CN104275167B - 一种刷型肼聚合物功能化磁性纳米材料及其制备和应用 - Google Patents
一种刷型肼聚合物功能化磁性纳米材料及其制备和应用 Download PDFInfo
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Abstract
本发明涉及一种刷型肼聚合物功能化磁性纳米材料制备及其在糖肽或糖蛋白富集中的应用。在纳米材料表面引入可逆加成断裂链转移(RAFT)试剂后，加入有机聚合反应功能单体和有机聚合反应引发剂，有机功能单体在可逆加成断裂链转移试剂的调控下进行可控自由基聚合反应，制备出含刷型聚合物的有机‑无机杂化纳米材料。该有机‑无机杂化纳米材料的制备过程简单、反应条件温和，并可以应用于复杂生物样品中糖肽或糖蛋白的富集。
Description
技术领域
本发明涉及糖基化肽的分离富集，具体地说是一种刷型肼聚合物功能化磁性纳米材料及其制备，以及其在糖肽或糖蛋白的选择性分离富集中的应用。
背景技术
蛋白质糖基化作为一种重要的翻译后修饰，在蛋白质折叠、构象稳定和活性等方面具有重要影响。糖基化蛋白质参与了蛋白质相互作用、免疫应答、细胞通讯、细胞凋亡等生命过程。糖基化蛋白质的异常变化可以作为肿瘤发生和发展的一种重要标志。
在糖基化蛋白质组分析中，高效液相色谱质谱联用是分析糖蛋白或者糖肽的一种有效工具。当样品直接进质谱分析时，由于糖肽或糖蛋白的含量相对于非糖肽或非糖蛋白的含量很低，糖肽或糖蛋白的离子信号强度往往会被非糖肽或糖蛋白的离子信号所抑制，因而在进行蛋白质糖基化分析时，对糖肽或糖蛋白进行预分离和富集是很有必要的。从复杂的体系中分离富集糖肽或糖蛋白较为有效的方法是酰肼化学法，该方法的主要原理是高碘酸钠将糖基上的顺式邻二醇氧化成醛，然后与固定在材料上的肼共价结合，从而达到了分离富集糖肽或糖蛋白的效果。
近年来，尽管有一些商品化的肼材料被广泛应用于细胞表面糖蛋白的提取，但材料的分离耗时，因而不适合高通量分析。将肼引入到磁性材料表面可以有效地克服这一缺陷(文献1.Zhiqing Zou et.al“Synthesis and Evaluationof Superparamagnetic Silica Particles for Extraction of Glycopeptidesin the Microtiter Plate Format”《Analytical Chemistry》,2008,80,1228-1234.文献2.Shisheng Sun et.al“Isolation of N-linkedglycopeptides by hydrazine-functionalized magnetic particles”《Analytical and bioanalytical chemistry》,2010,396,3071-3078.)，然而这些文献中键合到磁球表面的化合物只含有单个肼基团，这样材料表面的肼含量相对较低，因此富集到糖肽的量是很有限的。在无机纳米粒子表面键合刷型聚合物日益引起广泛关注，聚合物单体的多样性决定了聚合物类型的多样性，而且刷型聚合物容易后修饰，这样使得表面键合了聚合物的纳米材料特异性强，灵敏度高，捕捉量大。在磁核上以RAFT方式制备了刷型肼聚合物功能化磁性纳米材料并应用于糖肽或糖蛋白的分离富集得方法未见报道。
发明内容
本发明的目的在于提供一种刷型肼聚合物功能化磁性纳米材料制备及应用，其可在磁铁作用下简单快速地完成糖肽或糖蛋白从复杂生物样品中高效高选择性地分离富集。
为实现上述目的，本发明采用的技术方案如下：
一种刷型肼聚合物功能化磁性纳米材料，刷型肼聚合物功能化磁性纳米材料的结构示意如下，
所述刷型肼聚合物功能化磁性纳米材料的磁性微球平均粒径为300nm。可按如下步骤操作，
(1)四氧化三铁磁性纳米微球表面包覆一层二氧化硅；
具体为：取0.15-0.30g四氧化三铁纳米微球在超声作用下分散在60-260mL的无水乙醇中，加入15-52mL水，0.5-3mL浓氨水，超声10-60min，再加入1-5mL正硅酸乙酯，在25-55℃水浴中搅拌1-15h，取出磁球依次用水和无水乙醇洗涤；
(2)包覆上二氧化硅的磁球进行4-氯甲基苯基功能化反应；
具体为：将制备的包覆二氧化硅的磁球置于40-100℃的真空干燥箱中干燥2-24h后，将干燥的磁球加入10-50mL干燥甲苯，超声分散10-40min，在氮气保护下滴加50-300μL4-氯甲基苯基三氯硅烷，然后超声1-10min，再滴加120-720μL三乙胺，最终的混合物在氮气保护下回流6-36h，取出磁球依次用甲苯、水、乙醇洗涤，然后置于40-80℃的真空干燥箱中干燥2-24h；
(3)磁球表面原位生成RAFT试剂；
具体为：在氮气保护下，将6.9-41.5mg镁粉和22.0-46.0mg碘粒加入到反应瓶中，并向其中加入1-2mL四氢呋喃（内含溴苯1.4-8.7μL），吹风机加热引发后，滴入10-20mL四氢呋喃（内含溴苯28.9-173.6μL），在40-60℃时反应0.5-3.0h，然后冷却至0℃，再向其中滴入5-10mL四氢呋喃（内含二硫化碳23.7-118.4μL），0.5-4.0h后，向所得红色溶液中加入步骤(2)所得磁球，超声5-30min后，该反应液置于40-60℃的油浴中反应12-48h，依次用水、乙醇、丙酮洗涤后，置于40-80℃的真空干燥箱中干燥2-24h；
(4)甲基丙烯酸缩水甘油酯以RAFT方式聚合得到刷型聚合物磁球；
具体为：在希莱克试管中，加入步骤(3)所得磁球，10-30mL干燥四氢呋喃，超声分散5-30min后，再加入0.5-2.0mL甲基丙烯酸缩水甘油酯(GMA)，2.0-8.0mg偶氮二异丁腈，冷冻(-60至-80℃)-脱空气-溶解循环2-5次，在氮气保护下置于50-65℃的油浴中反应12-36h，产物依次用四氢呋喃、乙醇洗涤后，置于50℃的真空干燥箱中干燥2-24h；
(5)刷型聚合物磁球进行肼功能化；
具体为：将步骤(4)所得磁球分散到20-50mL无水乙醇中，超声5-60min后，加入0.5-3.0mL水合肼，在室温下搅拌6-36h，最终的产品用乙醇充分洗涤后，置于40-70℃的真空干燥箱中干燥2-24h，得刷型肼聚合物功能化磁性纳米微球。
所述刷型肼聚合物功能化磁性纳米材料可用于糖肽或糖蛋白的富集和纯化。蛋白酶解物在高碘酸钠氧化后刷型肼聚合物功能化磁性纳米材料与样品中的糖肽或糖蛋白共价结合，通过洗涤除去非糖肽或非糖蛋白，所富集到的糖肽经PNGase F酶切去糖链后释放出的肽段或蛋白可直接用质谱进行分析。
本发明具有如下优点：
1.磁核上包覆的二氧化硅可有效地防止四氧化三铁磁球被酸、碱腐蚀，提高材料的生物相容性，而且在二氧化硅层上可以进行有效的衍生化，减少了四氧化三铁磁球的非特异性吸附。
2.纳米磁球的超顺磁性使得材料在磁场作用下容易从溶液中分离出来，磁场撤销后容易分散开，因而操作简单，而且可以减少离心等前处理步骤带来的样品损失。
3.纳米磁核大的比表面积使得单位质量的材料上具有更多的功能基团，因而具备了高效的富集能力。
4.刷型肼聚合物功能化磁性纳米材料具有较好的亲水性和间隔臂，在生理条件下有很好的生物相容性和稳定性，在空间上可以与糖肽进行很好的相互作用。
5.刷型肼聚合物功能化磁性纳米材料具有较多的肼基团，因而具有特异性强，灵敏度高，捕捉量大等优势。
附图说明
图1为刷型肼聚合物功能化磁性纳米材料的制备示意图。
图2为刷型肼聚合物功能化磁性纳米材料的红外光谱图。
(a)Fe3O4@SiO2-GMA,(b)Fe3O4@SiO2-RAFT。
图3为刷型肼聚合物功能化磁性纳米材料的透射电镜图。
(a)Fe3O4@SiO2-RAFT,(b)Fe3O4@SiO2-GMA。
具体实施方式
实施例利用刷型肼聚合物功能化磁性纳米材料富集糖肽
刷型肼聚合物功能化磁性纳米材料的制备：
1）300μg Fe3O4颗粒分散到200mL乙醇、50mL水和1.4mL的浓氨水中，超声处理15min，然后加入1mL TEOS，在室温下搅拌10h，产物用30mL水和乙醇各洗5次，置于50℃的真空干燥箱中干燥24h，得Fe3O4@SiO2颗粒；
2）将200μg Fe3O4@SiO2颗粒分散到40mL干燥甲苯中，超声15min后，滴入含4-氯甲基三氯硅烷(90μL)的甲苯溶液8mL，再超声5min后，缓慢滴入含三乙胺(216μL)的甲苯溶液8mL，最终的反应液在氮气保护下回流24h，产物用30mL水和乙醇各洗5次，置于50℃的真空干燥箱中干燥24h，得Fe3O4@SiO2-Cl颗粒；
3）将60μg镁粉和1粒碘粒加入到反应瓶中，吹风机加热引发后，滴入含溴苯(238μL)的干燥四氢呋喃溶液5mL，在60℃时反应1.5h，然后冷却至0℃，再向其中滴入含二硫化碳(206μL)的干燥四氢呋喃溶液5mL，1.5h后，向所得红色溶液中加入200μg Fe3O4@SiO2-Cl颗粒，超声5min后，在氮气保护下，该反应液置于50℃的油浴中反应48h，用30mL水、乙醇、丙酮各洗4次后，置于50℃的真空干燥箱中干燥24h，得Fe3O4@SiO2-RAFT颗粒；
4）在希莱克试管中，加入100μg Fe3O4@SiO2-RAFT颗粒，17mL干燥四氢呋喃，超声分散15min后，再加入1mL甲基丙烯酸缩水甘油酯(GMA)，40μg AIBN，冷冻(-80℃)-脱空气-溶解循环三次，在氩气保护下置于60℃的油浴中反应24h，产物用20mL四氢呋喃洗6次，乙醇洗2次后，置于50℃的真空干燥箱中干燥24h，得Fe3O4@SiO2-GMA颗粒；
5）100μg Fe3O4@SiO2-GMA颗粒分散到30mL无水乙醇中，超声15min后，加入1mL水合肼，在室温下搅拌24h，最终的产品用乙醇充分洗涤后，置于50℃的真空干燥箱中干燥24h，得Fe3O4@SiO2-GMA-NHNH2颗粒。
6）纳米材料中肼含量测试，1.16mg Fe3O4@SiO2-GMA-NHNH2置于1.5mL离心管中，先用去离子水洗3次，然后再用冰醋酸甲醇溶液(0.8%，V/V)洗4次，再向其中加入过量的对硝基苯甲醛，1mL冰醋酸甲醇溶液(0.8%，V/V)，所得悬浮液室温反应4h。磁核分离后，用0.3mL冰醋酸甲醇溶液(0.8%，V/V)洗3次，所得的上清液合并到一起，根据对硝基苯甲醛的标准曲线计算出该纳米材料中的肼含量为1442nmol/mg。
产物表征
在Fe3O4@SiO2-RAFT(图2(b))的FT-IR谱中，442，575，1078cm-1的吸收峰分别属于Fe-O-Si,Fe-O-Fe和Si-O-Si的振动吸收峰。Fe3O4@SiO2@GMA(图2(a))的FT-IR谱中，新出现的2950，2875cm-1的吸收峰属于C-H振动吸收峰，1730cm-1属于C=O的振动吸收峰，这些特征峰的出现说明GMA成功接枝到磁核表面。
透射电镜图(图3)中清晰地看见，在图3(a)中，可以清晰地看到核壳结构的磁核，磁核外面包裹了一层二氧化硅；在图3(b)中，可以清晰地看到三明治结构的磁核，磁核粒径240nm，中间的二氧化硅层9nm，外层的PGMA为6nm，这说明GMA成功接枝到磁核表面。
样品溶液的制备：鸡蛋清卵清蛋白(Albumin from chicken egg white)、胎牛血清胎球蛋白(fetuin from fetal calf serum)、人血浆转铁蛋白(transferrin from human blood plasma)、人血浆α1-酸性糖蛋白(α1-acidglycoprotein from human plasma)各1mg混合溶解在含8M尿素的100mM的碳酸氢铵溶液中(pH=8.2)，加入80μmol二硫苏糖醇，在60℃恒温1h，再加入160μmol碘代乙酰胺，避光40min，用100mM的碳酸氢铵溶液将尿素浓度稀释成1M，按照与胰蛋白酶的质量比为1:40的加入胰蛋白酶，在37℃的水浴中反应时间为16h，获得的酶解液除盐，冻干后保存在-30℃的冰箱中备用。糖基化肽的富集及Triple TOF5600质谱分析：
1mg四种标准糖肽的混合物酶解物溶解于800μL氧化溶液中(100mM醋酸钠,150mM氯化钠，pH=5.5)，加入200μL50mM高点酸钠(NaIO4)，室温下避光反应1h，然后加入200μL100mM Na2S2O3，室温反应10min，再将反应液加入到5mg的刷型肼聚合物功能化磁球中，25℃下振荡过夜反应。反应完全成后，依次用1.5M氯化钠、无水甲醇、100mM碳酸氢铵洗去非特异吸附的非糖基化肽段。最终加入1μL PNGase F酶，于10mM碳酸氢铵中37℃孵育过夜，在外磁场作用下收集上清，冷冻干燥后0.1%FA复溶，再将样品进行Triple TOF5600质谱分析。
分析结果：来自于四个标准糖蛋白酶解的糖肽容易被刷型肼聚合物功能化磁球所捕获，非糖肽容易被洗脱，说明刷型肼聚合物功能化磁球能特异性地分离富集糖基化肽。
表1.在四种标准糖蛋白酶解液中检测到的糖基化肽
该有机-无机杂化纳米材料的制备过程简单、反应条件温和，并可以应用于复杂生物样品中糖肽或糖蛋白的富集。
Claims (4)
1.一种刷型肼聚合物功能化磁性纳米微球，磁性纳米微球是于四氧化三铁表面包裹硅胶后，通过硅胶上的硅烷化反应，于硅胶上键合刷型肼聚合物，其结构示意图如下，
2.一种权利要求1所述功能化磁性纳米微球的制备方法，其特征在于：
在四氧化三铁表面包裹二氧化硅的磁性纳米微球表面原位生成RAFT试剂，加入有机聚合反应功能单体和有机聚合反应引发剂，在RAFT试剂的调控下将功能单体接枝到纳米材料表面形成刷型肼聚合物功能化磁性纳米微球。
3.根据权利要求2所述的制备方法，其特征在于：按如下步骤操作，
(1)磁性纳米微球表面包覆一层二氧化硅：取0.15-0.30g四氧化三铁纳米微球在超声作用下分散在60-260mL的无水乙醇中，加入15-52mL水，0.5-3mL质量浓度25-28％的浓氨水，超声10-60min，再加入1-5mL正硅酸乙酯(TEOS)，在25-55℃水浴中搅拌1-15h，取出磁球依次用水和无水乙醇洗涤；
(2)包覆上二氧化硅的磁球进行4-氯甲基苯基功能化反应：将步骤(1)制备的包覆二氧化硅的磁球置于40-100℃的真空干燥箱中干燥2-24h后，将干燥的磁球加入10-50mL甲苯，超声分散10-40min，在氮气保护下滴加50-300μL4-氯甲基苯基三氯硅烷，然后超声1-10min，再滴加120-720μL三乙胺，最终的混合物在氮气保护下回流6-36h，取出磁球依次用甲苯、水、乙醇洗涤，然后置于40-80℃的真空干燥箱中干燥2-24h；
(3)磁球表面原位生成RAFT试剂：在氮气保护下，将6.9-41.5mg镁粉和22.0-46.0mg碘粒加入到反应瓶中，并向其中加入1-2mL内含溴苯的四氢呋喃，吹风机加热引发后，滴入10-20mL内含溴苯的四氢呋喃，在40-60℃时反应0.5-3.0h，然后冷却至0℃，再向其中滴入5-10mL内含二硫化碳的四氢呋喃，0.5-4.0h后，向所得红色溶液中加入步骤(2)所得磁球，超声5-30min后，该反应液置于40-60℃的油浴中反应12-48h，依次用水、乙醇、丙酮洗涤后，置于40-80℃的真空干燥箱中干燥2-24h；
(4)甲基丙烯酸缩水甘油酯以RAFT方式聚合得到刷型聚合物磁球：
在希莱克试管中，加入步骤(3)所得磁球，10-30mL四氢呋喃，超声分散5-30min后，再加入0.5-2.0mL甲基丙烯酸缩水甘油酯(GMA)，2.0-8.0mg偶氮二异丁腈(AIBN)，-60至-80℃冷冻-脱空气-溶解循环2-5次，在氮气保护下置于50-65℃的油浴中反应12-36h，产物依次用四氢呋喃、乙醇洗涤后，置于50℃的真空干燥箱中干燥2-24h；
(5)刷型聚合物磁球进行肼功能化：
将步骤(4)所得磁球分散到20-50mL无水乙醇中，超声5-60min后，加入0.5-3.0mL水合肼，在室温下搅拌6-36h，最终的产品用乙醇充分洗涤后，置于40-70℃的真空干燥箱中干燥2-24h，制备成刷型肼聚合物功能化磁性纳米微球。
4.一种权利要求1所述刷型肼聚合物功能化磁性纳米微球的应用，其特征在于：刷型肼聚合物功能化磁性纳米微球作为吸附剂或填料用于糖肽或糖蛋白的富集和/或纯化。
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| WO2008064973A1 (en) * | 2006-11-27 | 2008-06-05 | Unilever Plc | Composition comprising brush copolymer for treating hair |
| CN101747478A (zh) * | 2008-12-17 | 2010-06-23 | 中国科学院大连化学物理研究所 | 有机-无机杂化多孔整体材料的“一锅法”制备 |
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