CN108440551A - 一种检测生物硫醇的荧光探针 - Google Patents

一种检测生物硫醇的荧光探针 Download PDF

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CN108440551A
CN108440551A CN201810303835.2A CN201810303835A CN108440551A CN 108440551 A CN108440551 A CN 108440551A CN 201810303835 A CN201810303835 A CN 201810303835A CN 108440551 A CN108440551 A CN 108440551A
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宋相志
熊海青
苏远安
杨雷
张赟
韩金梁
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Abstract

本发明公开了一种检测生物硫醇的荧光探针，其分子结构式如下：该荧光探针有很弱的荧光，与生物硫醇响应后溶液发红光。本发明所述的探针分子不仅可以应用于纯水体系检测生物硫醇，同时也能够在细胞中快速识别并定量检测生物硫醇。本发明的荧光探针在生物化学领域具有重要的应用价值。

Description

一种检测生物硫醇的荧光探针
技术领域
本发明涉及的是荧光探针领域，涉及一种检测生物硫醇的荧光探针的制备与应用。
背景技术
生物硫醇促进生物体内的酶发挥作用并且是生理活动中的重要信号分子，同时也可以调节细胞的正常氧化还原状态，在生物体的生理活动中具有重要的功能。
用于检测生物硫醇的常规方法有色谱法、电化学方法、气质联用法。但这些常规方法通常具有诸如需要昂贵的仪器设备、复杂的操作过程、样品前处理繁琐等缺点。相对于常规方法的检测，荧光分析法具有操作简单、选择性好、灵敏度高等优点，同时可以用于细胞及生物活体成像研究。
发明内容
本发明目的之一是提供一种检测生物硫醇的荧光探针的合成方法；目的之二是提供一种灵敏度高、选择性好、抗干扰能力强、水溶性好并能够在细胞内检测生物硫醇的荧光探针。
本发明解决问题采取的技术方案为，一种可以用于纯水检测生物硫醇的荧光探针，其分子结构式如下：具体合成路线如下：具体合成方法如下：
(1)向50mL单口圆底烧瓶中加入10.0mL丙酮，然后将化合物1(0.2173g,1.0mmol)和3-溴丙炔(0.2380g,2.0mmol)溶于丙酮中，再加入无水碳酸钾(0.2764g,2.0mmol)，然后加热回流12小时，停止反应，将反应液过滤除去滤渣，旋干得到固体粗产品，最后经柱层析分离得到0.2002g黄色固体，产率78.4％。(2)将化合物2(0.2552g，1.0mmol)和4-氨基苯酚(0.1308g，1.2mmol)加至含有5.0mL无水DMF的25mL单口圆底烧瓶中，110℃反应4h，停止反应，冷却至室温，将反应液倒入50mL饱和食盐水中，二氯甲烷萃取(25.0mL×4)，饱和食盐水洗涤，无水硫酸钠干燥，减压旋干得到粗产品，再经柱层析分离得到产物0.0689g；产率20％。(3)将化合物3(0.1801g，0.52mmol)、5mL无水二氯甲烷加至20mL厚壁耐压瓶中，再加入碘甲烷(0.0863g，0.6mmol),90℃下避光反应12h，停止反应，冷却至室温，减压除去溶剂得到粗产品，最后经柱层析分离得到产物0.0932g，产率87％。(4)于25mL单口反应瓶中，将化合物4(0.0701g，0.2mmol)溶于5.0mL无水二氯甲烷中并加入三乙胺(0.0812g，0.8mmol)，冰水浴中搅拌10min，然后将2,4-二硝基苯磺酰氯(0.0873mg，0.33mmol)溶于二氯甲烷中并逐滴加到反应液中，继续搅拌1h，停止反应，将反应液直接经柱层析分离得到探针MCQ-DNBS0.0301g，产率21％。
本发明的荧光探针测试方法如下，将探针分子溶解在HEPES缓冲液(20.0mM，pH＝7.4)中，室温下进行测试。具体实施方法在实施实例中详细介绍。
本发明的荧光探针的响应机理如下：生物硫醇与探针分子响应后，其巯基与2,4-二硝基苯磺酰酯发生亲核取代反应并释放出染料4，溶液即时产生强烈的红色荧光。从而实现了荧光检测生物硫醇过程。探针分子的响应过程如下：
本发明的荧光探针在HEPES缓冲液(20.0mM，pH＝7.4)中有微弱的荧光，与生物硫醇响应后的荧光发射峰在613nm处，并且斯托克斯位移达到115nm。
本发明所述的探针分子合成路线简单，成本较低，可以于纯水体系中快速识别生物硫醇。
附图说明
图1为本发明的荧光探针(10.0μM)在HEPES缓冲液(20.0mM，pH＝7.4)中与不同氨基酸(Asp、Ala、Val、Phe、His、Leu、Ser、Ile、Trp、Lys、Arg、Pro、Gly、Met、Tyr、Glu、Thr，浓度分别为0.1mM；Cys、Hcy、GSH，浓度分别为20.0μM)响应后的荧光光谱。横坐标为波长，纵坐标为荧光强度。
图2为本发明的荧光探针(10.0μM)在HEPES缓冲液(20.0mM，pH＝7.4)中与不同浓度的Cys(0.0-20.0μM)响应后的荧光光谱。激发波长：498nm。横坐标为波长，纵坐标为荧光强度。
图3为本发明的荧光探针(10.0μM)在HEPES缓冲液(20.0mM，pH＝7.4)中与不同浓度Cys作用后溶液在613nm处的荧光强度。横坐标为Cys浓度，纵坐标为荧光强度。
图4为本发明的荧光探针(10.0μM)在HEPES缓冲液(20.0mM，pH＝7.4)中与不同浓度Cys作用后溶液在613nm处的荧光强度与Cys浓度之间的线性拟合关系。横坐标为Cys浓度，纵坐标为荧光强度。
图5为本发明的荧光探针(10.0μM)在HEPES缓冲液(20.0mM，pH＝7.4)中与不同浓度的Hcy(0.0-20.0μM)响应后的荧光光谱。激发波长：498nm。横坐标为波长，纵坐标为荧光强度。
图6为本发明的荧光探针(10.0μM)在HEPES缓冲液(20.0mM，pH＝7.4)中与不同浓度Hcy作用后溶液在613nm处的荧光强度。横坐标为Hcy浓度，纵坐标为荧光强度。
图7为本发明的荧光探针(10.0μM)在HEPES缓冲液(20.0mM，pH＝7.4)中与不同浓度Hcy作用后溶液在613nm处的荧光强度与Hcy浓度之间的线性拟合关系。横坐标为Hcy浓度，纵坐标为荧光强度。
图8为本发明的荧光探针(10.0μM)在HEPES缓冲液(20.0mM，pH＝7.4)中与不同浓度的GSH(0.0-20.0μM)响应后的荧光光谱。激发波长：498nm。横坐标为波长，纵坐标为荧光强度。
图9为本发明的荧光探针(10.0μM)在HEPES缓冲液(20.0mM，pH＝7.4)中与不同浓度GSH作用后溶液在613nm处的荧光强度。横坐标为GSH浓度，纵坐标为荧光强度。
图10为本发明的荧光探针(10.0μM)在HEPES缓冲液(20.0mM，pH＝7.4)中与不同浓度GSH作用后溶液在613nm处的荧光强度与GSH浓度之间的线性拟合关系。横坐标为GSH浓度，纵坐标为荧光强度。
图11为本发明荧光探针(10.0μM)在HEPES缓冲液(20.0mM，pH＝7.4)中分别与20.0μM的Cys、Hcy、GSH作用后溶液在613nm处的荧光强度与时间的关系。横坐标为时间，纵坐标为荧光强度。
图12为本发明荧光探针(10.0μM)在活细胞(HeLa)中与生物硫醇作用后细胞成像图。
具体实施实例
实施例1：中间产物2的合成
向50mL单口圆底烧瓶中加入10.0mL丙酮，然后将化合物1(0.2173g,1.0mmol)和3-溴丙炔(0.2380g,2.0mmol)溶于丙酮中，再加入无水碳酸钾(0.2764g,2.0mmol)，然后加热回流12小时，停止反应，将反应液过滤除去滤渣，旋干得到固体粗产品，最后经柱层析(硅胶200-300目，淋洗剂：V乙酸乙酯/V石油醚＝1/3)分离得到0.2002g黄色固体，产率78.4％。1H NMR(500MHz,CDCl3)δH:10.03(s,1H),7.34(s,1H),4.63(d,J＝2.4Hz,2H),3.52-3.05(m,4H),2.81(t,2H),2.73(t,2H),2.55(t,1H),2.01-1.82(m,4H).13C NMR(125MHz,CDCl3)δC:187.8,157.8,148.8,127.5,117.5,117.0,112.6,78.7,76.1,62.1,50.0,49.7,27.3,21.4,21.3,20.7.
实施例2：中间产物3的合成
将化合物2(0.2552g，1.0mmol)和4-氨基苯酚(0.1308g，1.2mmol)加至含有5.0mL无水DMF的25mL单口圆底烧瓶中，110℃反应4h，停止反应，冷却至室温，将反应液倒入50mL饱和食盐水中，二氯甲烷萃取(25.0mL×4)，饱和食盐水洗涤，无水硫酸钠干燥，减压旋干得到粗产品，再经柱层析(洗脱剂：V石油醚/V乙酸乙酯＝6/1至3/1)分离得到产物0.0689g；产率20％。1HNMR(400MHz,DMSO-d6)δH 9.85(s,1H),7.78(d,J＝9.2Hz,2H),7.65(s,1H),7.22(dd,J＝9.0,2.6Hz,1H),7.06(d,J＝2.6Hz,1H),5.19(s,2H),3.19–3.06(m,4H),2.72(t,J＝6.2Hz,2H),2.60(t,J＝6.4Hz,2H),2.52-2.47(m,1H),1.86(m,4H).13C NMR(100MHz,DMSO-d6)δC155.0,153.7,147.2,145.6,143.3,130.0,129.2,128.2,125.2,122.4,121.8,115.7,110.9,109.1,107.7,68.2,49.8,49.2,27.4,22.1,21.3,21.1.
实施例3：中间产物4的合成
将化合物3(0.1801g，0.52mmol)、5mL无水二氯甲烷加至20mL厚壁耐压瓶中，再加入碘甲烷(0.0863g，0.6mmol),90℃下避光反应12h，停止反应，冷却至室温，减压除去溶剂得到粗产品，最后经柱层析(洗脱剂：V二氯甲烷/V甲醇＝50/1至33/1)分离得到产物0.0932g，产率87％。1H NMR(500MHz,DMSO-d6)δH10.64(s,1H),8.45(s,1H),8.12(d,J＝9.3Hz,1H),7.61-7.42(m,2H),7.36(s,1H),5.19(s,2H),4.35(s,3H),2.72(d,J＝49.8Hz,4H),1.92-1.89(m,4H),1.40-1.12(m,4H).13C NMR(400MHz,DMSO-d6)δC 157.5,157.0,149.2 147.7,135.3135.0,130.5,128.7,127.8,124.5,121.2,117.2,111.3,107.5,103.3,67.9,50.1,49.5,44.5,27.3,21.3,20.6,20.3.
实施例4：探针的合成
于25mL单口反应瓶中，将化合物4(0.0701g，0.2mmol)溶于5.0mL无水二氯甲烷中并加入三乙胺(0.0812g，0.8mmol)，冰水浴中搅拌10min，然后将2,4-二硝基苯磺酰氯(0.0873mg，0.33mmol)溶于二氯甲烷中并逐滴加到反应液中，继续搅拌1h，停止反应，将反应液直接经柱层析(洗脱剂：V二氯甲烷/V甲醇＝50/1至10/1)分离得到探针MCQ-DNBS 0.0301g，产率21％。1H NMR(400MHz,DMSO-d6)δH 8.98(d,J＝2.5Hz,1H),8.54(dd,J＝9.2,2.6Hz,1H),8.45(s,1H),8.35(d,J＝9.4Hz,1H),8.03(d,J＝2.3Hz,1H),7.96(dd,J＝9.3,2.4Hz,1H),7.55(s,1H),7.40(d,J＝9.2Hz,1H),5.26(s,2H),4.39(s,3H),3.42(m,4H),2.79(t,2H),2.68(t,2H),1.94-1.90(m,J＝10.6,4.8Hz,5H).13C NMR(100MHz,DMSO-d6)δC158.0,154.3,152.8,150.2,149.8,142.9,140.5,138.7,135.1,131.7,130.3,128.9,127.4,126.1,122.6,122.4,121.3,118.3,117.9,107.4,103.4,67.7,50.4,49.7,45.0,32.0,27.3,21.2,20.5,20.1.
实施例5：本发明荧光探针的应用
将探针溶于pH为7.4的20.0mM HEPES缓冲液中，配制成1.0×10-5mol/L的探针溶液，分别向溶液中加入20倍当量的Cys、Hcy、GSH，激发波长为498nm时，溶液在613nm处均有一个明显的发射峰。本发明的荧光探针可以用于细胞内纯水体系中检测生物硫醇。

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1.一种检测生物硫醇的荧光探针，其结构为：
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