CN102893152A - 配体官能化的聚合物 - Google Patents
配体官能化的聚合物 Download PDFInfo
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- CN102893152A CN102893152A CN2011800101952A CN201180010195A CN102893152A CN 102893152 A CN102893152 A CN 102893152A CN 2011800101952 A CN2011800101952 A CN 2011800101952A CN 201180010195 A CN201180010195 A CN 201180010195A CN 102893152 A CN102893152 A CN 102893152A
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- polymkeric substance
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- alkyl
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Abstract
本发明公开了配体官能化基底、制备配体官能化基底的方法以及使用官能化基底的方法。
Description
相关专利申请的交叉引用
本专利申请要求提交于2010年2月18日的美国临时专利申请No.61/305740的权益,该专利申请的公开内容以引用方式全文并入本文。
技术领域
本发明涉及配体-官能化聚合物,和用于制备其的方法。该官能化聚合物可用于从生物样品中选择性结合和除去生物材料,例如病毒。
背景技术
靶标生物材料,例如病毒和生物大分子(包括活细胞的组分或产物,例如蛋白质、碳水化合物、脂质和核酸)的检测、定量、分离和纯化一直以来都是研究人员的目标。从诊断上来讲,检测和量化是重要的,例如,作为各种生理状况诸如疾病的指示。生物大分子的分离和纯化对治疗性使用和生物医学研究十分重要。生物大分子例如酶(其为特殊的一类能催化化学反应的蛋白质)在工业上也是有用的;已对酶进行了分离、纯化,然后用于制备甜味剂、抗生素和多种有机化合物(例如乙醇、乙酸、赖氨酸、天冬氨酸和生物有用的产品,例如抗体和类固醇)。
在活的有机体内的天然状态下,这些生物大分子的结构和相应的生物活性一般来讲保持在相当窄的pH和离子强度范围内。因此,任何分离和纯化操作必须考虑这些因素以得到具有效力的处理后生物大分子。
使用某些离子聚合物,尤其是阳离子聚合物来使细胞和/或细胞碎片絮凝,以及使蛋白质沉淀是已知的。相似地,已经使用离子聚合物来改变过滤介质以在深度过滤或膜吸收体类型应用中提高从工艺液流中移除杂质。随着被处理介质的传导率增加(即,随着含盐量增加),这些絮凝剂的效能通常降低。本领域需要在高离子强度条件下对生物物质具有提高的亲和力的聚合物材料。
根据溶质在流动相(其可以是气体或液体)和固定相之间的交换,可对生物产物混合物进行色谱分离和纯化操作。溶液混合物中各种溶质实现分离,是由于改变了各溶质与固定相的结合相互作用;当受到流动相的解离和置换作用时,与相互作用不太强的溶质相比,较强的结合相互作用一般导致保留时间较长,以该方式,可以实现分离和纯化。
当前的捕获或纯化色谱法是通过传统的柱色谱技术实现的。这些技术在下游纯化中具有严重的瓶颈问题,因为使用这种技术的通过量比较低。对于缓解这些问题的尝试包括增加色谱柱的直径,但这继而会由于装柱有效性和再生性困难而面临挑战。较大的色谱柱直径还会增加难以解决的沟流发生率。同样,在传统的色谱柱中,当检测到可取产物的漏过量高于某一水平时,所述吸收操作会被停止。这会引起吸附介质的动态吸附或有效吸附容量将显著小于总吸附或静态吸附容量。鉴于一些色谱树脂成本较高,这种有效性的缩减会导致严重的经济后果。
聚合物树脂被广泛用于各种目标化合物的分离和纯化。例如,可根据离子基团的存在、根据靶标化合物的大小、根据疏水相互作用、根据亲和相互作用或根据共价键的形成而将聚合物树脂用于纯化或分离靶标化合物。在本领域中,需要对病毒具有增强亲和力的聚合物基底,以使得能从生物样品选择性除去病毒。在本领域中还需要配体官能化膜,该膜可克服扩散和结合的限制,并且可以在高通过量和较低压降下操作。
发明内容
本发明涉及配体官能化的聚合物,和制备其的方法。更具体地讲,配体官能化的聚合物包括基体聚合物,具有羰基官能团,其已被改性以提供具有用于结合电中性或带负电的生物材料如细胞、细胞碎片、细菌、孢子、病毒、核酸和蛋白质的必要亲和力的接枝配体基团。
在一些实施例中,配体官能化的聚合物可以用作絮凝剂,从而生物样品(例如细胞培养流体)被接触,导致带负电和/或中性物种结合到所述聚合物并从溶液或悬浮液中沉淀。在另一个实施例中,基础基底(例如微孔膜或粒子)可以由所述配体官能化的聚合物涂布。在另一个实施例中,所述配体官能化的聚合物可以接枝到基础基底的表面。
可以将所述配体官能化的聚合物描述为羰基官能化聚合物的反应产物,例如二丙酮(甲基)丙烯酸酯(共)聚合物,和式I的配体化合物:
其中
R2为共价键、C2至C12亚烷基、C5-C12(杂)亚芳基、
R9为C2至C12亚烷基或C5-C12(杂)亚芳基,
各R3独立地为H、-OH、C1-C12烷基或C5-C12(杂)芳基,优选为H或C1-C4烷基,
R4为H、C1-C12烷基、C5-C12(杂)芳基或-N(R3)2,优选为H或C1-C4烷基。
提供了制备配体官能化基底的方法。在一些实施例中,所述方法包括任选地在存在酸催化剂的情况下使羰基官能化聚合物与式I的配体化合物反应。
提供具有接枝侧配体基团的官能化聚合物,所述配体基团具有式II:
其中
R1为H、C1-C12烷基或C5-C12(杂)芳基,优选为C1-C12烷基;
R2为共价键、C2至C12亚烷基或C5-C12(杂)亚芳基、
R9为C2至C12亚烷基或C5-C12(杂)亚芳基,
各R3独立地为H、-OH、C1-C12烷基或C5-C12(杂)芳基,优选为H或C1-C4烷基,
R4为H、C1-C12烷基、C5-C12(杂)芳基或–N(R3)2,优选为H或C1-C4烷基。
在其他实施例中,可以制备配体官能化的聚合物,其中所述亚胺连接基团(~~C(R1)=N-被还原成胺连接基团(~~CH(R1)-NH-。这可以通过用还原剂(例如氰基硼氢化钠)处理现存配体官能化的聚合物而实现,或者还原可以通过向羰基官能化聚合物和式I化合物的反应混合物添加所述还原剂而就地实现。
在本专利申请中,(甲基)丙烯酸类包括甲基丙烯酸类和丙烯酸类两者。
如本文所用,“烷基”或“亚烷基”包括直链的、支链的和环状的烷基并且包括未取代的和取代的烷基两者。除非另外指明,否则所述烷基基团通常包含1至20个碳原子。本文所使用的“烷基”的例子包括(但不限于)甲基、乙基、正丙基、正丁基、正戊基、异丁基、叔丁基、异丙基、正辛基、正庚基、乙基己基、环戊基、环己基、环庚基、金刚烷基和降冰片基等等。除非另外指明,否则烷基基团可为一价或多价的。
本文所使用的“芳基”或“亚芳基”是包含5-12个环原子的芳族基团并且可以包含任选的稠环,所述稠环可以是饱和的、不饱和的或芳族的稠环。芳基基团的例子包括苯基、萘基、联苯、菲基和蒽基。杂芳基为包含1-3个诸如氮、氧或硫之类的杂原子的芳基并且可以包含稠环。杂芳基基团的一些例子为吡啶基、呋喃基、吡咯基、噻吩基、噻唑基、噁唑基、咪唑基、吲哚基、苯并呋喃基和苯并噻唑基。除非另外指明,否则芳基和杂芳基可为一价或多价的。
附图说明
图1为实例1-5的牛血清白蛋白沉淀数据的图线。
具体实施方式
在本发明的制品和方法中,提供了配体官能化的聚合物,其具有,尤其在高离子强度介质中,对于电中性或带负电的生物材料如宿主细胞蛋白、DNA、RNA、病毒和其他微生物的增大的亲和力。对此种生物材料的亲和力允许纯化带正电的材料(例如抗体),因为它们不结合到配体官能团。该配体官能化基底使得配体基团能选择性捕获或结合靶标生物材料,而对配体基团缺少亲和力的其他材料能通过。在一些实施例中,配体官能化的聚合物用作絮凝剂,以选择性地结合靶生物材料,从溶液中沉淀它们,并且将沉淀加合物随后分离。
基体聚合物包含羰基官能化(共)聚合物;即,具有醛或酮基团(通常为聚合物链的侧基)的聚合物。所述聚合物包括具有羰基、优选酮基的烯键式不饱和单体的聚合单体单元,或烯键式不饱和单体和一氧化碳(一氧化碳共聚物)的共聚单体单元。
一般来讲,羰基官能化(共)聚合物选自:一氧化碳、丙烯醛、乙烯基甲基酮、乙烯基乙基酮、乙烯基异丁基酮、异丙烯基甲基酮、乙烯基苯基酮、二丙酮(甲基)丙烯酰胺、丙烯酸丙酮酯、(甲基)丙烯酸乙酰乙酸基乙酯和二丙酮(甲基)丙烯酸酯(共)聚合物。含一氧化碳共聚物的实例为ELVALOYTM741,其为乙烯/醋酸乙烯基酯/一氧化碳的三元共聚物。
聚合物可以为羰基官能化单体单元的共聚物。特别地,羰基官能化聚合物还可以包含烯键式不饱和亲水单体单元、和/或疏水单体单元。在一些实施例中,所述共聚物可以为交联共聚物。特别地,所述羰基官能化共聚物还可以包含具有不止一个烯键式不饱和基团的共聚单体单元。
如本文所用的“亲水单体”为具有水混溶性(单体中水)为至少1重量%、优选至少5重量%而未达浊点的那些可聚合的单体,并且其不含会妨碍生物物质与配体基结合的官能团。在单体溶液中,所述共聚物可以包含0至90重量%的这种单体单元。当存在时,基于100重量%总单体计,聚合物通常包含1重量%至90重量%的这种单体单元。
亲水单体的亲水基团可为中性的、具有正电荷、负电荷或它们的组合。在一些合适离子单体的情况下,离子基团可以为中性的或取决于pH状况而带电荷。此类单体通常用于向共聚物赋予所需亲水性(即水溶性或分散性)。这些共聚单体通常用于赋予配体官能化共聚物的所需水溶性/分散性。带负电的共聚单体可以被包含,只要其量足够小而不会妨碍配体结合相互作用。在病毒捕集的应用中,添加在选定pH下具有正电荷的亲水单体可以允许对病毒选择性结合和絮凝,同时排斥带正电的生物材料如抗体。
能够提供正电荷的一些示例性离子单体是式IV的氨基(甲基)丙烯酸酯类或氨基(甲基)丙烯酰胺类或者它们的季铵盐。季铵盐的抗衡离子通常是卤离子、硫酸根、磷酸根、硝酸根等。
其中X为–O-或–NR3-;
R7独立地为H或CH3,
R6为C2至C10亚烷基,优选为C2-C6。
各R8独立地为氢、烷基、羟烷基(即被羟基取代的烷基)或氨基烷基(即被氨基取代的烷基)。或者,两个R8基团与它们所连接的氮原子合在一起可形成芳族的、部分不饱和(即不饱和但不是芳族的)或饱和的杂环基团,其中杂环基团可任选稠合至芳族的另一个环(如苯)、部分不饱和的另一个环(如环己烯)或饱和的另一个环(如环己烷)。
应当理解,对于式IV,所述的(甲基)丙烯酸酯基团可被反应性降低的另一个烯键式不饱和基团,例如甲基丙烯酸酯、(甲基)丙烯酰胺、乙烯基、乙烯氧基、烯丙基、烯丙氧基和乙炔基取代。
在式IV的一些实施例中,两个R8基团均为氢。在其他实施例中,一个R8基团为氢而另一个为具有1至10个、1至6个或1至4个碳原子的烷基。在又一其他实施例中,至少一个R8基团为具有1至10个、1至6个或1至4个碳原子的羟基烷基或氨基烷基,其中羟基或氨基位于烷基的任何碳原子上。在其他实施例中,R8基团与氮原子结合,它们与所述氮原子连接以形成杂环基。杂环基团包含至少一个氮原子,并且可含有其他杂原子,例如氧或硫。示例性的杂环基团包括,但不限于咪唑基。杂环基团可稠合至另外的环,例如苯、环己烯或环己烷。稠合至另外环的示例性杂环基团包括,但不限于苯并咪唑基。
示例性的氨基丙烯酸酯类(即式IV中X为氧基)包括(甲基)丙烯酸N,N-二烷基氨基烷基酯,例如(甲基)丙烯酸N,N-二甲氨基乙酯、丙烯酸N,N-二甲氨基乙酯、丙烯酸N,N-二乙氨基乙酯、(甲基)丙烯酸N,N-二甲氨基丙酯、(甲基)丙烯酸N-叔丁基氨丙酯等等。
示例性氨基(甲基)丙烯酰胺(即式IV中X为-NR3-)包括例如N-(3-氨丙基)甲基丙烯酰胺、N-(3-氨丙基)丙烯酰胺、N-[3-(二甲氨基)丙基]甲基丙烯酰胺、N-[3-(二甲氨基)丙基]丙烯酰胺、N-(3-咪唑基丙基)甲基丙烯酰胺、N-(3-咪唑基丙基)丙烯酰胺、N-(2-咪唑基乙基)甲基丙烯酰胺、N-(1,1-二甲基-3-咪唑基丙基)甲基丙烯酰胺、N-(1,1-二甲基-3-咪唑基丙基)丙烯酰胺、N-(3-苯并咪唑基丙基)丙烯酰胺和N-(3-苯并咪唑基丙基)甲基丙烯烯酰胺。
式IV的单体的示例性季盐包括(但不限于)(甲基)丙烯酰胺基烷基三甲基铵盐(如3-甲基丙烯酰胺基丙基三甲基氯化铵和3-丙烯酰胺基丙基三甲基氯化铵)和(甲基)丙烯酰氧基烷基三甲基铵盐(如2-丙烯酰氧基乙基三甲基氯化铵、2-甲基丙烯酰氧基乙基三甲基氯化铵、3-甲基丙烯酰氧基-2-羟丙基三甲基氯化铵、3-丙烯酰氧基-2-羟丙基三甲基氯化铵和2-丙烯酰氧基乙基三甲基硫酸甲酯铵盐)。
可以向聚合物提供带正电基团的其他单体包括烯基吖内酯的二烷基氨基烷基胺加合物(如2-(二乙基氨基)乙胺、(2-氨基乙基)三甲基氯化铵以及乙烯基二甲基吖内酯的3-(二甲氨基)丙胺加合物)和二烯丙基胺单体(如二烯丙基氯化铵和二烯丙基二甲基氯化铵)。
在某些优选实施例中,第二亲水单体可以具有丙烯酸酯基,或其他烯键式不饱和基团和聚(环氧烷)基;例如,单丙烯酸酯化的聚环氧烷化合物,其中末端是羟基或烷基醚基团。这些单体具有以下通式:
R3-O-(CH(R3)-CH2-O)n-C(O)-C(R3)=CH2,V,
其中各R3独立地为H或C1-C4烷基,并且n为至少2。
在一个实施例中,该聚(环氧烷)基团(描述为-(CH(R3)-CH2-O)n-)是聚(环氧乙烷)(共)聚物。在另一个实施例中,该聚(环氧烷)基团是聚(环氧乙烷-共-环氧丙烷)共聚物。这些共聚物可以是嵌段共聚物、无规共聚物或梯度共聚物。
合适的亲水单体的其他代表性实例包括但不限于丙烯酸;甲基丙烯酸;2-丙烯酰胺-2-甲基-1-丙磺酸;(甲基)丙烯酸2-羟乙酯;N-乙烯基吡咯烷酮;N-乙烯基己内酰胺;丙烯酰胺;单-或二-N-烷基取代的丙烯酰胺;叔丁基丙烯酰胺;二甲基丙烯酰胺;N-辛基丙烯酰胺;聚(烷氧基烷基)(甲基)丙烯酸酯,包括(甲基)丙烯酸2-(2-乙氧基乙氧基)乙酯、(甲基)丙烯酸2-乙氧基乙酯、(甲基)丙烯酸2-甲氧基乙氧基乙酯、甲基丙烯酸2-甲氧基乙酯、聚乙二醇单(甲基)丙烯酸酯;烷基乙烯基醚,包括乙烯基甲基醚;以及它们的混合物。优选的亲水单体包括选自二甲基丙烯酰胺、(甲基)丙烯酸2-羟乙酯和N-乙烯基吡咯烷酮的那些。
共聚物还可以包含疏水单体单元,其量不会有害地影响配体聚合物结合性能及其水分散性。当存在时,基于100重量%总单体计,聚合物通常包含1至20重量%的这种单体单元。
疏水单体的可用类别包括丙烯酸烷基酯和酰胺,例子为含有C1-C30烷基的烷基酯和含有C1-C30烷基的单或二烷基丙烯酰胺的直链、环状和支链异构体。丙烯酸烷基酯的可用具体实例包括:丙烯酸甲酯、丙烯酸乙酯、丙烯酸正丙酯、丙烯酸正丁酯、丙烯酸异戊酯、丙烯酸正己酯、丙烯酸正庚基酯、丙烯酸异冰片酯、丙烯酸正辛酯、丙烯酸异辛酯、丙烯酸2-乙基己酯、丙烯酸异壬酯、丙烯酸癸酯、丙烯酸十一烷酯、丙烯酸十二烷基酯、丙烯酸月桂酯、丙烯酸十三酯和丙烯酸十四烷酯。烷基丙烯酰胺的可用具体实例包括可以使用的具有戊基、己基、庚基、异莰基、辛基、2-乙基己基、异壬基、癸基、十一烷基、十二烷基、十三烷基和十四烷基的单和二丙烯酰胺。可以使用对应的甲基丙烯酸酯。
可用类别的疏水单体还包括乙烯基单体如醋酸乙烯基酯、苯乙烯、和烷基乙烯基醚,马来酸酐和多官能单体。
配体官能化的聚合物可以通过缩合羰基官能化(共)聚合物与式I的配体化合物来制备:
其中
R2为共价键、C2至C12亚烷基、C5-C12(杂)亚芳基、
R9为C2至C12亚烷基或C5-C12(杂)亚芳基,
各R3独立地为H、-OH、C1-C12烷基或C5-C12(杂)芳基,优选为H或C1-C4烷基,
R4为H、C1-C12烷基、C5-C12(杂)芳基或–N(R3)2,优选为H或C1-C4烷基。
所得聚合物将具有下式的侧胍基基团:
其中
R1为H、C1-C12烷基或C5-C12(杂)芳基,
R2为共价键、C2至C12亚烷基、C5-C12(杂)亚芳基、
R9为C2至C12亚烷基或C5-C12(杂)亚芳基,
各R3独立地为H、-OH、C1-C12烷基或C5-C12(杂)芳基,优选为H或C1-C4烷基,
R4为H、C1-C12烷基、C5-C12(杂)芳基或–N(R3)2,优选为H或C1-C4烷基。
更具体地讲,侧配体基团将具有式:
R9为C2至C12亚烷基或C5-C12(杂)亚芳基,
各R3独立地为H、-OH、C1-C12烷基或C5-C12(杂)芳基,优选为H或C1-C4烷基,
R4为H、C1-C12烷基、C5-C12(杂)芳基或–N(R3)2,优选为H或C1-C4烷基。
该反应可以如下举例说明:
-(MCO)w-(MHydrophil)x-(Mhydrophob)z-→-(MLig)y-(MHydrophil)x--(Mhydrophob)z-(MCO)w*-,
其中
-(MCO)w为具有“w”个聚合的单体单元的羰基官能化单体单元,
-(MHydrophil)x-为具有“x”个聚合的单体单元的亲水单体单元,
-(Mhydrophob)z-为具有“z”个聚合的单体单元的疏水单体单元,
(MLig)y为具有“y”个聚合的单体单元的配体官能化单体单元,其中y小于或等于w;即所有或部分所述羰基由式I配体化合物官能化。w、x和z下标对应所用单体的重量范围:w可以包括10重量%至100重量%的单体混合物,x可以包括0重量%至90重量%的单体混合物,并且z可以包括0重量%至20重量%的单体混合物。“y”指示经配体基团官能化的羰基官能团的数目,并且w*指示未官能化羰基基团的数目。
对用式I的配体化合物官能化羰基官能化聚合物的另一种选择,配体官能化的聚合物可以通过聚合下式的单体而制备:
R1为H、C1-C12烷基或C5-C12(杂)芳基,
R2为共价键、C2至C12亚烷基、C5-C12(杂)亚芳基、
R9为C2至C12亚烷基或C5-C12(杂)亚芳基,
各R3独立地为H、-OH、C1-C12烷基或C5-C12(杂)芳基,优选为H或C1-C4烷基,
R4为H、C1-C12烷基、C5-C12(杂)芳基或–N(R3)2,优选为H或C1-C4烷基。
X为–O-或–NR3-,
R6为C2至C12亚烷基,和
R7为H或CH3。
式VI的单体可以与前述亲水单体共聚。
或者,配体官能化的聚合物可以通过聚合式VII的单体而制备。式VII的单体可以与前述亲水单体共聚。
其中
R1为H、C1-C12烷基,或C5-C12(杂)芳基,
R2为共价键、C2至C12亚烷基、C5-C12(杂)亚芳基、
R9为C2至C12亚烷基或C5-C12(杂)亚芳基,
各R3独立地为H、-OH、C1-C12烷基或C5-C12(杂)芳基,优选为H或C1-C4烷基,
R4为H、C1-C12烷基、C5-C12(杂)芳基或N(R3)2,优选为H或C1-C4烷基,并且R7为H或CH3。
本公开还提供官能性基底,其包含基础基底和其上的配体官能化的聚合物的接枝或未接枝涂层。优选地,基础基底为具有间隙表面和外表面的多孔基础基底。
基础基底可以从任何合适金属、热塑性材料或热固性材料形成。所述材料可以为有机或无机聚合物材料。合适的有机聚合物材料包括(但不限于):聚(甲基)丙烯酸酯、聚(甲基)丙烯酰胺、聚烯烃、聚(异戊二烯)、聚(丁二烯)、氟化聚合物、氯化聚合物、聚酰胺、聚酰亚胺、聚醚、聚(醚砜)、聚(砜)、聚(乙酸乙烯酯)、乙酸乙烯酯的共聚物,例如聚(乙烯)-聚(乙烯醇)共聚物、聚(磷腈)、聚(乙烯基酯)、聚(乙烯基醚)、聚(乙烯醇)以及聚(碳酸酯)。合适的无机聚合物材料包括(但不限于)石英、二氧化硅、玻璃、硅藻土和陶瓷材料。
合适的聚烯烃包括(但不限于):聚(乙烯)、聚(丙烯)、聚(1-丁烯)、乙烯和丙烯的共聚物、α烯烃共聚物(例如乙烯或丙烯与1-丁烯、1-己烯、1-辛烯和1-癸烯的共聚物)、聚(乙烯-共-1-丁烯)以及聚(乙烯-共-1-丁烯-共-1-己烯)。
合适的氟化聚合物包括(但不限于):聚(氟乙烯)、聚(偏二氟乙烯)、偏二氟乙烯的共聚物(例如聚(偏二氟乙烯-共-六氟丙烯))以及三氟氯乙烯的共聚物(例如聚(乙烯-共-三氟氯乙烯))。
合适的聚酰胺包括(但不限于):聚(亚胺基己二酰亚胺基六亚甲基)、聚(亚胺基己二酰亚胺基十亚甲基)以及聚己内酰胺。合适的聚酰亚胺包括但不限于聚(苯均四酸二酰亚胺)。
合适的聚(醚砜)包括但不限于聚(二苯醚砜)和聚(二苯砜-共-氧化二苯砜)。
合适的乙酸乙烯酯的共聚物包括(但不限于):聚(乙烯-共-乙酸乙烯酯)以及其中乙酸酯基团中的至少一些已被水解而提供多种聚(乙烯醇)的那些共聚物。
基础基底可以呈诸如粒子、纤维、膜或片的任何形式。合适的粒子包括(但不限于)磁粒子、有机粒子、无机粒子和多孔的和无孔的粒子。优选基础基底为多孔的。合适的多孔基础基底包括但不限于多孔粒子、多孔膜、多孔非织造幅材和多孔纤维。
在一些实施例中,该多孔基础基底由丙烯均聚物或共聚物形成,最优选由丙烯均聚物形成。聚丙烯聚合物常常是多孔制品(例如非织造物和微孔膜)所选材料,这是由于诸如无毒、惰性、低成本之类的性质以及可容易挤出、模制并成型为制品。
在多个实施例中,多孔基础基底具有通常大于约0.2微米的平均孔径以便使体积排阻分离最小化、使扩散限制最小化以及使基于靶标分子结合的表面积和分离最大化。一般来讲,当用于结合病毒时,孔径在0.1至10微米的范围内,优选0.5至3微米,最优选0.8至2微米。结合其他靶标分子的效率可导致不同的最佳范围。
合适的多孔基础基底包括(但不限于):多孔和微孔的膜、粒子、非织造幅材和纤维。在一些实施例中,所述多孔基础基底是微孔膜,例如热致相分离(TIPS)膜。经常通过形成热塑性材料以及大于该热塑性材料的熔点的第二材料的均相溶液来制备TIPS膜。在冷却时,所述热塑性材料结晶并且与第二材料实现相分离。结晶的热塑性材料常被拉伸。第二材料可选地在拉伸之前或之后被移除。微孔膜还公开于美国专利No.4,539,256(Shipman)、No.4,726,989(Mrozinski)、No.4,867,881(Kinzer)、No.5,120,594(Mrozinski)、No.5,260,360(Mrozinski等人)以及No.5,962,544(Waller)中,这些专利全部转让给了3M公司(圣保罗市,明尼苏达州)。另外,该微孔膜可如美国专利No.5,962,544(Waller)所述从乙烯-乙烯醇共聚物制备。
一些示例性的TIPS薄膜包括聚(偏二氟乙烯)(PVDF)、聚烯烃(例如聚乙烯均聚物或共聚物或者聚丙烯均聚物或共聚物)、含乙烯基聚合物或共聚物(例如乙烯-乙烯醇共聚物)以及含丁二烯聚合物或共聚物、以及含丙烯酸酯聚合物或共聚物。对于一些应用,包含PVDF的TIPS膜尤其可取。包含PVDF的TIPS膜进一步描述于U.S.7,338,692(Smith等人)。
在另一个示例性实施例中,多孔基础基底包含尼龙微孔薄膜或薄片,例如在美国专利No.6,056,529(Meyering等人)、6,267,916(Meyering等人)、6,413,070(Meyering等人)、6,776,940(Meyering等人)、3,876,738(Marinacchio等人)、3,928,517、4,707,265(Knight等人)和5,458,782(Hou等人)中描述的那些。
在其他实施例中,多孔基础基底是非织造幅材,其可包括由任何通常公知的制造非织造幅材的工艺制造的非织造幅材。如本文所用,术语“非织造幅材”是指这样的织物,该织物具有以毡状方式随机和/或单向插入的单纤维或细丝的结构。
例如,可通过湿法成网、梳理成网技术、气纺技术、射流喷网技术、纺粘技术或熔喷技术或它们的组合制备该纤维非织造幅材。纺粘纤维通常为小直径纤维,它们是通过喷丝头的多个细小的、通常为圆形的毛细管将熔融的热塑性聚合物以细丝形式挤出而形成的,其中挤出的纤维的直径迅速减小。熔喷纤维通常通过多个细小的通常圆形的模塑毛细管将熔融的热塑性材料以熔融的线或丝挤出到高速的通常被加热的气体(例如空气)气流中而形成的,该气流使熔融的热塑性材料的丝细化以减小它们的直径。此后,这些熔喷纤维由该高速气流运送并沉积在收集面上,以形成随机分配的熔喷纤维。非织造幅材中的任何者均可由单一类型的纤维或在热塑性聚合物的类型和/或厚度方面不同的两种或更多种纤维制成。
关于本发明的非织造幅材的制备方法的更多细节可见于Wente,Superfine Thermoplastic Fibers,48INDUS.Chem.1342(1956)(Wente的,超细热塑性纤维,工业工程化学)或Wente等人,Manufacture OfSuperfine Organic Fibers,(Naval Research Laboratories Report No.4364,1954)(超细有机纤维生产,(海洋研究实验报告No.4364,1954))中。
在一个实施例中,基础基底可以具有其表面上的配体官能化(共)聚合物的涂层。可用的涂层技术包括将(共)聚合物(任选地包括交联剂)的溶液或分散体涂布到基础基底上。聚合物涂敷通常继以蒸发所述溶剂来形成聚合物涂层。涂布方法包括常常称为浸涂、喷涂、刀涂、棒涂、狭缝式涂布、斜板式涂布、模具涂布、辊涂或凹版印刷涂布的技术。涂层品质一般取决于混合物均匀度,沉积液层的品质,和用于干燥或固化所述液层的方法。
在一些实施例中,首先将羰基官能化(共)聚合物涂布在基础基底上,并随后与式I配体化合物反应。在这些情况下用于涂布操作的可用交联剂包括羰基反应性的化合物,例如聚胺类、聚肼类和聚酰肼类。
在其它实施例中,配体官能化(共)聚合物其自身被涂布在基础基底上。这些情况下可用交联剂包括胺反应性化合物例如双和聚环氧化合物,多元羧酸和其衍生物(如酸性氯化物),多异氰酸酯和甲醛基交联剂例如羟甲基和烷氧基甲基官能化交联剂,例如衍生自尿素或三聚氰胺那些。
在其它实施例中,配体官能化共聚物通过例如EP 472,990中所述那些聚电解质叠层涂布技术被涂布在基础基底上。
在另一个实施例中,所述配体官能化的聚合物可以接枝到基础基底的表面;即共价键形成于配体官能化的聚合物和聚合物基础基底之间。共价键可以通过取代、缩合或自由基方法来形成。接枝的性质取决于用于基础基底的聚合物类型。
在一些实施例中,基体聚合物具有羰基反应性的官能团,例如其表面上的胺。这些表面官能团可以与配体官能化的聚合物上的现存羰基官能团反应。在另一个实施例中,基底表面可以提供有胺反应性官能团,例如可与配体官能化的聚合物的胍基反应的卤离子、环氧基、酯基、异氰酸酯基。
在一些实施例中,所述聚合物可以通过电离辐射引发的单体接枝聚合被接枝到基底表面,所述单体例如式VI或式VII的那些,任选地以及前述其他亲水性或疏水单体。或者,通过电离辐射引发的接枝聚合,然后通过与式I配体化合物反应而官能化,羰基官能化单体可以被接枝到基底表面。
在一些实施例中,基底表面可以用具有可自由基聚合基团和可与配体官能化的聚合物反应的第二官能团的接枝单体来自由基官能化。这种单体可以包括(甲基)丙烯酸异氰酸基乙酯或(甲基)丙烯酸缩水甘油酯。
当暴露于电离辐射、优选电子束或γ辐射时,接枝单体可以接枝(即形成共价键)到基础基底的表面。即,在存在电离辐射的情况下,接枝单体的(甲基)丙烯酰基与多孔基础基底的表面的反应导致经丙烯酸酯基烯键式不饱和可自由基聚合基团直接接枝到基础基底的反应,并还提供具有反应性官能团的基底表面,所述反应性官能团可以随后与配体官能化的聚合物反应。
本发明的方法涉及用电离辐射照射多孔或无孔基底表面以在其上接枝官能化单体的这种表面上制备自由基反应部位。官能化单体的官能团随后允许配体官能化的聚合物被接枝到基底表面。“电离辐射”意指导致在基础基底表面上形成自由基反应部位的足够剂量和能量的辐射。电离辐射可包括β、γ、电子束、x射线和其他电磁辐射。在某些情况下,电晕辐射可为具有足够高的能量的辐射。该辐射具有足够高的能量,使得当被基础基底表面吸收时,足够的能量被转移到该载体以导致在该载体中化学键的裂解以及在该载体上导致形成自由基位点。
将配体官能化的聚合物接枝(或涂布)到基底表面的方法改变基础基底的初始性质,因为所述基底承载有配体官能化的聚合物的接枝或未接枝涂层。本发明允许形成具有许多基础基底优点(如机械和热稳定性,孔隙度)的配体官能化的聚合物基底,而且具有由用于形成给定官能化基底的单体和步骤所得的对于生物物质例如病毒的增大亲和力。
具有配体官能化的聚合物的涂层的多孔基底特别适合用作过滤介质,以用于在生物样品中选择性结合和移除污染蛋白、细胞、细胞碎片、微生物、核酸、和/或病毒。本发明还提供通过使样品与本文所述配体聚合物官能性基底接触而从生物样品中移除靶生物物质的方法。
配体官能化(共)聚合物(聚合物自身,或具有其涂层的基底)可用于纯化包含生物衍生物种(生物物质)的生物或其他流体样品。生物物质包括(但不限于)细胞、细胞碎片、蛋白、核酸、内毒素和病毒。细胞和细胞碎片包括衍生于古细菌、细菌和真核生物的那些。细菌包括(但不限于)革兰氏阴性菌,例如假单胞菌类,大肠杆菌、幽门螺旋杆菌和粘质沙雷氏菌;革兰氏阳性菌,例如葡萄球菌类、肠球菌类、梭状芽孢杆菌类、芽孢杆菌类和乳酸杆菌类;传统上不被革兰氏方法染色的细菌,例如分枝杆菌类,和细菌的非繁殖体形式,例如芽孢。真核生物包括(但不限于)动物细胞、藻类、杂交瘤细胞、干细胞、癌细胞、植物细胞、真菌菌丝、真菌孢子、酵母细胞、寄生生物、寄生卵囊、昆虫细胞和蠕虫。蛋白包括(但不限于)天然蛋白、重组蛋白、酶和宿主细胞蛋白。病毒包括(但不限于)有包膜病毒类,例如疱疹病毒类、痘病毒类、腺病毒、乳多泡病毒类、冠状病毒类、逆转录病毒类如HIV、和原生病毒;和无包膜类,例如杯状病毒、覆盖噬菌体,肌病毒和小核糖核酸病毒。
在一些实施例中,纯化的目的在于从流体中移除所述生物物质。例如,重组蛋白或酶可以在细胞培养物中制备,可以添加(共)聚合物以絮凝蛋白或酶,并且所述沉淀可以作为蛋白或酶的纯化过程中的第一步骤被分离。又如,作为浓缩、清点、和/或辨识微生物的过程中的第一步骤,(共)聚合物或具有其涂层的基底可以用于从流体中捕集微生物。
在其它实施例中,从所述流体中移除的生物物质为在用于所述流体的附加处理步骤之前必须移除的污染物。
聚合物可以用作絮凝剂,以方便在离心或深度过滤操作之前、之后或代替离心或深度过滤操作而从细胞培养物或发酵肉汤中移除细胞和细胞碎片。例如,(共)聚合物可以用于在离心之前在细胞培养肉汤中絮凝细胞,并从而提高离心过程从液态离心滤液中分离细胞群的效率。或者,其可在离心步骤之后添加至液态离心滤液以絮凝悬浮细胞碎片和溶解的宿主细胞蛋白和核酸,从而增加后续深度过滤步骤的效率。其可以用于絮凝或沉淀悬浮细菌、病毒或其他微生物。其可以用于从溶液中沉淀所需或污染蛋白或核酸。显著地,配体官能化(共)聚合物或具有其涂层的基底在高盐浓度或高离子强度条件下是有用的,即,它们是“耐盐的”。术语“盐”包括有助于溶液传导率的所有低分子量离子物种。在存在盐的情况下配体官能化(共)聚合物的实用性的重要性在于,生物制药或酶制造中所使用的许多处理溶液的传导率为15-30mS/cm(大约150-300mM的盐)或更多。耐盐性可与常规季铵或Q配体(如三甲基-铵阳离子配体)的耐盐性进行比较来测量,所述季铵或Q配体与许多生物物质的主要静电相互作用在比目标范围小三至六倍的传导率下迅速劣化。例如,在NaCl浓度从0增加到50mM(大约5-6mS/cm的传导率)时,用常规Q配体衍生化的膜呈现的φX174病毒清除的对数下降值从六(LRV)降低至一(1)LRV。pIs接近于7(中性或接近中性)的病毒如φX174极难从处理液流中移除。当尝试从处理流体中移除其他生物物质时,观察到类似问题。例如,当尝试通过使用用常规Q配体官能化的过滤装置来移除带正电蛋白如宿主细胞蛋白时,处理流体可能必须稀释两倍或更多以将传导率降低至可接受范围。此举成本高并且极大增加总处理时间。
当用作絮凝剂时,相对于样品量的配体官能化(共)聚合物添加量可以在宽泛的范围内变化。一般来讲,所述添加量将产生约0.01μg/mL至约5000μg/mL的混合物中(共)聚合物的最终浓度。添加(共)聚合物的最佳量将取决于需要絮凝的物种的浓度。通常,聚合物量相对于被絮凝物种量将为0.01重量%至100重量%,优选为0.05重量%-30重量%,更优选为约0.1重量%-10重量%范围内。通过用如本领域熟知的一系列聚合物浓度测试所述样品,容易评估最佳量。虽然上述浓度范围是典型的,但本领域技术人员将了解在某些情况下其他范围可以有效。絮凝效率还取决于被絮凝物种的物理和化学特性。例如,我们发现,水性悬浮液中近中性病毒φX174的最佳絮凝发生于约800-1000%的聚合物与病毒重量比处。
使生物样品与配体官能化的聚合物(聚合物本身或具有其涂层的基底)接触一段时间,该时间足以当所述溶液包含0至约50mM的盐,优选当所述溶液包含0至约150mM的盐,更优选当所述溶液包含0至约300mM的盐或更高时与设置(溶解或悬浮)于溶液中的靶标生物物质相互作用并形成络合物,使得剩下的设置在溶液中的靶标生物物质的浓度小于其初始浓度的50%。更优选的是,使所述溶液与配体官能化的聚合物接触一段时间,所述时间足以当所述溶液包含0至约50mM的盐,优选当所述溶液包含0至约150mM的盐,更优选当所述溶液包含0至约300mM的盐或更高时与设置于所述溶液中的靶标生物物质相互作用并形成络合物,使得剩下的设置在溶液中的靶标生物物质的浓度小于其初始浓度的10%。还更优选的是,使所述溶液剂与配体官能化的聚合物接触一段时间,所述时间足以当所述溶液包含0至约50mM的盐,优选当所述溶液包含0至约150mM的盐,更优选当所述溶液包含0至约300mM的盐或更高时与设置于所述溶液中的靶标生物物质相互作用并形成络合物,使得剩下的设置在溶液中的靶标生物物质的浓度小于其初始浓度的1%。
在许多实施例中,水性介质中带正电的配体官能化(共)聚合物将近电中性或带负电的物种结合至式II配体官能团,而其他物种(如带正电的蛋白,例如单克隆抗体)将被排除或排斥于所述配体官能化基底之外。另外,如上文描述的,可将该基底直接或间接接枝有一种或多种离子单体。特别地,所述配体官能化的聚合物可以包含在生物样品溶液的选定pH下带正电以便提高蛋白质静电推斥的接枝离子基团,例如单克隆抗体,其中许多在中性pH下带正电,以及提供耐盐性的式II的配体官能团。
在一些实施例中,配体官能化的聚合物和含有界定生物物质的涂布基底是一次性的。在这种实施例中,生物物质与配体官能化的聚合物的结合优选是基本上不可逆的,因为没有必要回收所述结合的生物物质。尽管如此,如果需要,则可以通过增加离子强度或改变洗脱溶液的pH来颠倒生物物质的结合。
具有配体官能化的聚合物的接枝或未接枝涂层的基底可以是任何此前所述的基底,但优选为微孔膜。可取的膜孔尺寸为0.1至10μm,优选0.5至3μm且最优选为0.8至2μm。对于内孔结构,具有高表面积的膜是可取的,其通常对应于细小孔径。然而,如果孔径太小,则膜往往被存在于样品溶液中的细小颗粒堵塞。
如果需要,可通过使用多个堆叠的、配体官能化的聚合物涂布的多孔膜作为过滤元件来改善结合和捕获的效率。因此本发明提供一种过滤元件,其包括一层或多层多孔配体官能化的聚合物涂布的基底。各个层可以相同或不同,并且可具有不同孔隙度和上述接枝单体的接枝度的层。过滤元件还可包括上游预过滤层和下游支承层。根据需要,各个过滤元件可以是平面的或折叠的。
合适的预过滤器和支承层材料的例子包括聚丙烯、聚酯、聚酰胺、树脂粘合的或无粘合剂的纤维(例如玻璃纤维)以及其他合成材料(织造或非织造羊毛结构)的任何合适的多孔膜;烧结的材料,例如聚烯烃、金属和陶瓷;纱线;专用滤纸(例如纤维、纤维素、聚烯烃和粘合剂的混合物);聚合物膜,等等。
在另一个实施例中,提供了一种滤筒,其包括上述过滤元件。在另一个实施例中,提供一种过滤组件,其包括过滤元件和过滤壳体。在其他实施例中,本发明涉及一种捕集或移除靶标生物物质的方法,其包括以下步骤:
a)提供过滤元件,其包括一层或多层本发明的配体官能化基础基底,以及
b)使含有靶标生物物质的移动生物溶液喷射到过滤元件的上游表面上足够的时间,以实现靶标生物物质的结合。
上文描述了本发明,下面以举例的方式进一步说明本发明,这些实例不应当以任何方式被解释为对本发明的范围的强制限制。相反,应当清楚地理解,可以采用多种其他实施例、修改形式及其等同物。在阅读了本说明书之后,在不脱离本发明的精神和/或所附的权利要求书的范围的情况下,这些实施例、修改形式及其等同物对本领域内的技术人员将是显而易见的。
实例
实例1-5。
将二丙酮丙烯酰胺(40g)、乙醇(60g)和VAZO 67(0.2g)装填至8盎司玻璃瓶。混合物用缓慢氮气流吹扫5分钟,密封,并随后在水浴中翻转且平衡至55℃24小时,以使单体转换为聚合物。聚合物溶液的一部分(4.07g)用甲醇(16.48g)稀释并与氨基胍盐酸盐(1.08g,俄勒冈州波兰特的TCl美国公司(TCI America(Portland,OR)))混合。添加三氟乙酸(4滴)作为催化剂,并且溶液在环境温度下混合2小时。IR和1H-NMR分析确认形成了聚(双丙酮丙烯酰胺脒腙)(聚合物1)。
通过类似工序,将20%、40%、60%和80%的重复单元转换为脒腙官能团,制备聚合物2-5。
实例6-10。
通过实例1中所述工序,在甲醇溶液中制备二甲基丙烯酰胺和双丙酮丙烯酰胺的共聚物。通过实例1中所述工序,使氨基胍与共聚物(含有20重量%、40重量%、60重量%、80重量%和0重量%二甲基丙烯酰胺)反应,不同的是将浓盐酸而非三氟乙酸用作催化剂,以生产对应的脒腙(guanylhydrazone)共聚物6-10。
实例11。
根据以下工序,针对BSA沉淀分析脒腙聚合物1-5。结果示于图1中。
在pH 7.5的10mM MOPS缓冲液(4-吗啉丙磺酸)中制备牛血清白蛋白溶液(BSA,西格玛-奥德里奇(Sigma-Aldrich)),并确定具有4.0mg/mL的BSA浓度。根据下表1,制备含有各种氯化钠浓度的一系列BSA溶液:
表1
用去离子水将实例1-5的聚合物的溶液稀释至1%的固体重量百分比并调整至pH 7。
将5mL聚丙烯离心管装填2.0mL BSA溶液,然后125μL稀释的聚合物溶液。将离心管密封并上下位置颠倒地翻转30分钟,然后以2000rcf离心10分钟。将2mL初始BSA溶液与125μL MOPS缓冲液混合,制备BSA标准溶液。进行一系列1:1稀释以提供总共7个BSA标准物。这七个标准物一式三份地(200μL)被移取进96孔微滴定板的孔中,以及添加来自评估的各聚合物絮凝剂的上清液的一式三份样品。也包括含去离子水作为空白对照的三个孔。使用293nm波长通过SpectraMAX 250微板分光光度计系统(加利福尼亚州桑尼维尔的分子设备公司(Molecular Devices Corp,Sunnyvale,CA))分析所述板。将絮凝剂溶液的吸收与标准物的吸收相比,提供对沉淀BSA的百分比的量度。
比较例1。聚(甲基丙烯酰胺丙基三甲基氯化铵)(pMAPTAC)
将MAPTAC(160g的50重量%水溶液,得自威斯康星州密尔沃基的奥德里奇公司(Aldrich(Milwaukee,WI)))、乙醇(40g)和过硫酸钠(0.4g)装填至16盎司玻璃瓶。混合物用缓慢氮气流吹扫10分钟,密封,并随后在水浴中翻转且平衡至55℃保持24小时,以使单体转换为聚合物。该聚合物溶液用去离子水(80g)和乙醇(40g)稀释并充分混合。通过用pH 7去离子水将该聚合物的一部分稀释至1%固体重量百分比,制备作为絮凝剂评估的样品。如实例11中所述来进行BSA沉淀试验,并且发现pMAPTAC在0mM NaCl下为良好絮凝剂,但其分别在50mM、100mM和150mM NaCl的溶液中残留42%、73%和100%的BSA。
实例12。病毒絮凝剂
在含0,50mM和150mM NaCl的pH 8.010mM TRIS((羟甲基)氨基甲烷)中制备φX174噬菌体(大约109pfu/mL)的水性悬浮液。在pH 7的去离子水中以0.001%聚合物重量百分比制备絮凝剂聚合物的水溶液。将16μL聚合物溶液添加至离心管中2mL噬菌体悬浮液样品。将所述管密封,涡旋,并上下颠倒地转动2小时。然后,以3000rcf将所述管离心10分钟,并且所得悬浮液被过滤通过0.45微米无菌注射器过滤器(GHP Acrodisc,颇尔生命科学公司(Pall Life Sciences))。制备10倍稀释系列。
将1mL各稀释液与1mL大肠杆菌培养物(当在550nm处测量时,生长至0.3-0.6的光密度)混合。等待5分钟后,使用无菌吸移管来使4.5mL TSA顶层琼脂与稀释液/大肠杆菌混合物混合并接种到TSB板上。在顶层琼脂已硬化之后,将所述板倒置并放置于37℃培养箱中过夜。然后,从所述培养箱中移除板并且计数和记录φX174噬菌斑。也以类似方式评估初始病毒悬浮液的稀释系列。比较结果允许估算因絮凝剂处理所致LRV(病毒载量的对数下降值)。若干聚合物的结果列于下表2中:
表2
实例13。
将聚(乙烯基甲基酮)(1.0g,得自纽约安大略的科学聚合产品公司(Scientific Polymer Products,Ontario,New York))溶解于4g乙酸乙酯中。向该溶液添加甲醇(5g)、氨基胍盐酸盐(1.58g)和浓盐酸(1滴)。将混合物混合1小时,然后添加甲醇(5g)和去离子水(5g)以产生橙色溶液。红外线和NMR分析确认转化成了脒腙聚合物。用pH 7去离子水将所述聚合物稀释至1%固体重量百分比,以作为BSA沉淀剂评估。该聚合物在高达250mM NaCl浓度下表现出>50%的BSA沉淀。
比较例2。聚(二烯丙基二甲基氯化铵)(pDADMAC)
向配备有架空搅拌器、冷凝器、加热套膜、热电偶和氮气入口的1升3颈圆底烧瓶装填DADMAC(105.6g 65%固体重量百分比的水溶液,得自威斯康星州密尔沃基的奥德里奇公司(Aldrich(Milwaukee,WI)))、乙二胺四乙酸四钠(6μL 20重量%去离子水溶液)、去离子水(121.8g)和2,2’-偶氮二(2-脒基丙烷)二盐酸盐(1.74g)。开始搅拌,并且混合物用缓慢的氮气流吹扫15分钟。然后,经1小时将搅拌混合物的温度缓慢升高至60℃,然后维持在该温度额外24小时。NMR分析确认形成了期望的聚合物。
实例14-16。
通过类似于比较例2中所述的工序制备DADMAC与双丙酮丙烯酰胺的共聚物。通过实例1中所述工序,使含有20重量%、40重量%和80重量%双丙酮丙烯酰胺的共聚物与氨基胍反应以分别产生对应的20%、40%和80%脒腙共聚物14-16。这些共聚物和pDADMAC的溶液在去离子水(pH 7)中以1重量%制备并在BSA沉淀试验中进行评估。在100mM NaCl下,针对比较例2、实例14、实例15和实例16,这些絮凝剂分别显示0%、30%、62%和92%的BSA沉淀。
实例17。
3M提供嗜热脂肪土芽孢杆菌纯化孢子悬浮液,由大约1.4重量%细胞碎片和孢子组成。通过类似于实例11中所述的工序制备含有0mM、100mM、200mM和300mM NaCl的肉汤试验样本。由实例1、6和8的改性聚合物,在pH 7的去离子水中以1.0%固体百分比制备聚合物溶液。制备这些聚合物中每一个的1:4稀释系列以提供总共6个聚合物浓度。然后,将2mL肉汤样品与0.5mL聚合物溶液混合,并且将所述混合物翻转30分钟,然后以200rcf离心5分钟。通过混合2mL肉汤与0.5mL去离子水制备标准物,经相同混合/离心工序处理混合物,然后由上清液制备2倍系列稀释(6个样品)。将试验溶液的上清液和标准物的上清液移取至96孔微滴定板并通过650nm下吸光度测量进行分析。将絮凝剂溶液的吸收与标准物的吸收相比,提供对絮凝效率的量度。结果示于下表3中:
表3
实例18-20和比较例3-4
通过实例1所述工序在甲醇溶液中制备N,N-二甲氨基丙基丙烯酰胺(DMAPAm)和双丙酮丙烯酰胺(比较例3)的20:80w/w共聚物。
通过添加更多甲醇将该聚合物溶液的样品稀释至20%固体百分比,并且添加足够的丁基溴化物以烷基化共聚物(比较例4)的50%的DMAPAm单元。
通过类似于实例6的工序使比较例3聚合物溶液的样品与氨基胍盐酸盐反应,以产生其中分别有50%和100%的双丙酮丙烯酰胺单元转化为脒腙单元(实例18和19)的共聚物。
通过类似于实例6的工序,使比较例4的样品与氨基胍盐酸盐反应,以将所有双丙酮丙烯酰胺单元转化为脒腙单元(实例20)。
用去离子水将各个上述实例的样品稀释至1%固体百分比,调整至pH 7,并且针对BSA沉淀进行评估(表4)。
表4
通过分别与二甲基硫酸酯、苄基溴化物和十二烷基溴化物的烷基化制备类似共聚物,然后将酮基团转化为脒腙。当针对BSA沉淀进行测试时,再次对烷基化和鸟苷酸化观察到协同增强效应。
实例21。
通过类似于比较例2中所述的工序制备DADMAC与双丙酮丙烯酰胺的50:50w/w共聚物。用去离子水将此共聚物于甲醇中的溶液(1.32g 30%固体百分比溶液)稀释至2%固体百分比,与二氨基胍盐酸盐(74毫克)和浓盐酸(1滴)混合,并使其在室温下反应过夜以形成双-脒腙共聚物。将该溶液调整至pH 7并用去离子水稀释至1%固体百分比。该聚合物在含有高达250mM氯化钠的溶液中表现出对BSA的良好絮凝。
实例22。
将双丙酮丙烯酰胺(33.8g)、甲醇(400mL)和氨基胍盐酸盐(22.1g)放入1L圆底烧瓶并磁性搅拌,直至形成均相溶液。添加三氟乙酸(0.5mL)并且在环境温度下搅拌混合物过夜。在旋转蒸发仪上浓缩所述反应混合物,产生静置后结晶的淡黄油类。添加二乙醚(250mL)并且将结晶物粉碎,过滤,用额外的醚洗涤,并在真空下干燥3小时以提供对应的脒腙盐酸盐单体(53.5g,95.7%产率)。将该单体(10g)与去离子水(23g)、甲醇(7g)和2,2-偶氮二(2-咪唑啉-2-基)丙烷(0.2g,得自日本大阪的WAKO(Osaka,Japan))混合。所述混合物用氮气吹扫15分钟,然后如实例1所述在60℃下聚合24小时。该聚合物显示与实例1相同的絮凝性质。
实例23。
以逐层方法用实例1的聚合物涂布聚丙烯纺粘/熔喷/纺粘(SMS)非织造(50gsm基重)。制备三个涂布浴:
涂布浴#1:异丙醇中的1%wt/wt聚氮丙啶(70,000Mn);
涂布浴#2:去离子水中的0.5%wt/wt聚(2-丙烯酰胺-2-甲基-1-丙磺酸,钠盐);
涂布浴#3:去离子水中的1%wt/wt实例1聚合物。
进行以下涂布顺序(每个浴中5分钟停留时间),在施加各涂层之后用去离子水冲洗5分钟:#1、#2、#1、#2、#3、#2、#3、#2和#3。在室温下干燥过夜之后,从涂布幅材上切割16mm直径圆盘。该圆盘被放置于5mL离心管中,添加2mL产孢梭菌孢子悬浮液(含和不含添加的氯化钠),并且所述混合物在室温下翻转30分钟。在640nm处测量上清液溶液的UV吸光度并且与接触所述圆盘之前的吸光度比较,并指示在0mM和250mM氯化钠浓度下分别为46%和58%的孢子去除率。
实例24。
氨基硅烷涂布的玻璃显微镜载片(可购自威斯康星州麦迪逊的新来者供应公司(Newcomer Supply(Middleton,WI)))顺序地用实例23的涂层溶液#2浸涂,用去离子水冲洗,用实例23的涂层溶液#3浸涂,用去离子水冲洗,并在室温下干燥。然后,可将涂布的载片用于从水性介质中捕集细菌或孢子以便计数或识别。发现仅用涂层溶液#2涂布的对照氨基硅烷载片几乎未结合细菌或孢子。
实例25-28。
在异丙醇中以10重量%制备双丙酮丙烯酰胺溶液。将若干片材基底(大约4英寸×6英寸)(膜和非织造布,如下表所列)放入聚乙烯袋(ZiplocTM,威斯康辛州拉辛的S C约翰逊公司(S C Johnson(Racine,WI)))中。使用一次性移液管,将基底用双丙酮丙烯酰胺溶液完全润湿。将袋子拉紧关闭并用橡胶辊轧机在袋子上碾压,移除过量溶液。将收集的过量溶液用纸巾移除。然后,将所述袋真空包装到FoodsaverTM袋中。所述袋故意未排出氧,以最小化溶剂蒸发。将样品放入铝手提袋并暴露于Co-60γ辐射1小时。暴露剂量相当于5kGy。从袋中取出所述样品,并用足量水洗涤以去除任何均聚物痕迹。然后风干完全洗涤的样品。
然后,将双丙酮丙烯酰胺接枝膜转化为脒腙官能化膜。通过溶解65g氨基胍于1升甲醇并添加三氟乙酸(2.25mL)来制备氨基胍溶液。将各膜放入500mL聚乙烯瓶中,添加100mL氨基胍溶液,将瓶密封,并在室温下将混合物置于辊轧机上过夜。移除过量溶液,并且用去离子水充分洗涤所述膜并干燥。
从片材中冲出24mm圆盘并放入离心管中。在pH 8.025mM TRIS缓冲液(三(羟甲基)氨基甲烷,西格玛(Sigma))中,制备浓度0.75mg/mL的牛血清白蛋白溶液(BSA,西格玛奥德里奇公司(Sigma Aldrich))。将4.5mL BSA溶液移取到各离心管中,将所述管封盖,并且将管翻转过夜。通过UV-VIS光谱仪在279nm处分析上清液溶液,在325nm处施加背景校正。发现样品的静态结合容量为1mg/mL至4mg/mL。未接枝基底的分析显示结合容量为<0.2mg/mL。
表 | 基底 |
实例25 | 聚偏二氟乙烯膜,2μm标称孔尺寸 |
实例26 | 尼龙6,熔喷非织造幅材 |
实例27 | 尼龙66膜,单个增强层尼龙三区膜,标称孔尺寸1.8μm |
实例28 | 聚丙烯非织造幅材,作为3M DoodledusterTM布销售 |
实例29
4.3μm有效纤维直径和样品尺寸约30cm×43cm(1290cm2或200平方英寸)的60gsm尼龙6熔喷非织造基底用空气吹扫并在氮气气氛(小于20ppm氧)插入到手套箱中的拉锁袋内并密封。然后,从手套箱中移除所述拉锁袋,并使其通过电子束来受到剂量水平60kGy(千戈瑞)的辐射。将袋放回N2气氛控制的手套箱中。
打开拉锁袋,通过注入150g氮吹扫的吸取溶液来吸取非织造基底,该溶液包含:17%二丙酮丙烯酰胺单体、10%带羟基端基的聚乙二醇(平均分子量4,600g/mol(PEG 4600))、1.0%Sartomer SR-550聚乙二醇-丙烯酸酯和在具有非织造基底的拉锁袋内72重量%的水。使非织造布保持平坦,并完全且均匀地用轻微过量的接枝溶液饱和。将拉锁带密封。拉锁带留在氮气填充的手套箱内部,以允许有足够长的时间用于所有接枝单体通过与非织造基底的自由基反应而接枝共聚化。在最少6小时或最长约18小时(过夜)之后,将接枝尼龙非织造样品从手套箱和拉锁袋中移除,并且接枝非织造布通过浸泡于2升新鲜去离子水洗涤三次(以移除PEG和任何未反应单体),然后风干至环境条件。
制备去离子水中氨基胍(92g)和浓盐酸(3.45mL)的溶液(1500mL总溶液体积)。将一片接枝非织造布(大约12cm×40cm)放入1加仑塑料广口瓶内。一部分(500mL)氨基胍溶液添加至所述广口瓶,然后将其密封并放置在滚轧机上在室温下过夜反应。滗析出过量氨基胍溶液剂,将衍生的非织造片材在液流或去离子水下冲洗15分钟,然后使片材在室温下风干。从涂布幅材上切割24mm直径圆盘。将该圆盘放入5mL离心管,添加4.5mL的牛血清白蛋白(BSA)溶液(25mM TRIS中大约3mg/mL,pH 8.0),并且混合物在室温下翻转过夜。在279nm处测量上清液溶液的UV吸光度,并且与接触所述圆盘之前的吸光度比较以测定BSA的静态结合容量。发现官能化非织造布每克幅材材吸收152mgBSA。
实例30。
使用标准微生物工序,制备以下培养物:
a)萎缩芽孢杆菌(孢子和细胞碎片)
b)产孢梭菌(孢子)
c)大肠杆菌(细胞和细胞碎片)
d)中国地鼠卵巢(CHO)细胞
e)面包酵母
当在这些混合物上以类似于实例17中所述方式进行絮凝实验时,本发明的配体官能化的聚合物在存在氯化钠浓度超过50mM的情况下连贯地显示良好絮凝能力。
实例31。
在室温下搅拌氨基胍盐酸盐(1.11g)、甲醇(15g)和甲基丙烯酸乙酰乙酸乙酯(2.2g)并且用NMR周期性监测。在搅拌21小时之后,NMR确认甲基丙烯酸酯单体完全转化为对应的脒腙盐酸盐。
Claims (27)
1.一种配体官能化的聚合物,其包含经侧胍基官能化的羰基-官能化(共)聚合物。
4.根据权利要求1所述的配体官能化的聚合物,其中所述羰基官能化(共)聚合物选自:丙烯醛、乙烯基甲基酮、乙烯基乙基酮、乙烯基异丁基酮、双丙酮(甲基)丙烯酰胺、丙烯酸丙酮酯、一氧化碳共聚物、和双丙酮(甲基)丙烯酸酯(共)聚合物。
6.根据权利要求2所述的配体官能化的聚合物,其包含聚合的下式的单体单元:
其中
R1为H、C1-C12烷基或C5-C12(杂)芳基,
R2为共价键、C2至C12亚烷基或C5-C12(杂)亚芳基、
R9为C2至C12亚烷基或C5-C12(杂)亚芳基,
各R3独立地为H、C1-C12烷基或C5-C12(杂)芳基,优选为H或C1-C4烷基,
R4为H、C1-C12烷基、C5-C12(杂)芳基或–N(R3)2,优选为H或C1-C4烷基,和
R7为H或CH3。
7.根据权利要求4所述的配体官能化的聚合物,其还包括亲水单体单元。
8.根据权利要求2所述的配体官能化的聚合物,其具有下式:
-(MLig)y-(MHydrophil)x--(Mhydrophob)z-(MCO)w*-,
其中
-(MCO)w为具有“w”个聚合的单体单元的羰基官能化单体单元,
-(MHydrophil)x-为具有“x”个聚合的单体单元的亲水单体单元,
-(Mhydrophob)z-为具有“z”个聚合的单体单元的疏水单体单元,
(MLig)y为具有“y”个聚合的单体单元的配体官能化单体单元,
y为10至100重量%的所述单体单元;
x为0至90重量%的所述单体单元;和
w*可包含0至90重量%的所述单体单元,和
z为0至20重量%,基于100重量%总单体计。
9.一种聚合物絮凝剂,其包含权利要求1所述的配体官能化的聚合物。
10.一种官能化的基底,其包含基础基底,所述基础基底在其表面上具有权利要求1所述配体官能化的聚合物。
11.根据权利要求10所述的官能化的基底,其中所述配体官能化的聚合物被涂布在所述基底上。
12.根据权利要求10所述的官能化的基底,其中所述配体官能化的聚合物被接枝在所述基底上。
13.根据权利要求10所述的官能化的基底,其中所述基础基底是多孔的。
14.根据权利要求13所述的官能化的基底,其中所述多孔的基础基底为微孔的基础基底。
15.根据权利要求13所述的官能化的基底,其中所述多孔的基础基底为非织造幅材。
16.一种从流体中分离生物物质的方法,其包括:使所述流体与权利要求10所述的官能化的基底接触从而形成包含所述官能化的基底和所述生物物质的络合物,和分离所述络合物。
17.根据权利要求16所述的方法,其中所述生物物质选自细胞、细胞碎片、病毒、蛋白质、核酸和内毒素。
18.根据权利要求16所述的方法,其中所述官能化基底选自粒子、纤维、膜或片。
19.根据权利要求16所述的方法,其中所述官能化的基底为织造或非织造幅材。
20.一种从流体中分离生物物质的方法,其包括:使所述流体与权利要求1所述的聚合物接触从而形成包含所述聚合物和所述生物物质的沉淀或络合物,和分离所述沉淀或络合物。
21.根据权利要求20所述的方法,其中所述生物物质选自细胞、细胞碎片、病毒、蛋白质、核酸和内毒素。
22.根据权利要求21所述的方法,其中所述细胞选自古细菌、细菌和真核生物。
23.根据权利要求20所述的方法,其中所述生物流体衍生于细胞培养或发酵过程。
24.根据权利要求20所述的方法,其中所述流体在分离所述沉淀之后包含纯化的蛋白或酶的溶液。
25.根据权利要求20所述的方法,其中所述分离的沉淀包含纯化的蛋白或酶。
26.根据权利要求20所述的方法,其中所述流体的含盐量为至少50mM。
27.根据权利要求20所述的方法,其中所述流体的含盐量为至少100mM。
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EP3070472A1 (en) | 2016-09-21 |
US20130137158A1 (en) | 2013-05-30 |
EP2537028B1 (en) | 2016-04-27 |
US20110201078A1 (en) | 2011-08-18 |
US9296847B2 (en) | 2016-03-29 |
KR101808356B1 (ko) | 2018-01-18 |
US8945896B2 (en) | 2015-02-03 |
US20150166703A1 (en) | 2015-06-18 |
US8377672B2 (en) | 2013-02-19 |
EP2537028A1 (en) | 2012-12-26 |
KR20130009771A (ko) | 2013-01-23 |
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EP3070472B1 (en) | 2018-05-23 |
WO2011103106A1 (en) | 2011-08-25 |
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