CN112209942B - 一种区分检测半胱氨酸、同型半胱氨酸和谷胱甘肽的荧光探针 - Google Patents
一种区分检测半胱氨酸、同型半胱氨酸和谷胱甘肽的荧光探针 Download PDFInfo
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Abstract
本发明公开一种快速区分检测细胞和斑马鱼体内半胱氨酸、同型半胱氨酸和谷胱甘肽的荧光探针，其结构式为：
Description
技术领域
本发明属于化学分析检测技术领域，具体涉及一种快速区分检测细胞和斑马鱼体内半胱氨酸、同型半胱氨酸和谷胱甘肽的荧光探针及其应用。
背景技术
细胞内生物硫醇，包括半胱氨酸(Cys)、同型半胱氨酸(Hcy)和谷胱甘肽(GSH)在各种生理过程中发挥重要作用，如蛋白质合成、信号转导、细胞代谢和氧化应激的调节。因此，这些生物硫醇浓度异常可导致肝脏损伤、皮肤损伤、心血管疾病、阿尔茨海默病、HIV感染和癌变等一系列病理疾病。重要的是，人们发现这三种硫醇在其生产和代谢过程中有着密切的共生关系。为了阐明半胱氨酸/同型半胱氨酸与谷胱甘肽的复杂功能及其相互之间的关系，迫切需要开发一种有效的方法，在生物系统中对半胱氨酸、同型半胱氨酸与谷胱甘肽进行鉴别检测。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，这些方法可以再体外检测半胱氨酸、同型半胱氨酸和谷胱甘肽。与上述方法相比，荧光探针却是一种比较理想的体内检测手段，因为它具有检测方便，响应时间快，灵敏度高，检测限低，对细胞损害小等优点。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半胱氨酸/同型半胱氨酸和谷胱甘肽区分开，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，相应时间短，能够对细胞内或斑马鱼的半胱氨酸、同型半胱氨酸和谷胱甘肽进行快速监测或者细胞成像的荧光探针，其结构如下：
其合成路线为：
具体合成方法：化合物CC是根据文献合成。将化合物CC(84mg,0.3mmol)、苯乙炔(46mg,0.45mmol)、三苯基膦二氯化钯(11mg,0.05mmol)、碘化亚铜(5.7mg,0.1mmol)以及0.3mL的三乙胺加入到3mL无水四氢呋喃中，在氩气保护下室温搅拌1小时，将反应液旋干柱层析得到红色固体(80mg,产率77％)，即为探针CP。
本发明的探针的机理如下：
探针CP在半胱氨酸或同型半胱氨酸作用下，分子中的香豆素4位的炔键会被硫醇的巯基进攻生成加成产物CPC1和CPH1，接着硫醇的氨基会进一步进攻炔键加成后的双键生成CPC2和CPH2，脱去部分环化产物后为CA显示蓝色荧光(最大发射波长485nm)，但不同的是与半胱氨酸反应时，脱去五元环化产物时反应非常彻底且快速，最终只显示CA的蓝色荧光。而与同型半胱氨酸反应时，脱去六元环化产物则是较为缓慢的，最终显示CA的荧光和CPH1(最大发射波长600nm)的红色荧光。而与谷胱甘肽作用下香豆素部分不会发生脱去环化的反应，只显示CPG1的红色荧光(最大发射波长600nm),探针CP本身的红色荧光(最大发射波长608nm)在与半胱氨酸、同型半胱氨酸和谷胱甘肽的反应中显示不同的荧光，从而达到特异性区分检测半胱氨酸、同型半胱氨酸和谷胱甘肽。
本发明的荧光探针本身荧光发射峰在608nm,与半胱氨酸作用后荧光发射峰只在485nm处，与同型半胱氨酸作用后荧光发射峰在485nm和600nm处，与谷胱甘肽作用后荧光发射峰只出现在600nm处。
附图说明
图1为本发明的荧光探针(10.0×10-6mol/L)在pH为7.4的PBS缓冲溶液(10.0mM,VDMSO/VPBS＝1/1)中，与0.02mM的半胱氨酸响应后在3分钟内的紫外吸收变化图，横坐标为波长，纵坐标分别为吸收强度。
图2为本发明的荧光探针(10.0×10-6mol/L)在pH为7.4的PBS缓冲溶液(10.0mM,VDMSO/VPBS＝1/1)中，与0.02mM的同型半胱氨酸响应后在3分钟内的紫外吸收变化图，横坐标为波长，纵坐标分别为吸收强度。
图3为本发明的荧光探针(10.0×10-6mol/L)在pH为7.4的PBS缓冲溶液(10.0mM,VDMSO/VPBS＝1/1)中，与0.02mM的谷胱甘肽响应后在3分钟内的紫外吸收变化图，横坐标为波长，纵坐标分别为吸收强度。
图4为本发明的荧光探针(10.0×10-6mol/L)在pH为7.4的PBS缓冲溶液(10.0mM,VDMSO/VPBS＝1/1)中，与不同浓度的半胱氨酸作用后的荧光光谱变化，横坐标为波长，纵坐标分别为荧光强度。小图是与半胱氨酸浓度的线性关系，横坐标为浓度，纵坐标为荧光强度的比值。
图5为本发明的荧光探针(10.0×10-6mol/L)在pH为7.4的PBS缓冲溶液(10.0mM,VDMSO/VPBS＝1/1)中，与不同浓度的同型半胱氨酸作用后的荧光光谱变化，横坐标为波长，纵坐标分别为荧光强度。小图是与同型半胱氨酸浓度的线性关系，横坐标为浓度，纵坐标为荧光强度的比值。
图6为本发明的荧光探针(10.0×10-6mol/L)在pH为7.4的PBS缓冲溶液(10.0mM,VDMSO/VPBS＝1/1)中，与不同浓度的谷胱甘肽作用后的荧光光谱变化，横坐标为波长，纵坐标分别为荧光强度。小图是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7为本发明的荧光探针(10.0×10-6mol/L)在pH为7.4的PBS缓冲溶液(10.0mM,VDMSO/VPBS＝1/1)中，与半胱氨酸和同型半胱氨酸作用过程中485nm,608nm处荧光强度与探针本身在485nm,608nm处荧光强度的比值(F/F0)随时间的变化。小图是探针与谷胱甘肽作用过程中608nm处荧光强度的随时间的变化，横坐标为时间，纵坐标为荧光强度的比值。
图8中(a)图为本发明的荧光探针(10.0×10-6mol/L)在不同pH值缓冲溶液中，与半胱氨酸、同型半胱氨酸作用前后的荧光强度变化，横坐标为pH值，纵坐标为荧光强度的比值。(b)图是与谷胱甘肽作用前后的荧光强度变化，横坐标为pH值，纵坐标为荧光强度。
图9为本发明的荧光探针(10.0×10-6mol/L)在pH为7.4的PBS缓冲溶液(10.0mM,VDMSO/VPBS＝1/1)中与1.PBS；2.Cys；3.Hcy；4.GSH；5.Asn；6.Asp；7.Gly；8.His；9.Leu；10.Lys；11.Pro；12.Ser；13.Thr；14.Val；15.CO3 2-；16.F-；17.Zn2+；18.K+.等不同物质时响应时的选择性条形图，纵坐标为荧光强度的比值。
图10为本发明的荧光探针细胞适用性的毒性研究实验，横坐标为探针浓度，纵坐标为细胞存活率。
图11为本发明的荧光探针细胞内区分检测半胱氨酸、同型半胱氨酸和谷胱甘肽。
图12为本发明的荧光探针斑马鱼内区分检测半胱氨酸、同型半胱氨酸和谷胱甘肽。
具体实施实例
实施例1：探针分子的合成
化合物3的合成
将化合物CC(84mg,0.3mmol)、苯乙炔(46mg,0.45mmol)、三苯基膦二氯化钯(11mg,0.05mmol)、碘化亚铜(5.7mg,0.1mmol)以及0.3mL的三乙胺加入到3mL无水四氢呋喃中，在氩气保护下室温搅拌1小时，将反应液旋干柱层析得到红色固体(80mg,产率77％)，即为探针CP。探针分子的结构表征如下：1H NMR(400MHz,CDCl3)δ10.35(s,1H),7.72(d,J＝6.7Hz,2H),7.44(dd,J＝16.2,8.8Hz,4H),3.37(dd,J＝13.2,8.4Hz,4H),2.89-2.79(m,4H),2.06-1.96(m,4H).13C NMR(100MHz,CDCl3)δ187.81,160.87,152.45,149.14,139.88,132.70,130.44,128.69,126.15,121.68,119.94,112.35,108.92,108.64,105.97,83.63,50.43,49.99,31.44,29.70,27.64,21.08,20.09.MS(ESI)m/z calcd for C24H19NO3[M+Na+]:392.1257,found:392.1262.
实施例2：本发明的荧光探针的应用
荧光探针(10.0×10-6mol/L)在pH为7.4的PBS缓冲溶液(10.0mM,VDMSO/VPBS＝1/1)中加入氨基酸(Lys,Phe,Thr,Met,Val,His,Gly,Ser,Ala,Tyr,Arg,Glu,Ile,)后没有引起探针本身发射峰的明显变化，而加入氨基酸(Cys,Hcy,GSH)后，则引起了荧光变化，说明该探针具有优良的选择性，并且能够区分半胱氨酸、同型半胱氨酸和谷胱甘肽。而细胞毒性实验，细胞和斑马鱼中成像实验说明探针具有好的生物适用前景。
Claims (1)
1.一种检测半胱氨酸、同型半胱氨酸和谷胱甘肽的比值型荧光探针，其结构式如下:
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101892046A (zh) * | 2010-06-25 | 2010-11-24 | 北京理工大学 | 高选择性多元生物硫醇比色荧光探针及其制备方法 |
| CN105524055A (zh) * | 2016-01-15 | 2016-04-27 | 中南大学 | 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 |
| CN108383774A (zh) * | 2018-04-04 | 2018-08-10 | 郑州大学 | 一种基于端基炔酮的半胱氨酸荧光探针及其制备和应用 |
| CN110498786A (zh) * | 2019-09-04 | 2019-11-26 | 中南大学 | 一种检测半胱氨酸/同型半胱氨酸和谷胱甘肽的新型比值型荧光探针 |
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101892046A (zh) * | 2010-06-25 | 2010-11-24 | 北京理工大学 | 高选择性多元生物硫醇比色荧光探针及其制备方法 |
| CN105524055A (zh) * | 2016-01-15 | 2016-04-27 | 中南大学 | 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 |
| CN108383774A (zh) * | 2018-04-04 | 2018-08-10 | 郑州大学 | 一种基于端基炔酮的半胱氨酸荧光探针及其制备和应用 |
| CN110498786A (zh) * | 2019-09-04 | 2019-11-26 | 中南大学 | 一种检测半胱氨酸/同型半胱氨酸和谷胱甘肽的新型比值型荧光探针 |
Non-Patent Citations (2)
| Title |
|---|
| Rational Development of Dual-Ratiometric Fluorescent Probes for Distinguishing between H2S and SO2 in Living Organisms;Shaohui Han，等;《Anal. Chem.》;第第93卷卷(第第45期期);第15209-15215页 * |
| 选择性检测谷胱甘肽的荧光探针;王媛;陈潇潇;刘学良;陈玉哲;牛丽亚;吴骊珠;杨清正;;影像科学与光化学(04);摘要 * |
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