CN114805854A - 一种兼具ros清除及多重抗菌的聚赖氨酸导电水凝胶 - Google Patents
一种兼具ros清除及多重抗菌的聚赖氨酸导电水凝胶 Download PDFInfo
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Abstract
本发明属于生物医用高分子材料和医疗器械领域，具体涉及一种兼具ROS清除及多重抗菌的聚赖氨酸导电水凝胶，包括L‑精氨酸改性的聚赖氨酸、醛基功能化改性的天然粘多糖(例如透明质酸钠、海藻酸钠、羧甲基纤维素钠，等等)、化学交联剂(包括聚乙二醇二丙烯酸酯)以及具有近红外光响应的纳米复合材料(例如碳纳米管)。其制备方法包括：将通过化学改性L‑精氨酸修饰改性的聚赖氨酸、高碘酸钠氧化的天然粘多糖在席夫碱和化学交联剂作用下形成具有多重交联网络的水凝胶，并赋予其优异的机械强度、多重抗菌机制、组织兼容性以及ROS清除能力与电传导等多方面的优势，实施条件温和可控、性能可调，可广泛用于创伤修复、心血管、可穿戴设备以及组织工程等生物医学领域。
Description
技术领域
本发明属于生物医用高分子材料和医疗器械领域，具体涉及一种兼具ROS清除及多重抗菌的聚赖氨酸导电水凝胶。
背景技术
细菌感染作为严重影响人类生命健康安全的疾病之一，全球每年有超千万的患者正在遭受细菌的侵害。自1940年青霉素量产后，青霉素作为细菌性疾病的克星为临床相关疾病的治疗开辟了全新的途径，挽救了无数患者。然而，由于抗生素的过度使用或使用不当导致的抗生素滥用引发的细菌耐药性增加，严重影响抗生素的使用效率，导致医疗资源浪费所及临床高死亡率。因此，亟需开发全新的杀菌技术和抗菌材料消除或减缓耐药菌的出现。近年来，随着技术的发展，以抗菌材料为代表的新一代抗菌策略已经有望成为取代传统抗生素疗法的潜在手段。与单一方式相比通过结合多种杀菌手段的抗菌策略更有效、杀菌效率更高且不会或很少产生耐药菌。
在组织修复与再生过程中，其相对应的组织微环境过度表达的ROS严重影响受损组织的再生与重塑，引起组织生理环境紊乱，进而导致炎症性疾病的产生。因此，对受损组织部位过度表达的ROS进行及时有效地消除对于改善组织微环境的炎症水平促进组织部位的再生与修复具有十分重要的意义。
发明内容
针对现有技术的不足，本发明提供一种兼具ROS清除及多重抗菌性能的聚赖氨酸导电水凝胶。旨在通过席夫碱和化学交联剂作用构建具有多重交联网络的水凝胶，并赋予其优异的机械强度、多重抗菌性、组织兼容性以ROS清除能力与电传导等方面的优势，实施条件温和可控、性能可调，可广泛用于创伤修复、心血管、可穿戴设备以及组织工程等生物医学领域。
为实现上述目的，本发明采用以下的技术方案：
(1)向L-精氨酸盐酸盐溶液中依次加入1-(3-二甲氨基丙基)-3-乙基碳二亚胺盐酸盐和N-羟基丁二酰亚胺对L-精氨酸盐酸盐的羧基基团进行活化后加入聚赖氨酸进行反应，待反应结束后进行透析纯化后，冻干可得L-精氨酸改性的聚赖氨酸聚合物；
(2)在暗室中向含有邻二醇结构的粘多糖溶液中滴加高碘酸钠溶液并进行反应，待反应结束后加入乙二醇终止高碘酸钠对粘多糖结构的继续氧化后进行透析纯化，冻干可得醛基功能化改性的天然粘多糖；
(3)将所述的L-精氨酸改性的聚赖氨酸聚合物、醛基功能化改性的天然粘多糖、化学交联剂、近红外光响应的纳米复合材料以及光引发剂依次溶解混合后，使用紫外光照射固化，即得聚赖氨酸导电水凝胶。
优选的，步骤(1)所述聚赖氨酸溶液的浓度为1-30mg/mL，聚赖氨酸分子量为2000-5000Da；L-精氨酸盐酸盐的羧基与聚赖氨酸的氨基摩尔比为5∶1-1∶2；1-(3-二甲氨基丙基)-3-乙基碳二亚胺盐酸盐与L-精氨酸盐酸盐的摩尔比为2∶1-1∶3；1-(3-二甲氨基丙基)-3-乙基碳二亚胺盐酸盐与N-羟基丁二酰亚胺的摩尔比为3∶1-1∶1；反应温度为4-60℃，反应时间为12-72小时；透析温度为25-60℃，透析袋截留量大小为500-3000Da，透析时间为12-96小时。
优选的，步骤(2)所述高碘酸钠溶液的浓度为10-200mg/mL，高碘酸钠溶液的滴加时间为10-60分钟，滴加高碘酸钠溶液后的反应时间为1-3小时，滴加乙二醇后的反应时间为0.5-3小时，反应温度为25-60℃，透析温度为25-60℃，透析袋截留量大小为1000-12000Da，透析时间为12-96小时。
优选的，步骤(2)所述粘多糖包括但不限于透明质酸钠、海藻酸钠、羧甲基纤维素钠的至少一种；粘多糖的浓度为1-10mg/mL，溶解温度为25-60℃，溶解时间为3-36小时。
优选的，步骤(3)所述的聚赖氨酸L-精氨酸改性的聚赖氨酸聚合物的浓度为50-200mg/mL，醛基功能化改性的天然粘多糖浓度为10-100mg/mL，化学交联剂的浓度为30-150mg/mL，近红外光响应的纳米复合材料的浓度为1-5mg/mL，光引发剂的浓度0.5-20mg/mL，光照时间为0-90分钟。
优选的，步骤(3)所述的化学交联剂包括但不限于N，N′-亚甲基双丙烯酰胺、聚乙二醇二丙烯酸酯、聚醚二丙烯酸酯的至少一种。
优选的，步骤(3)所述的近红外光响应的纳米复合材料包括但不限于碳纳米管、石墨烯、四氧化三铁纳米粒子的至少一种。
优选的，步骤(3)所述的光引发剂包括但不限于I2959、LAP、α-酮戊二酸的至少一种。
本发明还提供由上述方法制备的聚赖氨酸导电水凝胶。
本发明还提供由上述方法制备的聚赖氨酸导电水凝胶在创伤修复、心血管、可穿戴设备以及组织工程等生物医学领域的应用。
与现有技术相比，本发明的有益效果在于：
本发明利用L-精氨酸盐酸盐对天然抗菌材料进行功能化改性后与醛基功能化的粘多糖材料进行混合，在生理条件下发生席夫碱的化学交联反应构建内源性广谱抗菌水凝胶支架，用于模拟细胞外基质的动态微环境，实现其促组织修复与重建的功能。此外，通过化学交联剂的引入，使得水凝胶在紫外光的照射下形成多重交联网络，通过席夫碱的动态交联和碳碳双键的共价交联形成的强弱结合使得聚赖氨酸水凝胶的机械强度得到进一步提升，确保水凝胶支架在发挥其生理功能的同时，基体不会崩塌。最后，通过负载具有近红外光响应的纳米复合材料赋予水凝胶支架在近红外照射下双重抗菌功效，并实现其良好的电传导性能。本发明所述聚赖氨酸水凝胶成胶方式温和、环保，无副产物产生，实施条件温和可控、性能可调，且由于聚赖氨酸和L-精氨酸的存在赋予水凝胶良好组织兼容性以及ROS清除能力，可广泛用于创伤修复、心血管、可穿戴设备以及组织工程等生物医学领域。
附图说明
图1是本发明所述L-精氨酸改性的聚赖氨酸聚合物的合成机理图。
图2是本发明所述L-精氨酸改性的聚赖氨酸聚合物的核磁共振氢谱。
图3是本发明所述聚赖氨酸导电水凝胶的导电性能示意图。
图4是本发明所述聚赖氨酸导电水凝胶的抗菌示意图。
图5本发明所述可聚赖氨酸导电水凝胶的热成像示意图。
图6是本发明所述聚赖氨酸导电水凝胶的DPPH清除示意图。
图7是本发明所述聚赖氨酸导电水凝胶的抗氧化数据图。
图8本发明所述可聚赖氨酸导电水凝胶清除活性氧示意图。
图9本发明所述可聚赖氨酸导电水凝胶的扫描电镜示意图。
具体实施方式
根据下述实施例和附图，可以更好地理解本发明并对本发明作进一步说明。然而，实施例所描述的内容仅用于说明本发明，而不是对本发明权利要求的限制。
实施例1
(1)向L-精氨酸盐酸盐溶液中依次加入1-(3-二甲氨基丙基)-3-乙基碳二亚胺盐酸盐和N-羟基丁二酰亚胺对L-精氨酸盐酸盐的羧基基团进行活化后加入聚赖氨酸在30℃进行反应12小时，待反应结束后将反应液转移至透析袋中透析24小时进行纯化，最后利用冷冻干燥机进行冻干，即得L-精氨酸改性的聚赖氨酸聚合物；其中聚赖氨酸溶液的浓度为10mg/mL，L-精氨酸盐酸盐的羧基与聚赖氨酸的氨基摩尔比为1∶1，1-(3-二甲氨基丙基)-3-乙基碳二亚胺盐酸盐与L-精氨酸盐酸盐的摩尔比为1∶1，1-(3-二甲氨基丙基)-3-乙基碳二亚胺盐酸盐与N-羟基丁二酰亚胺的摩尔比为1.2∶1，透析温度为37℃，透析袋截留量大小为3000Da。
(2)首先在30℃搅拌6小时溶解制备10mg/mL的海藻酸钠溶液，然后在暗室中使用恒压滴定漏斗向含有邻二醇结构的粘多糖溶液中滴加100mg/mL的高碘酸钠溶液进行反应2.5小时后，加入乙二醇继续反应2小时终止高碘酸钠对粘多糖结构的继续氧化后将反应液转移至透析袋中透析36小时进行纯化，冻干即得醛基功能化改性的海藻酸钠聚合物；其中滴加高碘酸钠溶液后的反应时间为1.5小时，反应温度为30℃，透析温度为37℃，透析袋截留量大小为3500Da。
(3)将所述的L-精氨酸改性的聚赖氨酸聚合物(100mg/mL)、醛基功能化改性的海藻酸钠(100mg/mL)、聚乙二醇二丙烯酸酯(40mg/mL)、碳纳米管(4mg/mL)以及光引发剂I2959(5mg/mL)溶解混合均匀后，使用365nm的紫外光照射10分钟固化，即得聚赖氨酸导电水凝胶。
实施例2
(1)向L-精氨酸盐酸盐溶液中依次加入1-(3-二甲氨基丙基)-3-乙基碳二亚胺盐酸盐和N-羟基丁二酰亚胺对L-精氨酸盐酸盐的羧基基团进行活化后加入聚赖氨酸在30℃进行反应12小时，待反应结束后将反应液转移至透析袋中透析24小时进行纯化，最后利用冷冻干燥机进行冻干，即得L-精氨酸改性的聚赖氨酸聚合物；其中聚赖氨酸溶液的浓度为20mg/mL，L-精氨酸盐酸盐的羧基与聚赖氨酸的氨基摩尔比为1∶2，1-(3-二甲氨基丙基)-3-乙基碳二亚胺盐酸盐与L-精氨酸盐酸盐的摩尔比为1∶1，1-(3-二甲氨基丙基)-3-乙基碳二亚胺盐酸盐与N-羟基丁二酰亚胺的摩尔比为2∶1，透析温度为30℃，透析袋截留量大小为1000Da。将5.0mg左右的L-精氨酸改性的聚赖氨酸聚合物溶解于0.6mL的D2O中，然后利用核磁共振氢谱仪进行1H-NMR表征，测试结如图2所示。
(2)首先在30℃搅拌12小时溶解制备10mg/mL的羧甲基纤维素钠溶液，然后在暗室中使用恒压滴定漏斗向含有邻二醇结构的粘多糖溶液中滴加10mg/mL的高碘酸钠溶液进行反应3小时后，加入乙二醇继续反应1小时终止高碘酸钠对粘多糖结构的继续氧化后将反应液转移至透析袋中透析48小时进行纯化，冻干即得醛基功能化改性的羧甲基纤维素钠聚合物；其中滴加高碘酸钠溶液后的反应时间为0.5小时，反应温度为30℃，透析温度为30℃，透析袋截留量大小为3500Da。
(3)将所述的L-精氨酸改性的聚赖氨酸聚合物(200mg/mL)、醛基功能化改性的羧甲基纤维素钠(50mg/mL)、聚乙二醇二丙烯酸酯(20mg/mL)、碳纳米管(1mg/mL)以及光引发剂I2959(1mg/mL)溶解混合均匀后，使用365nm的紫外光照射5分钟固化，即得聚赖氨酸导电水凝胶。
实施例3
(1)向L-精氨酸盐酸盐溶液中依次加入1-(3-二甲氨基丙基)-3-乙基碳二亚胺盐酸盐和N-羟基丁二酰亚胺对L-精氨酸盐酸盐的羧基基团进行活化后加入聚赖氨酸在30℃进行反应12小时，待反应结束后将反应液转移至透析袋中透析24小时进行纯化，最后利用冷冻干燥机进行冻干，即得L-精氨酸改性的聚赖氨酸聚合物；其中聚赖氨酸溶液的浓度为15mg/mL，L-精氨酸盐酸盐的羧基与聚赖氨酸的氨基摩尔比为2∶1，1-(3-二甲氨基丙基)-3-乙基碳二亚胺盐酸盐与L-精氨酸盐酸盐的摩尔比为2∶1，1-(3-二甲氨基丙基)-3-乙基碳二亚胺盐酸盐与N-羟基丁二酰亚胺的摩尔比为2∶1，透析温度为40℃，透析袋截留量大小为1000Da。
(2)首先在30℃搅拌24小时溶解制备5mg/mL的透明质酸钠溶液，然后在暗室中使用恒压滴定漏斗向含有邻二醇结构的粘多糖溶液中滴加20mg/mL的高碘酸钠溶液进行反应4小时后，加入乙二醇继续反应2小时终止高碘酸钠对粘多糖结构的继续氧化后将反应液转移至透析袋中透析48小时进行纯化，冻干即得醛基功能化改性的透明质酸钠聚合物；其中滴加高碘酸钠溶液后的反应时间为0.5小时，反应温度为30℃，透析温度为37℃，透析袋截留量大小为3500Da。
(3)将所述的L-精氨酸改性的聚赖氨酸聚合物(150mg/mL)、醛基功能化改性的透明质酸钠(50mg/mL)、聚醚二丙烯酸酯(10mg/mL)、碳纳米管(1mg/mL)以及光引发剂I2959(1mg/mL)溶解混合均匀后，使用365nm的紫外光照射5分钟固化，即得聚赖氨酸导电水凝胶。
实施例4
(1)向L-精氨酸盐酸盐溶液中依次加入1-(3-二甲氨基丙基)-3-乙基碳二亚胺盐酸盐和N-羟基丁二酰亚胺对L-精氨酸盐酸盐的羧基基团进行活化后加入聚赖氨酸在30℃进行反应24小时，待反应结束后将反应液转移至透析袋中透析24小时进行纯化，最后利用冷冻干燥机进行冻干，即得L-精氨酸改性的聚赖氨酸聚合物；其中聚赖氨酸溶液的浓度为15mg/mL，L-精氨酸盐酸盐的羧基与聚赖氨酸的氨基摩尔比为2∶1，1-(3-二甲氨基丙基)-3-乙基碳二亚胺盐酸盐与L-精氨酸盐酸盐的摩尔比为2∶1，1-(3-二甲氨基丙基)-3-乙基碳二亚胺盐酸盐与N-羟基丁二酰亚胺的摩尔比为2∶1，透析温度为40℃，透析袋截留量大小为1000Da。
(2)首先在30℃搅拌24小时溶解制备10mg/mL的透明质酸钠溶液，然后在暗室中使用恒压滴定漏斗向含有邻二醇结构的粘多糖溶液中滴加20mg/mL的高碘酸钠溶液进行反应2小时后，加入乙二醇继续反应1小时终止高碘酸钠对粘多糖结构的继续氧化后将反应液转移至透析袋中透析48小时进行纯化，冻干即得醛基功能化改性的透明质酸钠聚合物；其中滴加高碘酸钠溶液后的反应时间为1小时，反应温度为37℃，透析温度为37℃，透析袋截留量大小为12000Da。
(3)将所述的L-精氨酸改性的聚赖氨酸聚合物(100mg/mL)、醛基功能化改性的透明质酸钠(100mg/mL)、聚醚二丙烯酸酯(10mg/mL)、石墨烯(1mg/mL)以及光引发剂I2959(1mg/mL)溶解混合均匀后，使用365nm的紫外光照射10分钟固化，即得聚赖氨酸导电水凝胶。
(4)将所述的聚赖氨酸导电水凝胶与金色葡萄球菌和大肠杆菌分别共培养评价其抗菌性能，并利用热成像仪器评价其热传导性能。
实施例5
(1)向L-精氨酸盐酸盐溶液中依次加入1-(3-二甲氨基丙基)-3-乙基碳二亚胺盐酸盐和N-羟基丁二酰亚胺对L-精氨酸盐酸盐的羧基基团进行活化后加入聚赖氨酸在37℃进行反应24小时，待反应结束后将反应液转移至透析袋中透析24小时进行纯化，最后利用冷冻干燥机进行冻干，即得L-精氨酸改性的聚赖氨酸聚合物；其中聚赖氨酸溶液的浓度为30mg/mL，L-精氨酸盐酸盐的羧基与聚赖氨酸的氨基摩尔比为3∶1，1-(3-二甲氨基丙基)-3-乙基碳二亚胺盐酸盐与L-精氨酸盐酸盐的摩尔比为1∶1，1-(3-二甲氨基丙基)-3-乙基碳二亚胺盐酸盐与N-羟基丁二酰亚胺的摩尔比为1∶1，透析温度为37℃，透析袋截留量大小为500Da。
(2)首先在50℃搅拌12小时溶解制备10mg/mL的透明质酸钠溶液，然后在暗室中使用恒压滴定漏斗向含有邻二醇结构的粘多糖溶液中滴加50mg/mL的高碘酸钠溶液进行反应2小时后，加入乙二醇继续反应2小时终止高碘酸钠对粘多糖结构的继续氧化后将反应液转移至透析袋中透析96小时进行纯化，冻干即得醛基功能化改性的透明质酸钠聚合物；其中滴加高碘酸钠溶液后的反应时间为0.5小时，反应温度为50℃，透析温度为30℃，透析袋截留量大小为3000Da。
(3)将所述的L-精氨酸改性的聚赖氨酸聚合物(200mg/mL)、醛基功能化改性的透明质酸钠(80mg/mL)、聚乙二醇二丙烯酸酯(50mg/mL)、四氧化三铁纳米粒子(1mg/mL)以及光引发剂I2959(1mg/mL)溶解混合均匀后，使用365nm的紫外光照射20分钟固化，即得聚赖氨酸导电水凝胶。
(4)将所述的聚赖氨酸导电水凝胶进行DPPH清除测试评价其抗氧化性能，并利用H9C2细胞进行胞内ROS清除测试。
综上表明，本发明提供了一种利用光引发自由基聚合和席夫碱的动态化学协同交联策略构建一种兼具ROS清除及多重抗菌的聚赖氨酸导电水凝胶，用于模拟细胞外基质的动态微环境，实现其促组织修复与重建的功能。通过近红外光束激发赋予聚赖氨酸导电水凝胶双重抗菌功效，并实现其良好的电传导性能，此外，此水凝胶还具有良好组织兼容性以及ROS清除能力，可广泛用于创伤修复、心血管、可穿戴设备以及组织工程等生物医学领域。
Claims (10)
1.一种兼具ROS清除及多重抗菌的聚赖氨酸导电水凝胶，其特征在于，包括以下步骤：
(1)向L-精氨酸盐酸盐溶液中依次加入1-(3-二甲氨基丙基)-3-乙基碳二亚胺盐酸盐和N-羟基丁二酰亚胺对L-精氨酸盐酸盐的羧基基团进行活化后加入聚赖氨酸进行反应，待反应结束后进行透析纯化后，冻干可得L-精氨酸改性的聚赖氨酸聚合物；
(2)在暗室中向含有邻二醇结构的粘多糖溶液中滴加高碘酸钠溶液并进行反应，待反应结束后加入乙二醇继续反应后进行透析纯化，冻干可得醛基功能化改性的天然粘多糖；
(3)将所述的L-精氨酸改性的聚赖氨酸聚合物、醛基功能化改性的天然粘多糖、化学交联剂、近红外光响应的纳米复合材料以及光引发剂依次溶解混合后，使用紫外光照射固化，即得聚赖氨酸导电水凝胶。
2.根据权利要求1所述的聚赖氨酸导电水凝胶，其特征在于，步骤(1)所述聚赖氨酸溶液的浓度为1-30mg/mL，聚赖氨酸分子量为2000-5000Da；L-精氨酸盐酸盐的羧基与聚赖氨酸的氨基摩尔比为5∶1-1∶2；1-(3-二甲氨基丙基)-3-乙基碳二亚胺盐酸盐与L-精氨酸盐酸盐的摩尔比为2∶1-1∶3；1-(3-二甲氨基丙基)-3-乙基碳二亚胺盐酸盐与N-羟基丁二酰亚胺的摩尔比为3∶1-1∶1；反应温度为4-60℃，反应时间为12-72小时；透析温度为25-60℃，透析袋截留量大小为500-3000Da，透析时间为12-96小时。
3.根据权利要求1所述的聚赖氨酸导电水凝胶，其特征在于，步骤(2)所述高碘酸钠溶液的浓度为10-200mg/mL，高碘酸钠溶液的滴加时间为10-60分钟，滴加高碘酸钠溶液后的反应时间为1-3小时，滴加乙二醇后的反应时间为0.5-3小时，反应温度为25-60℃，透析温度为25-60℃，透析袋截留量大小为1000-12000Da，透析时间为12-96小时。
4.根据权利要求1所述聚赖氨酸导电水凝胶，其特征在于，步骤(2)所述粘多糖包括但不限于透明质酸钠、海藻酸钠、羧甲基纤维素钠的至少一种；粘多糖的浓度为1-10mg/mL，溶解温度为25-60℃，溶解时间为3-36小时。
5.根据权利要求1所述聚赖氨酸导电水凝胶，其特征在于，步骤(3)所述的聚赖氨酸L-精氨酸改性的聚赖氨酸聚合物的浓度为50-200mg/mL，醛基功能化改性的天然粘多糖浓度为10-100mg/mL，化学交联剂的浓度为30-150mg/mL，近红外光响应的纳米复合材料的浓度为1-5mg/mL，光引发剂的浓度0.5-20mg/mL，光照时间为0-90分钟。
6.根据权利要求1所述聚赖氨酸导电水凝胶，其特征在于，步骤(3)所述的化学交联剂包括但不限于N，N′-亚甲基双丙烯酰胺、聚乙二醇二丙烯酸酯、聚醚二丙烯酸酯的至少一种。
7.根据权利要求1所述聚赖氨酸导电水凝胶，其特征在于，步骤(3)所述的近红外光响应的纳米复合材料包括但不限于碳纳米管、石墨烯、四氧化三铁纳米粒子的至少一种。
8.根据权利要求1所述聚赖氨酸导电水凝胶，其特征在于，步骤(3)所述的光引发剂包括但不限于I2959、LAP、α-酮戊二酸的至少一种。
9.根据权利要求1-8所述即为聚赖氨酸导电水凝胶。
10.根据权利要求9所述的聚赖氨酸导电水凝胶具有优异的机械强度、多重抗菌机制、组织兼容性以及ROS清除能力与电传导等方面的优势，实施条件温和可控、性能可调，可广泛用于创伤修复、心血管、可穿戴设备以及组织工程等生物医学领域。
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| CN115634314B (zh) * | 2022-10-28 | 2023-08-04 | 广州贝奥吉因生物科技股份有限公司 | 一种非支撑骨修复凝胶微球及其制备方法 |
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