CN112300411B - 一种功能化卟啉水凝胶及其制备方法和应用 - Google Patents

一种功能化卟啉水凝胶及其制备方法和应用 Download PDF

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CN112300411B
CN112300411B CN202011285411.1A CN202011285411A CN112300411B CN 112300411 B CN112300411 B CN 112300411B CN 202011285411 A CN202011285411 A CN 202011285411A CN 112300411 B CN112300411 B CN 112300411B
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metalloporphyrin
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柴志华
王彦霞
王昊
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North China Institute of Science and Technology
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Abstract

本发明提出了一种功能化卟啉水凝胶及其制备方法和应用，制备方法包括以下步骤：（1）室温下，将功能单体溶解在pH=2.0的酸性溶液中，然后加入MBA和光敏剂金属卟啉，得到混合溶液，所述功能单体包括含氮杂环的烯类单体和丙烯酰胺；（2）混合溶液在室温下磁力搅拌，且通入氮气以排除体系内的氧气，然后加入引发剂APS，密封，在50‑80℃的恒温水浴下反应6‑10小时；（3）将步骤（2）反应得到的产物洗涤、浸泡和过滤，重复多次，低温冷冻干燥。本发明通过配合作用负载光敏剂金属卟啉，使得光敏剂金属卟啉可以在水凝胶中稳定存在，有效提高了金属卟啉的稳定性，而且制备方法简单、易于操作，易于推广应用，可广泛应用在光光动力学疗法和光催化等领域中。

Description

一种功能化卟啉水凝胶及其制备方法和应用
技术领域
本发明涉及生物与纳米材料技术领域领域，特别是指一种功能化卟啉水凝胶及其制备方法和应用。
背景技术
金属卟啉类化合物广泛存在于自然环境和生命体中，例如叶绿素的核心是镁卟啉，血红蛋白的核心是铁卟啉化合物。大部分金属卟啉都具有疏水性质，使其在水溶液中很难稳定存在，而光动力学疗法和光催化领域大部分都在水溶液中进行。而水溶性金属卟啉，由于其自身结构特点，在光照下容易分解失去活性，限制了其进一步的应用。而且，卟啉作为光敏剂在光动力学疗法中必须在肿瘤部位富集才能发挥作用，单独的金属卟啉很难到达肿瘤部位。因此，必须将金属卟啉负载到纳米材料中。
另外一面，水凝胶以其独特三维网状的结构特点，作为药物载体具有很大的优势。首先，水凝胶可以实现对光敏剂的负载，将其包载到凝胶内部有效防止光敏剂的释放，减少光敏剂对正常的组织得聚集，减少对正常器官的伤害。其次，水凝胶还可以负载多种类型的光敏剂和染料分子，扩大材料的吸光范围，协同作用，具有较高的光催化效率，实现更好的治疗效果。最后，水凝胶材料可以有效到达肿瘤部位，利用肿瘤部位的高通透性和EPR效应，将其靶向到达肿瘤区域。
水凝胶对金属卟啉的负载主要通过共价键和非共价键作用力两种方式。非共价键作用的组装以其简单高效的制备方法受到人们广泛的关注。但以这种方式的负载由于静电相互作用力比较弱，存在光敏剂从水凝胶释放的问题，从而降低了其光敏效率。
发明内容
本发明提出一种功能化卟啉水凝胶及其制备方法和应用，通过配合作用负载光敏剂金属卟啉，使得光敏剂金属卟啉可以在水凝胶中稳定存在，有效提高了金属卟啉的稳定性，而且制备方法简单、易于操作，易于推广应用，可广泛应用在光光动力学疗法和光催化等领域中。
本发明的技术方案是这样实现的：一种功能化卟啉水凝胶的制备方法，包括以下步骤：
（1）室温下，将功能单体溶解在pH=2.0的酸性溶液中，然后加入N,N-亚甲基双丙烯酰胺 （MBA ）和光敏剂金属卟啉，得到混合溶液，所述功能单体包括含氮杂环的烯类单体和丙烯酰胺，含氮杂环的烯类单体和丙烯酰胺的摩尔比为1:1-9，MBA加入量为功能单体质量的0.5-5%；
（2）步骤（1）中的混合溶液在室温下磁力搅拌，且通入氮气以排除体系内的氧气，然后加入引发剂过硫酸铵（APS），APS加入量为功能单体质量的0.5-3%，密封，在50-80℃的恒温水浴下反应6-10小时；
（3）将步骤（2）反应得到的产物洗涤、浸泡和过滤，重复多次，低温冷冻干燥，得到功能化卟啉水凝胶。
优选地，步骤（1）中，含氮杂环的烯类单体和丙烯酰胺的摩尔比1:1。
优选地，步骤（1）中，含氮杂环的烯类单体包括4-乙烯基吡啶或乙烯基吡咯烷酮。
优选地，步骤（1）中，光敏剂金属卟啉与功能单体的摩尔比为0.1-1:100。
优选地，步骤（1）中，光敏剂金属卟啉为5,10,15,20-四-(4-对磺酸基苯基)-锌卟啉（ZnTPPS）。
优选地，步骤（1）中，MBA的加入量为功能单体质量的5%。
优选地，步骤（2）中，APS加入量为功能单体质量的1%，密封，在60℃的恒温水浴下反应8小时。
一种功能化卟啉水凝胶，采用上述方法制备。
所述功能化卟啉水凝胶在光动力学疗法和光催化中的应用。
本发明的有益效果：
（1）本发明通过吡啶或者吡咯烷酮上的N与金属卟啉之间很强的配位作用，水凝胶可以高效负载光敏剂金属卟啉，使其具有较强产生单线态氧的能力，也解决了一般光敏剂从载体中容易释放的问题，有利于提高材料的稳定性，与静电作用对金属卟啉进行负载相比，配位作用具有更强的作用力和对金属卟啉更为高效的负载。
（2）本发明制备功能化卟啉水凝胶的方法简单、易于操作，成本低，而且在水凝胶交联过程中，直接把金属卟啉负载在水凝胶中，更有利于提高光敏剂的负载效率以及稳定性。水凝胶的三维网络结构在药物载体方面具有很大优势，可以负载多种金属卟啉和色素分子，使其在光催化和光化学等领域有着广阔的应用前景。
附图说明
为了更清楚地说明本发明实施例或现有技术中的技术方案，下面将对实施例或现有技术描述中所需要使用的附图作简单地介绍，显而易见地，下面描述中的附图仅仅是本发明的一些实施例，对于本领域普通技术人员来讲，在不付出创造性劳动的前提下，还可以根据这些附图获得其他的附图。
图1为实施例一功能化卟啉水凝胶的扫描电镜照片；
图2为实施例一功能化水凝胶催化降解ABDA的紫外光谱随时间变化曲线。
具体实施方式
下面将结合本发明实施例中的附图，对本发明实施例中的技术方案进行清楚、完整地描述，显然，所描述的实施例仅仅是本发明一部分实施例，而不是全部的实施例。基于本发明中的实施例，本领域普通技术人员在没有付出创造性劳动前提下所获得的所有其他实施例，都属于本发明保护的范围。
实施例一
一种功能化卟啉水凝胶的制备方法，包括以下步骤：
（1）采用自由基聚合方法，将4-乙烯基吡啶和丙烯酰胺（摩尔比为1:1）为功能单体溶解于pH=2.0的盐酸水溶液中，MBA 为交联剂、同时加入金属卟啉ZnTPPS，得到混合溶液，其中，MBA的加入量为功能单体质量的5%，ZnTPPS加入量为与功能单体摩尔比1：100；
（2）将步骤（1）中的混合溶液在室温下磁力搅拌30分钟，通入氮气3分钟以排除体系内的氧气。然后加入引发剂APS，加入量为功能单体质量的1%，密封，在60℃的恒温水浴下反应8小时；
（3）将步骤（2）反应得到的产物以去离子水进行洗涤，浸泡和过滤，重复6次，以除尽非水凝胶的成分，最后将产物低温冷冻干燥，得到水凝胶材料。
为了验证水凝胶形成，对制备出的水凝胶做了扫描电镜的表征，如图1所示。通过图1可以看到，制备出的水凝胶具有三维网状结构。
实施例二
本实施例与实施例一基本相同，不同之处在于：步骤1中，将4-乙烯基吡啶改为乙烯基吡咯烷酮。
为了验证水凝胶是否具有产生单线态氧的能力，用9,10-蒽基-双(亚甲基)二丙二酸（ABDA）作为单线态氧的捕捉剂。将水凝胶放入的ABDA溶液中，然后用氙灯光源下照射，其紫外光谱随时间的变化曲线如图2所示。可以看到，380nm处以及401nm处的ABDA特征吸收峰有下降趋势，随着光照时间的延长，产生单线态氧越来越多，ABDA特征吸收峰下降越明显，从而证明了水凝胶具有产生单线态的能力。
实施例三
一种功能化卟啉水凝胶的制备方法，包括以下步骤：
（1）采用自由基聚合方法，将4-乙烯基吡啶和丙烯酰胺（摩尔比为1:5）为功能单体溶解于pH=2.0的盐酸水溶液中，MBA 为交联剂、同时加入金属卟啉ZnTPPS，得到混合溶液，其中，MBA的加入量为功能单体质量的0.5%，ZnTPPS加入量为与功能单体摩尔比0.1：100；
（2）将步骤（1）中的混合溶液在室温下磁力搅拌30分钟，通入氮气3分钟以排除体系内的氧气。然后加入引发剂APS，加入量为功能单体质量的0.5%，密封，在50℃的恒温水浴下反应10小时；
（3）将步骤（2）反应得到的产物以去离子水进行洗涤，浸泡和过滤，重复6次，以除尽非水凝胶的成分，最后将产物低温冷冻干燥，得到水凝胶材料。
实施例四
一种功能化卟啉水凝胶的制备方法，包括以下步骤：
（1）采用自由基聚合方法，将4-乙烯基吡啶和丙烯酰胺（摩尔比为1:9）为功能单体溶解于pH=2.0的盐酸水溶液中，MBA 为交联剂、同时加入金属卟啉ZnTPPS，得到混合溶液，其中，MBA的加入量为功能单体质量的3.5%，ZnTPPS加入量为与功能单体摩尔比0.5：100；
（2）将步骤（1）中的混合溶液在室温下磁力搅拌30分钟，通入氮气3分钟以排除体系内的氧气。然后加入引发剂APS，加入量为功能单体质量的1.5%，密封，在80℃的恒温水浴下反应6小时；
（3）将步骤（2）反应得到的产物以去离子水进行洗涤，浸泡和过滤，重复6次，以除尽非水凝胶的成分，最后将产物低温冷冻干燥，得到水凝胶材料。
以上所述仅为本发明的较佳实施例而已，并不用以限制本发明，凡在本发明的精神和原则之内，所作的任何修改、等同替换、改进等，均应包含在本发明的保护范围之内。

Claims (8)

1.一种功能化卟啉水凝胶的制备方法，其特征在于，包括以下步骤：
（1）室温下，将功能单体溶解在pH=2.0的酸性水溶液中，然后加入MBA和光敏剂金属卟啉，得到混合溶液，所述功能单体为含氮杂环的烯类单体和丙烯酰胺，含氮杂环的烯类单体和丙烯酰胺的摩尔比为1:1-9，MBA加入量为功能单体质量的0.5-5%，光敏剂金属卟啉为ZnTPPS；
（2）步骤（1）中的混合溶液在室温下磁力搅拌，且通入氮气以排除体系内的氧气，然后加入引发剂APS，APS加入量为功能单体质量的0.5-3%，密封，在50-80℃的恒温水浴下反应6-10小时；
（3）将步骤（2）反应得到的产物洗涤、浸泡和过滤，重复多次，低温冷冻干燥，得到功能化卟啉水凝胶。
2.根据权利要求1所述的一种功能化卟啉水凝胶的制备方法，其特征在于，步骤（1）中，含氮杂环的烯类单体和丙烯酰胺的摩尔比1:1。
3.根据权利要求1或2所述的一种功能化卟啉水凝胶的制备方法，其特征在于，步骤（1）中，含氮杂环的烯类单体为4-乙烯基吡啶或乙烯基吡咯烷酮。
4.根据权利要求1所述的一种功能化卟啉水凝胶的制备方法，其特征在于，步骤（1）中，光敏剂金属卟啉与功能单体的摩尔比为0.1-1:100。
5.根据权利要求1所述的一种功能化卟啉水凝胶的制备方法，其特征在于，步骤（1）中，MBA的加入量为功能单体质量的5%。
6.根据权利要求1所述的一种功能化卟啉水凝胶的制备方法，其特征在于，步骤（2）中，APS加入量为功能单体质量的1%，密封，在60℃的恒温水浴下反应8小时。
7.一种采用权利要求1-6之一所述方法制备的功能化卟啉水凝胶。
8.一种权利要求7所述的功能化卟啉水凝胶在光催化中的应用。
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