一种香豆素pH荧光染料的开发及应用 |
点此下载全文 |
|
基金项目:国家自然基金(82003850);国家级大学生创新创业项目(201910632017) |
|
中文摘要:香豆素类化合物具有良好的荧光光谱,已广泛运用于抗肿瘤、抗氧化、抗炎等研究。前期研究中,作者发现3-苯并咪唑-7-羟基香豆素可作为荧光探针监测细胞内pH值变化(pKa = 7.20,pH 6.50 ~ 8.30)。因此,该文通过在3-苯并咪唑-7-羟基香豆素C-3位苯并咪唑上引入甲氧基给电子基团,得到化合物3-(6-甲氧基-1H-苯并咪唑)-7-羟基香豆素(BC),并通过核磁共振氢谱(1H NMR)、核磁共振碳谱(13C NMR)和高分辨质谱(HR-MS)确定了探针化合物的结构,考察了其荧光属性及pH值变化对检测的影响。结果表明,该探针具有较高的选择性和抗干扰能力,在pH 5.5 ~ 10.0范围内(pKa = 8.36),其荧光强度随着pH值的增大而增强。此外,BC可被成功应用于标记HeLa细胞内pH值的变化,展现出较好的生物医学应用前景。 |
中文关键词:pH 荧光探针 7-羟基香豆素 细胞成像 |
|
Development and Application of a Coumarin pH Fluorescent Dye |
|
|
Abstract:Coumarins are widely used in anti-tumor,anti-oxidation,anti-inflammatory and other pharmacological researches due to their good fluorescence spectrum characteristics. It was showed in the previous study that 3-benzimidazole-7-hydroxycoumarin could serve as a fluorescent probe to monitor intracellular pH changes(pKa = 7.20, pH 6.50-8.30). Herein, 3-(6-methoxy-1H-benzimidazole)-7-hydroxy coumarin(BC) was synthesized by introducing a methoxy electron donor group onto the C-3 benzimidazole of 3-methoxy-1H-benzimidazole. The structure of the probe compound was determined by hydrogen nuclear magnetic resonance spectroscopy(1H NMR), carbon nuclear magnetic resonance spectroscopy(13C NMR)and high resolution mass spectrometry(HR-MS). The fluorescence properties and pH value of the probe on the detection were investigated. Results showed that the probe has high selectivity and anti-interference ability. The fluorescence intensity of the probe increases with the increase of pH value in the range of pH 5.5-10.0(pKa = 8.36). Furthermore, BC could be successfully applied to mark pH changes in HeLa cells, showing a good prospect of biomedical applications. |
Key Words:pH fluorescent probe 7-hydroxycoumarin cell imaging |
引用本文:姜雪琴,刘 礼,李 昊,何阳森,吕沐瀚,吴建明,梁思成,詹会智,齐晓怡.一种香豆素pH荧光染料的开发及应用[J].分析测试学报,2021,40(9):1342-1347. |
摘要点击次数: 1208 |
全文下载次数: 872 |
查看全文 下载PDF阅读器 |
|