Biocidal Activity and Mechanism Study of Unsymmetrical Oligo-Phenylene-Ethynylenes
Biocidal Activity and Mechanism Study of Unsymmetrical Oligo-Phenylene-Ethynylenes
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不对称低聚亚苯基亚乙炔类化合物的杀菌活性及机理研究
DOI：
10.1021/acsabm.0c00267
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发表时间：
2020-09-21
影响因子：
4.7
通讯作者：
Wang, Jing
中科院分区：
文献类型：
--
作者：
Liao, Wei;Zhuo, Lian-gang;Wang, Jing
细菌污染和耐药性细菌的传播需要替代方法来处理细菌感染。光动力学疗法（PDT）具有独特的优点，是一种很有前途的方法。作为光动力疗法的光敏剂，寡聚对苯乙炔（oligo-p-phenylene-ethynylene，OPEs）等光致抗菌化合物得到了广泛的研究，但这些研究主要集中在含季铵盐的OPEs。在我们的前期研究中，发现含叔氨基的OPEs（T-OPEs）比相应的季铵盐具有更好的抗菌活性，这使得开发T-OPEs并进一步研究其构效关系变得非常重要。此外，已报道的OPEs的末端结构主要由季铵盐或叔氨基组成，不能与其他材料连接。因此，为了开发更有效和多功能的抗菌剂，我们设计并合成了四种具有末端氨基的不对称OPEs，它们可以通过共价键与其他功能单元连接。研究了它们对革兰氏阳性菌和革兰氏阴性菌的抗菌活性及其作用机制。在光纤光照射下，OPEs表现出有效的杀菌活性，没有观察到暗杀。其作用机制研究表明，光照射下OPEs可穿透细胞膜，扰动细胞膜，产生活性氧，从而影响其抗菌活性。OPEs的渗透能力部分取决于其亲脂性和细胞膜的结构和组成。
Bacterial contamination and the spread of antibiotic-resistant bacteria demand alternate methods to deal with bacterial infections. With particular advantages, photodynamic therapy (PDT) is a promising approach. As a kind of photosensitizer for PDT, light-induced antibacterial compounds like oligo-p-phenylene-ethynylenes (OPEs) have been widely investigated while these studies mainly focus on OPEs with quaternary ammonium salts. In our previous study, OPEs with tertiary amino groups (T-OPEs) were reported to exhibit a better antibacterial activity than the corresponding quaternary ammonium salts, which make it important to develop T-OPEs and further investigate their structure-activity relationship. Additionally, the terminal structure of the reported OPEs mainly consists of quaternary ammonium salts or tertiary amino groups, which could not be linked to other materials. Thus, to develop more effective and multifunctional antibacterial agents, we designed and synthesized four unsymmetrical OPEs having terminal amino groups, which could be linked to other functional units by covalent bonds. Their antibacterial activity against Gram-positive and Gram-negative bacteria and the mechanism have been investigated. The OPEs showed effective biocidal activity under fiber light irradiation, and no dark killing was observed. The mechanism study indicates that OPEs could penetrate and perturb the cell membrane and generate ROS under light irradiation, both of which could influence their antibacterial activity. The penetrating ability of OPEs is partly dependent on their lipophilicity and the structure and composition of the cell membrane.