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一种香豆素pH荧光染料的开发及应用
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作者单位
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 1. 西南医科大学 药学院四川 泸州 6460002. 西南医科大学附属医院 消化内科四川 泸州 6460003. 西南医科大学附属医院 皮肤科四川 泸州 6460004. 西南医科大学附属医院 胸外科四川 泸州 646000 
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.
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