Pyrene Functionalized Norbornadiene-Quadricyclane Fluorescent Photoswitches: Characterization of their Spectral Properties and Application in Imaging of Amyloid Beta Plaques
Artikel i vetenskaplig tidskrift, 2024
This study presents the synthesis and characterization of two fluorescent norbornadiene (NBD) photoswitches, each incorporating two conjugated pyrene units. Expanding on the limited repertoire of reported photoswitchable fluorescent NBDs, we explore their properties with a focus on applications in bioimaging of amyloid beta (Aβ) plaques. While the fluorescence emission of the NBD decreases upon photoisomerization, aligning with what has been previously reported, for the first time we observed luminescence after irradiation of the quadricyclane (QC) isomer. We deduce how the observed emission is induced by photoisomerization to the excited state of the parent isomer (NBD) which is then the emitting species. Thorough characterizations including NMR, UV-Vis, fluorescence, X-ray structural analysis and density functional theory (DFT) calculations provide a comprehensive understanding of these systems. Notably, one NBD-QC system exhibits exceptional durability. Additionally, these molecules serve as effective fluorescent stains targeting Aβ plaques in situ, with observed NBD/QC switching within the plaques. Molecular docking simulations explore NBD interactions with amyloid, unveiling novel binding modes. These insights mark a crucial advancement in the comprehension and design of future photochromic NBDs for bioimaging applications and beyond, emphasizing their potential in studying and addressing protein aggregates.
Norbornadienes
imaging
Alzheimer
photoswitches
photochromism
Författare
Shima Ghasemi
Chalmers, Kemi och kemiteknik, Kemi och biokemi
Monika Shamsabadi
Chalmers, Kemi och kemiteknik, Tillämpad kemi
Axel Olesund
Chalmers, Kemi och kemiteknik, Kemi och biokemi
Francisco Najera
Instituto de Investigación Biomédica de Málaga (IBIMA)
Universidad De Malaga
Andreas Erbs Hillers-Bendtsen
Köpenhamns universitet
Fredrik Edhborg
Chalmers, Kemi och kemiteknik, Kemi och biokemi
Muhammad Adil Salman Aslam
Chalmers, Kemi och kemiteknik, Tillämpad kemi
Wera Larsson
Chalmers, Kemi och kemiteknik, Kemi och biokemi
Zhihang Wang
University of Cambridge
Francoise Mystere Amombo Noa
Chalmers, Kemi och kemiteknik, Kemi och biokemi
Rebecca J. Salthouse
Universitat Politecnica de Catalunya
Lars Öhrström
Chalmers, Kemi och kemiteknik, Kemi och biokemi
Helen Hölzel
Universitat Politecnica de Catalunya
E. Perez-Inestrosa
Universidad De Malaga
Instituto de Investigación Biomédica de Málaga (IBIMA)
Kurt V. Mikkelsen
Köpenhamns universitet
Jörg Hanrieder
University College London (UCL)
Göteborgs universitet
Bo Albinsson
Chalmers, Kemi och kemiteknik, Kemi och biokemi
Ambra Dreos
Instituto de Investigación Biomédica de Málaga (IBIMA)
Göteborgs universitet
Kasper Moth-Poulsen
Chalmers, Kemi och kemiteknik, Tillämpad kemi
Institucio Catalana de Recerca i Estudis Avancats
Consejo Superior de Investigaciones Científicas (CSIC)
Universitat Politecnica de Catalunya
Chemistry - A European Journal
0947-6539 (ISSN) 1521-3765 (eISSN)
Vol. 30 34 e202400322Photo Thermal Management Materials (PHOTERM)
Europeiska kommissionen (EU) (EC/H2020/101002131), 2021-10-01 -- 2026-09-30.
Molecular Solar Thermal energy storage systems (MOST)
Energimyndigheten (2019-010724), 2019-05-07 -- 2019-09-03.
Europeiska kommissionen (EU) (EC/H2020/951801), 2020-09-01 -- 2024-02-29.
Ämneskategorier (SSIF 2011)
Atom- och molekylfysik och optik
Materialkemi
Organisk kemi
DOI
10.1002/chem.202400322