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具有乙酰胆碱酯酶、丁酰胆碱酯酶和碳酸酐酶抑制作用的新型抗氧化溴酚类化合物。

Novel antioxidant bromophenols with acetylcholinesterase, butyrylcholinesterase and carbonic anhydrase inhibitory actions.

作者信息

Öztaskın Necla, Taslimi Parham, Maraş Ahmet, Gülcin İlhami, Göksu Süleyman

机构信息

Department of Chemistry, Faculty of Science, Atatürk University, 25240 Erzurum, Turkey.

Department of Chemistry, Faculty of Science, Atatürk University, 25240 Erzurum, Turkey.

出版信息

Bioorg Chem. 2017 Oct;74:104-114. doi: 10.1016/j.bioorg.2017.07.010. Epub 2017 Jul 20.

Abstract

In this study, a series of novel bromophenols were synthesized from benzoic acids and methoxylated bromophenols. The synthesized compounds were evaluated by using different bioanalytical antioxidant assays including 2,2-diphenyl-1-picrylhydrazyl (DPPH) and 2,2'-azino-bis (3-ethylbenzothiazoline-6-sulphonic acid) (ABTS) radical scavenging assays. Also, reducing power of novel bromophenols were evaluated by Cu-Cu reducing, Fe-Fe reducing and [Fe-(TPTZ)]-[Fe-(TPTZ)]+ reducing and ferrous ions (Fe) chelating abilities. The compounds demonstrate powerful antioxidant activities when compared to standard antioxidant molecules of α-tocopherol, trolox, butylated hydroxyanisole (BHA), and butylated hydroxytoluene (BHT). Also in the last part of this studies novel bromophenols were tested against some metabolic enzymes including acetylcholinesterase (AChE), butyrylcholinesterase (BChE) enzymes and carbonic anhydrase I, and II (hCA I and hCA II) isoenzymes. The newly synthesized bromophenols showed Ki values in a range of 6.78±0.68 to 126.07±35.6nM against hCA I, 4.32±0.23 to 72.25±12.94nM against hCA II, 4.60±1.15 to 38.13±5.91nM against AChE and 7.36±1.31 to 29.38±3.68nM against BChE.

摘要

在本研究中,一系列新型溴酚由苯甲酸和甲氧基化溴酚合成。通过使用不同的生物分析抗氧化剂测定法对合成的化合物进行评估,包括2,2-二苯基-1-苦基肼(DPPH)和2,2'-偶氮双(3-乙基苯并噻唑啉-6-磺酸)(ABTS)自由基清除测定法。此外,通过铜-铜还原、铁-铁还原、[铁-(TPTZ)]-[铁-(TPTZ)]+还原以及亚铁离子(Fe)螯合能力来评估新型溴酚的还原能力。与α-生育酚、曲克芦丁、丁基羟基茴香醚(BHA)和丁基羟基甲苯(BHT)等标准抗氧化剂分子相比,这些化合物表现出强大的抗氧化活性。在本研究的最后部分,还对新型溴酚针对一些代谢酶进行了测试,包括乙酰胆碱酯酶(AChE)、丁酰胆碱酯酶(BChE)以及碳酸酐酶I和II(hCA I和hCA II)同工酶。新合成的溴酚对hCA I的Ki值范围为6.78±0.68至126.07±35.6nM,对hCA II的Ki值范围为4.32±0.23至72.25±12.94nM,对AChE的Ki值范围为4.60±1.15至38.13±5.91nM,对BChE的Ki值范围为7.36±1.31至29.38±3.68nM。

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