一种通过偶联菁和激发态分子内质子转移实现大斯托克斯位移的近红外发射溶酶体靶向探针。
An NIR-emitting lysosome-targeting probe with large Stokes shift via coupling cyanine and excited-state intramolecular proton transfer.
作者信息
Dahal Dipendra, McDonald Lucas, Bi Xiaoman, Abeywickrama Chathura, Gombedza Farai, Konopka Michael, Paruchuri Sailaja, Pang Yi
机构信息
Department of Chemistry, University of Akron, Akron, Ohio 44325, USA.
出版信息
Chem Commun (Camb). 2017 Mar 28;53(26):3697-3700. doi: 10.1039/c7cc00700k.
Abstract
An NIR-emitting probe (λ ∼ 700 nm) with a large Stokes shift (Δλ ≈ 234 nm) is synthesized by using excited-state intramolecular proton transfer (ESIPT). The phenolic proton, which controls ESIPT, acts as a switch to give strong fluorescence at pH ≈ 5. The probe can selectively show lysosome organelles, therefore leading to a lysosome probe without exhibiting "an alkalinizing effect".
摘要
通过利用激发态分子内质子转移（ESIPT）合成了一种具有大斯托克斯位移（Δλ≈234nm）的近红外发射探针（λ ∼ 700nm）。控制ESIPT的酚质子充当开关，在pH≈5时发出强荧光。该探针可以选择性地显示溶酶体细胞器，因此产生一种不会表现出“碱化效应”的溶酶体探针。
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本文引用的文献
1
Fluorescent Probes for Sensing and Imaging within Specific Cellular Organelles.用于特定细胞细胞器内传感和成像的荧光探针。
Acc Chem Res. 2016 Oct 18;49(10):2115-2126. doi: 10.1021/acs.accounts.6b00292. Epub 2016 Sep 23.
2
A Cyanine Dye to Probe Mitophagy: Simultaneous Detection of Mitochondria and Autolysosomes in Live Cells.一种用于探测线粒体自噬的花菁染料：活细胞中线粒体和自噬溶酶体的同时检测。
J Am Chem Soc. 2016 Sep 28;138(38):12368-74. doi: 10.1021/jacs.6b04048. Epub 2016 Sep 13.
3
A six-membered-ring incorporated Si-rhodamine for imaging of copper(ii) in lysosomes.一种用于溶酶体中铜（II）成像的含六元环硅罗丹明。
Org Biomol Chem. 2016 Jul 12;14(28):6720-8. doi: 10.1039/c6ob00894a.
4
Engineering Lysosome-Targeting BODIPY Nanoparticles for Photoacoustic Imaging and Photodynamic Therapy under Near-Infrared Light.工程化靶向溶酶体的 BODIPY 纳米颗粒用于近红外光下的光声成像和光动力治疗。
ACS Appl Mater Interfaces. 2016 May 18;8(19):12039-47. doi: 10.1021/acsami.6b02721. Epub 2016 May 5.
5
Lysosome triggered near-infrared fluorescence imaging of cellular trafficking processes in real time.溶酶体触发的细胞运输过程的近红外荧光实时成像。
Nat Commun. 2016 Mar 1;7:10855. doi: 10.1038/ncomms10855.
6
Aminobenzofuran-fused rhodamine dyes with deep-red to near-infrared emission for biological applications.用于生物应用的具有深红色至近红外发射的氨基苯并呋喃稠合罗丹明染料。
J Org Chem. 2015 Mar 20;80(6):3170-5. doi: 10.1021/acs.joc.5b00077. Epub 2015 Feb 26.
7
A Benzothiazole-Based Sensor for Pyrophosphate (PPi) and ATP: Mechanistic Insight for Anion-Induced ESIPT Turn-On.一种基于苯并噻唑的焦磷酸（PPi）和三磷酸腺苷（ATP）传感器：阴离子诱导的激发态分子内质子转移开启的机理洞察
J Mater Chem B. 2014 Oct 14;2(38):6634-6638. doi: 10.1039/C4TB01109K.
8
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ACS Appl Mater Interfaces. 2014 Dec 10;6(23):21669-76. doi: 10.1021/am506750m. Epub 2014 Nov 17.
9
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Chem Soc Rev. 2014 Jan 7;43(1):16-29. doi: 10.1039/c3cs60271k. Epub 2013 Sep 19.
10
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