有机磷类农药中毒的快速检测与诊断技术研究
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摘要
本文通过对一系列抗磷化丝氨酸(anti-phosphorserine, anti-Pser)和丁酰胆碱酯酶(anti-Butyrylcholinesterase, anti-BChE)抗体的筛选,获得了一对能够同时分别与OP-BChE结构中的磷化(OP结构)部分和蛋白(BChE结构)部分结合的抗体,并建立了一套能够快速检测动物血液中OP-BChE(一种有机磷神经毒剂中毒的检测靶标)的夹心ELISA体系。其中,anti-BChE作为捕捉抗体(capture antibody),能够公平识别磷化BChE (OP-BChE,以paraoxon-BChE为代表)和非磷化BChE,这样它能够将样品中的BChE/OP-BChE准确而快速地捕捉出来；另外,anti-Pser作为识别抗体(detection antibody)能够检测到OP-BChE中的OP结构。在组成的夹心ELISA体系中,对一系列因素包括anti-BChE、 anti-Pser的浓度和封闭液种类进行优化；优化后,我们得到一个线性范围在0.03-30nM,检测限处于0.03nM的检测OP-BChE的夹心ELISA系统。同时,我们将该体系成功应用于动物血样的体外检测实验：在大鼠血清中的添加回收率达到99%以上。故此,该方法的建立为能够实现快速,简便,经济的现场检测OP-BChE提供了一定的技术平台。
在已建立的检测OP-BChE的sELISA体系的基础上,我们建立了一种新型的能够高精确度地检测磷化丁酰胆碱酯酶(OP-BChE)的免疫电化学传感器。在该方法中,纳米材料氧化锆(ZrO2)是一种对“磷氧分子”(OP-)结构有较高特异性识别的物质,我们将它应用于捕捉OP-BChE结构中OP-部分,以达到捕获样品中OP-BChE的目的；并且利用已连有量子点(Quantum dot, QD)标记物的anti-BChE (anti-BChE-QD)来特异性识别被捕获的OP-BChE中的胆碱酯酶(BChE)部分。其中,QD标记物由灵敏度较高的电化学方法测定。本节选定神经毒剂二异丙基氟磷酸(Diisopropylfluorophosphate, DFP)为代表,与不同样品中的BChE结合形成OP-BChE.所建立的传感器的线性范围为0.1--30nM,并且检测限达到0.03nM(以信噪比为3),同时该方法具有较好重复性(相对标准偏差为4.5%)。在此基础上,该传感器成功地运用于实际样品(人血清)中添加的OP-BChE的检出。
本文同时成功研制了一种能够简便、快速、灵敏地检测由有机磷农药毒死蜱中毒后在动物体内产生的代谢产物----Trichloropyridinol (TCP)的免疫层析电化学生物传感器(Immunochromatographic Electrochemical Biosensor, IEB)。该方法利用IEB将免疫层析试纸条上的竞争性免疫反应和平面印刷碳电极(Screen-Printed Carbon Electrode)中的电化学反应相结合,将免疫层析试纸条上测试区域中捕获的酶标记物(HRP)转换为电化学信号,以达到快速、灵敏检测的目的。在实验过程中,为了获得更为灵敏的检测体系,我们有针对性的地将一系列实验条件包括免疫反应时间、封闭液种类、酶标HTCP的数量以及酶催化底物的浓度进行了优化。在优化条件下,该IEB体系的线性范围为0.1-100ng/ml,检测限为0.1ng/ml。同时,该IEB成功地应用于大鼠的活体实验：所建立的检测体系成功地检测出受Chlorpyrifos-oxon(CPF-oxon)污染的大鼠体内所产生的代谢产物TCP。该方法为能够实现现场快速诊断有机磷农药中毒提供了一条新的思路。
本文还报道了一种基于磁珠(Magnetic Beads,MB)平台下的免疫电化学传感器,用以定量检测受有机磷神经毒剂污染的样品中BChE的受抑制程度。该实验将anti-BChE和BChE分别与MB结合,并分别利用Ellman assay知competitive immunoassay同时测出样品中仍保留活性的BChE的浓度和BChE(包括失活部分)的总量,并将两者相减而获得样品中BChE的抑制量,从而达到诊断在受到有机磷神经毒剂侵染后动物体中毒情况的目的。其中,在竞争性免疫检测中,样品中的待测BChE与固定在MB上已知浓度的BChE同时竞争量子点(Quantum Dot,QD)标记的anti-BChE(QD-anti-BChE)上的活性位点.之后通过测定QD的电化学信号以确定样品中目标BChE的浓度。该方法能够测定的BChE的浓度范围为0.1-20nM。与此同时,我们利用联有微流控注射器的碳纳米管电极(Screen Printed Carbon nanotube Electrode)来测定被MB-anti-BChE捕获的样品中的BChE的活性来确定样品中仍有活性的BChE的浓度。由此,样品中BChE的受抑制程度便可以通过以上两个测定结果的差异来确定。该种检测方法表现出的灵敏度达到0.5nM,低于体内BChE总量(约50-80nM)的2%。
利用实验室已合成出的有机磷农药倍硫磷的5种半抗原(H1-H5),制备出能稳定分泌针对有机磷农药倍硫磷的高特异性的单克隆抗体的杂交瘤细胞株；并建立了一套特异性强、灵敏度高的倍硫磷残留免疫检测方法。其中,利用活泼酯法将能够最大程度地暴露芳香环结构的H3(6-{甲氧基[4-(甲硫基)苯氧基]硫代磷酰胺基}己酸)与Bovine Serum Albumin(BSA)偶联,作为免疫原；将H1(4-[2-(二甲氧基硫代磷酰氧基)-4-甲基-5(甲硫基)苯胺基]-4-羰基丁酸、H2(4-[4-(二甲氧基硫代磷酰氧基)-2-甲基苯基胺基]-4-羰基丁酸)、H3、H4(4-(二甲氧基硫代磷酰胺基)丁酸)以及H5(4-[3-甲级-4-(甲硫基)苯氧基]丁酸)与Ovalbumin(OVA)偶联,作为候选包被原。将获得的单克隆抗体分别与5种包被原组合,进行间接竞争ELISA分析,筛选到具备最高特异性与灵敏度的组合。分析结果显示,以H3-BSA为免疫原,以H5-OVA为包被原所组成的间接竞争ELISA体系能够获得较高的灵敏度和特异性。在对ELISA体系优化之后,抗体与农药对硫磷的交叉反应为0.5%,与其它受测类似结构农药的交叉反应更是小于0.2%；对倍硫磷的检测限达到了0.0028ng/ml(IC20)。并且将此体系运用于土、水、米以及大白菜的添加回收实验中,获得的平均回收率为80%--124%。该体系为倍硫磷农药在环境与农产品中的快速检测提供了一条经济与快速的方法。
A sandwich ELISA (sELISA) has been developed for detection of organophosphorylated butyrylcholinesterase (OP-BChE, paraoxon-BChE as a model), a potential biomarker for human exposure to organophophate insecticides and nerve agents. A pair of antibodies specific to OP-BChE adduct were identified through systematic screening of several anti BChE antibodies (anti-BChE) and anti-phosphoserine antibodies (anti-Pser) from different sources. The selected anti-BChE (set as capture antibody) recognized both phosphorylated and nonphosphorylated BChE. The anti-Pser (set as detecting antibody) was used to recognize the OP moiety of OP-BChE adducts. With the combination of the selected antibody pair, several key parameters (such as the concentration of anti-BChE and anti-Pser, and the blocking agent) were optimized to enhance the sensitivity and selectivity of the sELISA. Under the optimal conditions, the sELISA has shown a wide linear range from0.03nM to30nM, with a detection limit of0.03nM. Furthermore, the sELISA was successfully applied to detect OP-BChE from in vitro biological samples such as rat plasma spiked with OP-BChE with excellent adduct recovery (z>99%). These results demonstrate that this novel approach holds great promise to develop an ELISA kit and offers a simple and cost-effective tool for screening/evaluating exposure to organophosphate insecticides and nerve agents.
We present a novel disposable electrochemical immunosensor for highly selective and sensitive detection of organophosphorylated butyrylcholinesterase (OP-BChE), a specific biomarker for exposure to organophosphorus nerve agents. In our new approach, the zirconia nanoparticles (ZrO2) were employed to selectively capture the OP moiety of OP-BChE adducts, and followed by quantum dot (QD)-tagged anti-BChE antibodies for amplified quantification. The captured CdSe-QD tags can be sensitively detected by stripping voltammetry. The nerve agent, diisopropylfluorophosphate (DFP), was selected to prepare OP-BChE adducts in various matrices. The developed electrochemical immunosensor demonstrates a highly linear voltammetric response over the range of0.1to30nM OP-BChE, with a detection limit of0.03nM (based on S/N=3) coupled with a good reproducibility (R.S.D=4.5%). Moreover, the immunosensor can be successfully applied for diagnosis of in-vitro OP nerve agent exposure through biomonitoring of OP-BChE adducts in the plasma samples. This novel nanoparticle-based electrochemical immunosensor thus provides an alternative way for designing simple, fast, sensitive, and cost-effective sensing platform for on-site screening/evaluating exposure to a variety of OP nerve agents.
In this study, we also present a novel potable immunochromatographic electrochemical biosensor (IEB) for simple, rapid, and sensitive biomonitoring of trichloropyridinol (TCP), a metabolite biomarker of exposure to organophosphorus insecticides. Our new approach takes the advantage of immunochromatographic test strip for a rapid competitive immunoreaction and a disposable screen-printed carbon electrode for a rapid and sensitive electrochemical analysis of captured HRP labeling. Several key experimental parameters (e.g. immunoreaction time, the amount of HRP labeled TCP, concentration of the substrate for electrochemical measurements, and the blocking agents for the nitrocellulose membrane) were optimized to achieve a high sensitivity, selectivity and stability. Under optimal conditions, the IEB has been demonstrated a wide linear range (0.1-100ng/ml) with a detection limit as low as0.1ng/ml TCP. Furthermore, the IEB has been successfully applied for biomonitoring of TCP in the rat plasma samples with in vivo exposure to organophosphorous insecticides like Chlorpyrifos-oxon (CPF-oxon). The IEB thus opens up new pathways for designing a simple, rapid, clinically accurate and quantitative tool for TCP detection, as well as holds a great promise for in-field screening of metabolite biomarkers, e.g., TCP, for humans exposed to organophosphorous insecticides.
In this study, we also reported a new approach for electrochemical quantification of enzymatic (BChE) inhibition for biomonitoring of exposure to organophosphorous (OP) pesticides and nerve agents based on magnetic beads (MB) immunosensing platform. The principle of this approach is based on the combination of MB immunocapture-based enzyme activity assay and competitive immunoassay of the total amount of BChE for simultaneous detection of enzyme inhibition and phosphorylation in biological fluids. In competitive immunoassay, the target BChE in a sample competes with the BChE immobilized on the MBs to bind to limited sites of anti-BChE antibody labeled with quantum dots (QD-anti-BChE), followed by stripping voltammetric analysis of the bound QD conjugate on the MBs. This assay shows a linear response over the total BChE concentration range of0.1-20nM. Simultaneous real time BChE activity was measured on an electrochemical carbon nanotube-based sensor coupled with a microflow injection system after immunocapture by the MB-anti-BChE conjugate. Therefore, he formed phosphorylated BChE adduct (OP-BChE) can be estimated by the difference values of the total amount of BChE (including active and OP-inhibited) and active BChE from established calibration curves. Under the optimal conditions, it is sensitive enough to detect0.5nM OP-BChE, which is less than2%BChE inhibition.
A new specific monoclonal antibody (McAb) against the organophosphorous pesticide fenthion was generated based on5synthesized haptens (H1-H5), and a sensitive and specific Enzyme-Linked Immunosorbent Assay (ELISA) for detection of fenthion based on the new immunizing/coating hapten combination was developed. In this study, the H3(6-(methoxy(4-(methylthio) phenoxy) phosphorothioylamino) hexanoic acid) which attempts to expose the aromatic ring group was conjugated with Bovine Serum Albumin (BSA) used as immuogen; and H1(4-(2-(dimethoxyphosphorothioyloxy)-4-methyl-5-(methylthio)phenylamino)-4-oxobutanoic acid, H2(4-(4-(dimethoxyphosphorothioyloxy)-2-methylphenylamino)-4-oxobutanoic acid, H4(4-(dimethoxyphosphorothioylamino)butanoic acid) and H5(4-(3-methyl-4-(methylthio) phenoxy) butanoic acid) were conjugated with ovalbumin (OVA) for the coating antigen.
The BLAB/C mice were immunized by the BSA conjugation (H3-BSA, immunogen) with the intraperitoneal injection. The hybridoma cell lines which can stable secrete McAb with the high specificity to fenthion were established by hybridoma technology. All of the5OVA conjugations were used as coating antigen. The efficient antibody/coating antigen was selected from the5combinations. Furthermore, the optimal competitive indirect ELISA was developed, with the detection limit (IC20) of0.028ng/ml. The cross reactivity of the antibody with the organophophorous pesticide Parathion was0.5%, even lower than0.2%with the any other tested pesticides. Also, the average recovery of the optimal ELISA from real samples such as soil, water, rice and Chinese cabbages was80%-124%.
在已建立的检测OP-BChE的sELISA体系的基础上,我们建立了一种新型的能够高精确度地检测磷化丁酰胆碱酯酶(OP-BChE)的免疫电化学传感器。在该方法中,纳米材料氧化锆(ZrO2)是一种对“磷氧分子”(OP-)结构有较高特异性识别的物质,我们将它应用于捕捉OP-BChE结构中OP-部分,以达到捕获样品中OP-BChE的目的；并且利用已连有量子点(Quantum dot, QD)标记物的anti-BChE (anti-BChE-QD)来特异性识别被捕获的OP-BChE中的胆碱酯酶(BChE)部分。其中,QD标记物由灵敏度较高的电化学方法测定。本节选定神经毒剂二异丙基氟磷酸(Diisopropylfluorophosphate, DFP)为代表,与不同样品中的BChE结合形成OP-BChE.所建立的传感器的线性范围为0.1--30nM,并且检测限达到0.03nM(以信噪比为3),同时该方法具有较好重复性(相对标准偏差为4.5%)。在此基础上,该传感器成功地运用于实际样品(人血清)中添加的OP-BChE的检出。
本文同时成功研制了一种能够简便、快速、灵敏地检测由有机磷农药毒死蜱中毒后在动物体内产生的代谢产物----Trichloropyridinol (TCP)的免疫层析电化学生物传感器(Immunochromatographic Electrochemical Biosensor, IEB)。该方法利用IEB将免疫层析试纸条上的竞争性免疫反应和平面印刷碳电极(Screen-Printed Carbon Electrode)中的电化学反应相结合,将免疫层析试纸条上测试区域中捕获的酶标记物(HRP)转换为电化学信号,以达到快速、灵敏检测的目的。在实验过程中,为了获得更为灵敏的检测体系,我们有针对性的地将一系列实验条件包括免疫反应时间、封闭液种类、酶标HTCP的数量以及酶催化底物的浓度进行了优化。在优化条件下,该IEB体系的线性范围为0.1-100ng/ml,检测限为0.1ng/ml。同时,该IEB成功地应用于大鼠的活体实验：所建立的检测体系成功地检测出受Chlorpyrifos-oxon(CPF-oxon)污染的大鼠体内所产生的代谢产物TCP。该方法为能够实现现场快速诊断有机磷农药中毒提供了一条新的思路。
本文还报道了一种基于磁珠(Magnetic Beads,MB)平台下的免疫电化学传感器,用以定量检测受有机磷神经毒剂污染的样品中BChE的受抑制程度。该实验将anti-BChE和BChE分别与MB结合,并分别利用Ellman assay知competitive immunoassay同时测出样品中仍保留活性的BChE的浓度和BChE(包括失活部分)的总量,并将两者相减而获得样品中BChE的抑制量,从而达到诊断在受到有机磷神经毒剂侵染后动物体中毒情况的目的。其中,在竞争性免疫检测中,样品中的待测BChE与固定在MB上已知浓度的BChE同时竞争量子点(Quantum Dot,QD)标记的anti-BChE(QD-anti-BChE)上的活性位点.之后通过测定QD的电化学信号以确定样品中目标BChE的浓度。该方法能够测定的BChE的浓度范围为0.1-20nM。与此同时,我们利用联有微流控注射器的碳纳米管电极(Screen Printed Carbon nanotube Electrode)来测定被MB-anti-BChE捕获的样品中的BChE的活性来确定样品中仍有活性的BChE的浓度。由此,样品中BChE的受抑制程度便可以通过以上两个测定结果的差异来确定。该种检测方法表现出的灵敏度达到0.5nM,低于体内BChE总量(约50-80nM)的2%。
利用实验室已合成出的有机磷农药倍硫磷的5种半抗原(H1-H5),制备出能稳定分泌针对有机磷农药倍硫磷的高特异性的单克隆抗体的杂交瘤细胞株；并建立了一套特异性强、灵敏度高的倍硫磷残留免疫检测方法。其中,利用活泼酯法将能够最大程度地暴露芳香环结构的H3(6-{甲氧基[4-(甲硫基)苯氧基]硫代磷酰胺基}己酸)与Bovine Serum Albumin(BSA)偶联,作为免疫原；将H1(4-[2-(二甲氧基硫代磷酰氧基)-4-甲基-5(甲硫基)苯胺基]-4-羰基丁酸、H2(4-[4-(二甲氧基硫代磷酰氧基)-2-甲基苯基胺基]-4-羰基丁酸)、H3、H4(4-(二甲氧基硫代磷酰胺基)丁酸)以及H5(4-[3-甲级-4-(甲硫基)苯氧基]丁酸)与Ovalbumin(OVA)偶联,作为候选包被原。将获得的单克隆抗体分别与5种包被原组合,进行间接竞争ELISA分析,筛选到具备最高特异性与灵敏度的组合。分析结果显示,以H3-BSA为免疫原,以H5-OVA为包被原所组成的间接竞争ELISA体系能够获得较高的灵敏度和特异性。在对ELISA体系优化之后,抗体与农药对硫磷的交叉反应为0.5%,与其它受测类似结构农药的交叉反应更是小于0.2%；对倍硫磷的检测限达到了0.0028ng/ml(IC20)。并且将此体系运用于土、水、米以及大白菜的添加回收实验中,获得的平均回收率为80%--124%。该体系为倍硫磷农药在环境与农产品中的快速检测提供了一条经济与快速的方法。
A sandwich ELISA (sELISA) has been developed for detection of organophosphorylated butyrylcholinesterase (OP-BChE, paraoxon-BChE as a model), a potential biomarker for human exposure to organophophate insecticides and nerve agents. A pair of antibodies specific to OP-BChE adduct were identified through systematic screening of several anti BChE antibodies (anti-BChE) and anti-phosphoserine antibodies (anti-Pser) from different sources. The selected anti-BChE (set as capture antibody) recognized both phosphorylated and nonphosphorylated BChE. The anti-Pser (set as detecting antibody) was used to recognize the OP moiety of OP-BChE adducts. With the combination of the selected antibody pair, several key parameters (such as the concentration of anti-BChE and anti-Pser, and the blocking agent) were optimized to enhance the sensitivity and selectivity of the sELISA. Under the optimal conditions, the sELISA has shown a wide linear range from0.03nM to30nM, with a detection limit of0.03nM. Furthermore, the sELISA was successfully applied to detect OP-BChE from in vitro biological samples such as rat plasma spiked with OP-BChE with excellent adduct recovery (z>99%). These results demonstrate that this novel approach holds great promise to develop an ELISA kit and offers a simple and cost-effective tool for screening/evaluating exposure to organophosphate insecticides and nerve agents.
We present a novel disposable electrochemical immunosensor for highly selective and sensitive detection of organophosphorylated butyrylcholinesterase (OP-BChE), a specific biomarker for exposure to organophosphorus nerve agents. In our new approach, the zirconia nanoparticles (ZrO2) were employed to selectively capture the OP moiety of OP-BChE adducts, and followed by quantum dot (QD)-tagged anti-BChE antibodies for amplified quantification. The captured CdSe-QD tags can be sensitively detected by stripping voltammetry. The nerve agent, diisopropylfluorophosphate (DFP), was selected to prepare OP-BChE adducts in various matrices. The developed electrochemical immunosensor demonstrates a highly linear voltammetric response over the range of0.1to30nM OP-BChE, with a detection limit of0.03nM (based on S/N=3) coupled with a good reproducibility (R.S.D=4.5%). Moreover, the immunosensor can be successfully applied for diagnosis of in-vitro OP nerve agent exposure through biomonitoring of OP-BChE adducts in the plasma samples. This novel nanoparticle-based electrochemical immunosensor thus provides an alternative way for designing simple, fast, sensitive, and cost-effective sensing platform for on-site screening/evaluating exposure to a variety of OP nerve agents.
In this study, we also present a novel potable immunochromatographic electrochemical biosensor (IEB) for simple, rapid, and sensitive biomonitoring of trichloropyridinol (TCP), a metabolite biomarker of exposure to organophosphorus insecticides. Our new approach takes the advantage of immunochromatographic test strip for a rapid competitive immunoreaction and a disposable screen-printed carbon electrode for a rapid and sensitive electrochemical analysis of captured HRP labeling. Several key experimental parameters (e.g. immunoreaction time, the amount of HRP labeled TCP, concentration of the substrate for electrochemical measurements, and the blocking agents for the nitrocellulose membrane) were optimized to achieve a high sensitivity, selectivity and stability. Under optimal conditions, the IEB has been demonstrated a wide linear range (0.1-100ng/ml) with a detection limit as low as0.1ng/ml TCP. Furthermore, the IEB has been successfully applied for biomonitoring of TCP in the rat plasma samples with in vivo exposure to organophosphorous insecticides like Chlorpyrifos-oxon (CPF-oxon). The IEB thus opens up new pathways for designing a simple, rapid, clinically accurate and quantitative tool for TCP detection, as well as holds a great promise for in-field screening of metabolite biomarkers, e.g., TCP, for humans exposed to organophosphorous insecticides.
In this study, we also reported a new approach for electrochemical quantification of enzymatic (BChE) inhibition for biomonitoring of exposure to organophosphorous (OP) pesticides and nerve agents based on magnetic beads (MB) immunosensing platform. The principle of this approach is based on the combination of MB immunocapture-based enzyme activity assay and competitive immunoassay of the total amount of BChE for simultaneous detection of enzyme inhibition and phosphorylation in biological fluids. In competitive immunoassay, the target BChE in a sample competes with the BChE immobilized on the MBs to bind to limited sites of anti-BChE antibody labeled with quantum dots (QD-anti-BChE), followed by stripping voltammetric analysis of the bound QD conjugate on the MBs. This assay shows a linear response over the total BChE concentration range of0.1-20nM. Simultaneous real time BChE activity was measured on an electrochemical carbon nanotube-based sensor coupled with a microflow injection system after immunocapture by the MB-anti-BChE conjugate. Therefore, he formed phosphorylated BChE adduct (OP-BChE) can be estimated by the difference values of the total amount of BChE (including active and OP-inhibited) and active BChE from established calibration curves. Under the optimal conditions, it is sensitive enough to detect0.5nM OP-BChE, which is less than2%BChE inhibition.
A new specific monoclonal antibody (McAb) against the organophosphorous pesticide fenthion was generated based on5synthesized haptens (H1-H5), and a sensitive and specific Enzyme-Linked Immunosorbent Assay (ELISA) for detection of fenthion based on the new immunizing/coating hapten combination was developed. In this study, the H3(6-(methoxy(4-(methylthio) phenoxy) phosphorothioylamino) hexanoic acid) which attempts to expose the aromatic ring group was conjugated with Bovine Serum Albumin (BSA) used as immuogen; and H1(4-(2-(dimethoxyphosphorothioyloxy)-4-methyl-5-(methylthio)phenylamino)-4-oxobutanoic acid, H2(4-(4-(dimethoxyphosphorothioyloxy)-2-methylphenylamino)-4-oxobutanoic acid, H4(4-(dimethoxyphosphorothioylamino)butanoic acid) and H5(4-(3-methyl-4-(methylthio) phenoxy) butanoic acid) were conjugated with ovalbumin (OVA) for the coating antigen.
The BLAB/C mice were immunized by the BSA conjugation (H3-BSA, immunogen) with the intraperitoneal injection. The hybridoma cell lines which can stable secrete McAb with the high specificity to fenthion were established by hybridoma technology. All of the5OVA conjugations were used as coating antigen. The efficient antibody/coating antigen was selected from the5combinations. Furthermore, the optimal competitive indirect ELISA was developed, with the detection limit (IC20) of0.028ng/ml. The cross reactivity of the antibody with the organophophorous pesticide Parathion was0.5%, even lower than0.2%with the any other tested pesticides. Also, the average recovery of the optimal ELISA from real samples such as soil, water, rice and Chinese cabbages was80%-124%.
引文
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