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A NIR rhodamine fluorescent chemodosimeter specific for glutathione: Knoevenagel condensation, detection of intracellular glutathione and living cell imaging†
Journal of Materials Chemistry B ( IF 6.1 ) Pub Date : 2018-02-13 00:00:00 , DOI: 10.1039/c7tb03199h Lulu Tong 1, 2, 3, 4 , Ying Qian 1, 2, 3, 4
Journal of Materials Chemistry B ( IF 6.1 ) Pub Date : 2018-02-13 00:00:00 , DOI: 10.1039/c7tb03199h Lulu Tong 1, 2, 3, 4 , Ying Qian 1, 2, 3, 4
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A new near-infrared probe for detecting glutathione based on conjugate addition and intramolecular amino induced spirolactam opening named RhAN was designed and synthesized. Firstly, rhodamine was reacted with 2-(1,3,3-trimethylindolin-2-ylidene) acetaldehyde by a Knoevenagel condensation, and the conjugate chain was extended, obtaining M2. Then, M2 was connected with hydrazide to get M3. Finally, the target molecule RhAN was synthesized via the combination of M3 and acryloyl chloride. In the presence of GSH, RhAN exhibits high selectivity, which specifically identifies GSH over Cys and Hcy, the color change from yellow to green together with the fluorescence appeared within 5 s, and there was no interference from the presence of other biological thiols and amino acids. The absorption and emission wavelength of the probe RhAN reached 717 nm and 739 nm, the molar extinction coefficient is 4.36 × 104 M−1 cm−1 and quantum yield is 0.26. Its absorption and emission intensity were enhanced by more than 117-fold and 90-fold upon addition of GSH, respectively. In addition, it also has high sensitivity with a low detection limit of 0.1 μM, which is lower than most previously reported GSH probes. The probe works excellently within a wide pH range of 2–10. Moreover, RhAN was employed for endogenous and exogenous imaging in MCF-7 cells for GSH. MCF-7 cells incubated with RhAN with GSH or blank RhAN all showed significant fluorescence in the red channel, which indicated that the probe could not only detect exogenous GSH, but it also permeated into the cells and reacted with the intracellular GSH. This is an excellent design for a fluorescence sensor, RhAN, as a quick and effective method for detecting excess GSH in living cells, for maintaining the balance of amino acids in the body and ensuring normal life activities.
中文翻译：
专门针对谷胱甘肽的NIR罗丹明荧光化学计量仪：Knoevenagel缩合，细胞内谷胱甘肽的检测和活细胞成像†
设计并合成了一种新的基于共轭加成和分子内氨基诱导的螺内酰胺开口的谷胱甘肽检测近红外探针RhAN。首先，使罗丹明与2-（1,3,3-三甲基吲哚-2-亚基）乙醛经Knoevenagel缩合反应，并延伸共轭链，得到M 2。然后，将M 2与酰肼连接得到M 3。最后，通过M 3和丙烯酰氯的组合合成目标分子RhAN。在GSH存在下，RhAN表现出高选择性，可以特异性识别GSH超过Cys和Hcy，颜色从黄色变为绿色，并在5 s内出现荧光，并且不受其他生物硫醇和氨基酸的干扰。探针RhAN的吸收和发射波长分别达到717 nm和739 nm，摩尔消光系数为4.36×10 4 M -1 cm -1量子产率为0.26。加入GSH后，其吸收和发射强度分别提高了117倍和90倍以上。此外，它还具有高灵敏度，检测限低至0.1μM，低于大多数以前报道的GSH探针。该探针在2-10的宽pH范围内都能出色地工作。此外，RhAN被用于MCF-7细胞中GSH的内源性和外源性成像。与含有GSH的RhAN或空白RhAN一起孵育的MCF-7细胞在红色通道中均显示出明显的荧光，这表明该探针不仅可以检测外源GSH，而且可以渗透到细胞中并与细胞内GSH反应。这是荧光传感器RhAN的出色设计作为检测活细胞中过量GSH，维持体内氨基酸平衡和确保正常生活活动的一种快速有效的方法。
更新日期：2018-02-13
中文翻译：
专门针对谷胱甘肽的NIR罗丹明荧光化学计量仪：Knoevenagel缩合，细胞内谷胱甘肽的检测和活细胞成像†
设计并合成了一种新的基于共轭加成和分子内氨基诱导的螺内酰胺开口的谷胱甘肽检测近红外探针RhAN。首先，使罗丹明与2-（1,3,3-三甲基吲哚-2-亚基）乙醛经Knoevenagel缩合反应，并延伸共轭链，得到M 2。然后，将M 2与酰肼连接得到M 3。最后，通过M 3和丙烯酰氯的组合合成目标分子RhAN。在GSH存在下，RhAN表现出高选择性，可以特异性识别GSH超过Cys和Hcy，颜色从黄色变为绿色，并在5 s内出现荧光，并且不受其他生物硫醇和氨基酸的干扰。探针RhAN的吸收和发射波长分别达到717 nm和739 nm，摩尔消光系数为4.36×10 4 M -1 cm -1量子产率为0.26。加入GSH后，其吸收和发射强度分别提高了117倍和90倍以上。此外，它还具有高灵敏度，检测限低至0.1μM，低于大多数以前报道的GSH探针。该探针在2-10的宽pH范围内都能出色地工作。此外，RhAN被用于MCF-7细胞中GSH的内源性和外源性成像。与含有GSH的RhAN或空白RhAN一起孵育的MCF-7细胞在红色通道中均显示出明显的荧光，这表明该探针不仅可以检测外源GSH，而且可以渗透到细胞中并与细胞内GSH反应。这是荧光传感器RhAN的出色设计作为检测活细胞中过量GSH，维持体内氨基酸平衡和确保正常生活活动的一种快速有效的方法。
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