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河豚毒素天然产物家族的化学与生物学

The Chemistry and Biology of the Tetrodotoxin Natural Product Family.

作者信息

Nißl Benedikt, Mülbaier Marcel, Grisoni Francesca, Trauner Dirk, Bermúdez Marcel, Dialer Clemens, Konrad David B

机构信息

Department of Pharmacy, Ludwig-Maximilians-Universität München, Butenandtstr. 5-13, Haus C, 81377, Munich, Germany.

Drug Discovery Engine, Grünenthal GmbH, Zieglerstr. 6, 52078, Aachen, Germany.

出版信息

Angew Chem Int Ed Engl. 2025 Aug 25;64(35):e202502404. doi: 10.1002/anie.202502404. Epub 2025 Aug 1.

DOI:10.1002/anie.202502404
PMID:40528706
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC12377457/
Abstract

Tetrodotoxin is a neurotoxic marine alkaloid, first isolated in 1909 from pufferfish and named after the biological order tetraodontiformes. Since its structural elucidation in 1964, it has attracted the interest of synthetic organic chemists due to its exceptional polarity, complex architecture, and important biological activity. This review highlights the diversity of the tetrodotoxin natural product family and discusses the origins of derivatives, biosynthetic hypotheses, and biological activities. Furthermore, potential therapeutic applications and structure-activity relationship studies are covered, along with the total syntheses of the natural product and selected derivatives that were published to date.

摘要

河豚毒素是一种具有神经毒性的海洋生物碱，于1909年首次从河豚中分离出来，并以鲀形目生物命名。自1964年其结构被阐明以来，由于其特殊的极性、复杂的结构和重要的生物活性，它引起了有机合成化学家的兴趣。本综述重点介绍了河豚毒素天然产物家族的多样性，并讨论了其衍生物的起源、生物合成假说和生物活性。此外，还涵盖了潜在的治疗应用和构效关系研究，以及迄今为止已发表的该天然产物及其选定衍生物的全合成。

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本文引用的文献

[1]
Tetrodotoxin: The State-of-the-Art Progress in Characterization, Detection, Biosynthesis, and Transport Enrichment.

Mar Drugs. 2024-11-26

[2]
Tetrodotoxin Derivatization with a Newly Designed Boron Reagent Leads to Conventional Reversed-Phase Liquid Chromatography.

Toxins (Basel). 2024-6-4

[3]
Combining IC or Values from Different Sources Is a Source of Significant Noise.

J Chem Inf Model. 2024-3-11

[4]
Total syntheses of Tetrodotoxin and 9-epiTetrodotoxin.

Nat Commun. 2024-1-23

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A structural atlas of druggable sites on Na channels.

Channels (Austin). 2024-12

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Scalable generation of sensory neurons from human pluripotent stem cells.

Stem Cell Reports. 2023-4-11

[7]
Structure of human Na1.6 channel reveals Na selectivity and pore blockade by 4,9-anhydro-tetrodotoxin.

Nat Commun. 2023-2-23

[8]
Isolation and Biological Activity of 9-Tetrodotoxin and Isolation of Tb-242B, Possible Biosynthetic Shunt Products of Tetrodotoxin from Pufferfish.

J Nat Prod. 2022-9-23

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Science. 2022-7-22

[10]
Total Syntheses of the Proposed Biosynthetic Intermediates of Tetrodotoxin Tb-210B, Tb-226, Tb-242C, and Tb-258.

J Org Chem. 2022-7-15

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