CN105601658B - 一种能够区分生物硫醇的荧光探针的制备与应用 - Google Patents

一种能够区分生物硫醇的荧光探针的制备与应用 Download PDF

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CN105601658B
CN105601658B CN201610027345.5A CN201610027345A CN105601658B CN 105601658 B CN105601658 B CN 105601658B CN 201610027345 A CN201610027345 A CN 201610027345A CN 105601658 B CN105601658 B CN 105601658B
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fluorescence
fluorescence probe
cysteine
homocysteine
glutathione
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宋相志
刘兴江
谌文强
杨大雷
杨雷
齐风佩
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Abstract

本发明公开了一种能够区分生物硫醇的新型化合物，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，具有选择性好，抗干扰能力强，激发和发射波长处于近红外区等优点，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

一种能够区分生物硫醇的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生物硫醇的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生物硫醇方面的应用。
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)是生物体内常见的生物硫醇，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，比如半胱氨酸生理浓度的异常，会引起毛发色素脱色、水肿、嗜睡、肌肉损伤、皮肤松弛过敏、免疫能力下降等，同型半胱氨酸在临床上的应用主要作为心血管疾病，尤其是冠状动脉粥硬化和心肌梗塞的危险指标，它的浓度升高程度与疾病的危险性成正比，谷胱甘肽的浓度异常也可能会引起阿尔兹海默氏症、心血管疾病、癌症的发生。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。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、水溶性好、斯托克斯位移大、发射波长在近红外区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，发射波长在近红外区，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)称取原料1(0.04mmol,0.0201g)，4-氯-7-硝基苯并-2-氧杂-1,3-二唑 (NBD-Cl)(0.04mmol,0.0081g)和无水碳酸钾(0.15mmol,0.0213g)置于5mL单颈圆底烧瓶，加入2mL无水丙酮，氩气保护，室温搅拌4小时。待反应结束，除去丙酮，剩余物用柱层析进一步纯化(二氯甲烷:石油醚＝1:1,v/v)得到黑色固体。产量：0.0242g。收率：94％。
本发明的荧光探针使用方法如下，将探针分子溶解在含有10mM十六烷基三甲基溴化铵(CTAB)、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：(半胱氨酸：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705nm处，与谷胱甘肽作用后的荧光发射峰仅出现在705nm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，激发和发射波长处于近红外区，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(10mMCTAB，pH＝7.4)中，在650nm激发下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为本发明荧光探针的选择性，荧光探针(5.0×10-6mol/L)在PBS缓冲溶液(10mMCTAB，pH＝7.4)中，在476nm激发下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3为本发明的荧光探针(5.0×10-6mol/L)在PBS缓冲溶液(10mM CTAB，pH＝7.4)中，650nm激发下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4为本发明的荧光探针(5.0×10-6mol/L)在PBS缓冲溶液(10mM CTAB，pH＝7.4)中，650nm激发下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5为本发明的荧光探针(5.0×10-6mol/L)在PBS缓冲溶液(10mM CTAB，pH＝7.4)中，650nm激发下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6为本发明的荧光探针(5.0×10-6mol/L)在PBS缓冲溶液(10mM CTAB，pH＝7.4)中，650nm激发下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7为本发明的荧光探针(5.0×10-6mol/L)在PBS缓冲溶液(10mM CTAB，pH＝7.4)中，650nm激发下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8为本发明的荧光探针(5.0×10-6mol/L)在PBS缓冲溶液(10mM CTAB，pH＝7.4)中，650nm激发下与谷胱甘肽的线性关系，横坐标为浓度，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 CTAB，pH＝7.4)中，476nm激发下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10为本发明的荧光探针(5.0×10-6mol/L)在PBS缓冲溶液(10mM CTAB，pH＝7.4)中，476nm激发下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11为本发明的荧光探针(5.0×10-6mol/L)在PBS缓冲溶液(10mM CTAB，pH＝7.4)中，476nm激发下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12为本发明的荧光探针(5.0×10-6mol/L)在PBS缓冲溶液(10mM CTAB，pH＝7.4)中，476nm激发下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13为本发明的荧光探针(5.0×10-6mol/L)在PBS缓冲溶液(10mM CTAB，pH＝7.4)中，650nm激发下与10倍当量半胱氨酸的时间扫描，横坐标为时间，纵坐标为荧光强度。
图14为本发明的荧光探针(5.0×10-6mol/L)在PBS缓冲溶液(10mM CTAB，pH＝7.4)中，650nm激发下与10倍当量同型半胱氨酸的时间扫描，横坐标为时间，纵坐标为荧光强度。
图15为本发明的荧光探针(5.0×10-6mol/L)在PBS缓冲溶液(10mM CTAB，pH＝7.4)中，650nm激发下与10倍当量谷胱甘肽的时间扫描，横坐标为时间，纵坐标为荧光强度。
图16为本发明的荧光探针(5.0×10-6mol/L)在PBS缓冲溶液(10mM CTAB，pH＝7.4)中，476nm激发下与10倍当量半胱氨酸的时间扫描，横坐标为时间，纵坐标为荧光强度。
图17为本发明的荧光探针(5.0×10-6mol/L)在PBS缓冲溶液(10mM CTAB，pH＝7.4)中，476nm激发下与10倍当量同型半胱氨酸的时间扫描，横坐标为时间，纵坐标为荧光强度。
图18为本发明的荧光探针(5.0×10-6mol/L)在PBS缓冲溶液(10mM CTAB，pH＝7.4)中，476nm激发下与10倍当量谷胱甘肽的时间扫描，横坐标为时间，纵坐标为荧光强度。
图19为本发明的荧光探针(5.0×10-6mol/L)在PBS缓冲溶液(10mM CTAB，pH＝7.4)中，半胱氨酸抗干扰测试，横坐标为半胱氨酸和不同种类其他氨基酸混合类别，纵坐标为荧光比值。
图20为本发明的荧光探针(5.0×10-6mol/L)在PBS缓冲溶液(10mM CTAB，pH＝7.4)中，同型半胱氨酸抗干扰测试，横坐标为同型半胱氨酸和不同种类其他氨基酸混合类别，纵坐标为荧光比值。
图21为本发明的荧光探针(5.0×10-6mol/L)在PBS缓冲溶液(10mMCTAB，pH＝7.4)中，谷胱甘肽抗干扰测试，横坐标为谷胱甘肽和不同种类其他氨基酸混合类别，纵坐标为荧光比值。
图22为本发明的荧光探针(5.0×10-6mol/L)在PBS缓冲溶液(10mM CTAB，pH＝7.4)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23为本发明的荧光探针(5.0×10-6mol/L)在PBS缓冲溶液(10mM CTAB，pH＝7.4)中，与同型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24为本发明的荧光探针(5.0×10-6mol/L)在PBS缓冲溶液(10mM CTAB，pH＝7.4)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：探针分子的合成
称取原料1(0.04mmol,0.0201g)，4-氯-7-硝基苯并-2-氧杂-1,3-二唑(NBD-Cl)(0.04 mmol,0.0081g)和无水碳酸钾(0.15mmol,0.0213g)置于5mL单颈圆底烧瓶，加入2mL无水丙酮，氩气保护，室温搅拌4小时。待反应结束，除去丙酮，剩余物用柱层析进一步纯化(二氯甲烷:石油醚＝1:1,v/v)得到黑色固体。产量： 0.0242g。收率：94％。1H NMR(500MHz,CDCl3)δ8.53(d,J＝8.3Hz,1H),7.69 -7.63(m,1H),7.53(d,J＝8.4Hz,2H),7.41(d,J＝8.4Hz,2H),7.28-7.19(m,2H), 6.96(t,J＝7.4Hz,1H),6.89(d,J＝14.6Hz,1H),6.76(d,J＝7.9Hz,1H),6.63(d,J ＝8.3Hz,1H),6.57(s,1H),5.98(s,1H),5.72(d,J＝12.2Hz,1H),3.24(s,3H),2.59 (s,3H),1.65(s,5H),1.58(s,3H),1.50(s,3H).13C NMR(100MHz,CDCl3)δ162.0,156.6,153.7,153.2,150.3,145.2,144.4,144.1,142.3,139.2,137.2,136.8,135.0,133.7,133.5,133.2,131.6,131.3,131.1,130.4,128.4,128.0,121.6,121.3,120.9,119.8,118.4,113.6,108.0,107.0,98.5,46.6,46.4,29.6,29.3,28.7,15.0,14.2.ESI-MS:[M+H]+calcd for 687.2697,found 687.2706.
实施例2：本发明：荧光探针的应用
将探针溶于缓冲溶液(含10mM CTAB的PBS溶液，pH＝7.4)中配制成5.0×10-6mol/L的溶液，向溶液中加入氨基酸(Ala,Gln,Glu,His,Ile,Leu,Lys,Phe,Pro,Ser, Thr,Try,Tyr,Val.)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。

Claims (3)

1.一种能够区分生物硫醇的荧光探针，其结构为：
2.如权利要求1所述的能够区分生物硫醇的荧光探针的制备方法，其特征在于按以下步骤进行制备：
(a)称取原料14-氯-7-硝基苯并-2-氧杂-1,3-二唑(NBD-Cl)和无水碳酸钾置于单颈圆底烧瓶，加入无水丙酮，氩气保护，室温搅拌4小时；
(b)待反应结束，除去丙酮，剩余物用柱层析进一步纯化，得到黑色固体。
3.根据权利要求1所述的能够区分生物硫醇的荧光探针的非诊断或治疗目的的用途，其特征在于该荧光探针用于半胱氨酸/同型半胱氨酸和谷胱甘肽的区分以及环境或生物样品中半胱氨酸、同型半胱氨酸的荧光检测和分析。
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