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.

photoswitches

Norbornadienes

Alzheimer

photochromism

imaging

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

Universidad De Malaga

Instituto de Investigación Biomédica de Málaga y Plataforma en Nanomedicina

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 y Plataforma en Nanomedicina

Kurt V. Mikkelsen

Köpenhamns universitet

Jörg Hanrieder

University College London (UCL)

Göteborgs universitet

Bo Albinsson

Chalmers, Kemi och kemiteknik, Kemi och biokemi

Ambra Dreos

Göteborgs universitet

Instituto de Investigación Biomédica de Málaga y Plataforma en Nanomedicina

Kasper Moth-Poulsen

Chalmers, Kemi och kemiteknik, Tillämpad kemi

Universitat Politecnica de Catalunya

Institut de Ciència de Materials de Barcelona (ICMAB-CSIC)

Institucio Catalana de Recerca i Estudis Avancats

Chemistry - A European Journal

0947-6539 (ISSN) 1521-3765 (eISSN)

Vol. In Press

Photo Thermal Management Materials.Acronym: PHOTERM

Europeiska kommissionen (EU) (EC/H202/101002131), 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

Atom- och molekylfysik och optik

Materialkemi

Organisk kemi

DOI

10.1002/chem.202400322

Mer information

Senast uppdaterat

2024-06-10