CN116371366A - 一种广谱富集细菌的纳米磁小体及其制备方法与应用 - Google Patents
一种广谱富集细菌的纳米磁小体及其制备方法与应用 Download PDFInfo
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Abstract
Description
技术领域
本发明属于有机合成和细菌富集材料技术领域,具体涉及一种广谱富集细菌的纳米磁小体及其制备方法与应用。
背景技术
由病原微生物引起的疾病是世界范围内发病率和死亡率都较高的疾病,每年数百万次被细菌感染,给人们生命健康与社会经济发展造成重大损失。人类感染细菌后,可引起败血症、脑膜炎等相关疾病。近十年来,全球有超过一千万人死于由病原微生物引起的各种传染病。因此,开发致病菌的快速筛查方法是必要的。鉴于需要开发一种高效、快速、抗基质干扰性能强的检测方法,基于功能化纳米磁珠的样本前处理技术得到了迅速发展。
复合纳米磁珠是一种高通量的材料,可以快速提取生物、环境样本中的细菌、核酸以及蛋白等,磁性纳米材料是一直是生物医药、环境分析和材料物理等研究领域的研究热点。
这些复合纳米磁珠具有粒径小、生物相容性高、超顺磁性强等特点。其结构一般是含有可反应基团(羟基、羧基、氨基、巯基、炔基、叠氮基、醛基等)的磁颗粒、连接基和功能分子三部分,其中功能分子和磁颗粒之间是通过连接基连接而成。在连接过程中需要操作简便、成本低廉和条件温和(确保磁颗粒不团聚、磁性不失活以及功能分子的功能不失活)。因此、连接基团的结构和连接方式的设计或选择是一个至关重要的因素。
目前,关于连接基与磁珠与功能分子最常见的一种方式是通过羧基与氨基以酰胺键相连,但是需要加入缩合试剂活化羧基,需要严格控制pH值,需要严格无水条件,操作不简便,成本高。
发明内容
针对现有技术存在的不足,本发明的目的是提供一种广谱富集细菌的纳米磁小体及其制备方法与应用;本发明通过磁珠与功能分子之间一种简便的连接方式并获得一类具有优越细菌捕捉性能的具有全新结构的纳米磁小体:具体来说,利用连有拉电子的活化酯基可以与氨基磁珠中的氨基直接在溶剂中反应成酰胺,无需额外添加缩合剂和碱等特点,设计一种基于酰胺草酸酯与氨基磁珠直接相连的连接方式,进一步利用该方法,设计合成一种含草酰胺连接基的全新纳米磁小体结构。以同样的连接方式在氨基磁珠上连入聚乙二醇基以调节磁小体在水中分散性与减少磁小体之间团聚。另外连接基草酰胺本身具有络合金属离子的功能,会增强对细菌的捕捉能力。连接过程中不需要加入缩合试剂活化羧基,不需要严格无水条件,操作简便,成本低。含草酰胺与DPA双重金属离子络合功能的纳米磁小体具有优越的细菌捕捉能力。制备的纳米磁颗粒具有广谱的细菌富集能力,特别对革兰氏阴性菌有高度的亲和力,捕获率达98%以上。
本发明的目的通过以下技术方案实现:
一种广谱富集细菌的纳米磁小体,结构如下:
优选的,所述二价金属离子为Zn2+、Cu2+、Co2+、Ni2+;所述X为盐酸根、硫酸根或硝酸根。
优选的,所述的广谱富集细菌的纳米磁小体从溶液中完全分离的时间为3-5分钟。
上述的广谱富集细菌的纳米磁小体的制备方法,包括以下步骤:
R1和R2分别为C1-C17的烷基。
优选的,步骤(1)中,所述DPN-COCOOR1与PEG-NH-COCOOR2的质量比为1:100~100:1;所述DPN-COCOOR1与表面携带氨基的SiO2包裹的Fe3O4纳米颗粒的质量比为1:100~100:1;所述溶剂为苯、甲苯、邻二甲苯、氯苯、氟苯、二氯甲烷、二氯乙烷、乙腈、二甲基亚砜、二甲基甲酰胺、二甲基乙酰胺、乙酸乙酯、乙酸叔丁酯、四氢呋喃、乙醚、1,4-二氧六环、六氟异丙醇、1-甲基2-吡咯烷酮、丁酸甲酯中的一种或者多种的混合物;所述反应的温度为0-140摄氏度;所述PEG-NH-COCOOR2中PEG的分子量为200-2000。
优选的,步骤(2)中,所述的二价金属盐为二价金属的盐酸盐、硫酸盐或硝酸盐,二价金属为Zn2+、Cu2+、Co2+、Ni2+(ZnCl2,Zn(NO3)2,ZnSO4,CuCl2,Cu(NO3)2,CuSO4等);所述反应的溶剂为水、苯、甲苯、邻二甲苯、氯苯、氟苯、二氯甲烷、二氯乙烷、乙腈、二甲基亚砜、二甲基甲酰胺、二甲基乙酰胺、乙酸乙酯、乙酸叔丁酯、四氢呋喃、乙醚、1,4-二氧六环、六氟异丙醇、1-甲基2-吡咯烷酮、丁酸甲酯中的一种或者多种的混合物;所述反应的温度为0-140摄氏度。
优选的,所述表面携带氨基的SiO2包裹的Fe3O4纳米颗粒的制备方法为:
进一步优选的,步骤(a)中,所述二价铁盐为氯化亚铁及其水合物,溴化亚铁及其水合物,硫酸亚铁及其水合物,醋酸亚铁及其水合物中的至少一种;所述三价铁盐为氯化铁及其水合物,溴化铁及其水合物,硫酸铁及其水合物,醋酸铁及其水合物中的至少一种;所述二价铁盐和三价铁盐中的铁离子的物质的量比为1:5~5:1所述二价铁盐与氨水的质量比为1:1~1:100;所述合成的温度为0-40摄氏度;所述溶剂为水;所述Fe3O4纳米颗粒的直径为50nm-200nm。
进一步优选的,步骤(a)中,所述氨水的质量浓度为5-30%。
进一步优选的,步骤(b)中,所述Fe3O4纳米颗粒与四乙氧基硅烷的质量比为1:100~100:1;所述反应的温度为0-40摄氏度;所述反应在水中进行,所述Fe3O4纳米颗粒与氨水的质量比为1:1~1:100;所述SiO2包裹的Fe3O4纳米颗粒的直径为50nm-200nm;所述溶剂为乙醇。
进一步优选的,步骤(b)中,所述氨水的质量浓度为5-30%。
进一步优选的,步骤(c)中,所述SiO2包裹的Fe3O4纳米颗粒与3-氨丙基三乙氧基硅烷(简称APTES)的质量比为1:5~5:1;所述的溶剂为水、苯、甲苯、邻二甲苯、氯苯、氟苯、二氯甲烷、二氯乙烷、乙腈、二甲基亚砜、乙醇、二甲基甲酰胺、二甲基乙酰胺、乙酸乙酯、乙酸叔丁酯、四氢呋喃、乙醚、1,4-二氧六环、六氟异丙醇、1-甲基2-吡咯烷酮、丁酸甲酯中的一种或者多种的混合物;所述表面改性的温度为0-140摄氏度;所述表面携带氨基的SiO2包裹的Fe3O4纳米颗粒的直径为50nm-200nm。
进一步优选的,步骤(c)中,所述SiO2包裹的Fe3O4纳米颗粒与氨水的质量比为1:1~1:100;所述氨水的质量浓度为5-30%。
进一步优选的,所述DPN-COCOOR1的制备方法中,所述二吡啶甲基胺与草酰氯单酯ClCOCOOR1的质量比为1:10~10:1;二吡啶甲基胺与三乙胺的质量比为1:10~10:1;所述的溶剂为水、苯、甲苯、邻二甲苯、氯苯、氟苯、二氯甲烷、二氯乙烷、乙腈、二甲基亚砜、二甲基甲酰胺、二甲基乙酰胺、乙酸乙酯、乙酸叔丁酯、四氢呋喃、乙醚、1,4-二氧六环、六氟异丙醇、1-甲基2-吡咯烷酮、丁酸甲酯中的一种或者多种的混合物;所述反应的温度为0-140摄氏度。
优选的,所述PEG-NH-COCOOR2的制备方法为:聚乙二醇氨PEG-NH2、三乙胺与草酰氯单酯ClCOCOOR2在溶剂中反应生成聚乙二醇草酰胺单酯PEG-NH-COCOOR2。
进一步优选的,所述PEG-NH-COCOOR2的制备方法中,所述聚乙二醇氨PEG-NH2与ClCOCOOR2的质量比为1:10~10:1;聚乙二醇氨PEG-NH2与三乙胺的质量比为1:10~10:1;所述的溶剂为水、苯、甲苯、邻二甲苯、氯苯、氟苯、二氯甲烷、二氯乙烷、乙腈、二甲基亚砜、二甲基甲酰胺、二甲基乙酰胺、乙酸乙酯、乙酸叔丁酯、四氢呋喃、乙醚、1,4-二氧六环、六氟异丙醇、1-甲基2-吡咯烷酮、丁酸甲酯中的一种或者多种的混合物;所述反应的温度为0-140摄氏度;所述聚乙二醇氨PEG-NH2中聚乙二醇的分子量为200-2000。
上述的广谱富集细菌的纳米磁小体在富集细菌中的应用。
优选的,所述细菌为大肠杆菌、沙门氏菌、志贺氏菌、单增李斯特菌、植物乳杆菌。
本发明的纳米磁小体应用于科学研究、临床、食品安全和环境保护等领域的微生物样品分离与纯化,凭借电荷相互作用,对微生物有较强的捕获能力。
与现有技术相比,本发明具有如下优点和有益效果:
(1)本发明的制备方法简便、成本低;
(2)本发明的纳米磁小体具有广谱细菌富集能力,特别是革兰氏阴性菌,吸附率到达98%以上。
附图说明
图1为DPNCOCOEt的核磁谱图。
图2为氨基化磁珠颗粒的SEM图。
图3为纳米磁珠的细菌吸附实物图。
具体实施方式
以下结合说明书附图和具体实施例来进一步说明本发明,但实施例并不对本发明做任何形式的限定。除非特别说明,本发明采用的试剂、方法和设备为本技术领域常规试剂、方法和设备。
除非特别说明,以下实施例所用试剂和材料均为市购。
实施例1纳米磁珠合成
将3.0g氯化铁(III)六水合物和2.5g氯化亚铁(II)四水合物分别溶解在200mL去离子水中,然后将两种铁溶液在500mL圆底烧瓶中混合,剧烈搅拌下将10mL氨水(质量浓度为29%)加入混合物中。将溶液混合物连续搅拌过夜,用磁铁收集所得黑色产物并用去离子水和乙醇洗涤3次后得固体3.1g。
实施例2SiO2包裹纳米磁珠合成
将磁珠乙醇分散液(含有1.4g磁珠)350ml超声分散,加入氨水(15%)5ml。在氮气环境下搅拌15min.然后滴加4ml四乙氧基硅烷,室温搅拌过夜。产物进行乙醇洗涤3次后,分散在乙醇中。
实施例3氨基纳米磁珠合成
将由实施例2制备的磁珠(1.4g)在乙醇(350mL)中超声分散,加入氨水(5mL,质量浓度为29%)。通氮气搅拌15min.然后滴加3-氨丙基三乙氧基硅烷(4mL),搅拌过夜.产物过滤,并进行乙醇洗涤,得黑色固体1.6g。
实施例4DPNCOOMe合成
室温下将DPNH(1.99g 10mmol)和三乙胺(1.01g,10mmol)滴入二氯甲烷中(50mL),搅拌后缓慢滴入ClCOCOOMe(1.06g 10mmol),室温搅拌6小时。然后向反应体系中加入20mL水,溶液分层分出下层有机相,有机相用去离子水洗涤(3×20mL)。合并有机相,无水硫酸钠干燥后脱除溶剂,得粗产物2.4g,直接用于下一步。
实施例5DPNCOOEt合成
室温下将DPNH(1.99g 10mmol)和三乙胺(1.01g,10mmol)滴入二氯甲烷中(50mL),搅拌后缓慢滴入ClCOCOOEt(1.20g,10mmol),室温搅拌6小时。然后向反应体系中加入20mL水,溶液分层分出下层有机相,有机相用去离子水洗涤(3×20mL)。合并有机相,无水硫酸钠干燥后脱除溶剂,得粗产物2.52g,直接用于下一步。
实施例6PEGNCOOEt合成
室温下将PEGNH(3.0g)和三乙胺(1.01g,10mmol)滴入二氯甲烷中(50mL),搅拌后缓慢滴入ClCOCOOEt(1.20g,10mmol),室温搅拌6小时。然后向反应体系中加入20mL水,溶液分层分出下层有机相,有机相用去离子水洗涤(3×20mL)。合并有机相,无水硫酸钠干燥后脱除溶剂,得粗产物3.17g,直接用于下一步。
室温下将DPNCOOEt(1g),PEGNCOOEt(1g)和(500mg)与甲苯混合物用超声分散1小时,然后在氮气保护下加热回流48小时。冷却至室温,用磁分离器分理出固体,用20mL乙醇洗涤两次,晾干得固体520mg。
实施例9Zn-DPA-CONH-MNPs对细菌的吸附能力评价
本实验使用的对象菌为大肠杆菌、沙门氏菌、志贺氏菌、单增李斯特菌、植物乳杆菌。前三者为革兰氏阴性菌,后两个为革兰氏阳性菌。
LB液体培养基配制:酵母提取物5g,氯化钠10g,胰蛋白胨10g,蒸馏水1000mL。
LB固体培养基配制:酵母提取物5g,氯化钠10g,胰蛋白胨10g,琼脂粉15g,蒸馏水1000mL。
从冻存管中吸100μL细菌到装有5mL的液体培养基里面,于37℃培养箱中培养至稳定期。将培养好的大肠杆菌转移到离心管中,在6000rpm,10min条件下离心,去掉上清液重悬于无菌水中,重复2次。备用。
在装有5毫升生理盐水的试管中,加入上述实施例8的纳米磁性颗粒5mg,超声作用10分钟取出,吸取一定量菌悬液到试管中,震荡3min,在外磁场作用下,分离磁颗粒,取上清液进行梯度稀释计数。结果:大肠杆菌的吸附率为99%,沙门氏菌的吸附率为99%,志贺氏菌为吸附率为98%,单增李斯特菌吸附率为90%,植物乳杆菌为95%。磁珠颗粒吸附实物图如图3所示。
上述实施例仅例示性说明本发明的原理及其功效,而非用于限制本发明。本领域的技术人员不需要付出创造性的劳动即可联想到本发明的其他具体实施方式,这些方式都将落入本发明的保护范围之内。
Claims (10)
2.根据权利要求1所述的广谱富集细菌的纳米磁小体,其特征在于,所述二价金属离子为Zn2+、Cu2+、Co2+、Ni2+;
所述X为盐酸根、硫酸根或硝酸根;
所述的广谱富集细菌的纳米磁小体从溶液中完全分离的时间为3-5分钟。
4.根据权利要求3所述的制备方法,其特征在于,步骤(1)中,所述DPN-COCOOR1与PEG-NH-COCOOR2的质量比为1:100~100:1;所述DPN-COCOOR1与表面携带氨基的SiO2包裹的Fe3O4纳米颗粒的质量比为1:100~100:1;所述溶剂为苯、甲苯、邻二甲苯、氯苯、氟苯、二氯甲烷、二氯乙烷、乙腈、二甲基亚砜、二甲基甲酰胺、二甲基乙酰胺、乙酸乙酯、乙酸叔丁酯、四氢呋喃、乙醚、1,4-二氧六环、六氟异丙醇、1-甲基2-吡咯烷酮、丁酸甲酯中的一种或者多种的混合物;所述反应的温度为0-140摄氏度;所述PEG-NH-COCOOR2中PEG的分子量为200-2000;
步骤(2)中,所述的二价金属盐为二价金属的盐酸盐、硫酸盐或硝酸盐,二价金属为Zn2 +、Cu2+、Co2+、Ni2+;所述反应的溶剂为水、苯、甲苯、邻二甲苯、氯苯、氟苯、二氯甲烷、二氯乙烷、乙腈、二甲基亚砜、二甲基甲酰胺、二甲基乙酰胺、乙酸乙酯、乙酸叔丁酯、四氢呋喃、乙醚、1,4-二氧六环、六氟异丙醇、1-甲基2-吡咯烷酮、丁酸甲酯中的一种或者多种的混合物;所述反应的温度为0-140摄氏度。
6.根据权利要求5所述的制备方法,其特征在于,步骤(a)中,所述二价铁盐为氯化亚铁及其水合物,溴化亚铁及其水合物,硫酸亚铁及其水合物,醋酸亚铁及其水合物中的至少一种;所述三价铁盐为氯化铁及其水合物,溴化铁及其水合物,硫酸铁及其水合物,醋酸铁及其水合物中的至少一种;所述二价铁盐和三价铁盐中的铁离子的物质的量比为1:5~5:1所述二价铁盐与氨水的质量比为1:1~1:100;所述合成的温度为0-40摄氏度;所述溶剂为水;所述Fe3O4纳米颗粒的直径为50nm-200nm;
步骤(b)中,所述Fe3O4纳米颗粒与四乙氧基硅烷的质量比为1:100~100:1;所述反应的温度为0-40摄氏度;所述Fe3O4纳米颗粒与氨水的质量比为1:1~1:100;所述SiO2包裹的Fe3O4纳米颗粒的直径为50nm-200nm;所述溶剂为乙醇;
步骤(c)中,所述SiO2包裹的Fe3O4纳米颗粒与3-氨丙基三乙氧基硅烷的质量比为1:5~5:1;所述的溶剂为水、苯、甲苯、邻二甲苯、氯苯、氟苯、二氯甲烷、二氯乙烷、乙腈、二甲基亚砜、乙醇、二甲基甲酰胺、二甲基乙酰胺、乙酸乙酯、乙酸叔丁酯、四氢呋喃、乙醚、1,4-二氧六环、六氟异丙醇、1-甲基2-吡咯烷酮、丁酸甲酯中的一种或者多种的混合物;所述表面改性的温度为0-140摄氏度;所述表面携带氨基的SiO2包裹的Fe3O4纳米颗粒的直径为50nm-200nm。
8.根据权利要求7所述的制备方法,其特征在于,所述DPN-COCOOR1的制备方法中,所述二吡啶甲基胺与草酰氯单酯ClCOCOOR1的质量比为1:10~10:1;二吡啶甲基胺与三乙胺的质量比为1:10~10:1;所述的溶剂为水、苯、甲苯、邻二甲苯、氯苯、氟苯、二氯甲烷、二氯乙烷、乙腈、二甲基亚砜、二甲基甲酰胺、二甲基乙酰胺、乙酸乙酯、乙酸叔丁酯、四氢呋喃、乙醚、1,4-二氧六环、六氟异丙醇、1-甲基2-吡咯烷酮、丁酸甲酯中的一种或者多种的混合物;所述反应的温度为0-140摄氏度;
所述PEG-NH-COCOOR2的制备方法中,所述聚乙二醇氨PEG-NH2与ClCOCOOR2的质量比为1:10~10:1;聚乙二醇氨PEG-NH2与三乙胺的质量比为1:10~10:1;所述的溶剂为水、苯、甲苯、邻二甲苯、氯苯、氟苯、二氯甲烷、二氯乙烷、乙腈、二甲基亚砜、二甲基甲酰胺、二甲基乙酰胺、乙酸乙酯、乙酸叔丁酯、四氢呋喃、乙醚、1,4-二氧六环、六氟异丙醇、1-甲基2-吡咯烷酮、丁酸甲酯中的一种或者多种的混合物;所述反应的温度为0-140摄氏度;所述聚乙二醇氨PEG-NH2中聚乙二醇的分子量为200-2000。
9.权利要求1-2任一项所述的广谱富集细菌的纳米磁小体在富集细菌中的应用。
10.根据权利要求9所述的应用,其特征在于,所述细菌为大肠杆菌、沙门氏菌、志贺氏菌、单增李斯特菌、植物乳杆菌。
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