CN105524055B - 一种能够区分半胱氨酸/同型半胱氨酸和谷胱甘肽荧光探针的制备与应用 - Google Patents

一种能够区分半胱氨酸/同型半胱氨酸和谷胱甘肽荧光探针的制备与应用 Download PDF

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CN105524055B
CN105524055B CN201610030452.3A CN201610030452A CN105524055B CN 105524055 B CN105524055 B CN 105524055B CN 201610030452 A CN201610030452 A CN 201610030452A CN 105524055 B CN105524055 B CN 105524055B
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cysteine
homocysteine
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宋相志
刘兴江
谌文强
齐风佩
杨雷
杨大雷
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Abstract

本发明公开了一种可以区分半胱氨酸/同型半胱氨酸和谷胱甘肽的新型化合物，具体涉及一种新型荧光探针的制备方法及其应用，属于化学分析检测技术领域。其分子结构式如下：该荧光探针用于环境或生物样品中的半胱氨酸、同型半胱氨酸和谷胱甘肽的荧光传感分析，通过和探针分子作用后输出信号的差异，能够很好地区分半胱氨酸/同型半胱氨酸和谷胱甘肽，选择性好，抗干扰能力强，可以灵敏快速地从多种氨基酸中区分出半胱氨酸、同型半胱氨酸和谷胱甘肽，具有很好的应用前景。

Description

一种能够区分半胱氨酸/同型半胱氨酸和谷胱甘肽荧光探针 的制备与应用
技术领域
本发明涉及的是化学分析检测技术领域，具体涉及一种能够区分半胱氨酸/同型半胱氨酸和谷胱甘肽荧光探针的制备方法以及该荧光探针在实验环境和细胞环境检测半胱氨酸、同型半胱氨酸和谷胱甘肽方面的应用。
背景技术
氨基酸是构成蛋白质的基本物质，并且与生物的生命活动有着密切的联系。半胱氨酸(Cysteine，Cys)、同型半胱氨酸(Homocysteine，Hcy)和谷胱甘肽(Glutataione，GSH)是生物体内常见的巯基化合物，在维持生物的正常生理活动中起着重要的作用。医学研究表明不正常的生理浓度可能引起很多疾病，比如肾功能衰竭、老年痴呆症、帕金森疾病、心血管疾病、冠心病、肌肉损伤、皮肤松弛等，它们在生物体内含量变化可以作为这些疾病诊断的依据。因此，在生理条件下高选择性、高灵敏性地检测小分子生物硫醇是非常重要的，当前已引起广泛的关注及深入研究。目前已经应用的技术包括高效液相色谱法、毛细管电泳法、电化学检测、光学分析和质谱鉴定，这些方法仅可以在体外监测半胱氨酸、同型半胱氨酸和谷胱甘肽。荧光分子探针不仅灵敏度高选择性好，而且能够在活细胞中检测分析物，所以研究者们开始关注将荧光分子探针的这项技术应用于对体外和活细胞内的半胱氨酸、同型半胱氨酸和谷胱甘肽进行监测或者细胞荧光成像。目前已经报导了多种基于化学反应的该类荧光探针，例如Michael加成和亲核取代反应。在这些方法中，在荧光分子内引入荧光淬灭剂2,4-二硝基-苯磺酸盐、2,4-二硝基苯磺酰胺基团或者丙烯酰基团，导致荧光猝灭，在半胱氨酸、同型半胱氨酸和谷胱甘肽诱导下发生的裂解，荧光得以恢复，这是一种特别有效的方法。由于这三种氨基酸都含有巯基(-SH)并且在结构和反应活性上相差较小，所以这类荧光探针很难将谷胱甘肽和半胱氨酸/同型半胱氨酸区分开，因此研发能够输出不同响应信号的该类荧光探针是很有必要的。
发明内容
本发明目的之一是提供一种合成简单、反应条件温和、成本较低的荧光探针合成方法；目的之二是提供一种灵敏度高、选择性好，抗干扰能力强，能够对体外或者活细胞内的半胱氨酸、同型半胱氨酸和谷胱甘肽进行监测或者细胞荧光成像的荧光探针。
本发明解决问题采取的技术方案为，一种检测半胱氨酸、同型半胱氨酸和谷胱甘肽的“关-开”型荧光探针，其分子结构式如下：合成路线如下：
具体合成方法如下：(1)将4-(二甲氨基)肉桂醛(0.3505g，2.0mmol)，氢氧化钾(0.2076g，3.7mmol)和邻羟基苯乙酮(0.2723g，2.0mmol)溶于5mL的无水甲醇中，在氩气的保护下，加热回流4h。停止反应，冷却至室温，将反应体系倒入200g的碎冰中，得棕黄色澄清溶液。用4M的稀盐酸调节pH至2-3左右，有大量的深色固体析出，抽滤，依次用去离子水、10％的碳酸氢钠溶液，真空干燥。粗产物用无水乙醇重结晶，得深紫色针状晶体0.3988g，收率：68％。(2)将上步所得产物1(0.1001g，0.3mmol)溶于20mL甲醇和3mL 0.5M氢氧化钠溶液中，充分搅拌使得固体全部溶解，再向其中加入0.33mL 30％的双氧水溶液。升温70℃，反应3h，停止加热，冷却至室温，抽滤，粗产物用冷的无水甲醇洗涤2次，真空干燥，得红色固体粉末0.0544g，收率：59％。(3)将化合物2(0.0451g，0.15mmol)和4-氯-7-硝基苯并-2-氧杂-1,3-二唑(NBD-Cl)(0.0307g，0.15mmol)溶于2mL无水乙腈，加入三乙胺(0.025mL，0.16mmol)，在室温下搅拌过夜。停止反应，抽滤，用无水乙醇洗涤2次，真空干燥，得深棕色固体0.0371g，收率：56％。
本发明的荧光探针使用方法如下，将探针分子溶解在含有30％乙腈、pH为7.4的PBS缓冲溶液中，室温下进行测试。并且对低浓度的半胱氨酸、同型半胱氨酸和谷胱甘肽可以进行定量检测，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作用机理如下，探针分子与半胱氨酸或同型半胱氨酸作用后，NBD部分从探针分子上离去，并伴随重排现象，探针分子的荧光由无到有，并有双荧光信号输出，探针分子与谷胱甘肽作用后，NBD部分从探针分子上离去，探针分子的荧光由无到有，从而实现了对半胱氨酸、同型半胱氨酸和谷胱甘肽的检测过程。探针分子与半胱氨酸和同型半胱氨酸的响应过程：
酸：n＝1；同型半胱氨酸：n＝2)。探针分子与谷胱甘肽的响应过程：
本发明的荧光探针与半胱氨酸或同型半胱氨酸作用后荧光发射峰在545nm和621nm处，与谷胱甘肽作用后的荧光发射峰仅出现在621nm处。
本发明所述的探针分子合成简单，成本较低，对半胱氨酸、同型半胱氨酸和谷胱甘肽的选择性好、抗干扰能力强、响应速度快，并能通过输出信号不同特异性区分半胱氨酸/同型半胱氨酸和谷胱甘肽，使得该荧光探针在生物化学，环境科学等领域具有实际的应用价值。
附图说明
图1为本发明荧光探针的选择性，荧光探针(5.0×10-6mol/L)在PBS缓冲溶液(10mM，V乙腈/VPBS＝3/7，pH＝7.4)中，与不同种类氨基酸作用后的荧光光谱，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(5.0×10-6mol/L)在PBS缓冲溶液(10mM，V乙腈/VPBS＝3/7，pH＝7.4)中，与不同浓度半胱氨酸作用后的荧光光谱变化，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(5.0×10-6mol/L)在PBS缓冲溶液(10mM，V乙腈/VPBS＝3/7，pH＝7.4)中，与不同浓度同型半胱氨酸作用后的荧光光谱变化，横坐标为波长，纵坐标为荧光强度。
图4为本发明的荧光探针(5.0×10-6mol/L)在PBS缓冲溶液(10mM，V乙腈/VPBS＝3/7，pH＝7.4)中，与不同浓度谷胱甘肽作用后的荧光光谱变化，横坐标为波长，纵坐标为荧光强度。
图5为本发明的荧光探针(5.0×10-6mol/L)在PBS缓冲溶液(10mM，V乙腈/VPBS＝3/7，pH＝7.4)中，与半胱氨酸浓度的线性关系，横坐标为浓度，纵坐标为荧光强度。
图6为本发明的荧光探针(5.0×10-6mol/L)在PBS缓冲溶液(10mM，V乙腈/VPBS＝3/7，pH＝7.4)中，与同型半胱氨酸浓度的线性关系，横坐标为浓度，纵坐标为荧光强度。
图7为本发明的荧光探针(5.0×10-6mol/L)在PBS缓冲溶液(10mM，V乙腈/VPBS＝3/7，pH＝7.4)中，与谷胱甘肽浓度的线性关系，横坐标为浓度，纵坐标为荧光强度。
图8为本发明的荧光探针(5.0×10-6mol/L)在PBS缓冲溶液(10mM，V乙腈/VPBS＝3/7，pH＝7.4)中，与半胱氨酸作用过程中545nm，621nm处荧光强度与探针本身在545nm，621nm处荧光强度的比值(I/I0)随时间的变化，横坐标为时间，纵坐标为荧光强度。
图9为本发明的荧光探针(5.0×10-6mol/L)在PBS缓冲溶液(10mM，V乙腈/VPBS＝3/7，pH＝7.4)中，与同型半胱氨酸作用过程中545nm，621nm处荧光强度与探针本身在545nm，621nm处荧光强度的比值(I/I0)随时间的变化，横坐标为时间，纵坐标为荧光强度。
图10为本发明的荧光探针(5.0×10-6mol/L)在PBS缓冲溶液(10mM，V乙腈/VPBS＝3/7，pH＝7.4)中，与谷胱甘肽作用过程中545nm，621nm处荧光强度与探针本身在545nm，621nm处荧光强度的比值(I/I0)随时间的变化，横坐标为时间，纵坐标为荧光强度。
图11为本发明的荧光探针(5.0×10-6mol/L)在不同pH值缓冲溶液中，与半胱氨酸作用前后的荧光强度，横坐标为pH，纵坐标为荧光强度。
图12为本发明的荧光探针(5.0×10-6mol/L)在不同pH值缓冲溶液中，与谷胱甘肽作用前后的荧光强度，横坐标为pH，纵坐标为荧光强度。
具体实施实例
实施例1：化合物1的合成
将4-(二甲氨基)肉桂醛(0.3505g，2.0mmol)，氢氧化钾(0.2076g，3.7mmol)和邻羟基苯乙酮(0.2723g，2.0mmol)溶于5mL的无水甲醇中，在氩气的保护下，加热回流4h。停止反应，冷却至室温，将反应体系倒入200g的碎冰中，得棕黄色澄清溶液。用4M的稀盐酸调节pH至2-3左右，有大量的深色固体析出，抽滤，依次用去离子水、10％的碳酸氢钠溶液，真空干燥。粗产物用无水乙醇重结晶，得深紫色针状晶体0.3988g，收率：68％。探针分子的结构表征如下：1H NMR(400MHz,CDCl3)δ7.82(dd,J＝8.0,1.2Hz,1H),7.73(dd,J＝14.4,11.2Hz,1H),7.47–7.38(m,3H),7.12(d,J＝14.6Hz,1H),7.03–6.98(m,2H),6.93–6.84(m,2H),6.71(d,J＝7.8Hz,2H),3.02(s,6H).HRMS(EI)m/z计算[C19H19NO2+Na]+的分子量为316.1416,发现:316.1308。
实施例2：化合物2的合成
将上步所得产物1(0.1001g，0.3mmol)溶于20mL甲醇和3mL 0.5M氢氧化钠溶液中，充分搅拌使得固体全部溶解，再向其中加入0.33mL 30％的双氧水溶液。升温700C，反应3h，停止加热，冷却至室温，抽滤，粗产物用冷的无水甲醇洗涤2次，真空干燥，得红色固体粉末0.0544g，收率：59％。探针分子的结构表征如下：1H NMR(400MHz,d6-DMSO)δ7.96(d,J＝8.3Hz,1H),7.42(dd,J＝17.1,9.0Hz,3H),7.33(d,J＝8.7Hz,2H),7.18(dd,J＝7.8,5.1,2.8Hz,1H),6.98(d,J＝16.2Hz,1H),6.67(d,J＝8.8Hz,2H),2.87(s,6H).HRMS(EI)m/z计算[C19H17NO3+H]+的分子量为:308.1208,发现:308.1278。
实施例3：探针分子3的合成
将化合物2(0.0451g，0.15mmol)和4-氯-7-硝基苯并-2-氧杂-1,3-二唑(NBD-Cl)(0.0307g，0.15mmol)溶于2mL无水乙腈，加入三乙胺(0.025mL，0.16mmol)，在室温下搅拌过夜。停止反应，抽滤，用无水乙醇洗涤2次，真空干燥，得深棕色固体0.0371g，收率：56％。探针分子的结构表征如下：1HNMR(500MHz,d6-DMSO)δ8.61(d,J＝8.4Hz,1H),8.06(dd,J＝7.9,1.4Hz,1H),7.93–7.81(m,3H),7.60(d,J＝8.9Hz,2H),7.54(t,J＝7.4Hz,1H),7.16(d,J＝8.4Hz,1H),7.00(d,J＝15.8Hz,1H),6.71(d,J＝9.0Hz,2H),2.99(s,6H).13C NMR(125MHz,d6-DMSO)δ170.06,157.52,155.24,152.67,152.35,145.44,144.83,140.88,138.21,135.81,134.89,132.66,130.97,130.89,125.77,125.55,124.09,122.53,118.76,112.25,111.44,109.85,107.75,9.27.
实施例4：本发明：荧光探针的应用
将探针溶于缓冲溶液(V乙腈/VPBS＝3/7，pH＝7.4)中配制成5.0×10-6mol/L的溶液，向溶液中加入氨基酸(Asn,Ala,Val,Phe,His,Leu,Ser,Ile,Trp,Lys,Arg,Pro,Gly,Met,Tyr,Glu,Thr)没有引起荧光的变化，加人氨基酸(Cys,Hcy,GSH)引起了荧光变化，该荧光探针对半胱氨酸、同型半胱氨酸和谷胱甘肽表现出很高灵敏度并且能够区分半胱氨酸/同型半胱氨酸和谷胱甘肽。当半胱氨酸、同型半胱氨酸和谷胱甘肽与干扰物质(Asn,Ala,Val,Phe,His,Leu,Ser,Ile,Trp,Lys,Arg,Pro,Gly,Met,Tyr,Glu,Thr)共存时，探针不受干扰因素的影响，表现出来很好的抗干扰能力。该探针分子与半胱氨酸、同型半胱氨酸和谷胱甘肽作用后荧光信号明显，即可观察到荧光的变化。探针分子在pH为6至10的范围内都可以对半胱氨酸/同型半胱氨酸和谷胱甘肽选择性区分识别，表现出了较好的检测范围。

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1.一种能够区分半胱氨酸/同型半胱氨酸和谷胱甘肽的荧光探针，其结构为：
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