CN103804369B - 一种裸眼和荧光比率检测含氰离子荧光分子探针的合成及应用 - Google Patents

一种裸眼和荧光比率检测含氰离子荧光分子探针的合成及应用 Download PDF

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CN103804369B
CN103804369B CN201210460218.6A CN201210460218A CN103804369B CN 103804369 B CN103804369 B CN 103804369B CN 201210460218 A CN201210460218 A CN 201210460218A CN 103804369 B CN103804369 B CN 103804369B
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宋相志
陈颂
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SUZHOU LUOLAN BIOLOGICAL SCIENCE & TECHNOLOGY Co Ltd
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Abstract

本发明涉及的是一种兼具裸眼识别和荧光比值检测氰离子荧光分子探针的制备方法以及该荧光分子探针在检测氰离子方面的应用。本发明的荧光分子以二乙胺基香豆素为原料，与苯并噻唑-2-乙腈，在哌啶做碱的条件下合成的。合成简便，反应条件温和。本发明所述的探针分子灵敏度较高，荧光性能稳定，合成产率较高，选择性好，响应范围宽，检测限低，并且适用于裸眼检测。所述荧光探针不受AcO-，H2PO4 2-，NO3 -，ClO4 -，HSO4 -，F-，Cl-，Br-，I-等阴离子的影响。比值型荧光探针可以克服因为激发光强度、探针浓度、环境因素所带来的外界误差，使得该荧光分子探针在生物化学，环境科学等领域具有实际的应用价值。

Description

一种裸眼和荧光比率检测含氰离子荧光分子探针的合成及应用
技术领域
本发明涉及的是化学分析检测技术领域，具体涉及一种裸眼及荧光比值检测氰离子荧光分子探针的制备方法以及该荧光分子探针在检测氰离子方面的应用。
背景技术
氰化物作为一种碱性试剂广泛应用于塑料、纤维、黄金、染料、水处理以及药物等生产活动中，具有重要的意义；但是，氰化物又是一种非常危险的化学品，可以通过肺、胃肠道以及皮肤进入体内与血红素中的细胞色素c氧化酶活性位点结合，造成线粒体电子传递链受到破坏，正常的呼吸过程被抑制，并且氰化物的吸入会提高钙离子的浓度，诱导一系列的酶促反应使活性氧物种含量增加，抗氧化能力受到抑制，从而给生物体带来巨大安全隐患甚至造成生命影响。环境中释放出的氰化物主要来源于黄金开采、电镀以及冶金等行业，并且一些食品或植物中也存在氰化物。因此，开发出一种灵敏高效的检测和监测氰根离子的荧光传感器具有十分重要的意义(JoJ，LeeD.Turn-OnFluorescencedetectionofcyanideinwater：activationoflatentfluorophoresthroughremotehydrogenbondsthatmimicpeptideβ-turnmotif.[J]JournalofAmericanChemicalSociety2009；131，16283-16291.XuZ，ChenX，KimHN，YoonJ.Sensorsfortheopticaldetectionofcyanideion.[J]ChemicalSocietyReviews2010；39，127-137.KoenigR.Wildlifedeathsareagrimwake-upcallinEasternEurope.[J]Science2000；287(5459)，1737-1738.)。
迄今，依托多样性的实验方案和检测技术，一些标准方法实现了对微量氰离子的检测，如电位分析法、色谱法、流动注射技术等。但这些传统的方法存在费时、选择性差、处理复杂、仪器昂贵等缺点。相对于传统的检测氰离子的方法，荧光光谱法由于其灵敏度高、快速、操作方便的特点在分子传感器领域发挥着重要的作用。尤其，比值传感器通过裸眼观测颜色的变化便可以实现对分析物的监测已成为最理想的检测手段。因此，设计合成一种兼具荧光光谱移动和颜色变化的比值荧光探针在氰离子检测领域具有重要的应用前景(GaneshV，SanzMPC，Mareque-RivasJC..Effectiveanionsensingbasedontheabilityofcoppertoaffectelectrontransportacrossself-assembledmonolayers.[J]ChemicalCommunications2007；5010-5012.SafaviA，MalekiN，ShahbaaziHR.Indirectdeterminationofcyanideionandhydrogencyanidebyadsorptivestrippingvoltammetryatamercuryelectrode.[J]AnalyticaChimicaActa2004：503，213-221.ChristisonTT，RohrerJS，Directdeterminationoffreecyanideindrinkingwaterbyionchromatographywithpulsedamperometricdetection.[J]JournalofChromatographyA2007；1155，31-39.)。
发明内容
对于上述情况，本发明的目的在于提供一种合成简便、成本低廉的比值荧光探针的合成方法以及该探针在检测环境中氰离子浓度的应用。
本发明使用的裸眼检测和荧光比值检测氰离子分子探针，由二烷胺基香豆素醛和苯并杂环-2-乙腈在碱的存在下合成，并且苯并杂环-2-乙腈部分作为识别基团。
本发明解决问题采取的技术方案为，一种裸眼检测和荧光比率检测氰离子荧光分子探针，具有下列结构通式：
其中：R1为C1-C12的直链烷基；R2为O，N，S原子中的一种；
本发明代表性的化合物的合成原理，当R1为乙基，R2为S时，其合成路线如上式所示：1)将N，N-二甲基甲酰胺在冰浴下冷却，向其滴加三氯氧磷，滴加完毕后升温至室温反应一小时，然后将二烷胺基香豆素溶于N，N-二甲基甲酰胺中滴加到上述溶液中，升温，反应18小时降至室温，倒入冰水中，剧烈搅拌，析出橙黄色固体，用乙醇重结晶得到二乙胺基香豆素醛衍生物。2)将二乙胺基香豆素醛衍生物和苯并噻唑-2-乙腈溶解在无水乙醇中，加入1滴哌啶，室温搅拌3小时，析出紫红色固体，抽滤，用乙醇洗涤，柱层析分离即得探针化合物。
在本说明书的实施例中更详细地说明了该探针的合成和检测方法。本发明的荧光分子探针使用方法没有特殊限制。通常可以将探针分子溶解在二甲基亚砜中，室温下进行测试。当加入氰离子时，由于氰离子可以进攻不饱和双建(见下式)，进而中断了探针原有的分子内电荷转移(ICT)过程，使得探针在紫外和荧光光谱上发生蓝移，同时溶液颜色由红色变为黄色。
该分子荧光探针在二甲基亚砜中溶解性好，其最大吸收波长和发射波长分别为532nm和616nm，光学性能稳定，荧光量子产率较高。当加入氰离子时，探针分子的最大吸收峰由532nm蓝移至350nm，溶液的颜色由红色变成了黄色，明显的颜色变化也可用于裸眼检测。在荧光发射光谱中，探针分子在616nm处的最大发射峰随着氰离子的增加荧光强度下降，在488nm处出现一个新的发射峰，探针分子的发射光谱蓝移了大约128nm。
本发明所述的探针分子合成简便且，易纯化且产率较高。探针荧光性能稳定，对氰离子具有很好的灵敏性性和选择性，AcO-，H2PO4 2-，NO3 -，ClO4 -，HSO4 -，F-，Cl-，Br-，I-等阴离子对检测没有响应，检测范围宽，检测限低，并且适合裸眼检测。同时，本发明所述的比值型荧光探针可以克服因为激发光强度、探针浓度、环境因素所带来的外界误差，使得该荧光分子探针在生物化学，环境科学等领域具有实际的应用价值。
附图说明
图1为本发明的荧光探针在二甲基亚砜溶液中，紫外吸收光谱随着加入氰离子浓度增加的变化情况，横坐标为波长，纵坐标为吸光度。
图2为本发明的荧光探针在二甲基亚砜溶液中，加入等浓度不同阴离子的紫外吸收光谱的变化情况，横坐标为波长，纵坐标为吸光度。
图3为本发明的荧光探针在二甲基亚砜溶液中，加入等浓度不同阴离子的紫外吸收比值(A350/A532)的变化情况，横坐标为离子，纵坐标为吸收比值。
图4为本发明的荧光探针在二甲基亚砜溶液中，逐渐加入氰离子的荧光发射光谱变化情况，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在二甲基亚砜溶液中，逐渐加入氰根离子的荧光强度比值(I488/I616)的变化情况，横坐标为氰离子的浓度，纵坐标为荧光强度比值；插入图片为加入低浓度氰离子荧光强度比值的变化情况，横坐标为氰离子的浓度，纵坐标为荧光强度比值。
图6为本发明的荧光探针在二甲基亚砜溶液中，加入等浓度不同阴离子的荧光发射光谱的变化情况，横坐标为波长，纵坐标为荧光强度。
图7为本发明的荧光探针在二甲基亚砜溶液中，加入等浓度不同阴离子的荧光强度比值(I488/I616)的变化情况，横坐标为离子，纵坐标为荧光强度比值。
图8为本发明的荧光探针制备中二乙胺基香豆素醛的核磁共振氢谱。
图9为本发明的荧光探针的核磁共振氢谱。
具体实施方式
实施例1：二乙胺基香豆素醛的制备
氩气保护下，将2mLN，N-二甲基甲酰胺在冰浴冷却并剧烈搅拌下，缓慢滴加2mL三氯氧磷，滴加完毕后继续搅拌1小时；然后将二乙基香豆素(1.33g.6.12mmol)溶解在10mL无水N，N-二甲基甲酰胺中，滴加到上述溶液中，升温至70度反应18小时。反应结束后降至室温，倒入100mL冰水中，剧烈搅拌，析出橙黄色固体。抽滤，水洗，乙醇洗，用无水乙醇重结晶得到0.6g黄色针状晶体，即为二乙胺基香豆素醛(40％)。
1HNMR(300MHz，CDCl3)：δppm＝10.11(1H，d，J4.5)，8.24(1H，d，J4.7)，7.41(1H，dd，J9.0，2.8)，6.64(1H，d，J9.0)，6.48(1H，s)，3.65-3.32(4H，m)，1.26(6H，dd，J7.1，5.5).
实施例2：分子荧光探针的制备
将二乙胺基香豆素醛(25mg.0.1mmol)和苯并噻唑-2-乙腈(18mg.0.1mmol)溶于10mL无水乙醇中，加入1滴哌啶，室温搅拌3小时。反应结束后，抽滤，用乙醇洗涤，柱层析分离(石油醚/二氯甲烷＝1∶2)得到产品28mg(70％)即为分子荧光探针。
1HNMR(400MHz，DMSO-d6)：δppm＝8.91(1H，s)，8.43(1H，d，J0.4)，8.12-8.08(1H，m)，7.90-7.88(1H，m)，7.52-7.42(3H，m)，6.61(1H，s)，6.60(1H，s)，3.49(4H，dd，J9.4，9.6)，1.28(6H，d，J9.6).
实施例3：裸眼和荧光增强检测含巯基氨基酸荧光探针的应用
将该荧光探针溶于二甲基亚砜溶液中配置成浓度为2.0×10-5mol/L和1.0×10-5mol/L的溶液，加入相应的阴离子，分别测定紫外吸收光谱和荧光发射光谱的变化。图1-图5表明，在紫外吸收光谱和荧光发射光谱中，该荧光探针均显示出对氰离子很高的选择性，随着加入氰离子浓度的增加，紫外吸收峰和荧光发射峰均发生较大的蓝移，同时明显的颜色变化也适用于裸眼检测。并且该荧光探针不受其他阴离子如：AcO-，H2PO4 2-，NO3 -，ClO4 -，HSO4 -，F-，Cl-，Br-，I-等离子的影响，表现出该荧光探针对氰离子具有高灵敏的专一选择性。

Claims (1)

1.一种荧光分子探针在裸眼或荧光比值检测氰离子中的应用，其中所述荧光分子探针的结构为
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CN114836200B (zh) * 2022-06-16 2023-05-05 郑州大学 基于人血清蛋白的复合荧光探针及其制备方法和在检测赭曲霉毒素a中的应用

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