Synthetic Route to Oscillatoxin D and Its Analogues

Nokura, Yoshihiko; Araki, Yasutomo; Nakazaki, Atsuo; Nishikawa, Toshio

doi:10.1021/acs.orglett.7b03032

Cited by 15 publications

(17 citation statements)

References 56 publications

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“…S37 †), the absolute conguration of 2 was tentatively assigned as 2S, 4R, 7R, 10S, 11R, 12S and 15S. 17,18 Oscillatoxin F (3) was obtained as white solid. The HRESIMS data assigned its molecular formula as C 26 H 38 O 4 showing 58 mass fewer than compound 2.…”

Section: Resultsmentioning

confidence: 99%

Chemical and biological study of aplysiatoxin derivatives showing inhibition of potassium channel Kv1.5

Tang

Fan

et al. 2019

RSC Adv.

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Section: Resultsmentioning

confidence: 99%

Chemical and biological study of aplysiatoxin derivatives showing inhibition of potassium channel Kv1.5

Tang

Fan

et al. 2019

RSC Adv.

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“…(2) the AB spirobicyclic ring system (e.g., Oscillatoxin D) [152], and (3) acyclic structures such as Nhatrangins [153].…”

Section: Aplysiatoxin Derivativesmentioning

confidence: 99%

“…Structure of representative Aplysiatoxin derivatives from References[152,153]: Me indicates a methyl group.…”

mentioning

confidence: 99%

Marine Toxins Targeting Kv1 Channels: Pharmacological Tools and Therapeutic Scaffolds

et al. 2020

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Toxins from marine animals provide molecular tools for the study of many ion channels, including mammalian voltage-gated potassium channels of the Kv1 family. Selectivity profiling and molecular investigation of these toxins have contributed to the development of novel drug leads with therapeutic potential for the treatment of ion channel-related diseases or channelopathies. Here, we review specific peptide and small-molecule marine toxins modulating Kv1 channels and thus cover recent findings of bioactives found in the venoms of marine Gastropod (cone snails), Cnidarian (sea anemones), and small compounds from cyanobacteria. Furthermore, we discuss pivotal advancements at exploiting the interaction of κM-conotoxin RIIIJ and heteromeric Kv1.1/1.2 channels as prevalent neuronal Kv complex. RIIIJ’s exquisite Kv1 subtype selectivity underpins a novel and facile functional classification of large-diameter dorsal root ganglion neurons. The vast potential of marine toxins warrants further collaborative efforts and high-throughput approaches aimed at the discovery and profiling of Kv1-targeted bioactives, which will greatly accelerate the development of a thorough molecular toolbox and much-needed therapeutics.

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“…(2) the AB spirobicyclic ring system (e.g., Oscillatoxin D) [152], and (3) acyclic structures such as Nhatrangins [153]. In addition to their various structures, ATX derivatives exhibit selectivity and potency against Kv1.5 channels, a possible pivotal target for new treatment of atrial tachyarrhymias with minimal potential for deleterious side effect [151,154,155].…”

Section: Aplysiatoxin Derivativesmentioning

confidence: 99%

Ion Channels as Marine Drug Targets

Sabatier¹

2020

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Synthetic Route to Oscillatoxin D and Its Analogues

Abstract: O-Methyloscillatoxin D and its analogues were concisely synthesized by a bioinspired intramolecular Mukaiyama aldol reaction as a key step, which involves the construction of a novel spiro-ether moiety.

Cited by 15 publications

References 56 publications

Chemical and biological study of aplysiatoxin derivatives showing inhibition of potassium channel Kv1.5

Chemical and biological study of aplysiatoxin derivatives showing inhibition of potassium channel Kv1.5

Marine Toxins Targeting Kv1 Channels: Pharmacological Tools and Therapeutic Scaffolds

Ion Channels as Marine Drug Targets

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