Kuki, Ákos - Malinovská, Lenka - Naesens, Lieve - Wimmerová, Michaela - Borbás, Anikó - Herczegh, Pál - Bereczki, Ilona
PY  - 2023
TI  - Amphiphilic Sialic Acid Derivatives as Potential Dual-Specific Inhibitors of Influenza Hemagglutinin and Neuraminidase
JF  - International Journal of Molecular Sciences
VL  - 24
IS  - 24
SP  - 1-23
EP  - 1-23
PB  - MDPI
SN  - 16616596
KW  - influenza
KW  - sialic acid
KW  - neuraminidase
KW  - hemagglutinin
KW  - aggregates
UR  - https://www.mdpi.com/1422-0067/24/24/17268
N2  - 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.
ER  -

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. \textit{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.

Detailed Information on Publication Record