Discovery of a size-record breaking green-emissive fluorophore: small, smaller, HINA

被引：15
作者：
Kang, Rui [1 ]
Talamini, Laura [2 ]
D'Este, Elisa [3 ]
Estevao, Bianca Martins [2 ]
De Cola, Luisa [1 ,2 ]
Klopper, Wim [1 ,4 ]
Biedermann, Frank [1 ]
机构：
[1] Karlsruhe Inst Technol KIT, Inst Nanotechnol INT, Hermann Von Helmholtz Pl 1, D-76344 Eggenstein Leapaldshafen, Germany
[2] Univ Strasbourg, Inst Sci & Ingn Supramol ISIS, CNRS, 8Rue Gaspard Mange, F-67083 Strasbourg, France
[3] Max Plank Inst Med Res, Opt Microscopy Facil, Jahnstr 29, D-69120 Heidelberg, Germany
[4] Karlsruhe Inst Technol KIT, Inst Phys Chem IPC, Fritz Haber Weg 6, D-76131 Karlsruhe, Germany
来源：
CHEMICAL SCIENCE | 2021年 / 12卷 / 04期
基金：
巴西圣保罗研究基金会;
关键词：
53;
D O I：
10.1039/d0sc05557c
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Astonishingly, 3-hydroxyisonicotinealdehyde (HINA) is despite its small size a green-emitting push-pull fluorophore in water (QY of 15%) and shows ratiometric emission response to biological relevant pH differences (pK(a2) similar to 7.1). Moreover, HINA is the first small-molecule fluorophore reported that possesses three distinctly emissive protonation states. This fluorophore can be used in combination with metal complexes for fluorescent-based cysteine detection in aqueous media, and is readily taken up by cells. The theoretical description of HINA's photophysics remains challenging, even when computing Franck-Condon profiles via coupled-cluster calculations, making HINA an interesting model for future method development.
引用
收藏
页码：1392 / 1397
页数：6
相关论文
共 53 条
[1]   General Time Dependent Approach to Vibronic Spectroscopy Including Franck-Condon, Herzberg-Teller, and Duschinsky Effects [J].
Baiardi, Alberto ;
Bloino, Julien ;
Barone, Vincenzo .
JOURNAL OF CHEMICAL THEORY AND COMPUTATION, 2013, 9 (09) :4097-4115
[2]   Excited-State Proton Transfer in Confined Medium. 4-Methy1-7-hydroxyflavylium and β-Naphthol Incorporated in Cucurbit[7]uril [J].
Basilio, Nuno ;
Laia, Cesar A. T. ;
Pina, Fernando .
JOURNAL OF PHYSICAL CHEMISTRY B, 2015, 119 (06) :2749-2757
[3]   SCOTfluors: Small, Conjugatable, Orthogonal, and Tunable Fluorophores for InVivo Imaging of Cell Metabolism [J].
Benson, Sam ;
Fernandez, Antonio ;
Barth, Nicole D. ;
de Moliner, Fabio ;
Horrocks, Mathew H. ;
Herrington, C. Simon ;
Abad, Jose Luis ;
Delgado, Antonio ;
Kelly, Lisa ;
Chang, Ziyuan ;
Feng, Yi ;
Nishiura, Miyako ;
Hori, Yuichiro ;
Kikuchi, Kazuya ;
Vendrell, Marc .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (21) :6911-6915
[4]   Fluorescent artificial receptor-based membrane assay (FARMA) for spatiotemporally resolved monitoring of biomembrane permeability [J].
Biedermann, Frank ;
Ghale, Garima ;
Hennig, Andreas ;
Nau, Werner M. .
COMMUNICATIONS BIOLOGY, 2020, 3 (01)
[5]   On the dual emission of p-dimethylaminobenzonitrile and its photophysical implications [J].
Catalan, Javier .
PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 2013, 15 (22) :8811-8820
[6]   Vibronic Coupling Analysis of the Ligand-Centered Phosphorescence of Gas-Phase Gd(III) and Lu(III) 9-Oxophenalen-1-one Complexes [J].
Chmela, Jiri ;
Greisch, Jean-Francois ;
Harding, Michael E. ;
Klopper, Wim ;
Kappes, Manfred M. ;
Schooss, Detlef .
JOURNAL OF PHYSICAL CHEMISTRY A, 2018, 122 (09) :2461-2467
[7]   Dual fluorescence and fast intramolecular charge transfer with 4-(diisopropylamino) benzonitrile in alkane solvents [J].
Demeter, A ;
Druzhinin, S ;
George, M ;
Haselbach, E ;
Roulin, JL ;
Zachariasse, KA .
CHEMICAL PHYSICS LETTERS, 2000, 323 (3-4) :351-360
[8]   Dual-Self-Restricted GFP Chromophore Analogues with Significantly Enhanced Emission [J].
Deng, Hongping ;
Yu, Chunyang ;
Yan, Deyue ;
Zhu, Xinyuan .
JOURNAL OF PHYSICAL CHEMISTRY B, 2020, 124 (05) :871-880
[9]   Solvatochromism of the green fluorescence protein chromophore and its derivatives [J].
Dong, Jian ;
Solntsev, Kyril M. ;
Tolbert, Laren M. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (37) :12038-12039
[10]   Fluorescent Dyes and Their Supramolecular Host/Guest Complexes with Macrocycles in Aqueous Solution [J].
Dsouza, Roy N. ;
Pischel, Uwe ;
Nau, Werner M. .
CHEMICAL REVIEWS, 2011, 111 (12) :7941-7980
123456