Literature DB >> 25338021

Synthesis and biology of cyclic imine toxins, an emerging class of potent, globally distributed marine toxins.

Craig E Stivala1, Evelyne Benoit, Rómulo Aráoz, Denis Servent, Alexei Novikov, Jordi Molgó, Armen Zakarian.   

Abstract

From a small group of exotic compounds isolated only two decades ago, Cyclic Imine (CI) toxins have become a major class of marine toxins with global distribution. Their distinct chemical structure, biological mechanism of action, and intricate chemistry ensures that CI toxins will continue to be the subject of fascinating fundamental studies in the broad fields of chemistry, chemical biology, and toxicology. The worldwide occurrence of potent CI toxins in marine environments, their accumulation in shellfish, and chemical stability are important considerations in assessing risk factors for human health. This review article aims to provide an account of chemistry, biology, and toxicology of CI toxins from their discovery to the present day.

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Year:  2015        PMID: 25338021      PMCID: PMC4344380          DOI: 10.1039/c4np00089g

Source DB:  PubMed          Journal:  Nat Prod Rep        ISSN: 0265-0568            Impact factor:   13.423


  97 in total

Review 1.  Drugs from the sea: conotoxins as drug leads for neuropathic pain and other neurological conditions.

Authors:  D Alonso; Z Khalil; N Satkunanthan; B G Livett
Journal:  Mini Rev Med Chem       Date:  2003-11       Impact factor: 3.862

2.  Synthesis of the bis-spiroacetal moiety of spirolides B and D.

Authors:  Kai Meilert; Margaret A Brimble
Journal:  Org Lett       Date:  2005-08-04       Impact factor: 6.005

3.  Total synthesis of pinnatoxins A and G and revision of the mode of action of pinnatoxin A.

Authors:  Romulo Araoz; Denis Servent; Jordi Molgó; Bogdan I Iorga; Carole Fruchart-Gaillard; Evelyne Benoit; Zhenhua Gu; Craig Stivala; Armen Zakarian
Journal:  J Am Chem Soc       Date:  2011-06-17       Impact factor: 15.419

4.  Pinnatoxins and spirolides in Norwegian blue mussels and seawater.

Authors:  Thomas Rundberget; John A Bunæs Aasen; Andrew I Selwood; Christopher O Miles
Journal:  Toxicon       Date:  2011-09-08       Impact factor: 3.033

5.  Isolation, structural determination and acute toxicity of pinnatoxins E, F and G.

Authors:  Andrew I Selwood; Christopher O Miles; Alistair L Wilkins; Roel van Ginkel; Rex Munday; Frode Rise; Paul McNabb
Journal:  J Agric Food Chem       Date:  2010-05-26       Impact factor: 5.279

6.  Studies toward a marine toxin immunogen: enantioselective synthesis of the spirocyclic imine of (-)-gymnodimine.

Authors:  Ke Kong; Ziad Moussa; Daniel Romo
Journal:  Org Lett       Date:  2005-11-10       Impact factor: 6.005

7.  Characterization of a Dispiroketal Spirolide Subclass from Alexandrium ostenfeldii.

Authors:  Joy S Roach; Patricia Leblanc; Nancy I Lewis; Rex Munday; Michael A Quilliam; Shawna L Mackinnon
Journal:  J Nat Prod       Date:  2009-07       Impact factor: 4.050

8.  Nicotinic receptor agonists and antagonists increase sAPPalpha secretion and decrease Abeta levels in vitro.

Authors:  M Mousavi; E Hellström-Lindahl
Journal:  Neurochem Int       Date:  2008-12-07       Impact factor: 3.921

9.  Graphene based pipette tip solid phase extraction of marine toxins in shellfish muscle followed by UPLC-MS/MS analysis.

Authors:  Qing Shen; Like Gong; Joewel T Baibado; Wei Dong; Yixuan Wang; Zhiyuan Dai; Hon-Yeung Cheung
Journal:  Talanta       Date:  2013-07-26       Impact factor: 6.057

10.  Activation and allosteric modulation of a muscarinic acetylcholine receptor.

Authors:  Andrew C Kruse; Aaron M Ring; Aashish Manglik; Jianxin Hu; Kelly Hu; Katrin Eitel; Harald Hübner; Els Pardon; Celine Valant; Patrick M Sexton; Arthur Christopoulos; Christian C Felder; Peter Gmeiner; Jan Steyaert; William I Weis; K Christopher Garcia; Jürgen Wess; Brian K Kobilka
Journal:  Nature       Date:  2013-11-20       Impact factor: 49.962

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  21 in total

1.  Marine Macrocyclic Imines, Pinnatoxins A and G: Structural Determinants and Functional Properties to Distinguish Neuronal α7 from Muscle α1(2)βγδ nAChRs.

Authors:  Yves Bourne; Gerlind Sulzenbacher; Zoran Radić; Rómulo Aráoz; Morgane Reynaud; Evelyne Benoit; Armen Zakarian; Denis Servent; Jordi Molgó; Palmer Taylor; Pascale Marchot
Journal:  Structure       Date:  2015-05-21       Impact factor: 5.006

Review 2.  Cyclic imine toxins from dinoflagellates: a growing family of potent antagonists of the nicotinic acetylcholine receptors.

Authors:  Jordi Molgó; Pascale Marchot; Rómulo Aráoz; Evelyne Benoit; Bogdan I Iorga; Armen Zakarian; Palmer Taylor; Yves Bourne; Denis Servent
Journal:  J Neurochem       Date:  2017-03-21       Impact factor: 5.372

Review 3.  Current Situation of Palytoxins and Cyclic Imines in Asia-Pacific Countries: Causative Phytoplankton Species and Seafood Poisoning.

Authors:  Young-Sang Kim; Hyun-Joo An; Jaeseong Kim; You-Jin Jeon
Journal:  Int J Environ Res Public Health       Date:  2022-04-18       Impact factor: 4.614

4.  Cyclic imine toxins survey in coastal european shellfish samples: Bioaccumulation and mode of action of 28-O-palmitoyl ester of pinnatoxin-G. first report of portimine-A bioaccumulation.

Authors:  Rómulo Aráoz; Paul Barnes; Véronique Séchet; Muriel Delepierre; Sophie Zinn-Justin; Jordi Molgó; Armen Zakarian; Philipp Hess; Denis Servent
Journal:  Harmful Algae       Date:  2020-08-12       Impact factor: 4.273

Review 5.  Alternative methods for the detection of emerging marine toxins: biosensors, biochemical assays and cell-based assays.

Authors:  Laia Reverté; Lucía Soliño; Olga Carnicer; Jorge Diogène; Mònica Campàs
Journal:  Mar Drugs       Date:  2014-11-26       Impact factor: 5.118

6.  Prorocentrolide-A from Cultured Prorocentrum lima Dinoflagellates Collected in Japan Blocks Sub-Types of Nicotinic Acetylcholine Receptors.

Authors:  Muriel Amar; Rómulo Aráoz; Bogdan I Iorga; Takeshi Yasumoto; Denis Servent; Jordi Molgó
Journal:  Toxins (Basel)       Date:  2018-02-28       Impact factor: 4.546

Review 7.  Solid Phase Adsorption Toxin Tracking (SPATT) Technology for the Monitoring of Aquatic Toxins: A Review.

Authors:  Mélanie Roué; Hélène Taiana Darius; Mireille Chinain
Journal:  Toxins (Basel)       Date:  2018-04-20       Impact factor: 4.546

8.  The Dinoflagellate Toxin 20-Methyl Spirolide-G Potently Blocks Skeletal Muscle and Neuronal Nicotinic Acetylcholine Receptors.

Authors:  Aurélie Couesnon; Rómulo Aráoz; Bogdan I Iorga; Evelyne Benoit; Morgane Reynaud; Denis Servent; Jordi Molgó
Journal:  Toxins (Basel)       Date:  2016-08-24       Impact factor: 4.546

Review 9.  Ladder-Shaped Ion Channel Ligands: Current State of Knowledge.

Authors:  Yuri B Shmukler; Denis A Nikishin
Journal:  Mar Drugs       Date:  2017-07-20       Impact factor: 5.118

10.  Regioselective Mercury(I)/Palladium(II)-Catalyzed Single-Step Approach for the Synthesis of Imines and 2-Substituted Indoles.

Authors:  Rsuini U Gutiérrez; Mayra Hernández-Montes; Aarón Mendieta-Moctezuma; Francisco Delgado; Joaquín Tamariz
Journal:  Molecules       Date:  2021-07-05       Impact factor: 4.411

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