CN109970777B - 一种具有检测过氧化氢功能的荧光探针及其制备方法和应用 - Google Patents
一种具有检测过氧化氢功能的荧光探针及其制备方法和应用 Download PDFInfo
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Abstract
本发明公开了一种具有检测过氧化氢(H2O2)功能的荧光探针及其制备方法和应用。该荧光探针是以4‑吡啶甲醛、二硫代草酰胺、4‑溴甲基苯硼酸频呐醇酯作为原料制备的一种新型荧光探针。进一步研究表明，这种探针可以实现对H2O2的快速灵敏检测。相对于现有的荧光检测技术，本发明得到的荧光探针对于H2O2具有选择性较高，无有机溶剂残留，响应灵敏，合成路线简单，检测方法简便等特点。本方法适用于实际生产应用，在分析化学，医药领域，生命科学和环境工程等技术领域具有巨大的应用前景。
Description
技术领域
本发明属于小分子荧光探针材料技术领域，特别涉及一种可检测过氧化氢(H2O2)的水溶性小分子荧光探针及其制备方法和应用。
背景技术
H2O2是生物体内一种常见的活性氧，在细胞活动中发挥着重要的作用。H2O2是产生其他活性氧的前体，也是其它活性氧的副产物。当生物体内的H2O2过量时，可能会发生氧化应激，产生某些疾病，比如癌症、糖尿病、心血管疾病、神经变性、阿尔茨海默氏病等，因此在化学科学，环境科学，生命科学，临床诊断等领域对H2O2的检测具有重要的意义。目前，H2O2检测的常规方法有分光光度法、滴定法、色谱法、电化学分析法等，这些方法在检测H2O2的过程中，可能会存在检测时间较长、检测过程复杂、仪器比较庞大价格昂贵等问题。与上述检测方法相比较，荧光探针法具有操作相对简单，响应灵敏，能够实时检测等优点，一些荧光探针分子不仅与H2O2反应还与其他活性氧反应，比如羟基自由基，超氧化合物等。另外在生物体内存在H2O2含量较低，容易被生物体内的酶分解的现象。目前报道的H2O2荧光探针普遍存在检测范围较窄，合成路线较复杂等问题。因此合成能与微量的H2O2进行专一反应的荧光探针分子尤为重要。为了克服现有技术的缺陷，本发明设计出一种水溶性荧光探针分子，通过荧光探针分子与H2O2的微量反应能够实现由发出较强荧光到荧光迅速减弱的过程。
发明内容
本发明的首要目的在于提供一种水溶性的能快速检测H2O2的小分子荧光探针。
本发明属于小分子荧光探针材料技术领域，公开了一种可检测H2O2的水溶性小分子荧光探针及其制备和应用。该荧光探针是以4-吡啶甲醛、二硫代草酰胺、4-溴甲基苯硼酸频呐醇酯作为原料制备的一种新型荧光探针。进一步研究表明，这种探针可以实现对过氧化氢H2O2的快速灵敏检测。
该荧光探针具有如下式(一)所示结构：
本发明的目的通过下述方案实现：本发明提供了一种所述可检测水中H2O2的水溶性小分子荧光探针的制备方法，包括以下步骤：
(1)制备2,5-双(4-吡啶基)噻唑并[5,4-d]噻唑：在通氧气条件下(流速10mL/min)，将二硫代草酰胺和4-吡啶甲醛溶于无水N,N’-二甲基甲酰胺中，150℃加热回流，反应6-10h，过滤，然后用去离子水冲洗，真空干燥，得到2,5-双(4-吡啶基)噻唑并[5,4-d]噻唑。
(2)制备水溶性小分子荧光探针N,N’-二(4-亚甲基甲基苯硼酸)2,5-双(4-吡啶盐)噻唑并[5,4-d]噻唑二溴：将2,5-双(4-吡啶基)噻唑并[5,4-d]噻唑和4-溴甲基苯硼酸频呐醇酯溶于乙腈中，加热到85～95℃反应5～8h，过滤，用正己烷冲洗，真空干燥，得到小分子荧光探针N,N’-二(4-亚甲基甲基苯硼酸)2,5-双(4-吡啶盐)噻唑并[5,4-d]噻唑二溴。
所述步骤(1)中反应物的摩尔份数配方如下：
二硫代草酰胺1份
4-吡啶甲醛2.5～4份
所述步骤(2)中反应物的摩尔份数配方如下：
2,5-双(4-吡啶基)噻唑并[5,4-d]噻唑1份
4-溴甲基苯硼酸频呐醇酯65～75份
根据上述制备方法制备的荧光探针具体的反应过程如下所示：
本法本发明还提供了基于上述方法制备的荧光探针在快速检测H2O2中的应用。
本发明将4-吡啶甲醛、二硫代草酰胺、4-溴甲基苯硼酸频呐醇酯反应制备得荧光探针，该荧光探针的水溶液在有H2O2存在时，会随着浓度的增加出现显著的荧光减弱现象，并且能达到高灵敏度检测的效果。相比于一些现有的技术，本发明中荧光探针材料制备路线简单，合成成本较低，处理方便，比较适合于实际应用和放大生产。
附图说明
图1为发明所制备的小分子荧光探针的核磁谱图(1H NMR)。
图2为荧光探针对H2O2的识别示意图。
图3为在不同H2O2浓度下，荧光探针的荧光发射光谱谱图变化(λex＝395nm)，[H2O2]＝0μM(a)，15μM(b)，20μM(c)，100μM(d)。
图4为H2O2浓度为(100μM)随着反应时间探针的荧光强度变化，荧光探针的荧光强度变化值对应的拟合曲线。
下面通过实施例对本发明的技术方案及其实施方式予以说明。
具体实施方式
下面结合实施例和附图对本发明作进一步详细的描述，但本发明的实施方式不限于此。
实施例1：
一种能够检测H2O2的荧光探针的制备方法，包括以下步骤：
(1)2,5-双(4-吡啶基)噻唑并[5,4-d]噻唑的制备：在通氧气条件下(流速10mL/min)，将二硫代草酰胺(1mmol)和4-吡啶甲醛(3mmol)溶于10mL无水N,N’-二甲基甲酰胺中，150℃加热回流，反应8h后，过滤，然后用去离子水冲洗，真空干燥，得到2,5-双(4-吡啶基)噻唑并[5,4-d]噻唑。
(2)荧光探针N,N’-二(4-亚甲基甲基苯硼酸)2,5-双(4-吡啶盐)噻唑并[5,4-d]噻唑二溴制备：将2,5-双(4-吡啶基)噻唑并[5,4-d]噻唑(0.1mmol)和4-溴甲基苯硼酸频呐醇酯(7mmol)溶解于10mL乙腈中，加热到90℃反应6h，过滤，用正己烷冲洗，真空干燥，得到小分子荧光探针N,N’-二(4-亚甲基甲基苯硼酸)2,5-双(4-吡啶盐)噻唑并[5,4-d]噻唑二溴。
实施例2：
用蒸馏水配置11份的荧光探针溶液，溶液浓度为2.5μM，体积为3mL，然后，分别将含有不同浓度的H2O2 0μM(a)，15μM(b)，20μM(c)，100μM(d)的30μL的H2O2溶液加入每份探针溶液中，室温搅拌30S后，测定每份溶液的荧光强度，395nm作为激发波长，则得到每份溶液的荧光发射光谱变化图谱(图3)。测试结果表明，随着H2O2浓度的增加，荧光探针的荧光强度下降。且H2O2浓度大于20μM时，荧光强度明显下降。
实施例3：
用蒸馏水配置1份的荧光探针溶液，溶液浓度为2.5μM，体积为3mL，然后加入100μM(d)的30μL的H2O2溶液到探针溶液中，室温搅拌后，测定溶液的随着反应时间的荧光强度，395nm作为激发波长，则得到溶液的荧光发射光谱变化图谱(图4)。测试结果表明，随着反应时间的增长，荧光探针的荧光强度下降，在反应时间为3分钟时，荧光强度明显下降。
上述实施例为本发明较佳的实施方式，但本发明的实施方式并不受上述实施例的限制，其他的任何未背离本发明的精神实质与原理下所作的改变、修饰、替代、组合、简化，均应为等效的置换方式，都包含在本发明的保护范围之内。
Claims (6)
1.一种水溶性小分子荧光探针，其特征在于具有如下式1所示结构：
2.根据权利要求1所述的水溶性小分子荧光探针的制备方法，其特征在于包括以下具体步骤：
(1)制备2,5-双(4-吡啶基)噻唑并[5,4-d]噻唑：在通氧气条件下，流速为10mL/min，将二硫代草酰胺和4-吡啶甲醛溶于溶剂中，加热回流，反应，过滤，冲洗，得到2,5-双(4-吡啶基)噻唑并[5,4-d]噻唑；
(2)制备水溶性小分子荧光探针N,N’-二(4-亚甲基甲基苯硼酸频哪醇酯)2,5-双(4-吡啶盐)噻唑并[5,4-d]噻唑二溴：将2,5-双(4-吡啶基)噻唑并[5,4-d]噻唑和4-溴甲基苯硼酸频呐醇酯，加热反应，过滤，冲洗，得到小分子荧光探针N,N’-二(4-亚甲基甲基苯硼酸频哪醇酯)2,5-双(4-吡啶盐)噻唑并[5,4-d]噻唑二溴。
3.根据权利要求2所述的水溶性小分子探针的制备方法，其特征在于：
所述步骤(1)中反应物的摩尔份数配方如下：
二硫代草酰胺1份
4-吡啶甲醛2.5～4份
所述步骤(2)中反应物的摩尔份数配方如下：
2,5-双(4-吡啶基)噻唑并[5,4-d]噻唑1份
4-溴甲基苯硼酸频呐醇酯65～75份。
4.根据权利要求3所述的基于水溶性小分子荧光探针的制备方法，其特征在于：步骤(1)中所述的加热回流是指150℃加热回流，反应是指反应6-10h，所述的溶剂指的是无水有机溶剂，所述无水有机溶剂是无水N,N’-二甲基甲酰胺；冲洗则是指用去离子水冲洗，步骤(2)中所述的加热反应是指加热到85～95℃反应5～8h，冲洗则指的是用正己烷冲洗。
5.基于权利要求1所述水溶性小分子荧光探针在检测H2O2的应用。
6.根据权利要求5所述的应用，其特征在于：荧光探针与H2O2进行专一性反应，在H2O2存在时，其395nm处荧光明显减弱。
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