CN112592297A - 一种基于丹磺酰氯的甲醛荧光传感器及其制备方法和应用 - Google Patents
一种基于丹磺酰氯的甲醛荧光传感器及其制备方法和应用 Download PDFInfo
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Abstract
本发明公开了一种基于丹磺酰氯的甲醛荧光传感器及其制备方法和应用，该方法以丹磺酰氯为前体合成了一种甲醛荧光传感器。该甲醛荧光传感器可在水相中选择性识别甲醛；通过采用紫外‑可见分光光度计以及荧光分光光度计测定水相中该甲醛荧光传感器的特征峰的强度变化，检测甲醛的存在。本发明提供了目标产物在甲醛检测中的应用，发现其对甲醛的检测效果良好。与现有技术相比，本发明使用的原料价格低廉，合成步骤简单，后处理方便，较易实现大规模生产，在检测甲醛方面有很大的应用前景。
Description
技术领域
本发明属于生物化学技术领域，尤其涉及一种基于丹磺酰氯的甲醛荧光传感器及其制备方法和应用。
背景技术
甲醛是一种常见的现代工业品，同时也是具有挥发性的化学污染物，是一种致癌物质。外源性甲醛的接触多是通过吸入或摄入，内源性生产的甲醛是通过酶系统介导的一个生理过程，如对氨基脲敏感的胺氧化酶(SSAO)可以生成甲醛，而机体中也存在相应的分子机制来除掉甲醛。在人的健康大脑中，甲醛的含量是0.2～0.4mM，适量甲醛在人的记忆存储、保留及长时间的记忆检索方面有很重要的作用。然而甲醛过量会损害中枢神经系统，减弱人的记忆和认知能力，引起神经元退行性病变，如阿尔兹海默症。
测定甲醛含量的常见方法有分光光度法、电化学检测法、气相色谱法、液相色谱法、传感器法等，但是大都灵敏度低，有的需要侵入性破坏生物组织。近年来，光学成像分析得到了广泛的研究。小分子有机荧光探针是一种将分子间的相互作用转换为光学信号传递给外界的工具。因其具有高选择性，高的检测灵敏度、并能实时在线检测等优点。它在与特定目标分析物发生作用后，荧光信号会发生变化，以达到检测目的。
发明内容
本发明的目的在于针对现有技术的不足，提供一种基于丹磺酰氯的甲醛荧光传感器及其制备方法和应用。
本发明的目的是通过以下技术方案来实现的：一种基于丹磺酰氯的甲醛荧光传感器，结构如下：
一种上述基于丹磺酰氯的甲醛荧光传感器的制备方法，包括以下步骤：
第一步：将对羟基苯甲醛与三乙胺溶于第一溶剂二氯甲烷中，加入丹磺酰氯，在0℃搅拌0.5～1h，然后加热至室温反应3～4h，反应完成之后，减压蒸馏除去第一溶剂，萃取，硅胶柱分离，得到第一化合物。
第二步：将烯丙基三氟硼酸钾溶解于第二溶剂氨水溶液中，室温下搅拌0.5～1h，加入第一化合物和蒸馏水，室温下反应16～18h，减压除去第二溶剂，经硅胶柱分离得到第二化合物。第二化合物为甲醛荧光传感器。
进一步地，所述羟基苯甲醛和丹磺酰氯的摩尔比是1:1。
一种上述基于丹磺酰氯的甲醛荧光传感器用于检测溶液中是否存在甲醛。
与现有技术相比，本发明的有益效果是：
(1)本发明以丹磺酰氯为主体，具有良好的光稳定性，斯托克斯位移大量子产率高；
(2)本发明所选用原料获取容易成本低，合成步骤简单，后处理亦很方便，较易实现大规模生产；
(3)本发明合成方法简单，反应条件温和，且产率较高；
(4)本发明所涉及的传感器水溶性好，能在水溶液中选择性检测甲醛变化，且灵敏度较高，在检测环境中的甲醛方面具有很大的应用前景。
附图说明
图1为本发明的甲醛荧光传感器1H NMR示意图；
图2为本发明的甲醛荧光传感器13C NMR示意图；
图3为本发明的甲醛荧光传感器的荧光选择性示意图；
图4为本发明的甲醛荧光传感器的紫外选择性示意图。
具体实施方式
本发明一种基于丹磺酰氯的甲醛荧光传感器，该甲醛荧光传感器的结构如下：
通过采用紫外-可见分光光度计以及荧光分光光度计测定水相中该甲醛荧光传感器的特征峰的强度变化，检测甲醛的存在。本发明发现该甲醛荧光传感器可在水相中选择性识别甲醛，对甲醛有很好的检测效果，提供了目标产物在甲醛检测中的应用。
(一)传感器化合物的合成
本发明合成路线如下：
(二)荧光性能测试
将乙醛、丙酮、苯甲醛、4-硝基苯甲醛、4-甲氧基苯甲醛、甲基乙二醛、H2O2、GSH、Cys、Hcy、葡萄糖等溶液加入甲醛荧光传感器溶液中，进行荧光响应测试。
(三)紫外测试
将甲醛加入甲醛荧光传感器中和空白样(只有甲醛荧光传感器)对比，进行紫外响应测试
下面结合附图和具体实施例对本发明进一步说明。
实施例
(1)本发明一种基于丹磺酰氯的甲醛荧光传感器的制备方法如下：
(1.1)第一化合物的合成：
将对羟基苯甲醛(122mg,1.0mmol)和三乙胺(304mg,3.0mmol，催化剂)溶解于在CH2Cl2(15mL)中冷却至0℃，然后在氮气下滴加5mL溶解于CH2Cl2中的丹磺酰氯(269mg,1.0mmol)溶液。将混合物在0℃下搅拌30min，然后将反应混合物加热至室温，搅拌3h，通过TLC检测反应完成。将反应混合物倒入100mL H2O中，用每次50mL CH2Cl2萃取3次。有机层用50mL盐水清洗，在Na2SO4上干燥，过滤和浓缩。粗品经硅胶柱层析纯化得到第一化合物。
(1.2)第二化合物的合成：
将220mg三氟硼酸烯丙基钾(1.50mmol)溶于5mL NH3溶液(氨水中的铵离子过量)中，室温氮气下搅拌30min。将第一化合物(178mg,0.50mmol)溶解于10mL NH3溶液中，加入蒸馏水(20μL)。该混合物在常温氮气条件下反应16h。溶剂减压除去后，粗品经硅胶柱层析纯化得到第二化合物，即甲醛荧光传感器。
(2)荧光选择性能测试
将甲醛荧光传感器溶于PBS缓冲液(pH 7.4,1.0wt.％DMSO)；其中甲醛荧光传感器的浓度为1×10-3mol/L，得到甲醛荧光传感器溶液。将甲醛、乙醛、丙酮、苯甲醛、4-硝基苯甲醛、4-甲氧基苯甲醛、甲基乙二醛、H2O2、GSH、Cys、Hcy、葡萄糖等均分别配置成浓度为5×10-3mol/L的待测水溶液。
荧光选择性实验如图3所示，取3mL PBS缓冲液置于液体池中，加入60μL甲醛荧光传感器溶液，测其初始荧光强度值，然后分别加入配置好的各种待测水溶液60μL，测量其稳定时的荧光强度。观察图3可知，甲醛荧光传感器对甲醛有明显响应效果，并且在530nm处荧光强度达到最大值，也即甲醛荧光传感器对甲醛有很好的选择性。
(3)紫外性能测试
紫外选择性实验如图4所示，取3mL PBS缓冲液置于液体池中，加入60μL甲醛荧光传感器溶液，测其初始吸光度，然后分别加入配置好的甲醛水溶液60μL，测量其稳定时的吸光度。观察图4可知，甲醛荧光传感器加入甲醛后，在255nm处和285nm处吸光度变化，甲醛荧光传感器对甲醛有明显响应效果，即甲醛荧光传感器对甲醛有很好的选择性；其中，反应传感器和甲醛反应后变为了第一化合物的结构。
Claims (4)
1.一种基于丹磺酰氯的甲醛荧光传感器，其特征在于，结构如下：
2.一种权利要求1所述基于丹磺酰氯的甲醛荧光传感器的制备方法，其特征在于，包括以下步骤：
第一步：将对羟基苯甲醛与三乙胺溶于第一溶剂二氯甲烷中，加入丹磺酰氯，在0℃搅拌0.5～1h，然后加热至室温反应3～4h，反应完成之后，减压蒸馏除去第一溶剂，萃取，硅胶柱分离，得到第一化合物。
第二步：将烯丙基三氟硼酸钾溶解于第二溶剂氨水溶液中，室温下搅拌0.5～1h，加入第一化合物和蒸馏水，室温下反应16～18h，减压除去第二溶剂，经硅胶柱分离得到第二化合物。第二化合物为甲醛荧光传感器。
3.根据权利要求2所述基于丹磺酰氯的甲醛荧光传感器的制备方法，其特征在于，所述羟基苯甲醛和丹磺酰氯的摩尔比是1:1。
4.一种权利要求1所述基于丹磺酰氯的甲醛荧光传感器用于检测是否存在甲醛。
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| CN108047060A (zh) * | 2017-12-01 | 2018-05-18 | 河南省农业科学院农业质量标准与检测技术研究所 | 一种识别检测甲醛的芘衍生物荧光探针分子及其制备方法和应用 |
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