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Sugar-based synthesis of Tamiflu and its inhibitory effects on cell secretion

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Sugar-based synthesis of Tamiflu and its inhibitory effects on cell secretion

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dc.contributor.author Ma, Jimei
dc.contributor.author Zhao, Yanying
dc.contributor.author Ng, Simon
dc.contributor.author Zhang, Jing
dc.contributor.author Zeng, Jing
dc.contributor.author Than, Aung
dc.contributor.author Chen, Peng
dc.contributor.author Liu, Xue-Wei
dc.date.accessioned 2012-01-31T04:16:57Z
dc.date.available 2012-01-31T04:16:57Z
dc.date.copyright 2010
dc.date.issued 2012-01-31
dc.identifier.citation Ma, J., Zhao, Y., Ng, S., Zhang, J., Zeng, J., Than, A., et al. (2010). Sugar-Based Synthesis of Tamiflu and Its Inhibitory Effects on Cell Secretion. Chemistry - a European Journal, 16(15), 4533-4540.
dc.identifier.uri http://hdl.handle.net/10220/7486
dc.description.abstract Tamiflu is currently the most effective drug for the treatment of influenza, but the insufficient supply and side-effects of this drug demand urgent solutions. We present a practical synthesis of Tamiflu by using novel synthetic routes, cheap reagents, and the abundantly available starting material D-glucal. The strategy features a Claisen rearrangement of hexose to obtain the cyclohexene backbone and introduction of diamino groups through tandem intramolecular aziridination and ring opening. In addition, this synthetic protocol allows late-stage functionalization for the flexible synthesis of Tamiflu analogues. By using the synthesized Tamiflu and its active metabolite (oseltamivir carboxylate), we investigated their influences on neuroendocrine PC12 cells in various aspects. It was discovered that oseltamivir carboxylate significantly inhibits the vesicular exocytosis (regulated secretion) of PC12 cells, and suggests a mechanism underlying the Tamiflu side-effects, in particular its possible adverse influences on neurotransmitter release in the central nervous system.
dc.language.iso en
dc.relation.ispartofseries Chemistry - a European journal
dc.rights © 2010 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
dc.subject DRNTU::Science::Biological sciences::Biochemistry.
dc.title Sugar-based synthesis of Tamiflu and its inhibitory effects on cell secretion
dc.type Journal Article
dc.contributor.school School of Physical and Mathematical Sciences
dc.identifier.doi http://dx.doi.org/10.1002/chem.200902048
dc.identifier.rims 149060

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