Latorre-Sánchez Alejandro, Johansson Mats, Zhang Yuning, Malkoch Michael, Pomposo José A
Centro de Física de Materiales (CSIC, UPV/EHU) and Materials Physics Center MPC, Paseo Manuel de Lardizabal 5, E-20018 San Sebastián, Spain.
J Mater Chem B. 2018 Jan 7;6(1):98-104. doi: 10.1039/c7tb02739g. Epub 2017 Dec 6.
The fabrication of antibacterial films based on renewable materials (e.g., chitosan) has attracted significant interest in fields such as food packaging, health care and medicine. However, exploiting the antibacterial properties of cinchona alkaloids to design active nanostructured films able to release quinine-based antimicrobial compounds has not been considered previously. Herein, we develop two different routes to produce active quinine-based nanostructured cross-linked films by exploiting the multiple reactive sites of quinine and, specifically, both the nitrogen atom and the vinyl group of the quinuclidine portion of the molecule, as well as their corresponding orthogonal quaternization and thiol-ene coupling reactions. The first synthetic strategy produces stiff and brittle nanostructured quinine-based films of limited utility for practical applications. Conversely, the second approach produces active, flexible and nanostructured quinine-based films (T = -14 °C, Young's modulus = 1.3 GPa), which are able to release antimicrobial compounds against E. coli that, remarkably, are noncytotoxic against mouse macrophage and human dermal fibroblast cells. These kinds of active cinchona alkaloid-based coatings are easy to prepare by means of simple, solvent-free, melt quaternization/spreading procedures at a relatively low temperature (120 °C), making this second approach one of the most facile reported procedures to date to produce active nanostructured bio-based films.
基于可再生材料（如壳聚糖）制备抗菌薄膜在食品包装、医疗保健和医学等领域引起了广泛关注。然而，利用金鸡纳生物碱的抗菌特性来设计能够释放基于奎宁的抗菌化合物的活性纳米结构薄膜，此前尚未被考虑过。在此，我们开发了两种不同的途径，通过利用奎宁的多个反应位点，特别是分子喹核碱部分的氮原子和乙烯基，以及它们相应的正交季铵化和硫醇-烯偶联反应，来制备基于奎宁的活性纳米结构交联薄膜。第一种合成策略制备出的基于奎宁的纳米结构薄膜坚硬且易碎，在实际应用中的实用性有限。相反，第二种方法制备出了活性、柔性且基于奎宁的纳米结构薄膜（玻璃化转变温度(T = -14 °C)，杨氏模量( = 1.3 GPa)），该薄膜能够释放对大肠杆菌具有抗菌作用的化合物，并且显著地对小鼠巨噬细胞和人皮肤成纤维细胞无细胞毒性。这类基于金鸡纳生物碱的活性涂层易于通过简单的无溶剂熔融季铵化/铺展程序在相对较低的温度（(120 °C)）下制备，使得第二种方法成为迄今为止报道的制备活性纳米结构生物基薄膜的最简便方法之一。
