A sialosyl sulfonate as a potent inhibitor of influenza virus replication

Ádám Hadházi, Mauro Pascolutti, Benjamin Bailly, Jeffrey C. Dyason, A. Borbás, Robin J. Thomson, Mark Von Itzstein

Research output: Contribution to journalArticle

1 Citation (Scopus)

Abstract

A new direction for influenza virus sialidase inhibitor development was identified using a sulfonate congener of 2-deoxy-2-β-H N-acetylneuraminic acid. Sialosyl sulfonates can be synthesised efficiently in four steps from N-acetylneuraminic acid via a microwave assisted decarboxylation. The presence of the sulfonate group significantly increases inhibition of influenza virus sialidase and viral infection when compared to the carboxylate congener, and also to the benchmark sialidase inhibitor 2,3-dehydro-2-deoxy-N-acetylneuraminic acid, Neu5Ac2en.

Original languageEnglish
Pages (from-to)5249-5253
Number of pages5
JournalOrganic and Biomolecular Chemistry
Volume15
Issue number25
DOIs
Publication statusPublished - Jan 1 2017

Fingerprint

influenza
Neuraminidase
viruses
Virus Replication
sulfonates
Orthomyxoviridae
Viruses
inhibitors
congeners
N-Acetylneuraminic Acid
Virus Diseases
acids
Benchmarking
decarboxylation
Decarboxylation
infectious diseases
Microwaves
carboxylates
microwaves
2-deoxy-2,3-dehydro-N-acetylneuraminic acid

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Cite this

Hadházi, Á., Pascolutti, M., Bailly, B., Dyason, J. C., Borbás, A., Thomson, R. J., & Von Itzstein, M. (2017). A sialosyl sulfonate as a potent inhibitor of influenza virus replication. Organic and Biomolecular Chemistry, 15(25), 5249-5253. https://doi.org/10.1039/c7ob00947j

A sialosyl sulfonate as a potent inhibitor of influenza virus replication. / Hadházi, Ádám; Pascolutti, Mauro; Bailly, Benjamin; Dyason, Jeffrey C.; Borbás, A.; Thomson, Robin J.; Von Itzstein, Mark.

In: Organic and Biomolecular Chemistry, Vol. 15, No. 25, 01.01.2017, p. 5249-5253.

Research output: Contribution to journalArticle

Hadházi, Á, Pascolutti, M, Bailly, B, Dyason, JC, Borbás, A, Thomson, RJ & Von Itzstein, M 2017, 'A sialosyl sulfonate as a potent inhibitor of influenza virus replication', Organic and Biomolecular Chemistry, vol. 15, no. 25, pp. 5249-5253. https://doi.org/10.1039/c7ob00947j
Hadházi, Ádám ; Pascolutti, Mauro ; Bailly, Benjamin ; Dyason, Jeffrey C. ; Borbás, A. ; Thomson, Robin J. ; Von Itzstein, Mark. / A sialosyl sulfonate as a potent inhibitor of influenza virus replication. In: Organic and Biomolecular Chemistry. 2017 ; Vol. 15, No. 25. pp. 5249-5253.
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