Manibalan Kesavan, Chen Sin-Ming, Mani Veerappan, Huang Tsung-Tao, Huang Sheng-Tung
Department of Chemical Engineering and Biotechnology, National Taipei University of Technology, Taipei, 10608, Taiwan, Republic of China.
Institue of Biochemical and Biomedical Engineering, National Taipei University of Technology, Taipei, 10608, Taiwan, Republic of China.
J Fluoresc. 2016 Jul;26(4):1489-95. doi: 10.1007/s10895-016-1844-x. Epub 2016 Jun 11.
The development of sensitive fluorescence probes to detect biothiols such as cysteine and homocysteine has attracted great attention in recent times. Herein, we described the design and synthesis of coumarin based long-wavelength fluorescence probe, Bromo-2-benzothiazolyl-3-cyano-7-hydroxy coumarin (BBCH, 2) for selective detections of cysteine and homocysteine. The probe is rationally designed in such a way that both sulfhydryl and adjacent amino groups of thiols are involved in sensing process. Only cysteine/homocysteine able to react with BBCH to release fluorescence reporter (BCH, 1); while, glutathione and other amino acids unable to react with BBCH due to the absence of adjacent amino groups. In presence of cysteine, the color of BBCH is turns from colorless to red and thus BBCH is a naked eye fluorescence indicator for cysteine. Besides, BBCH can discriminate cysteine and homocysteine based on color changes and different reaction rates. The described sensing platform showed good sensing performances to detect cysteine and homocysteine with detection limits of 0.87 and 0.19 μM, respectively. Practical applicability was verified in biological and pharmaceutical samples.
近年来，开发用于检测半胱氨酸和高半胱氨酸等生物硫醇的灵敏荧光探针引起了极大关注。在此，我们描述了基于香豆素的长波长荧光探针溴-2-苯并噻唑基-3-氰基-7-羟基香豆素（BBCH，2）的设计与合成，用于选择性检测半胱氨酸和高半胱氨酸。该探针经过合理设计，使硫醇的巯基和相邻氨基都参与传感过程。只有半胱氨酸/高半胱氨酸能够与BBCH反应释放荧光报告基团（BCH，1）；而谷胱甘肽和其他氨基酸由于没有相邻氨基而不能与BBCH反应。在半胱氨酸存在下，BBCH的颜色从无色变为红色，因此BBCH是一种用于半胱氨酸的肉眼荧光指示剂。此外，BBCH可以根据颜色变化和不同的反应速率区分半胱氨酸和高半胱氨酸。所描述的传感平台在检测半胱氨酸和高半胱氨酸方面表现出良好的传感性能，检测限分别为0.87和0.19μM。在生物和药物样品中验证了其实际适用性。
