The Chemical Synthesis of Tetrodoxin: An Ongoing Quest

Chau, Jaclyn; Ciufolini, Marco A.

doi:10.3390/md9102046

Cited by 47 publications

(35 citation statements)

References 81 publications

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“…Several total syntheses of TTX ( 1 ) and the approaches toward its construction were already reviewed . However, for the sake of completeness they will be covered in this manuscript as well, albeit only briefly with only the key strategic steps discussed.…”

Section: Synthesis Of Ttxmentioning

confidence: 99%

Tetrodotoxin: History, Biology, and Synthesis

et al. 2019

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This review provides a comprehensive coverage of the history, biology and chemistry of tetrodotoxin (TTX). It traces the origin of this remarkable molecule all the way back to the ancient Chinese medicine records. The discovery of biological activity, isolation, and a brief overview of structure elucidation are summarized. Next, the biology of TTX is discussed, primarily in the context of its activity in the sodium channels, its anesthetic properties, and its potential use in cancer treatment or drug addiction. Biosynthesis of TTX is covered before the discussion of the total syntheses. All total, formal or partial syntheses are covered but those total syntheses that have been discussed in previous reviews are only briefly summarized. Finally, the synthesis of natural and unnatural derivatives is surveyed, and a conclusion and outlook are provided for this very extensive field of endeavor. To the best of our knowledge the literature coverage is complete up to December 2018.

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Section: Synthesis Of Ttxmentioning

confidence: 99%

Tetrodotoxin: History, Biology, and Synthesis

et al. 2019

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“…A more efficient synthesis requiring less chromatography followed (Jacobi et al 1984), but in both of these syntheses, the STX analogue decarbamoyl STX was an intermediate which is then converted to STX in the final step. Methods to chemically synthesize TTX are now quite numerous (Chau and Ciufolini 2011), but of interest is that some start with readily available and cheap chemicals like glucose (Sato et al 2008) and levoglucosenone (Urabe et al 2006) reducing the overall cost of their production. The syntheses are becoming more efficient with recent syntheses having increasingly fewer steps (Bhonde and Looper 2011).…”

Section: Chemical Productionmentioning

confidence: 99%

Biological Toxins and Bioterrorism

Gopalakrishnakone¹,

Balali-Mood²,

Llewellyn³

et al. 2015

Toxinology

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In recent years, the field of toxinology has expanded substantially. On the one hand it studies venomous animals, plants and micro organisms in detail to understand their mode of action on targets. While on the other, it explores the biochemical composition, genomics and proteomics of toxins and venoms to understand their three interaction with life forms (especially humans), development of antidotes and exploring their pharmacological potential. Therefore, toxinology has deep linkages with biochemistry, molecular biology, anatomy and pharmacology. In addition, there is a fast-developing applied subfield, clinical toxinology, which deals with understanding and managing medical effects of toxins on human body. Given the huge impact of toxin-based deaths globally, and the potential of venom in generation of drugs for so-far incurable diseases (for example, diabetes, chronic pain), the continued research and growth of the field is imminent. This has led to the growth of research in the area and the consequent scholarly output by way of publications in journals and books. Despite this ever-growing body of literature within biomedical sciences, there is still no all-inclusive reference work available that collects all of the important biochemical, biomedical and clinical insights relating to toxinology. Composed of 11 volumes, Toxinology provides comprehensive and authoritative coverage of the main areas in toxinology, from fundamental concepts to new developments and applications in the field. Each volume comprises a focused and carefully chosen collection of contributions from leading names in the subject.

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“…The syntheses are becoming more efficient with recent syntheses having increasingly fewer steps (Bhonde and Looper 2011). Methods to chemically synthesize TTX are now quite numerous (Chau and Ciufolini 2011), but of interest is that some start with readily available and cheap chemicals like glucose (Sato et al 2008) and levoglucosenone (Urabe et al 2006) reducing the overall cost of their production.…”

Section: Chemical Productionmentioning

confidence: 99%

Marine Biotoxins in History: Misuse and Mayhem

Llewellyn

2014

Toxinology

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Saxitoxin (STX) and tetrodotoxin (TTX) have a colorful history. Two of the most toxic natural toxins known, they have been used as weapons to commit suicide, attempt, or successfully commit murder, and STX has been officially declared a chemical weapon by the world's governments. This meant that it was no longer a natural marine chemical of interest to toxinologists, pharmacologists, and at times seafood producers (because it can taint their product); it had now come upon the radar of many government agencies. TTX has its own mystique more renowned as the toxin of "fugu" fame, but also been blamed as the active agent in the zombification rituals in some Caribbean cultures. However, deliberate intoxications by these toxins remain far fewer than accidental deaths through eating poorly prepared fugu meals or saxitoxin-infested shellfish. Diagnosis, rather than detection, remains the best means of identifying whether a victim has been purposefully intoxicated. Treatment of intoxication by STX or TTX is still relatively crude, relying mostly upon gastric evacuation to remove unabsorbed toxin and symptomatic relief to nurse the victim through the acute phase of an intoxication and then relying upon the body's natural recovery mechanisms. Some potential pharmaceutical treatment options exist, but these have only been tested in small mammal studies, upon few test animals, and under limited conditions and would require significant investment in resources to progress them beyond the laboratory.

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The Chemical Synthesis of Tetrodoxin: An Ongoing Quest

Abstract: This contribution reviews all the synthetic work on tetrodotoxin that has appeared in the literature through June 2011.

Cited by 47 publications

References 81 publications

Tetrodotoxin: History, Biology, and Synthesis

Tetrodotoxin: History, Biology, and Synthesis

Biological Toxins and Bioterrorism

Marine Biotoxins in History: Misuse and Mayhem

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