Recent Advances in Applications of Fluorescent Perylenediimide and Perylenemonoimide Dyes in Bioimaging, Photothermal and Photodynamic Therapy

被引:33
作者
Krupka, Oksana [1 ]
Hudhomme, Pietrick [2 ]
机构
[1] Univ Angers, Inserm, CNRS, MINT,SFR ICAT, F-49000 Angers, France
[2] Univ Angers, CNRS, MOLTECH Anjou, SFR MATRIX, F-49000 Angers, France
关键词
perylenediimide; perylenemonoimide; dyes; fluorescence; bioimaging; photothermal therapy; photodynamic therapy; cancer therapy; theranostics; EFFICIENT PHOTOACOUSTIC AGENTS; NON-FULLERENE ACCEPTORS; SOLAR-CELLS; DIIMIDES SYNTHESIS; BISIMIDE DYES; WATER; NANOPARTICLES; DERIVATIVES; STATE; DESIGN;
D O I
10.3390/ijms24076308
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
The emblematic perylenediimide (PDI) motif which was initially used as a simple dye has undergone incredible development in recent decades. The increasing power of synthetic organic chemistry has allowed it to decorate PDIs to achieve highly functional dyes. As these PDI derivatives combine thermal, chemical and photostability, with an additional high absorption coefficient and near-unity fluorescence quantum yield, they have been widely studied for applications in materials science, particularly in photovoltaics. Although PDIs have always been in the spotlight, their asymmetric counterparts, perylenemonoimide (PMI) analogues, are now experiencing a resurgence of interest with new efforts to create architectures with equally exciting properties. Namely, their exceptional fluorescence properties have recently been used to develop novel systems for applications in bioimaging, biosensing and photodynamic therapy. This review covers the state of the art in the synthesis, photophysical characterizations and recently reported applications demonstrating the versatility of these two sister PDI and PMI compounds. The objective is to show that after well-known applications in materials science, the emerging trends in the use of PDI- and PMI-based derivatives concern very specific biomedicinal applications including drug delivery, diagnostics and theranostics.
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页数:51
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共 157 条
[1]   Energy/Electron Transfer Switch for Controlling Optical Properties of Silicon Quantum Dots [J].
Abdelhameed, Mohammed ;
Aly, Shawkat ;
Lant, Jeremy T. ;
Zhang, Xiaoran ;
Charpentier, Paul .
SCIENTIFIC REPORTS, 2018, 8
[2]   Novel near infra-red fluorescent pH sensors based on 1-aminoperylene bisimides covalently grafted onto poly(acryloylmorpholine) [J].
Aigner, Daniel ;
Borisov, Sergey M. ;
Petritsch, Peter ;
Klimant, Ingo .
CHEMICAL COMMUNICATIONS, 2013, 49 (21) :2139-2141
[3]   Bay- and peri-functionalized donor-acceptor perylene monoimides via nitration and nucleophilic substitution/reduction pathway [J].
Altas, A. ;
Gultekin, D. D. ;
Acar, M. ;
Cucu, E. ;
Karatay, A. ;
Elmali, A. ;
Atalay, A. ;
Demircan, C. A. ;
Bozkaya, U. ;
Kazaz, C. ;
Sahin, E. ;
Bozdemir, O. . A. .
MATERIALS TODAY CHEMISTRY, 2022, 24
[4]   2,5,8,11-Tetraboronic Ester Perylenediimides: A Next Generation Building Block for Dye-Stuff Synthesis [J].
Battagliarin, Glauco ;
Li, Chen ;
Enkelmann, Volker ;
Muellen, Klaus .
ORGANIC LETTERS, 2011, 13 (12) :3012-3015
[5]   A review on energy storage devices based on rylene imide dyes: Synthesis, applications and challenges [J].
Biradar, Madan R. ;
Bhosale, Sidhanath, V ;
Morajakar, Pranay P. ;
Bhosale, Sheshanath, V .
FUEL, 2022, 310
[6]   Recent Advances in Heterocyclic Nanographenes and Other Polycyclic Heteroaromatic Compounds [J].
Borissov, Arseni ;
Maurya, Yogesh Kumar ;
Moshniaha, Liliia ;
Wong, Wai-Shing ;
Zyla-Karwowska, Marika ;
Stepien, Marcin .
CHEMICAL REVIEWS, 2022, 122 (01) :565-788
[7]   THE PREPARATION, REACTIONS, AND PROPERTIES OF TRIPHENYLENES [J].
BUESS, CM ;
LAWSON, DD .
CHEMICAL REVIEWS, 1960, 60 (04) :313-330
[8]   Influence of core extension and side chain nature in targeting G-quadruplex structures with perylene monoimide derivatives [J].
Busto, Natalia ;
Garcia-Calvo, Jose ;
Cuevas, Jose Vicente ;
Herrera, Antonio ;
Mergny, Jean-Louis ;
Pons, Sebastian ;
Torroba, Tomas ;
Garcia, Begona .
BIOORGANIC CHEMISTRY, 2021, 108
[9]   Enzyme-Triggered Disassembly of Perylene Monoimide-based Nanoclusters for Activatable and Deep Photodynamic Therapy [J].
Cai, Yang ;
Ni, Dongqi ;
Cheng, Wenyu ;
Ji, Chendong ;
Wang, Yaling ;
Muellen, Klaus ;
Su, Zhiqiang ;
Liu, Ying ;
Chen, Chunying ;
Yin, Meizhen .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2020, 59 (33) :14014-14018
[10]   A water-soluble perylene dye functionalised with a 17β-estradiol: a new fluorescent tool for steroid hormones [J].
Cespedes-Guirao, Francisco J. ;
Ropero, Ana B. ;
Font-Sanchis, Enrique ;
Nadal, Angel ;
Fernandez-Lazaro, Fernando ;
Sastre-Santos, Angela .
CHEMICAL COMMUNICATIONS, 2011, 47 (29) :8307-8309