基于卟啉及其阵列对农药残留传感检测的新方法及作用机制研究
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摘要
农药作为目前最有效、最方便和最经济的防治农作物病虫害的手段，在农业增产中发挥着巨大的作用。然而，农药的大量使用也严重威胁着生态环境、人类健康甚至社会安全。经典检测技术虽然具有高灵敏性和准确定量等优点，但检测步骤冗繁，耗时过长，且需要昂贵的大型仪器和专业技术人员，不适于现场检测使用。因此，农药残留检测亟需一种同时兼具灵敏度和便携性、可以大规模使用的检测方法，实现农药残留快速而灵敏的检测，才能真正保障环境、人身和社会的和谐统一。因此，本论文不仅着重研究了卟啉可视化阵列传感芯片的制备及其检测效果，研究了卟啉与农药的相互作用机理，还探索了纳米化卟啉材料的制备条件及其对农药的检测效果，为最终构建出一种新型的基于纳米卟啉材料的阵列传感器，实现对农药残留的定性和定量检测奠定了基础。具体研究工作如下：
（1）以毒死蜱（有机磷类农药）、三唑酮和林丹（有机氯类）、多菌灵（氨基甲酸酯类）和溴氰菊酯（拟除虫菊酯类）等五种典型农药为检测对象，利用紫外-可见吸收光谱，筛选出了具有敏感响应性的卟啉材料。结果表明，ZnTPP对林丹、多菌灵和溴氰菊酯具有敏感性，而对毒死蜱和三唑酮无响应；CoTPP只对毒死蜱无响应，对其余四种农药均具有敏感性；MnTPPCl对毒死蜱、三唑酮和溴氰菊酯有响应。基于阵列交叉敏感性的考虑，ZnTPP、CoTPP和MnTPPCl可作为构成可视化阵列的敏感材料。
（2）利用筛选出的光学敏感卟啉材料，辅以极性指示剂等光敏材料，制备成6×6的可视化阵列传感芯片，并对毒死蜱、三唑酮、林丹、多菌灵和溴氰菊酯进行了检测。结果表明，与待测农药作用后，阵列传感芯片上的大部分敏感单元的颜色会发生明显变化。将阵列传感芯片与农药反应前后的图像相减，可得到农药的特征性指纹图谱。将差谱RGB数据采用主成分分析、聚类分析和判别分析等模式识别分析方法进行分析和处理后，发现该传感阵列对五种待测农药有显著的识别和鉴定能力，稳定性和重现性良好，可用于农药残留的定性检测。
（3）为阐明卟啉材料对农药分子的检测机理，结合分子对接法、动力学、热力学等研究手段，进一步研究了卟啉-农药相互作用关系。分子对接计算结果表明，卟啉大环以及大环上的苯环取代基同农药分子上的苯环结构之间的π-π作用明显提高了其对农药分子的亲和作用。对比三种金属卟啉与五种农药相互作用的结合常数及分子对接计算所得的打分结果，可知与毒死蜱、三唑酮、林丹、多菌灵和溴氰菊酯五种农药结合作用最强的卟啉依次为：MnTPPCl、MnTPPCl、CoTPP、ZnTPP和MnTPPCl，作用体系的结合常数分别为：5.73×108、8.51×107、3.04×108、8.02×107和1.53×108。结果与单体卟啉对农药的检测效果相一致。
（4）依据自组装的原理，通过混合溶剂方法制备出MnTPPCl纳米材料和CoTPP纳米材料，通过表面活性剂辅助自组装法利用表面活性剂聚乙二醇制备出了ZnTPP纳米材料。利用FE-SEM对三种卟啉纳米材料的形貌进行了表征：MnTPPCl纳米材料是圆盘状纳米颗粒，纳米颗粒的平均粒径约为150nm，颗粒大小较均匀；CoTPP纳米材料是棒状纳米颗粒，CoTPP纳米颗粒的平均宽度为100nm，长度为700nm；ZnTPP纳米材料是不规则纳米颗粒，ZnTPP纳米颗粒的平均粒径为300nm。由于纳米颗粒的纳米效应，MnTPPCl、CoTPP和ZnTPP纳米化后，荧光效应均强于单体，其荧光强度分别提高了2.37、2.13和5.22倍。
（5）利用紫外-可见吸收光谱，结合荧光光谱，研究了纳米卟啉材料对毒死蜱、多菌灵、三唑酮、林丹和溴氰菊酯的敏感响应性。结果表明，纳米CoTPP只对毒死蜱和多菌灵有响应，对其余三种农药无响应。而纳米MnTPPCl和纳米ZnTPP对五种农药均具有良好响应。不仅如此，除了纳米MnTPPCl-三唑酮和纳米ZnTPP-溴氰菊酯体系外，其余检测体系中，荧光强度的变化值与农药浓度均呈现良好的线性关系，为实现农药残留的定量检测奠定了基础。
As the most effective, convenient and economical control, pesticides play key rolesin agriculture. However, large-scale use of pesticides seriously threaten ecologicalenvironment, personal health and even social security. Although traditional detectiontechniques show the advantages of high sensitivity and reliability, they requiretime-consuming analysis, expensive instruments and highly trained personnel, which isunsuitable for field analysis. Therefore, rapid and sensitive detection methods ofpesticides become more and more important. In this thesis, the study was not onlyfocused on the selection of porphyrins and the interaction of porphyrins with pesticides,but the preparation and application in the detection of pesticides of nano-porphyrinswere also explored to prepare a novel array sensor based on nano-porphyrins array andrealize the qualitative and quantitative detection of pesticides finally. Researches werecarried out as follows:
(1) The responses of porphyrins for five common pesticides were investigated withUV-Vis absorption spectroscopy. As the results showed, ZnTPP was sensitive tolindane, carbendazim, and deltamethrin. CoTPP was sensitive to triadimefon, lindane,carbendazim, and deltamethrin. But there was not any apparent response in theCoTPP-chlopyrifos system. MnTPPCl was sensitive to chlopyrifos, carbendazim, anddeltamethrin. Considering the cross reactivity of sensor array, ZnTPP, CoTPP andMnTPPCl could be used as sensing material for the preparation of visualized sensorarray.
(2) According to the optical properties of porphyrins, the colorimetric array sensorwas created. Cross-reactivity of multiple sensing elements can improve the ability todiscriminte several different pesticides. The6×6sensor array was prepared byhandiwork spotting to detect pesticides. Owing to the obvious colour changes of thesensor arrays, the characteristic difference maps of every analyte were gained. RGBdata from the sensor array was analyzed with pattern recognition methods, includingprinciple component, hierarchical cluster and discriminant analysis. As a result, that thedetection of pesticides with the sensor array showed good repeatability, and the fivepesticides can be completely distinguished. Qualitative detection of pesticides could beobtained with this sensor array.
(3) To evaluate the detection mechanism with porphyrins, the interaction ofporphyrins with peticides were investigated with molecular docking method andUV-Vis absorption spectroscopy. Computational simulation demonstrated that π-πinteraction, which resulted from the macro-structure as well as the substituted benzenering in the porphyrin systems with the benzene structures of the pesticides, contributed alot to their affinity. In addition, it was found that the strongest binding occurred in thesystems of MnTPPCl-chlopyrifos, MnTPPCl-triadimefon, CoTPP-lindane,ZnTPP-carbendazim, and MnTPPCl-deltamethrin. The binding constant was5.73×108,8.51×107,3.04×108,8.02×107and1.53×108, respectively. These results were consistentwith the detection results.
(4) Based on the principle of self-assembly, nano-MnTPPCl and nano-CoTPP weresuccessfully prepared by the mixed-solvent method, and nano-ZnTPP was prepared bysurfactant-assisted self-assembly method using poly (ethylene glycol) as surfactant.Three porphyrin nanomaterials were characterized using FE-SEM. Nano-MnTPPCl wasdisc-shaped nanoparticles, and the average particle size was150nm. Nano-CoTPP wasrod-like nanoparticles, with the average width of100nm and the length of700nm.Nano-ZnTPP was irregular nanoparticles, and the average diameter was300nm.Because of the nanometer effect of nanoparticles, the fluorescence intensity of threenano-porphyrins (MnTPPCl, CoTPP and ZnTPP) was stronger than that of porphyrinmonomer with2.37,2.13and5.22times, respectively.
(5) The sensitivity of nano-porphyrins for five common pesticides, were studiedwith UV-Vis absorption and fluorescence spectroscopies. The results indicated thatnano-CoTPP was sensitive to triadimefon and carbendazim. But there were not anyapparent responses in the CoTPP-three other pesticides systems. Nano-MnTPPCl andnano-ZnTPP showed good sensitivity to all the five pesticides. Expect the systems ofnano-MnTPPCl-triadimefon and nano-ZnTPP-deltamethrin, there were good linearrelationship in other nano-porphyrins-pesiticides systems. Therefore, nano-porphyrinswere considered to be sensing material for quantitative detection of pesticides.
（1）以毒死蜱（有机磷类农药）、三唑酮和林丹（有机氯类）、多菌灵（氨基甲酸酯类）和溴氰菊酯（拟除虫菊酯类）等五种典型农药为检测对象，利用紫外-可见吸收光谱，筛选出了具有敏感响应性的卟啉材料。结果表明，ZnTPP对林丹、多菌灵和溴氰菊酯具有敏感性，而对毒死蜱和三唑酮无响应；CoTPP只对毒死蜱无响应，对其余四种农药均具有敏感性；MnTPPCl对毒死蜱、三唑酮和溴氰菊酯有响应。基于阵列交叉敏感性的考虑，ZnTPP、CoTPP和MnTPPCl可作为构成可视化阵列的敏感材料。
（2）利用筛选出的光学敏感卟啉材料，辅以极性指示剂等光敏材料，制备成6×6的可视化阵列传感芯片，并对毒死蜱、三唑酮、林丹、多菌灵和溴氰菊酯进行了检测。结果表明，与待测农药作用后，阵列传感芯片上的大部分敏感单元的颜色会发生明显变化。将阵列传感芯片与农药反应前后的图像相减，可得到农药的特征性指纹图谱。将差谱RGB数据采用主成分分析、聚类分析和判别分析等模式识别分析方法进行分析和处理后，发现该传感阵列对五种待测农药有显著的识别和鉴定能力，稳定性和重现性良好，可用于农药残留的定性检测。
（3）为阐明卟啉材料对农药分子的检测机理，结合分子对接法、动力学、热力学等研究手段，进一步研究了卟啉-农药相互作用关系。分子对接计算结果表明，卟啉大环以及大环上的苯环取代基同农药分子上的苯环结构之间的π-π作用明显提高了其对农药分子的亲和作用。对比三种金属卟啉与五种农药相互作用的结合常数及分子对接计算所得的打分结果，可知与毒死蜱、三唑酮、林丹、多菌灵和溴氰菊酯五种农药结合作用最强的卟啉依次为：MnTPPCl、MnTPPCl、CoTPP、ZnTPP和MnTPPCl，作用体系的结合常数分别为：5.73×108、8.51×107、3.04×108、8.02×107和1.53×108。结果与单体卟啉对农药的检测效果相一致。
（4）依据自组装的原理，通过混合溶剂方法制备出MnTPPCl纳米材料和CoTPP纳米材料，通过表面活性剂辅助自组装法利用表面活性剂聚乙二醇制备出了ZnTPP纳米材料。利用FE-SEM对三种卟啉纳米材料的形貌进行了表征：MnTPPCl纳米材料是圆盘状纳米颗粒，纳米颗粒的平均粒径约为150nm，颗粒大小较均匀；CoTPP纳米材料是棒状纳米颗粒，CoTPP纳米颗粒的平均宽度为100nm，长度为700nm；ZnTPP纳米材料是不规则纳米颗粒，ZnTPP纳米颗粒的平均粒径为300nm。由于纳米颗粒的纳米效应，MnTPPCl、CoTPP和ZnTPP纳米化后，荧光效应均强于单体，其荧光强度分别提高了2.37、2.13和5.22倍。
（5）利用紫外-可见吸收光谱，结合荧光光谱，研究了纳米卟啉材料对毒死蜱、多菌灵、三唑酮、林丹和溴氰菊酯的敏感响应性。结果表明，纳米CoTPP只对毒死蜱和多菌灵有响应，对其余三种农药无响应。而纳米MnTPPCl和纳米ZnTPP对五种农药均具有良好响应。不仅如此，除了纳米MnTPPCl-三唑酮和纳米ZnTPP-溴氰菊酯体系外，其余检测体系中，荧光强度的变化值与农药浓度均呈现良好的线性关系，为实现农药残留的定量检测奠定了基础。
As the most effective, convenient and economical control, pesticides play key rolesin agriculture. However, large-scale use of pesticides seriously threaten ecologicalenvironment, personal health and even social security. Although traditional detectiontechniques show the advantages of high sensitivity and reliability, they requiretime-consuming analysis, expensive instruments and highly trained personnel, which isunsuitable for field analysis. Therefore, rapid and sensitive detection methods ofpesticides become more and more important. In this thesis, the study was not onlyfocused on the selection of porphyrins and the interaction of porphyrins with pesticides,but the preparation and application in the detection of pesticides of nano-porphyrinswere also explored to prepare a novel array sensor based on nano-porphyrins array andrealize the qualitative and quantitative detection of pesticides finally. Researches werecarried out as follows:
(1) The responses of porphyrins for five common pesticides were investigated withUV-Vis absorption spectroscopy. As the results showed, ZnTPP was sensitive tolindane, carbendazim, and deltamethrin. CoTPP was sensitive to triadimefon, lindane,carbendazim, and deltamethrin. But there was not any apparent response in theCoTPP-chlopyrifos system. MnTPPCl was sensitive to chlopyrifos, carbendazim, anddeltamethrin. Considering the cross reactivity of sensor array, ZnTPP, CoTPP andMnTPPCl could be used as sensing material for the preparation of visualized sensorarray.
(2) According to the optical properties of porphyrins, the colorimetric array sensorwas created. Cross-reactivity of multiple sensing elements can improve the ability todiscriminte several different pesticides. The6×6sensor array was prepared byhandiwork spotting to detect pesticides. Owing to the obvious colour changes of thesensor arrays, the characteristic difference maps of every analyte were gained. RGBdata from the sensor array was analyzed with pattern recognition methods, includingprinciple component, hierarchical cluster and discriminant analysis. As a result, that thedetection of pesticides with the sensor array showed good repeatability, and the fivepesticides can be completely distinguished. Qualitative detection of pesticides could beobtained with this sensor array.
(3) To evaluate the detection mechanism with porphyrins, the interaction ofporphyrins with peticides were investigated with molecular docking method andUV-Vis absorption spectroscopy. Computational simulation demonstrated that π-πinteraction, which resulted from the macro-structure as well as the substituted benzenering in the porphyrin systems with the benzene structures of the pesticides, contributed alot to their affinity. In addition, it was found that the strongest binding occurred in thesystems of MnTPPCl-chlopyrifos, MnTPPCl-triadimefon, CoTPP-lindane,ZnTPP-carbendazim, and MnTPPCl-deltamethrin. The binding constant was5.73×108,8.51×107,3.04×108,8.02×107and1.53×108, respectively. These results were consistentwith the detection results.
(4) Based on the principle of self-assembly, nano-MnTPPCl and nano-CoTPP weresuccessfully prepared by the mixed-solvent method, and nano-ZnTPP was prepared bysurfactant-assisted self-assembly method using poly (ethylene glycol) as surfactant.Three porphyrin nanomaterials were characterized using FE-SEM. Nano-MnTPPCl wasdisc-shaped nanoparticles, and the average particle size was150nm. Nano-CoTPP wasrod-like nanoparticles, with the average width of100nm and the length of700nm.Nano-ZnTPP was irregular nanoparticles, and the average diameter was300nm.Because of the nanometer effect of nanoparticles, the fluorescence intensity of threenano-porphyrins (MnTPPCl, CoTPP and ZnTPP) was stronger than that of porphyrinmonomer with2.37,2.13and5.22times, respectively.
(5) The sensitivity of nano-porphyrins for five common pesticides, were studiedwith UV-Vis absorption and fluorescence spectroscopies. The results indicated thatnano-CoTPP was sensitive to triadimefon and carbendazim. But there were not anyapparent responses in the CoTPP-three other pesticides systems. Nano-MnTPPCl andnano-ZnTPP showed good sensitivity to all the five pesticides. Expect the systems ofnano-MnTPPCl-triadimefon and nano-ZnTPP-deltamethrin, there were good linearrelationship in other nano-porphyrins-pesiticides systems. Therefore, nano-porphyrinswere considered to be sensing material for quantitative detection of pesticides.
引文
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