CN105498721B - 一种黄曲霉毒素分子印迹材料及其制备方法 - Google Patents

一种黄曲霉毒素分子印迹材料及其制备方法 Download PDF

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CN105498721B
CN105498721B CN201510820896.2A CN201510820896A CN105498721B CN 105498721 B CN105498721 B CN 105498721B CN 201510820896 A CN201510820896 A CN 201510820896A CN 105498721 B CN105498721 B CN 105498721B
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方国臻
张璐璐
王俊平
王硕
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Abstract

本发明提供了一种黄曲霉毒素分子印迹材料，以负载型离子液体为载体。本发明还公开了这种分子印迹材料的制备方法：(1)将黄曲霉毒素的结构类似物1,4‑萘二甲酸为模板分子加入DMF溶液中，搅拌使其充分溶解，加入功能单体负载型离子液体，搅拌30min，再加入四乙氧基硅烷和催化剂氨水，40℃水浴孵化24h；(2)抽滤。本发明优点是：本发明引入负载型离子液体，使其作为载体提供较大表面积，采用表面溶胶‑凝胶法合成分子印迹材料。本发明成本低廉，合成过程简单，反应条件容易控制，颗粒粒径均一、对黄曲霉毒素具有较高的选择性。该分子印迹材料可用于固相萃取富集与高效液相色谱连用，结合起来，可以用于各种食品样品中黄曲霉毒素的分离富集，具有广阔的应用前景。

Description

一种黄曲霉毒素分子印迹材料及其制备方法
技术领域
本发明属于高分子材料技术领域，尤其是涉及一种富集痕量黄曲霉毒素(B1、B2、G1、G2)的分子印迹材料及其制备方法。
背景技术
黄曲霉毒素(AFT)是一组化学结构类似的化合物，目前已分离鉴定出12种，主要分子型式含B1、B2、G1、G2、M1、M2等。黄曲霉毒素被世界卫生组织(WHO)的癌症研究机构划定为1类致癌物，是一种毒性极强的剧毒物质。黄曲霉毒素存在于土壤、动植物、各种坚果，特别是花生和核桃中。在大豆、稻谷、玉米、通心粉、调味品、牛奶、奶制品、食用油等制品中也经常发现黄曲霉毒素。
随着人们对食品安全关注度的快速上升，毒素的快速检测已成为国内外研究的发展趋势。但是薄膜层析法、液相色谱法、金标试纸法和免疫亲和柱法具有检测周期长，程序复杂所需试剂繁多，检测费用过高等缺点，已远远不能满足现代检测要求。随着分子印迹技术的发展和真菌毒素检测要求的不断提高，分子印迹技术在真菌毒素检测中的应用越来越广泛。将分子印迹聚合物填充于固相萃取小柱中，可用于样品的分离、纯化和浓缩，与抗体相比，分子印迹聚合物制备步骤简单、稳定性好、使用寿命长。但目前由于没有合适的对黄曲霉毒素具有很强识别功能的分子印记材料，所以还没有广泛使用分子印迹方法检测黄曲霉毒素。
发明内容
有鉴于此，本发明创造旨在提出一种对黄曲霉毒素(B1、B2、G1、G2)具有高选择性的分子印迹材料。
本发明利用功能单体负载型离子液体为载体，表面溶胶-凝胶方法合成出一种用于选择性富集痕量黄曲霉毒素(B1、B2、G1、G2)的吸附材料。该材料可用作固相萃取材料，可克服环境样品体系复杂的预处理过程，为样品的富集和分离提供很大的方便，与免疫亲和柱相比，成本也低。在食品领域的痕量分析中起重要作用，具有可适用性。
为达到上述目的，本发明创造的技术方案是这样实现的：
采用功能单体负载型离子液体作为载体，合成了一种黄曲霉毒素(B1、B2、G1、G2)分子印迹材料。
本发明的分子印迹材料对黄曲霉毒素(B1、B2、G1、G2)有很强的识别功能。
本发明还公开了这种分子印迹材料的制备方法：
一种黄曲霉毒素分子印迹材料的制备方法，包括如下步骤：
(1)将黄曲霉毒素的结构类似物DMC作为模板分子加入到DMF溶液中，搅拌使其充分溶解，加入功能单体负载型离子液体，搅拌30min，再加入四乙氧基硅烷和催化剂，40℃水浴孵化24h；
(2)将步骤(1)所得产物先用DMF淋洗，再用甲醇淋洗除去未反应物，50℃真空干燥老化8h；将老化后的反应产物放于索氏萃取器中，洗去模板分子；50℃真空干燥，得到对黄曲霉毒素具有高选择性的分子印迹材料。
进一步，步骤(1)中DMC与负载型离子液体的质量比为0.5-1:1；四乙氧基硅烷与催化剂的体积比为5-6:1。
进一步，步骤(1)所述催化剂是氨水。
进一步，步骤(2)中洗去模板分子是使用体积比为8-10:1甲醇和冰乙酸混合溶液索氏提取48h后，再用甲醇索氏提取12h，直至萃取液中无DMC检出为止。得到本发明的分子印迹聚合物(MIP)。
以功能单体负载型离子液体为支持体，合成对黄曲霉毒素具有高选择性的分子印迹材料；所使用的功能单体负载型离子液体是核心为咪唑环的一类物质，的结构式为：
X-＝Br-、NTf2 -、BF4 -、PF6 -
按照上述方法，但不加模板分子DMC，制备本发明对应的非印迹聚合物(NIP)。
本发明黄曲霉毒素分子印迹材料，用于食品中黄曲霉毒素的快速检测。
相对于现有技术，本发明创造所述的黄曲霉毒素分子印迹材料的制备方法及应用在黄曲霉毒素检测中具有以下优势：
本发明利用表面溶胶-凝胶方法合成的分子印迹材料，具有传质速度快，比表面积大，颗粒粒径均一的优点。该材料可以快速吸附黄曲霉毒素，对目标物具有强的选择性；该材料用化学方法制备，具有较好的稳定性，较长的使用寿命。本发明成本低廉，实验操作简单，反应条件容易控制，制得的黄曲霉毒素分子印迹聚合物作为固相萃取的填料与液相色谱联用，适用于食品中痕量黄曲霉毒素的分离与富集。与商品化的免疫亲和柱相比，该材料具有制备方便，选择性高，成本低的优点。
附图说明
构成本发明创造的一部分的附图用来提供对本发明创造的进一步理解，本发明创造的示意性实施例及其说明用于解释本发明创造，并不构成对本发明创造的不当限定。
附图说明
图1分子印迹聚合物和非印迹聚合物动力学实验；
图2赭曲霉毒素A(OTA)为黄曲霉毒素(B1、B2、G1、G2)的竞争物，研究该分子印迹材料的选择性能。
具体实施方式
为了使本发明上述特征和优点更加清楚和容易理解，下面将结合附图对本发明的实施方式作进一步详细描述。
下述实施例中所述负载型离子液体为自己合成，其他(DMC、黄曲霉毒素(B1、B2、G1、G2)、四乙氧基硅烷、氨水、DMF、甲醇、冰乙酸)均为市售，使用前未经任何处理。
实施例1
一种黄曲霉毒素(B1、B2、G1、G2)分子印迹材料的制备：
(1)将0.6mmol DMC加入到1.7ml DMF中，搅拌15min至完全溶解，加入100mg负载型离子液体，继续搅拌30min，随后加入9mmol四乙氧基硅烷，搅拌反应30min，再加入0.4ml氨水(3.0mol/L)，搅拌反应20min，40℃水浴孵化24h；
(2)抽滤，先用DMF淋洗，再用甲醇进一步洗去未反应物，于真空干燥箱中50℃老化8h，用体积比为9:1的甲醇乙酸反复萃取48h，再用甲醇萃取12h，直至萃取液中无DMC检出为止。50℃真空干燥，得到对黄曲霉毒素(B1、B2、G1、G2)具有高选择性的分子印迹材料。
按照上述方法，不添加DMC，制备本发明对应的非印迹聚合物。
实施例2
研究该分子印迹材料的吸附性能。将4mg的分子印迹聚合物置于2ml离心管中，分别加入1.5ml不同浓度(10、20、30、40、50、60、80、100、120、150、200mg/L)的DMC甲醇标准溶液，在室温下振荡4h，并在15℃和4000r/min下离心15min。准确移取400μl的上清液稀释至4ml，在紫外-可见分光光度计(λ＝327nm)处测定DMC的吸光度值，根据标准曲线计算DMC的浓度，最后计算吸附容量。同时平行做非印迹聚合物对DMC的吸附选择性实验，其中分子印迹聚合物和非印迹聚合物都需要做空白实验，即将4mg的分子印迹聚合物置于2ml离心管中，分别加入1.5ml DMC的甲醇。随着DMC浓度的升高，吸附容量逐渐增大，最后逐渐保持平衡。在相同浓度下，分子印迹聚合物的吸附容量大于非印迹聚合物的吸附容量(图1)。
实施例3
研究该分子印迹材料的动力学性能。将4mg的分子印迹聚合物置于2ml离心管中，加入1.5ml 100mg/L的DMC甲醇标准溶液，在室温下分别振荡10、20、30、40、60、90、120、160、200、300、360min，在15℃和4000r/min条件下离心15min。准确移取400μl的上清液稀释至4ml，在紫外-可见分光光度计(λ＝327nm)处测定DMC的吸光度值，根据标准曲线计算DMC的浓度，最后计算吸附容量。同时平行做非印迹聚合物对DMC的吸附选择性实验，其中分子印迹聚合物和非印迹聚合物都需要做空白实验，即将4mg的分子印迹聚合物置于2ml离心管中，分别加入1.5ml DMC的甲醇。印迹聚合物对目标物的吸附在60min时几乎达到平衡。
实施例4
选择赭曲霉毒素A(OTA)为黄曲霉毒素(B1、B2、G1、G2)的竞争物，研究该分子印迹材料的选择性能。分别配制浓度为1.0μg/L的OTA与黄曲霉毒素(B1、B2、G1、G2)的单标溶液。将4mL配制好的溶液通过固相萃取小柱，用甲醇洗脱，用高效液相色谱检测。(图2)
以上所述仅为本发明创造的较佳实施例而已，并不用以限制本发明创造，凡在本发明创造的精神和原则之内，所作的任何修改、等同替换、改进等，均应包含在本发明创造的保护范围之内。

Claims (7)

1.一种黄曲霉毒素分子印迹材料的制备方法，所述黄曲霉毒素分子印迹材料使用功能单体负载型离子液体为载体，其特征在于，包括如下步骤：
(1)将黄曲霉毒素的结构类似物DMC作为模板分子加入到DMF溶液中，搅拌使其充分溶解，加入功能单体负载型离子液体，搅拌30min，再加入四乙氧基硅烷和催化剂，40℃水浴孵化24h；
(2)将步骤(1)所得产物先用DMF淋洗，再用甲醇淋洗除去未反应物，50℃真空干燥老化8h；将老化后的反应产物放于索氏萃取器中，洗去模板分子；50℃真空干燥，得到对黄曲霉毒素具有高选择性的分子印迹材料。
2.根据权利要求1所述的一种黄曲霉毒素分子印迹材料的制备方法，其特征在于：步骤(1)中DMC与负载型离子液体的质量比为0.5-1:1；四乙氧基硅烷与催化剂的体积比为5-6:1。
3.根据权利要求1所述的一种黄曲霉毒素分子印迹材料的制备方法，其特征在于：步骤(1)中DMC与负载型离子液体的质量比为0.97:1；四乙氧基硅烷与催化剂的体积比为5.01:1。
4.根据权利要求1-3任一权利要求所述的一种黄曲霉毒素分子印迹材料的制备方法，其特征在于，步骤(1)所述催化剂是氨水。
5.根据权利要求1所述的一种黄曲霉毒素分子印迹材料的制备方法，其特征在于：步骤(2)中洗去模板分子是使用体积比为8-10:1甲醇和冰乙酸混合溶液索氏提取48h后，再用甲醇索氏提取12h，直至萃取液中无DMC检出为止。
6.根据权利要求1所述的一种黄曲霉毒素分子印迹材料的制备方法，其特征在于：步骤(2)中洗去模板分子是使用体积比为9:1甲醇和冰乙酸混合溶液索氏提取48h后，再用甲醇索氏提取12h，直至萃取液中无DMC检出为止。
7.根据权利要求1-6任一权利要求的制备方法制备的一种黄曲霉毒素分子印迹材料，其特征在于，用于食品中黄曲霉毒素的快速检测。
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