Benzofurazan sulfides for thiol imaging and quantification in live cells through fluorescence microscopy.
Benzofurazan sulfides for thiol imaging and quantification in live cells through fluorescence microscopy.
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DOI：
10.1021/ac301306s
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发表时间：
2012-08-07
影响因子：
7.4
通讯作者：
Guan, Xiangming
中科院分区：
文献类型：
--
作者：
Li, Yinghong;Yang, Yang;Guan, Xiangming
巯基在各种细胞功能中起重要作用。细胞巯基浓度可受各种生理或病理因素影响。可以通过荧光显微术有效且特异性地使活细胞中的硫醇成像的荧光成像剂对于活细胞硫醇监测是期望的。合成了苯并呋咱硫化物1a-e，发现除了1d之外，它们都是硫醇特异性荧光剂。它们不发荧光，但通过硫化物-硫醇交换反应与硫醇反应后形成强荧光硫醇加合物。另一方面，它们不与其他生物学相关的亲核官能团如-NH 2、-OH或-COOH反应，这揭示了硫醇检测的特异性。选择硫化物1a以确认其通过荧光显微镜成像细胞硫醇的能力。该化合物被证明可以通过荧光显微镜分别使用430 nm和520 nm作为激发和发射波长有效地成像和定量活细胞中的巯基变化。通过HPLC/UV总巯基测定方法验证了从荧光显微镜获得的活细胞中总巯基的定量结果。该试剂和方法对巯基氧化还原相关研究具有重要的参考价值。
Thiol groups play a significant role in various cellular functions. Cellular thiol concentrations can be affected by various physiological or pathological factors. A fluorescence imaging agent that can effectively and specifically image thiols in live cells through fluorescence microscopy is desirable for live cell thiol monitoring. Benzofurazan sulfides 1a–e were synthesized and found to be thiol specific fluorogenic agents except 1d. They are not fluorescent but form strong fluorescent thiol adducts after reacting with thiols through a sulfide-thiol exchange reaction. On the other hand, they exhibit no reaction with other biologically relevant nucleophilic functional groups such as -NH2, -OH, or -COOH revealing the specificity for the detection of thiols. Sulfide 1a was selected to confirm its ability to image cellular thiols through fluorescence microscopy. The compound was demonstrated to effectively image and quantify thiol changes in live cells through fluorescence microscopy using 430 nm and 520 nm as the excitation and emission wavelengths respectively. The quantification results of total thiol in live cells obtained from fluorescence microscopy were validated by an HPLC/UV total thiol assay method. The reagents and method will be of a great value to thiol redox-related research.
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DOI：
10.1016/j.jpba.2008.08.033
发表时间：
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影响因子：
3.4
作者：
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