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dc.contributor.authorZhang, Jun
dc.contributor.authorSandberg, Alexander
dc.contributor.authorWu, Xiongyu
dc.contributor.authorNyström, Sofie
dc.contributor.authorLindgren, Mikael
dc.contributor.authorKonradsson, Peter
dc.contributor.authorHammarström, Per
dc.date.accessioned2018-06-07T10:56:53Z
dc.date.available2018-06-07T10:56:53Z
dc.date.created2017-08-22T09:40:35Z
dc.date.issued2017
dc.identifier.citationACS Omega. 2017, 2 (8), 4693-4704.nb_NO
dc.identifier.issn2470-1343
dc.identifier.urihttp://hdl.handle.net/11250/2500800
dc.description.abstractIt was previously reported that two naphthyl-based trans-stilbene probes, (E)-4-(2-(naphthalen-1-yl)vinyl)benzene-1,2-diol (1) and (E)-4-(2-(naphthalen-2-yl)vinyl)benzene-1,2-diol (3), can bind to both native transthyretin (TTR) and misfolded protofibrillar TTR at physiological concentrations, displaying distinct emission maxima bound to the different conformational states (>100 nm difference). To further explore this amyloid probe scaffold to obtain extended fluorescence lifetimes, two new analogues with expanded aromatic ring systems (anthracene and pyrene), (E)-4-(2-(anthracen-2-yl)vinyl)benzene-1,2-diol (4) and (E)-4-(2-(pyren-2-yl)vinyl)benzene-1,2-diol (5), were synthesized employing the palladium-catalyzed Mizoroki–Heck reaction. (E)-4-Styrylbenzene-1,2-diol (2), 3, 4, and 5 were investigated with respect to their photophysical properties in methanol and when bound to insulin, lysozyme, and Aβ1-42 fibrils, including time-resolved fluorescence measurements. In conclusion, 4 and 5 can bind to both native and fibrillar TTR, becoming highly fluorescent. Compounds 2–5 bind specifically to insulin, lysozyme, and Aβ1-42 fibrils with an apparent fluorescence intensity increase and moderate binding affinities. The average fluorescence lifetimes of the probes bound to Aβ1-42 fibrils are 1.3 ns (2), 1.5 ns (3), 5.7 ns (4), and 29.8 ns (5). In summary, the variable aromatic moieties of the para-positioned trans-stilbenoid vinyl-benzene-1,2-diol with benzene, naphthalene, anthracene, and pyrene showed that the extended conjugated systems retained the amyloid targeting properties of the probes. Furthermore, both the anthracene and pyrene moieties extensively enhanced the fluorescence intensity and prolonged lifetimes. These attractive probe properties should improve amyloid detection and characterization by fluorescence-based techniques.nb_NO
dc.language.isoengnb_NO
dc.publisherACS Publicationsnb_NO
dc.titletrans-Stilbenoids with Extended Fluorescence Lifetimes for the Characterization of Amyloid Fibrilsnb_NO
dc.title.alternativetrans-Stilbenoids with Extended Fluorescence Lifetimes for the Characterization of Amyloid Fibrilsnb_NO
dc.typeJournal articlenb_NO
dc.typePeer reviewednb_NO
dc.description.versionpublishedVersionnb_NO
dc.source.pagenumber4693-4704nb_NO
dc.source.volume2nb_NO
dc.source.journalACS Omeganb_NO
dc.source.issue8nb_NO
dc.identifier.doi10.1021/acsomega.7b00535
dc.identifier.cristin1487784
dc.description.localcode© 2017 American Chemical Society. This is an open access article published under an ACS AuthorChoice License, which permits copying and redistribution of the article or any adaptations for non-commercial purposes.nb_NO
cristin.unitcode194,66,20,0
cristin.unitnameInstitutt for fysikk
cristin.ispublishedtrue
cristin.fulltextoriginal
cristin.qualitycode1


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