CN111732718B - 一种具有抗菌和抗病毒功能的水溶性共轭聚合物及其制备与应用 - Google Patents

一种具有抗菌和抗病毒功能的水溶性共轭聚合物及其制备与应用 Download PDF

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CN111732718B
CN111732718B CN202010541408.5A CN202010541408A CN111732718B CN 111732718 B CN111732718 B CN 111732718B CN 202010541408 A CN202010541408 A CN 202010541408A CN 111732718 B CN111732718 B CN 111732718B
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展永
邢成芬
高冬
齐俊杰
安海龙
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Hebei kaierwei Biotechnology Co., Ltd
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Abstract

本发明提供一种具有抗菌、抗病毒功能的水溶性共轭聚合物及其制备与应用。以水溶性聚噻吩为主要组分，通过将形成所述水溶性聚噻吩的单体与其他受体单元共聚而成；形成所述水溶性聚噻吩的单体至少包括下述结构式所示的单体：
Figure DDA0002538982180000011
所述水溶性共轭聚合物结构式如式I所示：

Description

一种具有抗菌和抗病毒功能的水溶性共轭聚合物及其制备与 应用
技术领域
本发明属于生物技术领域，具体涉及一种具有抗菌、抗病毒功能的水溶性共轭聚合物及其制备与应用，更具体地涉及一种可以避免细菌以及病毒耐药性的光功能高分子及其制备方法与应用。
背景技术
细菌的耐药性以及病毒的抗药性已经成为了临床治疗的难题，造成了巨大的经济损失以及社会负担。由于抗生素的滥用以及病毒自身变异性强的特点，新型的可以有效避免细菌以及病毒耐药性的治疗方式已经成为了医学、生物学等领域的研究热点。
光动力治疗和光热治疗的方法是针对细菌或者病毒的抗药性的一种非常有效的治疗方式，该方法通过光化学反应产生生物分子毒性物质(如活性氧或者热量)，从而可以高效的杀伤病毒或者细菌并且不会导致其产生耐药性从而达到对精准的、耐突变性的杀伤的目的。由于光动力治疗方法是通过外界光源进行控制的，因而采用光化学治疗方法具有计量可控，区域可控，生物毒性小以及副作用低等特点。有机共轭分子作为光动力治疗的光敏试剂，具有优异的光学稳定性，同时克服了传统无机光热试剂稳定性、生物相容性差的缺点，近年来在生物成像、肿瘤的光动力治疗、光热治疗及联合治疗等领域得到广泛关注。
有必要研究可以无视病毒变异特性、持续有效的抗菌或者抗病毒的方法，从而在医学、防护等领域得到应用。
发明内容
本发明的一个目的在于公开一种同时具有抗菌、抗病毒功能的水溶性共轭聚合物。该聚合物可以高效地对细菌或病毒进行杀伤，同时能够有效地避免抗菌、抗病毒治疗过程中产生耐药性。
本发明所提供的具有抗菌、抗病毒功能的水溶性共轭聚合物，以水溶性聚噻吩为主要组分，通过将形成所述水溶性聚噻吩的单体与其他受体单元共聚而成；
所述水溶性共轭聚合物中，以摩尔百分含量计，形成所述水溶性聚噻吩的单体占85～100％，其他受体单元占0～15％(端点值0不可取)；
形成所述水溶性聚噻吩的单体以噻吩为母体，其侧链含有水溶性基团，
具体地，形成所述水溶性聚噻吩的单体至少包括下述结构式所示的单体：
Figure RE-GDA0002631192640000021
其中，X-可为F-、Cl-、Br-、OH、SO4 -、NO2 -等阴离子基团；
n为2-12的整数，具体可为3，R可为C1-C6的烷基，具体可为甲基；
其他受体单元具体可为吡咯并吡咯二酮结构单元。
具体地，所述水溶性共轭聚合物由95％的形成所述水溶性聚噻吩的单体与5％的吡咯并吡咯二酮结构单元共聚合成；
更具体地，所述水溶性共轭聚合物由各噻吩单元通过2,5位相连，然后与吡咯并吡咯二酮结构相连，组成共轭主链，同时侧链含有水溶性基团，其结构式如式I所示：
Figure RE-GDA0002631192640000022
式I中，m1+m2+m3+m4＝1-40；m1＝0-20；m2＝0-20；m3＝1-20；m4＝1-5，并且 m4/(m1+m2+m3+m4)不高于5％；
具体地，所述式I所示水溶性共轭聚合物的结构式如下所示：
Figure RE-GDA0002631192640000031
m1+m3+m4＝1-40；m1＝1-20；m3＝1-20；m4＝1-5，并且m4/(m1+m3+m4)不高于5％；
上述式I所示水溶性共轭聚合物通过如下方法制备得到：将各单体通过氧化偶联反应进行聚合，即得。
具体地，上述式I所示水溶性共轭聚合物通过包括如下步骤的方法制备得到：在反应瓶中依次加入10mL氯仿,无水三氯化铁(325mg,2mmol)，按照比例然后滴加不同单体使其量的和为1mmol，室温下反应24-72小时；使用甲醇猝灭反应并且离心，甲醇/ 氯仿(1:1)洗涤，然后加入氯化四丁基铵，生成黑色沉淀；将沉淀过滤后使用甲醇溶解，旋干，洗涤，利用截留分子量为3500Da的透析袋透析2天；减压除去溶剂后真空干燥得到固体。
上述水溶性共轭聚合物在制备具有抗菌、抗病毒功能的产品中的应用也属于本发明的保护范围。
所述应用中，所述共轭聚合物通过溶液状态或薄膜状态在外界光源光照射下产生活性氧或者光热效应实现抗菌、抗病毒功能；
所述菌具体可为大肠杆菌；
所述病毒具体可为EV71病毒、流感病毒和2019-nCoV病毒。
所述具有抗菌、抗病毒功能的水溶性共轭聚合物的溶液通过如下方法进行制备：将水溶性共轭聚合物溶于水溶液中，超声，即可；
其中，所述水溶性共轭聚合物的浓度可为0.1mg/mL～10mg/mL。
具有抗菌、抗病毒功能的水溶性共轭聚合物的薄膜通过如下方法进行制备：通过超声分散将水溶性共轭聚合物分散于水中，然后采用涂覆法或浸泡法组装在基膜上，之后将基膜置于真空干燥箱中干燥，即可；
所述水溶性共轭聚合物的浓度可为0.1mg/mL～10mg/mL；
所述干燥的条件为：在真空度小于500Pa的条件下，20-70℃干燥12-72小时；
所述基膜可为无纺布；
所述浸泡法包括以下步骤：将基膜浸泡在水溶性共轭聚合物的水溶液中，浸泡1-12 小时后，使用抽滤的方式将目标化合物负载在基膜上；
所述涂覆法包括以下步骤：将水溶性共轭聚合物溶液涂到基膜表面，涂覆次数为1-20次，使目标化合物负载在基膜上。
所述光源为波长含有400nm-900nm的连续光源或者波长处于400nm-900nm区域的单一波长的光源。
本发明的实质性特点为：本发明中共轭聚合物由多个噻吩单元共聚而成，其较强的共轭效应使得其有极强的光响应能力，而在侧链中引入亲水性侧链可以有效的调节其聚集行为，从而提高单线态氧产生的量子效率。水溶性共轭聚合物与细菌、真菌和病毒等表面有较强结合能力，因而能够作为光敏材料在白光照射下产生单线态氧达到对其进行杀伤的目的。这种杀伤效果与抗生素相比，不容易诱导耐药性，是一种高效优良的抗菌、抗病毒方法。同时，在共轭骨架中引入吡咯并吡咯二酮结构可以利用共轭单元之间的给受体相互作用对能级进行调节，从而赋予其对不同波长的光的响应能力，同时也具备一定程度的光热转换能力。
本发明的有益效果为：本发明得到的抗菌、抗病毒的水溶性共轭聚合物，与传统的抗菌、抗病毒药物相比，具有高效、使用时间长等特点。本发明中共轭聚合物在光照条件下具有较好的抗菌、抗病毒效果，同时，本发明中共轭聚合物抗菌不容易产生耐药性，且开发周期相对于抗菌、抗病毒药物短，因而可以高效的应用于临床抗菌、抗病毒治疗当中。
附图说明
图1为本发明实施例1制备的水溶性共轭聚合物用于杀灭大肠杆菌实验结果。
图2为本发明实施例3中水溶性共轭聚合物材料对EV71病毒杀灭的效果。
图3为本发明实施例4中水溶性共轭聚合物材料对流感病毒抑制作用研究结果。
图4为本发明实施例5中水溶性共轭聚合物材料对2019-nCoV病毒抑制作用研究结果。
具体实施方式
下面通过具体实施例对本发明进行说明，但本发明并不局限于此。
下述实施例中所使用的实验方法如无特殊说明，均为常规方法；下述实施例中所用的试剂、生物材料等，如无特殊说明，均可从商业途径得到。
下述实施例中所使用的单体M1，结构式如下：
Figure RE-GDA0002631192640000051
参照文献Synthetic Communications,1996,26(20),3725–3732合成；
下述实施例中所使用的单体M3，结构式如下：
Figure RE-GDA0002631192640000052
参照文献Chemical Communications,2013,49,5538-5540合成；
下述实施例中所使用的单体M4，结构式如下：
Figure RE-GDA0002631192640000053
参照文献European Journal of Organic Chemistry,2016(15),2617-2627合成。
实施例1、水溶性共轭聚合物的合成
在反应瓶中依次加入10mL氯仿,无水三氯化铁(325mg,2mmol)，以及单体M120.2mg(0.1mmol)，单体M3 224.2mg(0.8mmol)，单体M4 59.3mg(0.1mmol)，使其总的物质的量为1mmol，室温下反应24小时。使用甲醇猝灭反应并且离心，甲醇/ 氯仿(1:1)洗涤，然后加入氯化四丁基铵，生成黑色沉淀。将沉淀过滤后使用甲醇溶解，旋干，洗涤，利用截留分子量为3500Da的透析袋透析2天；减压除去溶剂后真空干燥得到紫黑色固体。
实施例2、水溶性共轭聚合物用于杀灭大肠杆菌
使用超纯水配制100μL水溶性共轭聚合物(实施例1制得)溶液，使其浓度达到30μg/mL。加入OD600＝1的大肠杆菌悬浮液100μL。将体系在4℃静置5min，通过震荡使细菌和水溶性共轭聚合物混合均匀。之后放入37℃培养箱孵育十分钟，并且用0.5W的白光光照5分钟，之后吸取10μL菌液稀释104倍，取20μL涂板，培养皿37℃培养箱培养12小时后对菌落数进行计数。其中，未加水溶性共轭聚合物的溶液以及加入了水溶性共轭聚合物但是没有光照的实验组作为对照。其结果如附图1所示，结果表明该水溶性共轭聚合物在光照条件下具有良好的抗菌性能。
实施例3、水溶性聚噻吩复合物用于杀灭EV71病毒
将水溶性共轭聚合物(实施例1制备的聚合物)配制成溶液，使水溶性共轭聚合物的浓度为1mM，分别放入到1.5mL离心管中，按照下表中的加样量配制溶液
Figure RE-GDA0002631192640000061
之后加入0.2mLEV71病毒毒液，混匀。将实验组Tn室温光照30分钟，光源强度不小于40mW/cm2(50W卤钨灯，光照距离30cm)，将对照组C置于室温暗盒中30分钟。对取下的样本进行病毒半数感染剂量(TCID50)的测定，其处理结果如附图2所示。根据附图结果可以观察到材料光照后对病毒有明显的抑制效果。
实施例4、水溶性聚噻吩复合物用于杀灭流感病毒
将水溶性共轭聚合物(实施例1制备的聚合物)稀释得到最终浓度为166.67 ug/mL、55.56ug/mL、18.52ug/mL、6.17ug/mL、2.058ug/mL的水溶液，之后与流感病毒PR8进行混合，30mW的功率下照射20min，置于黑暗环境中20min后，加入到MDCK细胞中，利用噬斑测定流感病毒滴度。结果显示(附图3：高浓度条件光照对流感病毒有完全抑制作用，2.058ug/mL作用后流感病毒空斑少于不加高分子材料只加病毒孔的空斑数，有部分抑制作用。此外，此浓度下的高分子材料同培养基DMEM 一样本身不会影响病毒形成空斑。因此，该水溶性共轭聚合物具有良好的抑制流感病毒的效果。
实施例5、水溶性聚噻吩共轭聚合物用于杀灭新型冠状病毒2019-nCoV
配制一系列水溶性共轭聚合物(实施例1制备的聚合物)的浓度从0.1ug/mL到15ug/mL的水溶液，之后与新型冠状病毒2019-nCoV进行混合，之后在0.05W的功率下照射15min，置于黑暗环境中20min后，加入到MDCK细胞中，利用噬斑计算病毒杀伤效率。其结果如附图4所示，结果显示该共轭聚合物具有明显的杀灭新型冠状病毒2019-nCoV的效果。

Claims (5)

1.一种水溶性共轭聚合物，由各噻吩单元通过2,5位相连，然后与吡咯并吡咯二酮结构相连，组成共轭主链，同时侧链含有水溶性基团，其结构式如下所示：
Figure FDA0003045997550000011
m1+m3+m4＝1-40；m1＝1-20；m3＝1-20；m4＝1-5，并且m4/(m1+m3+m4)不高于5％。
2.权利要求1所述的水溶性共轭聚合物在制备具有抗菌、抗病毒功能的产品中的应用；
所述菌为大肠杆菌；
所述病毒为EV71病毒、流感病毒和2019-nCoV病毒。
3.一种活化权利要求1所述的共轭聚合物的方法，为：将所述共轭聚合物以溶液状态或薄膜状态在外界光源光照射下产生活性氧或者光热效应。
4.根据权利要求3所述的方法，其特征在于：所述光源为波长含有400nm-900nm的连续光源或者波长处于400nm-900nm区域的单一波长的光源。
5.一种具有抗菌、抗病毒功能的产品，由权利要求1所述的水溶性共轭聚合物制成；
所述菌为大肠杆菌；
所述病毒为EV71病毒、流感病毒和2019-nCoV病毒。
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