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© Nadia Naffakh, Institut Pasteur
Immunofluorescence detection of influenza virus nucleoprotein in infected cells
Publication : Organic & biomolecular chemistry

Synthesis and evaluation of novel 3-C-alkylated-Neu5Ac2en derivatives as probes of influenza virus sialidase 150-loop flexibility

Scientific Fields
Diseases
Organisms
Applications
Technique

Published in Organic & biomolecular chemistry - 21 Nov 2012

Rudrawar S, Kerry PS, Rameix-Welti MA, Maggioni A, Dyason JC, Rose FJ, van der Werf S, Thomson RJ, Naffakh N, Russell RJ, von Itzstein M

Link to Pubmed [PMID] – 22976385

Org. Biomol. Chem. 2012 Nov;10(43):8628-39

Novel 3-C-alkylated-Neu5Ac2en derivatives have been designed to target the expanded active site cavity of influenza virus sialidases with an open 150-loop, currently seen in X-ray crystal structures of influenza A virus group-1 (N1, N4, N5, N8), but not group-2 (N2, N9), sialidases. The compounds show selectivity for inhibition of H5N1 and pdm09 H1N1 sialidases over an N2 sialidase, providing evidence of the relative 150-loop flexibility of these sialidases. In a complex with N8 sialidase, the C3 substituent of 3-phenylally-Neu5Ac2en occupies the 150-cavity while the central ring and the remaining substituents bind the active site as seen for the unsubstituted template. This new class of inhibitors, which can ‘trap’ the open 150-loop form of the sialidase, should prove useful as probes of 150-loop flexibility.

https://www.ncbi.nlm.nih.gov/pubmed/22976385