Pyrene Functionalized Norbornadiene-Quadricyclane Fluorescent Photoswitches: Characterization of their Spectral Properties and Application in Imaging of Amyloid Beta Plaques

被引：0

作者：

Ghasemi, Shima ^{[1
]}

Shamsabadi, Monika ^{[1
]}

Olesund, Axel ^{[1
]}

Najera, Francisco ^{[2
,3
]}

Hillers-Bendtsen, Andreas Erbs ^{[4
]}

Edhborg, Fredrik ^{[1
]}

Aslam, Adil S. ^{[1
]}

Larsson, Wera ^{[1
]}

Wang, Zhihang ^{[5
]}

Noa, Francoise M. Amombo ^{[1
]}

Salthouse, Rebecca Jane ^{[10
]}

Ohrstrom, Lars ^{[1
]}

Holzel, Helen ^{[10
]}

Perez-Inestrosa, E. ^{[2
,3
]}

Mikkelsen, Kurt V. ^{[4
]}

Hanrieder, Jorg ^{[6
,7
]}

Albinsson, Bo ^{[1
]}

Dreos, Ambra ^{[2
,6
]}

Moth-Poulsen, Kasper ^{[1
,8
,9
,10
]}

机构：

[1] Chalmers Univ Technol, Dept Chem & Chem Engn, S-41296 Gothenburg, Sweden

[2] Inst Invest Biomed Malaga & Plataforma Nanomed IBI, Malaga 29590, Spain

[3] Univ Malaga, Fac Ciencias, Dept Quim Organ, Malaga 29071, Spain

[4] Univ Copenhagen, Dept Chem, Univ Pk 5, Copenhagen, Denmark

[5] Univ Cambridge, Dept Mat Sci & Met, 27 Charles Babbage Rd, Cambridge CB3 0FS, England

[6] Univ Gothenburg, Sahlgrenska Acad, Dept Psychiat & Neurochem, S-43180 Molndal, Sweden

[7] UCL, Queen Sq Inst Neurol, Dept Neurodegenerat Dis, London WC1N 3BG, England

[8] ICMAB CSIC, Inst Mat Sci Barcelona, Barcelona 08193, Spain

[9] ICREA, Catalan Inst Res & Adv Studies, Pg Lluis Co 23, Barcelona 08010, Spain

[10] Univ Politecn Cataluna, Dept Chem Engn, EEBE, Eduard Maristany 10-14, Barcelona 08019, Spain

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2024年 / 30卷 / 34期

关键词：

Norbornadienes; photochromism; photoswitches; imaging; Alzheimer; DIARYLETHENE; PROBE;

D O I：

10.1002/chem.202400322

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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 (A beta) 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 A beta 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. In this study we synthesize and characterise two novel fluorescent norbornadiene derivatives bearing pyrene moieties. In depth spectral and physico-chemical characterisation is presented; moreover, their application as dyes for imaging of amyloid beta aggregates in Alzheimer's mice models is investigated, with implications for bioimaging and protein aggregate studies. image

引用

页数：9