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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.

DOI:10.3390/biom10121594
PMID:33255306
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC7760079/
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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本文引用的文献

1
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Mediators Inflamm. 2020 Jul 8;2020:4070419. doi: 10.1155/2020/4070419. eCollection 2020.
2
Water Behavior at the Phase Transition of Phospholipid Matrixes Assessed by FTIR Spectroscopy.通过傅里叶变换红外光谱法评估磷脂基质相变过程中的水行为。
J Phys Chem B. 2020 Jul 23;124(29):6236-6244. doi: 10.1021/acs.jpcb.0c03719. Epub 2020 Jul 14.
3
Quorum sensing molecule N-(3-oxododecanoyl)-l-homoserine lactone: An all-rounder in mammalian cell modification.
查尔酮衍生的内酯:合成、全细胞生物转化及其抗菌和抗真菌活性评价。
Molecules. 2023 Apr 28;28(9):3800. doi: 10.3390/molecules28093800.
4
Microbial Transformations of Halolactones and Evaluation of Their Antiproliferative Activity.卤内酯的微生物转化及其抗增殖活性评价。
Int J Mol Sci. 2023 Apr 20;24(8):7587. doi: 10.3390/ijms24087587.
5
Antimicrobial Activity of Lactones.内酯的抗菌活性。
Antibiotics (Basel). 2022 Sep 29;11(10):1327. doi: 10.3390/antibiotics11101327.
6
Derivatives of Plastics as Potential Carcinogenic Factors: The Current State of Knowledge.塑料衍生物作为潜在致癌因素:当前的知识状况
Cancers (Basel). 2022 Sep 24;14(19):4637. doi: 10.3390/cancers14194637.
7
Evaluation of the Physico-Chemical Properties of Liposomes Assembled from Bioconjugates of Anisic Acid with Phosphatidylcholine.评价阿魏酸与磷脂酰胆碱生物缀合物组装而成的脂质体的物理化学性质。
Int J Mol Sci. 2021 Dec 5;22(23):13146. doi: 10.3390/ijms222313146.
8
Interaction of 4'-methylflavonoids with biological membranes, liposomes, and human albumin.4'-甲基黄酮类化合物与生物膜、脂质体和人血清白蛋白的相互作用。
Sci Rep. 2021 Aug 6;11(1):16003. doi: 10.1038/s41598-021-95430-8.
9
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Int J Mol Sci. 2021 Mar 9;22(5):2769. doi: 10.3390/ijms22052769.
10
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PLoS One. 2021 Mar 26;16(3):e0248960. doi: 10.1371/journal.pone.0248960. eCollection 2021.
群体感应分子N-(3-氧代十二烷酰基)-L-高丝氨酸内酯:哺乳动物细胞修饰中的多面手。
J Oral Biosci. 2020 Mar;62(1):16-29. doi: 10.1016/j.job.2020.01.001. Epub 2020 Jan 23.
4
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Biomolecules. 2020 Jan 6;10(1):95. doi: 10.3390/biom10010095.
5
Synthesis and Antimicrobial Activity of Methoxy- Substituted γ-Oxa-ε-lactones Derived from Flavanones.甲氧基取代的γ-氧代-ε-内酰胺的合成及其抗菌活性。
Molecules. 2019 Nov 16;24(22):4151. doi: 10.3390/molecules24224151.
6
Antifungal Activity of the Essential Oil of Origanum syriacum L.叙利亚牛至精油的抗真菌活性
J Food Prot. 1995 Oct;58(10):1147-1149. doi: 10.4315/0362-028X-58.10.1147.
7
Preparation of Enantiomeric β-(2',5'-Dimethylphenyl)Bromolactones, Their Antiproliferative Activity and Effect on Biological Membranes.对映体β-(2',5'-二甲基苯基)溴代内酯的制备、其抗增殖活性及对生物膜的影响。
Molecules. 2018 Nov 20;23(11):3035. doi: 10.3390/molecules23113035.
8
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J Membr Biol. 2018 Dec;251(5-6):735-745. doi: 10.1007/s00232-018-0051-x. Epub 2018 Oct 22.
9
Bacterial infections and cancer.细菌感染与癌症。
EMBO Rep. 2018 Nov;19(11). doi: 10.15252/embr.201846632. Epub 2018 Oct 22.
10
Antioxidant Status in the Soleus Muscle of Sprague-Dawley Rats in Relation to Duodenal-Jejunal Omega Switch and Different Dietary Patterns.与十二指肠空肠ω 转换和不同饮食模式相关的 Sprague-Dawley 大鼠比目鱼肌中的抗氧化状态。
Oxid Med Cell Longev. 2018 Jul 8;2018:3795070. doi: 10.1155/2018/3795070. eCollection 2018.