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The role of the arylidene linkage on the antimicrobial enhancement of new tert-butylcyclohexanone-based polyketones
Polymer Bulletin ( IF 3.1 ) Pub Date : 2020-10-03 , DOI: 10.1007/s00289-020-03365-3
Samar J. Almehmadi , Khalid A. Alamry , M. A. Elfaky , Abdullah M. Asiri , Mostafa A. Hussien , S. Z. Al-Sheheri , Mahmoud A. Hussein

Six promising biologically active polymers based on a 4-tert-butylcyclohexanone moiety have been synthesized through the Friedel–Crafts reaction as new polyketone derivatives. The polymerization occurred by the interaction of three different arylidene-based monomers, with adipoyl and sebacoyl diacid chlorides. The role of such arylidene linkages on the overall performance of these new polyketones was investigated with a special attention to its antimicrobial enhancement probability. The resulting polyketones were characterized by common characterization techniques including solubility, FTIR, X-ray diffraction, and morphological properties. The thermal properties of all the resulting polyketones were evaluated using TGA and associated with their structural units. The PDTmax results indicated that all the polymers had almost similar PDTmax patterns, which appeared in the range from 440 to 630 °C. The biological activity of all the synthesized polyketones was examined and showed that most of the synthesized polyketones had antibacterial activity against microbial strains. The role of the arylidene linkage on the antimicrobial enhancement of these new polyketone derivatives was also evaluated. The tested polyketones showed significant activity against most microbial strains, and the maximum activity was observed against E. coli and P. Aeruginosa. Polymer 5b showed the maximum inhibition zone of 13 mm amongst the other polymers. Furthermore, the tested polyketones showed no significant activity against B. subtilis or the fungus C. albicans. Furthermore, molecular docking studies were applied to all polymers with the “5FSA” protein, and the results have been investigated. Polymer 5b also showed the highest docking score of − 5.84 kcal/mol. Therefore, polymer 5b was classified as a promising biologically active polymer.

中文翻译:

亚芳基键对新型叔丁基环己酮基聚酮抗菌增强的作用

六种基于 4-叔丁基环己酮部分的有前景的生物活性聚合物已通过 Friedel-Crafts 反应合成为新的聚酮衍生物。聚合通过三种不同的亚芳基单体与己二酰和癸二酰二酰氯的相互作用发生。研究了这种亚芳基键对这些新聚酮的整体性能的作用,并特别关注其抗菌增强可能性。所得聚酮通过常见的表征技术进行表征,包括溶解度、FTIR、X 射线衍射和形态特性。使用 TGA 评估所有所得聚酮的热性能并与其结构单元相关联。PDTmax 结果表明所有聚合物具有几乎相似的 PDTmax 模式,出现在 440 到 630 °C 的范围内。对所有合成的聚酮的生物活性进行了检测,结果表明大多数合成的聚酮对微生物菌株具有抗菌活性。还评估了亚芳基键对这些新聚酮衍生物的抗菌增强作用。测试的聚酮对大多数微生物菌株显示出显着的活性,并且观察到对大肠杆菌和铜绿假单胞菌的最大活性。聚合物 5b 在其他聚合物中显示出 13 毫米的最大抑菌圈。此外,测试的聚酮对枯草芽孢杆菌或真菌白色念珠菌没有显着活性。此外,分子对接研究适用于所有含有“5FSA”蛋白的聚合物,并研究了结果。聚合物 5b 还显示出最高的对接分数 - 5.84 kcal/mol。因此,聚合物5b被归类为有前途的生物活性聚合物。
更新日期:2020-10-03
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