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

被引:13
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
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
    Baiardi, Alberto
    Bloino, Julien
    Barone, Vincenzo
    [J]. 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
    Basilio, Nuno
    Laia, Cesar A. T.
    Pina, Fernando
    [J]. JOURNAL OF PHYSICAL CHEMISTRY B, 2015, 119 (06) : 2749 - 2757
  • [3] SCOTfluors: Small, Conjugatable, Orthogonal, and Tunable Fluorophores for InVivo Imaging of Cell Metabolism
    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
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (21) : 6911 - 6915
  • [4] Fluorescent artificial receptor-based membrane assay (FARMA) for spatiotemporally resolved monitoring of biomembrane permeability
    Biedermann, Frank
    Ghale, Garima
    Hennig, Andreas
    Nau, Werner M.
    [J]. COMMUNICATIONS BIOLOGY, 2020, 3 (01)
  • [5] On the dual emission of p-dimethylaminobenzonitrile and its photophysical implications
    Catalan, Javier
    [J]. 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
    Chmela, Jiri
    Greisch, Jean-Francois
    Harding, Michael E.
    Klopper, Wim
    Kappes, Manfred M.
    Schooss, Detlef
    [J]. 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
    Demeter, A
    Druzhinin, S
    George, M
    Haselbach, E
    Roulin, JL
    Zachariasse, KA
    [J]. CHEMICAL PHYSICS LETTERS, 2000, 323 (3-4) : 351 - 360
  • [8] Dual-Self-Restricted GFP Chromophore Analogues with Significantly Enhanced Emission
    Deng, Hongping
    Yu, Chunyang
    Yan, Deyue
    Zhu, Xinyuan
    [J]. JOURNAL OF PHYSICAL CHEMISTRY B, 2020, 124 (05) : 871 - 880
  • [9] Solvatochromism of the green fluorescence protein chromophore and its derivatives
    Dong, Jian
    Solntsev, Kyril M.
    Tolbert, Laren M.
    [J]. 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
    Dsouza, Roy N.
    Pischel, Uwe
    Nau, Werner M.
    [J]. CHEMICAL REVIEWS, 2011, 111 (12) : 7941 - 7980