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Select item 70243291.

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

Kanna Adachi, Hayate Ishizuka, Minami Odagi, Kazuo Nagasawa

Mar Drugs. 2020 Jan; 18(1): 24. Published online 2019 Dec 26. doi: 10.3390/md18010024

PMCID:: PMC7024329

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The structure of zetekitoxin AB, a saxitoxin analog from the Panamanian golden frog Atelopus zeteki: A potent sodium-channel blocker

Mari Yotsu-Yamashita, Yong H. Kim, Samuel C. Dudley, Jr., Gaurav Choudhary, Arnold Pfahnl, Yasukatsu Oshima, John W. Daly

Proc Natl Acad Sci U S A. 2004 Mar 30; 101(13): 4346–4351. Published online 2004 Mar 22. doi: 10.1073/pnas.0400368101

PMCID:: PMC384749

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Preparation of a 1,2-isoxazolidine synthon for the synthesis of zetekitoxin AB

Srinivas R. Paladugu, Ryan E. Looper

Tetrahedron Lett. Author manuscript; available in PMC 2016 Nov 18.

Published in final edited form as: Tetrahedron Lett. 2015 Nov 18; 56(46): 6332–6334. doi: 10.1016/j.tetlet.2015.09.070

PMCID:: PMC4649947

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Silylpyrrole Oxidation En Route to Saxitoxin Congeners Including 11-Saxitoxinethanoic Acid

Doris T. Y. Tang, Jeffrey E. Merit, T. Aaron Bedell, J. Du Bois

J Org Chem. Author manuscript; available in PMC 2022 Feb 19.

Published in final edited form as: J Org Chem. 2021 Dec 17; 86(24): 17790–17803. Published online 2021 Dec 7. doi: 10.1021/acs.joc.1c02116

PMCID:: PMC8857915

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Synthetic studies towards Zetekitoxin AB: preparation of 4,5-epi-11-hydroxy-saxitoxinol

Aaron D. Pearson, Robert M. Williams

Tetrahedron. Author manuscript; available in PMC 2015 Oct 28.

Published in final edited form as: Tetrahedron. 2014 Oct 28; 70(43): 7942–7949. doi: 10.1016/j.tet.2014.08.058

PMCID:: PMC4192658

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A review of chemical defense in harlequin toads (Bufonidae: Atelopus)

Kannon C. Pearson, Rebecca D. Tarvin

Toxicon X. 2022 Mar; 13: 100092. Published online 2022 Jan 22. doi: 10.1016/j.toxcx.2022.100092

PMCID:: PMC8801762

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A Direct C11 Alkylation Strategy on the Saxitoxin Core: A Synthesis of (+)-11-Saxitoxinethanoic Acid

Srinivas R. Paladugu, Chintelle K. James, Ryan E. Looper

Org Lett. Author manuscript; available in PMC 2021 Nov 4.

Published in final edited form as: Org Lett. 2019 Oct 4; 21(19): 7999–8002. Published online 2019 Sep 25. doi: 10.1021/acs.orglett.9b02986

PMCID:: PMC8567775

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Natural voltage-gated sodium channel ligands: Biosynthesis and biology

April L. Lukowski, Alison R. H. Narayan

Chembiochem. Author manuscript; available in PMC 2020 May 15.

Published in final edited form as: Chembiochem. 2019 May 15; 20(10): 1231–1241. Published online 2019 Mar 27. doi: 10.1002/cbic.201800754

PMCID:: PMC6579537

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Military Importance of Natural Toxins and Their Analogs

Vladimír Pitschmann, Zdeněk Hon

Molecules. 2016 May; 21(5): 556. Published online 2016 Apr 28. doi: 10.3390/molecules21050556

PMCID:: PMC6273326

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Neurotoxic Alkaloids: Saxitoxin and Its Analogs

Maria Wiese, Paul M. D’Agostino, Troco K. Mihali, Michelle C. Moffitt, Brett A. Neilan

Mar Drugs. 2010; 8(7): 2185–2211. Published online 2010 Jul 20. doi: 10.3390/md8072185

PMCID:: PMC2920551

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Tetrodotoxin, a Potential Drug for Neuropathic and Cancer Pain Relief?

Rafael González-Cano, M. Carmen Ruiz-Cantero, Miriam Santos-Caballero, Carlos Gómez-Navas, Miguel Á. Tejada, Francisco R. Nieto

Toxins (Basel) 2021 Jul; 13(7): 483. Published online 2021 Jul 12. doi: 10.3390/toxins13070483

PMCID:: PMC8310002

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Select item 1072536212.

Eco-Metabolomics Applied to the Chemical Ecology of Poison Frogs (Dendrobatoidea)

Mabel Gonzalez, Chiara Carazzone

J Chem Ecol. 2023; 49(9-10): 570–598. Published online 2023 Aug 18. doi: 10.1007/s10886-023-01443-0

PMCID:: PMC10725362

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Recent Progress in Neuroactive Marine Natural Products

Ryuichi Sakai, Geoffrey T. Swanson

Nat Prod Rep. Author manuscript; available in PMC 2015 Jan 17.

Published in final edited form as: Nat Prod Rep. 2014 Jan 17; 31(2): 273–309. doi: 10.1039/c3np70083f

PMCID:: PMC3955223

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On the Chemistry, Toxicology and Genetics of the Cyanobacterial Toxins, Microcystin, Nodularin, Saxitoxin and Cylindrospermopsin

Leanne Pearson, Troco Mihali, Michelle Moffitt, Ralf Kellmann, Brett Neilan

Mar Drugs. 2010; 8(5): 1650–1680. Published online 2010 May 10. doi: 10.3390/md8051650

PMCID:: PMC2885083

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Mutant cycle analysis with modified saxitoxins reveals specific interactions critical to attaining high-affinity inhibition of hNa_V1.7

Rhiannon Thomas-Tran, J. Du Bois

Proc Natl Acad Sci U S A. 2016 May 24; 113(21): 5856–5861. Published online 2016 May 9. doi: 10.1073/pnas.1603486113

PMCID:: PMC4889396

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A Convenient Synthesis of (16S,20S)-3β-Hydroxy-5α-pregnane-20,16-carbolactam and Its N-alkyl Derivatives

Agnieszka Wojtkielewicz, Damian Pawelski, Przemysław Bazydło, Aneta Baj, Stanisław Witkowski, Jacek W. Morzycki

Molecules. 2020 May; 25(10): 2377. Published online 2020 May 20. doi: 10.3390/molecules25102377

PMCID:: PMC7287600

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Absolute Structure Determination and Kv1.5 Ion Channel Inhibition Activities of New Debromoaplysiatoxin Analogues

Sicheng Shen, Weiping Wang, Zijun Chen, Huihui Zhang, Yuchun Yang, Xiaoliang Wang, Peng Fu, Bingnan Han

Mar Drugs. 2021 Nov; 19(11): 630. Published online 2021 Nov 11. doi: 10.3390/md19110630

PMCID:: PMC8622842

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Select item 853789918.

Voltage-Gated Sodium Channels: A Prominent Target of Marine Toxins

Rawan Mackieh, Rita Abou-Nader, Rim Wehbe, César Mattei, Christian Legros, Ziad Fajloun, Jean Marc Sabatier

Mar Drugs. 2021 Oct; 19(10): 562. Published online 2021 Oct 5. doi: 10.3390/md19100562

PMCID:: PMC8537899

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Select item 642645219.

Divergent Synthesis of Natural Derivatives of (+)-Saxitoxin Including 11-Saxitoxinethanoic Acid

James R. Walker, Jeffrey E. Merit, Rhiannon Thomas-Tran, Doris T. Y. Tang, J. Du Bois

Angew Chem Int Ed Engl. Author manuscript; available in PMC 2020 Feb 4.

Published in final edited form as: Angew Chem Int Ed Engl. 2019 Feb 4; 58(6): 1689–1693. Published online 2019 Jan 2. doi: 10.1002/anie.201811717

PMCID:: PMC6426452

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Select item 285737220.

The Chemical and Evolutionary Ecology of Tetrodotoxin (TTX) Toxicity in Terrestrial Vertebrates

Charles T. Hanifin

Mar Drugs. 2010; 8(3): 577–593. Published online 2010 Mar 10. doi: 10.3390/md8030577

PMCID:: PMC2857372

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PMC Images search for "zetekitoxin AB"

Scheme 1

Retrosythetic analysis of zetekitoxin AB

Synthetic studies towards Zetekitoxin AB: preparation of 4,5-epi-11-hydroxy-saxitoxinol

Tetrahedron. ;70(43):7942-7949.
Fig. 1.

Proposed structure of zetekitoxin AB (1) and an energy-minimized conformation, determined by molecular modeling, together with the structure of saxitoxin (2), and an excluded alternative structure (3) for zetekitoxin AB.

The structure of zetekitoxin AB, a saxitoxin analog from the Panamanian golden frog Atelopus zeteki: A potent sodium-channel blocker

Proc Natl Acad Sci U S A. 2004 Mar 30;101(13):4346-4351.
Figure 1

Structures of Zetekitoxin AB (left) and saxitoxin (right)

Synthetic studies towards Zetekitoxin AB: preparation of 4,5-epi-11-hydroxy-saxitoxinol

Tetrahedron. ;70(43):7942-7949.
Figure 1

Structures of zetekitoxin AB 1 and saxitoxin 2.

Preparation of a 1,2-isoxazolidine synthon for the synthesis of zetekitoxin AB

Tetrahedron Lett. ;56(46):6332-6334.