CN112694466B - 一种硫化氢检测分子探针、制备方法、检测用品和应用 - Google Patents

一种硫化氢检测分子探针、制备方法、检测用品和应用 Download PDF

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CN112694466B
CN112694466B CN202011425908.9A CN202011425908A CN112694466B CN 112694466 B CN112694466 B CN 112694466B CN 202011425908 A CN202011425908 A CN 202011425908A CN 112694466 B CN112694466 B CN 112694466B
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肖鹏
刘建军
陶风波
杨立恒
袁光宇
郭东亮
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Electric Power Research Institute of State Grid Jiangsu Electric Power Co Ltd
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Abstract

本发明公开了一种硫化氢检测分子探针、制备方法、检测用品和应用。该硫化氢检测分子探针的化学结构如式I，所述检测用品为包含上述分子探针的检测试纸、检测试剂或检测试剂盒。该分子探针水中可溶，无需添加有机试剂，对硫化氢检测灵敏度高、响应速度快，可以制备为检测试纸、检测试剂、检测试剂盒等多种形式，应用于不同的检测环境，均可以有效检出硫化氢，并且该类检测探针的合成方法简便，易操作。
Figure DDA0002824833050000011

Description

一种硫化氢检测分子探针、制备方法、检测用品和应用
技术领域
本发明涉及一种硫化氢检测分子探针、制备方法、检测用品和应用，尤其涉及一种检测灵敏度高、响应速度快的硫化氢检测分子探针、制备方法、检测用品和应用。
背景技术
硫化氢(H2S)是一种高毒性、无色、具有臭鸡蛋气味的气体，可溶于水、乙醇及甘油中，化学性质不稳定。硫化氢为易燃危险气体化学品，能与空气混合形成爆炸性混合气体，遇明火、高热能引起燃烧爆炸。硫化氢也是一种强烈的神经毒素，对粘膜有强烈刺激作用，吸入少量高浓度硫化氢可快速致命，低浓度的硫化氢对眼、呼吸系统及中枢神经都有影响。研究发现，储能用锂离子电池在发生热失控的初期，有机电解液会在电池内部发生无氧分解产生硫化氢等气体，并且能在电池安全阀打开之前扩散到环境中。因此，对硫化氢进行实时监测，可作为评估电池状态、指示设备安全的一种有效手段。
分子探针是一类具有发色基团(C)和识别基团(R)(或结合基团)结构的分子。其中，识别基团能够与诸多活性小分子发生特异性反应，并将所识别的气体分子信息传递给发色基团并表达出可直接感知的色变或荧光信号。利用分子探针进行特征气体探测具有低成本、高灵敏度、免驱动等显著优势，且反应前后的光学变化还可通过光纤进行信号的远距离传输，从而能够对复杂环境内部活性小分子进行检测。
现有探针均针对活细胞内检测硫化氢设计，其分子往往具有较小的结构和一定的亲水亲油平衡常数以适应生理环境。
发明内容
发明目的：本发明的第一目的是提供一种硫化氢检测分子探针，第二目的是提供所分子探针的制备方法，第三目的是提供一种包含所述分子探针的检测用品，第四目的是提供所述分子探针在制备硫化氢检测用品中的应用，第五目的是提供所述检测用品在检测硫化氢中的应用。
技术方案：本发明的硫化氢检测分子探针具有式I的结构：
Figure BDA0002824833030000021
其中：A为
Figure BDA0002824833030000022
或化学键；n为5-100的整数。
优选，所述分子探针结构中：n为21-100的整数。
进一步优选，所述分子探针为以下任一化合物：
Figure BDA0002824833030000023
上述分子探针以萘酰亚胺为母体，以PEG链为保湿基团，以2,4-二硝基苯磺酸酯作为识别基团。在分子探针结构中引入PEG结构，可提高探针的水溶性，从而增加探针在水溶液中检测硫化氢的灵敏度及响应速度；也可增加探针在滤纸、薄膜等载体材料上的吸附力，以及在干燥环境中保湿和吸收硫化氢分子的能力。该探针分子能通过其颜色及荧光的变化信号指示环境中硫化氢分子的存在及浓度信息；上述分子探针理化性质稳定，吸附在载体材料上之后也具有稳定的性质，易于保存，可有效检测复杂环境中的微量硫化氢。
上述分子探针通过以下任一方法制备得到：
方法一：
化合物1经酰化、羟基化、酰化和加成反应得到化合物I；
Figure BDA0002824833030000031
方法二：
化合物1经酰化、羟基化和酰化反应得到化合物I；
Figure BDA0002824833030000032
其中，n的定义如前所述。
将上述的分子探针添加硫化氢检测可接受的载体，可制备为用于检测硫化氢的检测用品；所述的检测用品具体为检测试纸、检测试剂或检测试剂盒。
其中，所述检测试纸由滤纸、聚合物薄膜、硅胶颗粒、水凝胶或树脂颗粒吸附所述分子探针制得，所述分子探针的吸附量为1×10-9mg/cm2～1mg/cm2。其制备方法是滤纸或高分子聚合物经1μM～1M分子探针的母液(溶剂可为二氯甲烷、氯仿、丙酮、甲醇、水等常见溶剂)浸泡1s～60min后晾干而得，浸泡晾干过程可多次反复以增加吸附效果。
上述分子探针及检测用品均可应用在硫化氢检测中。
有益效果：与现有技术相比，本发明具有如下显著优点：
(1)分子探针水溶性提高并且具有保湿效果，从而提高了分子探针在水溶液中及其试纸的检测灵敏度和响应速度；
(2)分子探针对载体材料的吸附能力强，性质稳定，易于保存，适宜制备为多种检测用品，尤其是检测试纸使用更便捷；
(3)分子探针制备方法简便、易操作。
附图说明
图1为分子探针I-2的质谱图；
图2为分子探针I-2的1H NMR谱图；
图3为分子探针I-2在水溶液中的检测吸收光谱图；
图4为分子探针I-2在水溶液中的检测发射光谱图。
具体实施方式
下面结合附图和实施例对本发明的技术方案作进一步说明。
实施例1：分子探针I-1的合成
Figure BDA0002824833030000041
(1)中间体2的合成
将4-溴-1,8-萘二甲酸酐(5g，18.18mM，1eq)与丙炔胺(1.10g，20.00mM，1.1eq)溶于100mL无水乙醇中，70℃反应3h，反应结束后冷却至室温导入水中析出固体，抽滤，水洗滤饼三次，将滤饼烘干后得到5.3g中间体2，收率94％。不经进一步纯化直接用于下一步。ESI-MS m/z:313.9817[M+H]+。
(2)中间体3的合成
将中间体2(4g，12.82mM，1eq)，N-羟基丁二酰亚胺(1.62g，14.10mM，1.1eq)，碳酸钾(5.81g，42.02mM，3.3eq)加入到60mL DMSO中，80℃反应3h，反应结束后冷却至室温倒入水中，用1M的HCl调节pH＝3，析出固体，抽滤，水洗滤饼烘干，得到2.83g中间体3，黄色粉末，收率88％。ESI-MS m/z:252.0661[M+H]+。
(3)中间体4的合成
将中间体3(1g，3.98mM，1eq)，2,4-二硝基苯磺酰氯(1.27g，4.78mM，1.2eq)，三乙胺(0.70mL)加入到30mL四氢呋喃中，室温反应12h，反应结束后倒入水中，析出白色固体，抽滤，水洗滤饼烘干，得到1.82g中间体4，收率95％。ESI-MS m/z:482.0294[M+Na]+。
(4)分子探针I-1的合成
中间体4(1g，2.1mM，1eq)，叠氮PEG100(0.69g，2.49mM，1.2eq)无水硫酸铜(100mg)，抗坏血酸钠(100mg)加入到50mL四氢呋喃与水的混合溶剂(四氢呋喃∶水＝3∶1)中，在氩气保护下反应24h，反应结束后加入200mL二氯甲烷稀释，经50mL水洗后，分液保留二氯甲烷相，经无水硫酸镁干燥，减压除去有机溶剂，使用硅胶柱分离，展开剂二氯甲烷∶甲醇＝20∶1，得到1.03g分子探针I-1，淡黄色油状固体，产率65％。
采用与实施例1相似的操作，制得下列分子探针：
Figure BDA0002824833030000051
实施例2：分子探针I-6的合成
Figure BDA0002824833030000052
(1)中间体5-1的合成
将4-溴-1,8-萘二甲酸酐(5g，18.18mM，1eq)与胺基PEG4400(88.62g，20.00mM，1.1eq)溶于500mL无水乙醇中，70℃反应24h，反应结束后加入400mL二氯甲烷稀释，经50mL水洗后，分液保留二氯甲烷相，经无水硫酸镁干燥，减压除去有机溶剂，使用硅胶柱分离，展开剂二氯甲烷∶甲醇＝15∶1，得到70.74g中间体5-1，无色油状固体，产率83％。
(2)中间体6-1的合成
将中间体5-1(4g，0.85mM，1eq)，N-羟基丁二酰亚胺(0.11g，0.94mM，1.1eq)，碳酸钾(0.38g，2.81mM，3.3eq)加入到60mL DMSO中，80℃反应24h，反应结束后冷却至室温倒入水中，用1M的HCl调节pH＝3，使用二氯甲烷萃取三遍，分液保留二氯甲烷相，经无水硫酸镁干燥，减压除去有机溶剂，使用硅胶柱分离，展开剂二氯甲烷∶甲醇＝10∶1，得到3.30g中间体6-1，黄色油状固体，产率84％。
(4)分子探针I-6的合成
将中间体6-1(1g，0.22mM，1eq)，2,4-二硝基苯磺酰氯(0.07g，0.26mM，1.2eq)，三乙胺(0.07mL)加入到30mL四氢呋喃中，室温反应24h，反应结束后倒入水中，使用二氯甲烷萃取三遍，分液保留二氯甲烷相，经无水硫酸镁干燥，减压除去有机溶剂，使用硅胶柱分离，展开剂二氯甲烷∶甲醇＝15∶1，得到0.97g分子探针I-6，黄无色油状固体，产率91％。
采用与实施例2相似的操作，制得下列分子探针：
Figure BDA0002824833030000061
实施例3：分子探针检测试纸的制备
滤纸条经1mM分子探针的DMSO母液浸泡1s，后晾干备用，浸泡晾干过程可多次反复以增加吸附效果。
实施例4：分子探针在水溶液中的检测性能
1、具体操作方法：
将50M的分子探针溶于水中，分别加入不同当量的硫化钠溶液，进行检测。
2、检测结果：
表1分子探针在水溶液中的检测性能
Figure BDA0002824833030000071
注：颜色由浅至深评价标准依次为无色、微黄色、浅黄色、黄色、深黄色。
如表1所示，与对比例的分子探针相比，本申请的分子探针在较低的检测浓度下具有更高的检测灵敏度；加入硫化钠即可显色，并且颜色显色稳定，说明本申请的分析探针具有更快速的检测响应速度。
如图3～图4所示，本申请的分子探针可对不同浓度硫化氢分子做出吸收光谱及发射光谱的响应，即随硫化氢当量增加探针在430nm处的吸收强度随之增加，550nm处荧光发射也随之增强。
实施例5：分子探针试纸的检测性能
1、具体操作方法：
滤纸条经5mM分子探针的DMSO母液浸泡1s，后晾干备用，浸泡晾干过程可多次反复以增加吸附效果；滴加不同当量的硫化钠溶液，进行检测。
2、检测结果：
表2分子探针检测试纸的检测性能
Figure BDA0002824833030000072
注：颜色由浅至深评价标准依次为无色、微黄色、浅黄色、黄色、深黄色。
如表2所示，本申请的分子探针试纸在较低的检测浓度下具有更高的检测灵敏度；加入硫化钠后即可显色，并且颜色显色稳定，说明本申请的分析探针试纸具有更快速的检测响应速度。

Claims (9)

1.一种硫化氢检测分子探针，其特征在于，所述硫化氢检测分子探针具有式I的结构：
Figure FDA0003369005930000011
其中：A为
Figure FDA0003369005930000012
或化学键；n为5-100的整数。
2.根据权利要求1所述的分子探针，其特征在于，所述分子探针结构中：n为21-100的整数。
3.根据权利要求1所述的分子探针，其特征在于，所述分子探针为以下任一化合物：
Figure FDA0003369005930000013
4.一种权利要求1～3任一所述的分子探针的制备方法，其特征在于，所述制备方法为以下任一方法：
方法一：
化合物1经酰化、羟基化、酰化和加成反应得到化合物I；
Figure FDA0003369005930000021
方法二：
化合物1经酰化、羟基化和酰化反应得到化合物I；
Figure FDA0003369005930000022
其中，n的定义如权利要求1～3任一所述。
5.一种检测用品，其特征在于，所述检测用品包含权利要求1～3任一所述的分子探针以及硫化氢检测可接受的载体。
6.根据权利要求5所述的检测用品，其特征在于，所述检测用品为检测试纸、检测试剂或检测试剂盒。
7.根据权利要求6所述的检测用品，其特征在于，所述检测试纸由滤纸、聚合物薄膜、硅胶颗粒、水凝胶或树脂颗粒吸附所述分子探针制得。
8.根据权利要求7所述的检测用品，其特征在于，在所述检测试纸中，所述分子探针的吸附量为1×10-9mg/cm2～1mg/cm2。
9.一种权利要求1～3任一所述的分子探针在制备硫化氢检测用品中的应用。
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