Please use this identifier to cite or link to this item: https://hdl.handle.net/10356/94305
Title: Sugar-based synthesis of Tamiflu and its inhibitory effects on cell secretion
Authors: Ma, Jimei
Zhao, Yanying
Ng, Simon
Zeng, Jing
Than, Aung
Chen, Peng
Liu, Xue-Wei
Zhang, Jing
Keywords: DRNTU::Science::Biological sciences::Biochemistry
Issue Date: 2010
Source: 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.
Series/Report no.: Chemistry - a European journal
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.
URI: https://hdl.handle.net/10356/94305
http://hdl.handle.net/10220/7486
DOI: 10.1002/chem.200902048
Rights: © 2010 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Fulltext Permission: none
Fulltext Availability: No Fulltext
Appears in Collections:SPMS Journal Articles

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