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一种基于高量子产率 BODIPY 衍生物的近红外荧光探针,用于选择性检测生物样品中外源和内源性半胱氨酸。

A near-infrared fluorescent probe based on BODIPY derivative with high quantum yield for selective detection of exogenous and endogenous cysteine in biological samples.

机构信息

Key Laboratory for Green Organic Synthesis and Application of Hunan Province, Key Laboratory of Environmentally Friendly Chemistry and Application of Ministry of Education, College of Chemistry, Xiangtan University, Xiangtan, 411105, PR China.

Key Laboratory for Green Organic Synthesis and Application of Hunan Province, Key Laboratory of Environmentally Friendly Chemistry and Application of Ministry of Education, College of Chemistry, Xiangtan University, Xiangtan, 411105, PR China; State Key Laboratory of Chemo/Biosensing and Chemometrics, College of Chemistry & Chemical Engineering, Hunan University, Changsha, 410082, PR China.

出版信息

Anal Chim Acta. 2017 Nov 22;994:73-81. doi: 10.1016/j.aca.2017.09.031. Epub 2017 Oct 3.

DOI:10.1016/j.aca.2017.09.031
PMID:29126471
Abstract

Cysteine (Cys) is involved in cellular growth and Cys deficiency is related with many diseases. So far, a number of fluorescent probes have been constructed for the detection of Cys successfully. However, the probes are difficult to discriminate Cys from Hcy and the emission wavelength of the probes is in ultraviolet or visible range. Herein, a NIR fluorescent probe named NIR-BODIPY-Ac is synthesized and used to detect Cys. The emission wavelength of the probe is at 708 nm that belongs to near-infrared (NIR) region by attaching indolium to BODIPY core, which is suitable for bioimaging in vivo. Moreover, the probe exhibits high fluorescence quantum yield (Φ = 0.51) after the addition of Cys and high sensitivity toward Cys with 81-fold fluorescence enhancement. The linear range of the probe for Cys covers from 0.2 to 30 μM with a detection limit of 0.05 μM. Furthermore, the probe shows high selectivity towards Cys owing to the fact that there is more fast reaction rate between the probe and Cys than that of Hcy. In particular, the NIR fluorescent probe is applied for the detection of exogenous and endogenous Cys in biological samples such as cell, tissue and mouse with satisfactory results.

摘要

半胱氨酸(Cys)参与细胞生长,Cys 缺乏与许多疾病有关。迄今为止,已经成功构建了许多用于检测 Cys 的荧光探针。然而,这些探针很难将 Cys 与 Hcy 区分开来,并且探针的发射波长在紫外光或可见光范围内。在此,合成了一种名为 NIR-BODIPY-Ac 的近红外(NIR)荧光探针用于检测 Cys。通过将吲哚鎓连接到 BODIPY 核心上,探针的发射波长在 708nm 处,属于近红外(NIR)区域,适用于体内生物成像。此外,探针在加入 Cys 后表现出高荧光量子产率(Φ=0.51)和对 Cys 的高灵敏度,荧光增强 81 倍。探针对 Cys 的线性范围从 0.2 到 30μM,检测限为 0.05μM。此外,由于探针与 Cys 之间的快速反应速率大于与 Hcy 之间的快速反应速率,因此探针对 Cys 表现出高选择性。特别地,该近红外荧光探针已成功应用于细胞、组织和小鼠等生物样品中外源和内源性 Cys 的检测,结果令人满意。

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