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Synthetic Approaches to Zetekitoxin AB, a Potent Voltage-Gated Sodium Channel Inhibitor

Department of Biotechnology and Life Science, Tokyo University of Agriculture and Technology (TUAT), 2-24-16, Naka-cho, Koganei city, Tokyo 184-8588, Japan
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Mar. Drugs 2020, 18(1), 24; https://doi.org/10.3390/md18010024
Received: 7 December 2019 / Revised: 23 December 2019 / Accepted: 24 December 2019 / Published: 26 December 2019
(This article belongs to the Special Issue Ion Channels as Marine Drug Targets)
Voltage-gated sodium channels (NaVs) are membrane proteins that are involved in the generation and propagation of action potentials in neurons. Recently, the structure of a complex made of a tetrodotoxin-sensitive (TTX-s) NaV subtype with saxitoxin (STX), a shellfish toxin, was determined. STX potently inhibits TTX-s NaV, and is used as a biological tool to investigate the function of NaVs. More than 50 analogs of STX have been isolated from nature. Among them, zetekitoxin AB (ZTX) has a distinctive chemical structure, and is the most potent inhibitor of NaVs, including tetrodotoxin-resistant (TTX-r) NaV. Despite intensive synthetic studies, total synthesis of ZTX has not yet been achieved. Here, we review recent efforts directed toward the total synthesis of ZTX, including syntheses of 11-saxitoxinethanoic acid (SEA), which is considered a useful synthetic model for ZTX, since it contains a key carbon–carbon bond at the C11 position. View Full-Text
Keywords: saxitoxin; zetekitoxin AB; voltage-gated sodium channel; guanidine alkaloid saxitoxin; zetekitoxin AB; voltage-gated sodium channel; guanidine alkaloid
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MDPI and ACS Style

Adachi, K.; Ishizuka, H.; Odagi, M.; Nagasawa, K. Synthetic Approaches to Zetekitoxin AB, a Potent Voltage-Gated Sodium Channel Inhibitor. Mar. Drugs 2020, 18, 24.

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