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用于成像应用的具有大斯托克斯位移的近红外发射苯乙烯基染料:从细胞质膜、线粒体到斑马鱼神经丘。

NIR-emitting styryl dyes with large Stokes' shifts for imaging application: From cellular plasma membrane, mitochondria to Zebrafish neuromast.

作者信息

Dahal Dipendra, Ojha Krishna R, Pokhrel Sabita, Paruchuri Sailaja, Konopka Michael, Liu Qin, Pang Yi

机构信息

Department of Chemistry, The University of Akron, Akron, OH 44325, USA.

Department of Biology, The University of Akron, Akron, OH 44325, USA.

出版信息

Dyes Pigm. 2021 Oct;194. doi: 10.1016/j.dyepig.2021.109629. Epub 2021 Jul 6.

Abstract

Near-infrared (NIR) emitting probes with very large Stokes' shifts play a crucial role in bioimaging applications, as the optical signals in this region exhibit high signal to background ratio and allow deeper tissue penetration. Herein we illustrate NIR-emitting probe with very large Stokes' shifts (Δλ ≈ 260 - 272 nm) by integrating the excited-state intramolecular proton transfer (ESIPT) unit 2-(2'-hydroxyphenyl)benzoxazole (HBO) into a pyridinium derived cyanine. The ESIPT not only enhances the Stokes' shifts but also improves the quantum efficiency of the probe (ф = 0.27 - 0.40 in DCM). The application of in live cells imaging reveals that compound stains mitochondria in eukaryotic cells, normal human lungs fibroblast (NHLF), Zebrafish's neuromast hair cells, and support cells, and inner plasma membrane in prokaryotic cells, ().

摘要

具有非常大斯托克斯位移的近红外(NIR)发射探针在生物成像应用中起着至关重要的作用,因为该区域的光信号表现出高信噪比,并允许更深的组织穿透。在此,我们通过将激发态分子内质子转移(ESIPT)单元2-(2'-羟基苯基)苯并恶唑(HBO)整合到吡啶鎓衍生的花菁中,展示了具有非常大斯托克斯位移(Δλ≈260 - 272 nm)的近红外发射探针。ESIPT不仅增强了斯托克斯位移,还提高了探针的量子效率(在二氯甲烷中ф = 0.27 - 0.40)。在活细胞成像中的应用表明,化合物对真核细胞中的线粒体、正常人肺成纤维细胞(NHLF)、斑马鱼的神经丘毛细胞和支持细胞以及原核细胞中的内膜进行染色。

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