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β-芳基-δ-碘-γ-内酰胺的抗增殖、抗菌和抗病毒活性及其对细胞氧化应激标志物和生物膜的影响。

Antiproliferative, Antimicrobial and Antiviral Activity of β-Aryl-δ-iodo-γ-lactones, Their Effect on Cellular Oxidative Stress Markers and Biological Membranes.

机构信息

Department of Physics and Biophysics, Wrocław University of Environmental and Life Sciences, C.K. Norwida 25, 50-375 Wrocław, Poland.

Department of Physiology in Zabrze, Medical University of Silesia, Poniatowskiego 15, 40-751 Katowice, Poland.

出版信息

Biomolecules. 2020 Nov 24;10(12):1594. doi: 10.3390/biom10121594.

Abstract

The aim of this work was the examination of biological activity of three selected racemic cis-β-aryl-δ-iodo-γ-lactones. Tested iodolactones differed in the structure of the aromatic fragment of molecule, bearing isopropyl (), methyl (), or no substituent () on the position of the benzene ring. A broad spectrum of biological activity as antimicrobial, antiviral, antitumor, cytotoxic, antioxidant, and hemolytic activity was examined. All iodolactones showed bactericidal activity against , and lactones , were active against . The highest cytotoxic activity towards HeLa and MCF7 cancer cell lines and NHDF normal cell line was found for lactone . All assessed lactones significantly disrupted antioxidative/oxidative balance of the NHDF, and the most harmful effect was determined by lactone . Contrary to lactone , lactones and did not induce the hemolysis of erythrocytes after 48 h of incubation. The differences in activity of iodolactones - in biological tests may be explained by their different impact on physicochemical properties of membrane as the packing order in the hydrophilic area and fluidity of hydrocarbon chains. This was dependent on the presence and type of alkyl substituent. The highest effect on the membrane organization was observed for lactone due to the presence of bulky isopropyl group on the benzene ring.

摘要

这项工作的目的是研究三种手性顺式-β-芳基-δ-碘-γ-内酰胺的生物活性。测试的碘内酯在分子芳香片段的结构上有所不同,苯环的 位上带有异丙基()、甲基()或无取代基()。研究了它们作为抗菌、抗病毒、抗肿瘤、细胞毒性、抗氧化和溶血活性的广谱生物活性。所有碘内酯对 都表现出杀菌活性,而内酯 和 对 有效。内酯 对 HeLa 和 MCF7 癌细胞系和 NHDF 正常细胞系表现出最高的细胞毒性活性。所有评估的内酯都显著破坏了 NHDF 的抗氧化/氧化平衡,内酯 确定了最有害的影响。与内酯 相反,内酯 和 在用内酯孵育 48 小时后不会引起红细胞溶血。碘内酯在生物测试中的活性差异可能是由于它们对膜的物理化学性质的不同影响,如亲水区的堆积顺序和烃链的流动性。这取决于烷基取代基的存在和类型。由于苯环上存在大体积的异丙基,内酯 对膜组织的影响最大。

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