Pyrene Functionalized Norbornadiene-Quadricyclane Fluorescent Photoswitches: Characterization of their Spectral Properties and Application in Imaging of Amyloid Beta Plaques
Journal article, 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.
imaging
photoswitches
Alzheimer
photochromism
Norbornadienes
Author
Shima Ghasemi
Chalmers, Chemistry and Chemical Engineering, Chemistry and Biochemistry
Monika Shamsabadi
Chalmers, Chemistry and Chemical Engineering, Applied Chemistry
Axel Olesund
Chalmers, Chemistry and Chemical Engineering, Chemistry and Biochemistry
Francisco Najera
University of Malaga
Instituto de Investigación Biomédica de Málaga y Plataforma en Nanomedicina
Andreas Erbs Hillers-Bendtsen
University of Copenhagen
Fredrik Edhborg
Chalmers, Chemistry and Chemical Engineering, Chemistry and Biochemistry
Muhammad Adil Salman Aslam
Chalmers, Chemistry and Chemical Engineering, Applied Chemistry
Wera Larsson
Chalmers, Chemistry and Chemical Engineering, Chemistry and Biochemistry
Zhihang Wang
University of Cambridge
Francoise Mystere Amombo Noa
Chalmers, Chemistry and Chemical Engineering, Chemistry and Biochemistry
Rebecca J. Salthouse
Polytechnic University of Catalonia
Lars Öhrström
Chalmers, Chemistry and Chemical Engineering, Chemistry and Biochemistry
Helen Hölzel
Polytechnic University of Catalonia
E. Perez-Inestrosa
University of Malaga
Instituto de Investigación Biomédica de Málaga y Plataforma en Nanomedicina
Kurt V. Mikkelsen
University of Copenhagen
Jörg Hanrieder
University College London (UCL)
University of Gothenburg
Bo Albinsson
Chalmers, Chemistry and Chemical Engineering, Chemistry and Biochemistry
Ambra Dreos
Instituto de Investigación Biomédica de Málaga y Plataforma en Nanomedicina
University of Gothenburg
Kasper Moth-Poulsen
Institute of Material Science of Barcelona (ICMAB)
Chalmers, Chemistry and Chemical Engineering, Applied Chemistry
Polytechnic University of Catalonia
Catalan Institution for Research and Advanced Studies
Chemistry - A European Journal
0947-6539 (ISSN) 1521-3765 (eISSN)
Vol. 30 34 e202400322Photo Thermal Management Materials (PHOTERM)
European Commission (EC) (EC/H2020/101002131), 2021-10-01 -- 2026-09-30.
Molecular Solar Thermal energy storage systems (MOST)
European Commission (EC) (EC/H2020/951801), 2020-09-01 -- 2024-02-29.
Swedish Energy Agency (2019-010724), 2019-05-07 -- 2019-09-03.
Subject Categories
Atom and Molecular Physics and Optics
Materials Chemistry
Organic Chemistry
DOI
10.1002/chem.202400322