Odrobińska Justyna, Neugebauer Dorota
Department of Physical Chemistry and Technology of Polymers, Faculty of Chemistry, Silesian University of Technology, 44-100 Gliwice, Poland.
Materials (Basel). 2020 Aug 5;13(16):3455. doi: 10.3390/ma13163455.
The amphiphilic copolymers of poly(ethylene glycol) methyl ether methacrylate (MPEGMA) and alkyne functionalized 2-hydroxyethyl methacrylate (AlHEMA) were synthesized by controlled atom transfer radical polymerization (ATRP). The reactions were carried out using the standard ATRP initiator ethyl α-bromoisobutyrate, (EiBBr) and the "bio"initiator bromoester derivative of 4--butylresorcinol (4nBREBr). Two substances with antioxidant activity used in cosmetology, (±)-α-lipoic acid (LA) and ferulic acid (FA), were subjected to esterification reactions to introduce azide groups. The "click" reactions between the alkyne contained copolymers and functionalized acids (LA-N, FA-N) were performed to obtain polymer-antioxidant conjugates (P((HEMA--FA)--MPEGMA) and P((HEMA--LA)--MPEGMA)). The conjugation was performed with an efficiency of 20-75%. In vitro experiments in a phosphate buffer saline (PBS) solution at neutral conditions demonstrated that the sufficient release was reached after 2.5 h for FA and 1 h for LA. The rapid release kinetics as well as the polymer carriers, which were applied to regulate the delivery of antioxidant substances, are beneficial in cosmetology.
通过可控原子转移自由基聚合（ATRP）合成了聚（乙二醇）甲基醚甲基丙烯酸酯（MPEGMA）和炔基官能化甲基丙烯酸2-羟乙酯（AlHEMA）的两亲性共聚物。反应使用标准的ATRP引发剂α-溴代异丁酸乙酯（EiBBr）和4-丁基间苯二酚的溴代酯衍生物（4nBREBr）这种“生物”引发剂来进行。对美容领域中使用的两种具有抗氧化活性的物质，（±）-α-硫辛酸（LA）和阿魏酸（FA）进行酯化反应以引入叠氮基团。使含炔基的共聚物与官能化酸（LA-N、FA-N）之间发生“点击”反应，以获得聚合物-抗氧化剂共轭物（P((HEMA-FA)-MPEGMA)和P((HEMA-LA)-MPEGMA)）。共轭反应的效率为20%-75%。在中性条件下于磷酸盐缓冲盐水（PBS）溶液中进行的体外实验表明，FA在2.5小时后达到充分释放，LA在1小时后达到充分释放。快速释放动力学以及用于调节抗氧化物质递送的聚合物载体在美容领域是有益的。
