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dc.contributor.authorMoodie, Lindon
dc.contributor.authorZuzek, Monika
dc.contributor.authorFrangez, Robert
dc.contributor.authorAndersen, Jeanette hammer
dc.contributor.authorHansen, Espen
dc.contributor.authorOlsen, Elisabeth Klungerbo
dc.contributor.authorCergolj, Marija
dc.contributor.authorSepcic, Kristina
dc.contributor.authorHanssen, Kine Østnes
dc.contributor.authorSvenson, Johan
dc.date.accessioned2022-05-03T11:55:06Z
dc.date.available2022-05-03T11:55:06Z
dc.date.issued2016-11-09
dc.description.abstractThe marine secondary metabolite stryphnusin (1) was isolated from the boreal sponge Stryphnus fortis, collected off the Norwegian coast. Given its resemblance to other natural acetylcholinesterase antagonists, it was evaluated against electric eel acetylcholinesterase and displayed inhibitory activity. A library of twelve synthetic phenethylamine analogs, 2a–7a and 2b–7b, containing tertiary and quaternary amines respectively were synthesized to investigate the individual structural contributions to the activity. Compound 7b was the strongest competitive inhibitor of both acetylcholinesterase and butyrylcholinesterase with IC<sub>50</sub> values of 57 and 20 μM, respectively. This inhibitory activity is one order of magnitude higher than the positive control physostigmine, and is comparable with several other marine acetylcholinesterase inhibitors. The physiological effect of compound 7b on muscle function and neuromuscular transmission was studied and revealed a selective mode of action at the investigated concentration. This data is of importance as the interference of therapeutic acetylcholinesterase inhibitors with neuromuscular transmission can be problematic and lead to unwanted side effects. The current findings also provide additional insights into the structure–activity relationship of both natural and synthetic acetylcholinesterase inhibitors.en_US
dc.identifier.citationMoodie L, Zuzek, Frangez, Andersen Jh, Hansen E, Olsen EK, Cergolj M, Sepcic K, Hanssen KØ, Svenson J. Synthetic analogs of stryphnusin isolated from the marine sponge Stryphnus fortis inhibit acetylcholinesterase with no effect on muscle function or neuromuscular transmission. Organic and biomolecular chemistry. 2016;14(47):11220-11229en_US
dc.identifier.cristinIDFRIDAID 1412101
dc.identifier.doi10.1039/c6ob02120d
dc.identifier.issn1477-0520
dc.identifier.issn1477-0539
dc.identifier.urihttps://hdl.handle.net/10037/24983
dc.language.isoengen_US
dc.publisherRoyal Society of Chemistryen_US
dc.relation.journalOrganic and biomolecular chemistry
dc.rights.accessRightsopenAccessen_US
dc.rights.holderCopyright 2016 Royal Society of Chemistryen_US
dc.titleSynthetic analogs of stryphnusin isolated from the marine sponge Stryphnus fortis inhibit acetylcholinesterase with no effect on muscle function or neuromuscular transmissionen_US
dc.type.versionpublishedVersionen_US
dc.typeJournal articleen_US
dc.typeTidsskriftartikkelen_US
dc.typePeer revieweden_US


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