CN103788076A - 一种检测半胱氨酸的试剂和方法 - Google Patents

一种检测半胱氨酸的试剂和方法 Download PDF

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CN103788076A
CN103788076A CN201410033092.3A CN201410033092A CN103788076A CN 103788076 A CN103788076 A CN 103788076A CN 201410033092 A CN201410033092 A CN 201410033092A CN 103788076 A CN103788076 A CN 103788076A
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阴彩霞
霍方俊
杨瑜涛
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Abstract

本发明提供了一种检测半胱氨酸（Cys）的试剂，它是马来酰亚胺衍生物:N-[4-甲基香豆素-7-基]马来酰亚胺。此试剂由7-氨基-4-甲基香豆素和顺丁烯二酸酐在冰乙酸回流5小时制得，原料便宜，反应条件简单，易于生产。本发明提供了半胱氨酸的定量检测方法，是基于N-[4-甲基香豆素-7-基]马来酰亚胺，在pH为7.4的HEPES溶液中定量地检测半胱氨酸的含量。该检测方法，对半胱氨酸显示了高的灵敏性和选择性，检测过程简便、灵敏、快速，检测结果准确。

Description

一种检测半胱氨酸的试剂和方法
技术领域
本发明涉及半胱氨酸检测技术，具体涉及一种试剂及其合成方法，以及这种试剂在检测半胱氨酸中的应用。
背景技术
L-半胱氨酸（L-Cys）是20种天然氨基酸中唯一具有还原性基团巯基（-SH）的氨基酸，它在生物体内参与细胞的还原过程及蛋白质、谷胱甘肽的合成。半胱氨酸在医药、食品添加剂及化妆品领域也有着广泛的应用，它可以用于一些抗生素以及治疗皮肤损伤，增强生物体的抗病能力，具有重要的生物化学研究价值。此外，它也可以作为抗辐射剂及抗氧化剂。目前，关于L-Cys的分析方法主要有高效液相色谱法（潘峰，孙玮，张青，等.高效液相色谱法测定血浆中同型半胱氨酸[J].氨基酸和生物资源，2010，32（4）：55-57.）、光度法(陈亚红，李占灵，张会霞.酶抑制动力学光度法测定L-半胱氨酸[J].分析试验室，2008，27（1）：38-41.；刘养清，韩素琴.亚硝酰铁氰化钠法测定复杂样品中半胱氨酸含量的方法研究[J].山西师范大学学报：自然科学版，2000，14（2）：42-45.)、电化学方法(Mohammad K.Amini，Jafar H.Khorasani，Shokooh S.Khaloo，et al.Cobalt（II）salophen-modified carbon-paste electrode for potentiometric and voltammetricdetermination of cysteine[J].Anal.Biochem，2003，320：32-38.；N.Maleki，A.Safavi，F.Sedaghati，et al.Efficient electrocatalysis of L-cysteine oxidationat carbon ionic liquid electrode[J].Anal.Biochem，2007，369：149-153.)等。
在本发明中，合成了一种基于马来酰亚胺的化合物，通过Cys和化合物在Michael加成反应前后荧光强度的变化，实现Cys的检测。
发明内容：
本发明的目的是提供一种合成简单、操作方便、选择性高、水溶性好的定量检测Cys的试剂，以及该试剂在Cys检测中的应用。
本发明提供的快速检测Cys的试剂和方法，是基于一种马来酰亚胺衍生物N-[4-甲基香豆素-7-基]马来酰亚胺（N-[4-Methylcoumarin-7-yl]maleimide），在pH为7.4的HEPES溶液中定量地检测Cys的含量。该检测方法，对Cys显示了高的灵敏性和选择性，检测过程简便、灵敏、快速，检测结果准确。
该试剂的结构式：
Figure BDA0000460042000000021
该试剂的合成方法，步骤为：7-氨基-4-甲基香豆素和顺丁烯二酸酐按摩尔比1︰1完全溶解在冰乙酸中，回流5小时，停止反应；浓缩、冷却后抽滤，并用碳酸钠溶液洗涤，最后用苯重结晶得到土黄色固体。
用该试剂检测Cys的方法，步骤为：
（1）、配制pH=7.4、浓度为10mM的HEPES缓冲溶液，配制2mM的N-[4-甲基香豆素-7-基]马来酰亚胺的甲醇溶液；
（2）、按体积比20000:1，将HEPES缓冲溶液和N-[4-甲基香豆素-7-基]马来酰亚胺的甲醇溶液加到干净的荧光比色皿中，在荧光分光光度仪上检测，随着待测样的加入,398nm的荧光强度逐渐增强；
（3）、把2mL的HEPES缓冲溶液、0.1μL的N-[4-甲基香豆素-7-基]马来酰亚胺甲醇溶液加到另一个荧光比色皿中，分别在加入Cys溶液的体积为0.25、0.50、0.75、1.00、1.25、1.50、1.75、2.00μL时，在荧光分光光度仪上测定398nm对应的荧光强度F为104、168、236、304、372、436、503、569，以Cys浓度为横坐标，以相对荧光强度F－F0为纵坐标绘制图，F0﹦39，得到Cys浓度的工作曲线；线性回归方程为：F－F0=-1.61+264.9c，c的单位为μM；
（4）、将HEPES缓冲溶液2000uL和N-[4-甲基香豆素-7-基]马来酰亚胺甲醇溶液0.1uL加到干净的荧光比色皿中，用微量进样器吸取V ul待测样品溶液，加入到此干净的荧光比色皿中，在荧光分光光度仪上检测，将测得的荧光强度代入（3）的线性回归方程，得到浓度c，待测样品C待测样=2000uL×c×10-6/VuL,即可求得Cys的浓度。
与现有技术相比，本发明具有如下优点和效果：1、检测体系成本低廉，试剂由7-氨基-4-甲基香豆素和顺丁烯二酸酐一步反应得到；2、本发明的检测方法，对Cys显示了高的灵敏性和选择性，Hcy和GSH不干扰测定；3、检测过程在水相中进行；4、检测手段简单，只需要借助荧光分光光度仪即可实现。
附图说明：
图1实施例1为该试剂的制备步骤及其表征
图2实施例2试剂与Cys作用的荧光发射图
图3实施例3试剂与各种分析物的荧光柱状图
图4实施例4测定Cys的工作曲线
图5实施例5测定样品的荧光发射图
具体实施方式：
实施例1
0.175g，7-氨基-4-甲基香豆素和0.098g，完全溶解在10mL冰乙酸中，回流5小时，停止反应；浓缩、冷却后抽滤，并用20mL碳酸钠饱和溶液洗涤，最后用30mL苯重结晶得到土黄色固体即为该试剂。
1H NMR(DMSO-d6):δ7.89(d,J=8.2Hz,1H),7.82(d,J=13.7Hz,1H),7.39(s,2H),7.24((s,1H),6.44(d,J=1.2Hz,1H),2.46(s,3H)（图1a）.13C NMR(DMSO-d6):d=172.7,168.9,156.5,156.1,148.2,138.1,128.9,125.1,122.1,117.8,117.1,20.9（图1b）.元素分析(calcd.%)forC14H9NO4:C,65.88;H,3.55,Found:C,68.82;H,3.63.ESI-MS m/z:[试剂+H]+，256.17,.[试剂+Na]+,278.08,[试剂+K]+,294.17（图1c）.
实施例2
配制pH=7.4、浓度为10mM的HEPES缓冲溶液，并用甲醇配制2mM的N-[4-甲基香豆素-7-基]马来酰亚胺溶液；把2mL的HEPES缓冲溶液及0.1μL的N-[4-甲基香豆素-7-基]马来酰亚胺甲醇溶液加到干净的荧光比色皿中，取Cys的溶液，逐渐用微量进样器加到此比色皿中，边加样边在荧光分光光度仪上检测，随着Cys的加入，398nm处荧光强度逐渐增强。荧光发射图见图2。
实施例3
配制pH=7.4、浓度为10mM的HEPES缓冲溶液，并用甲醇配制2mM的N-[4-甲基香豆素-7-基]马来酰亚胺溶液；在27个荧光比色皿中，各加入2mL的HEPES缓冲溶液和0.1μL的N-[4-甲基香豆素-7-基]马来酰亚胺甲醇溶液，再分别加入20摩尔当量的Cys，以及500摩尔当量的各种分析物：Cys，Hcy，GSH，Ala,Arg,Asn,Asp,Gln,Glu,Gly,His,IIe,Leu，Lys,Met,Phe,Pro,Ser,Thr,Trp,Tyr,VaL,ME,MPA,CN-,HS-,SCN-在荧光分光光度仪上检测，绘制不同分析物对应的398nm相对荧光强度的柱状图，（见图3）。Cys使得N-[4-甲基香豆素-7-基]马来酰亚胺的荧光强度由39变到589，其它的分析物基本没有引起N-[4-甲基香豆素-7-基]马来酰亚胺荧光强度的变化。
经实验证明，其它分析物不干扰体系对Cys的测定。
实施例4
配制pH=7.4、浓度为10mM的HEPES缓冲溶液，并用甲醇配制2mM的N-[4-甲基香豆素-7-基]马来酰亚胺溶液，用蒸馏水配制2mM的Cys溶液；把2mL的HEPES缓冲溶液和0.1μL的N-[4-甲基香豆素-7-基]马来酰亚胺甲醇溶液加到荧光比色皿中，分别在加入Cys溶液的体积为0.25、0.50、0.75、1.00、1.25、1.50、1.75、2.00μL时，在荧光分光光度仪上测定398nm对应的荧光强度F为104、168、236、304、372、436、503、569，以Cys浓度为横坐标，以相对荧光强度F－F0为纵坐标绘制图，F0﹦39，得到Cys浓度的工作曲线（见图4）；线性回归方程为：F－F0=-1.61+264.9c，c的单位为μM；
实施例5
配制pH=7.4的的HEPES（10mM）缓冲溶液，配制2mM的Cys水溶液，并用甲醇配制2mM的N-[4-甲基香豆素-7-基]马来酰亚胺溶液；把2mL的HEPES缓冲溶液和0.1μL的N-[4-甲基香豆素-7-基]马来酰亚胺甲醇溶液加到干净的荧光比色皿中，取Cys的溶液1.36μL，用微量进样器加到此比色皿中，同时在荧光光谱仪上测定398nm的对应的荧光强度F为397，相对荧光强度F﹣F0﹦358，通过实施例4的线性回归方程，求得c=1.357×10-6mol/L，偏差为0.22%。（见图5）。

Claims (3)

1.一种试剂：特征在于它是N-[4-甲基香豆素-7-基]马来酰亚胺,其结构式为：
Figure FDA0000460041990000011
2.如权利要求1所述的一种试剂的合成方法，其特征在于，步骤为：7-氨基-4-甲基香豆素和顺丁烯二酸酐按摩尔比1︰1完全溶解在冰乙酸中，回流5小时，停止反应；浓缩、冷却后抽滤，并用碳酸钠溶液洗涤，最后用苯重结晶得到土黄色固体。
3.一种检测半胱氨酸的方法：其特征在于，步骤为：
（1）、配制pH=7.4、浓度为10mM的HEPES缓冲溶液，配制2mM的N-[4-甲基香豆素-7-基]马来酰亚胺的甲醇溶液；
（2）、按体积比20000:1，将HEPES缓冲溶液和N-[4-甲基香豆素-7-基]马来酰亚胺的甲醇溶液加到干净的荧光比色皿中，在荧光分光光度仪上检测，随着待测样的加入,398nm的荧光强度逐渐增强；
（3）、把2mL的HEPES缓冲溶液、0.1μL的N-[4-甲基香豆素-7-基]马来酰亚胺甲醇溶液加到另一个荧光比色皿中，分别在加入Cys溶液的体积为0.25、0.50、0.75、1.00、1.25、1.50、1.75、2.00μL时，在荧光分光光度仪上测定398nm对应的荧光强度F为104、168、236、304、372、436、503、569，以Cys浓度为横坐标，以相对荧光强度F－F0为纵坐标绘制图，F0﹦39，得到Cys浓度的工作曲线；线性回归方程为：F－F0=-1.61+264.9c，c的单位为μM；
（4）、将HEPES缓冲溶液2000uL和N-[4-甲基香豆素-7-基]马来酰亚胺甲醇溶液0.1uL加到干净的荧光比色皿中，用微量进样器吸取V ul待测样品溶液，加入到此干净的荧光比色皿中，在荧光分光光度仪上检测，将测得的荧光强度代入（3）的线性回归方程，得到浓度c，待测样品C待测样=2000uL×c×10-6/VuL,即可求得Cys的浓度。
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CN104597008A (zh) * 2014-11-30 2015-05-06 陈燕婷 基于核酸适体荧光探针HCy3的同型半胱氨酸试剂盒及其检测方法
CN105181666A (zh) * 2015-09-23 2015-12-23 山西大学 一种荧光检测半胱氨酸的试剂和方法
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CN110143954A (zh) * 2019-06-03 2019-08-20 山西大学 一种香豆素衍生物及其合成方法和应用
CN111233804A (zh) * 2020-03-03 2020-06-05 山西大学 苯并吡喃氧鎓离子-香豆素衍生物及其合成方法和应用
CN111303072A (zh) * 2020-02-27 2020-06-19 山西大学 一种区分检测半胱氨酸的试剂及其合成方法和应用

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CN104597008A (zh) * 2014-11-30 2015-05-06 陈燕婷 基于核酸适体荧光探针HCy3的同型半胱氨酸试剂盒及其检测方法
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CN104535755A (zh) * 2015-01-20 2015-04-22 湖北出入境检验检疫局检验检疫技术中心 一种用于毛发水酱油检测的试剂及其制备方法
WO2016166773A1 (en) 2015-04-16 2016-10-20 Council Of Scientific & Industrial Research Novel coumarin derivative for detection of cysteine and process for the synthesis thereof
CN105181666A (zh) * 2015-09-23 2015-12-23 山西大学 一种荧光检测半胱氨酸的试剂和方法
CN110143954A (zh) * 2019-06-03 2019-08-20 山西大学 一种香豆素衍生物及其合成方法和应用
CN111303072A (zh) * 2020-02-27 2020-06-19 山西大学 一种区分检测半胱氨酸的试剂及其合成方法和应用
CN111233804A (zh) * 2020-03-03 2020-06-05 山西大学 苯并吡喃氧鎓离子-香豆素衍生物及其合成方法和应用

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