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新型化合物4-甲氧基-2-(4-甲氧基苯基)苯并[d][1,3,2]二氧硼烷的体外抗氧化、抗胆碱酯酶、抗脲酶、抗酪氨酸酶及细胞毒性特性研究

Investigation of the In Vitro Antioxidant, Anticholinesterase, Antiurease, Antityrosinase, and Cytotoxic Properties of a Novel Compound: 4-Methoxy-2-(4-Methoxyphenyl)Benzo[d][1,3,2]Dioxaborole.

作者信息

Temel Hamdi, Baydan Emine

机构信息

Department of Pharmacology, Faculty of Medicine, Yozgat Bozok University, Yozgat, Turkey.

Department of Pharmacology and Toxicology, Institute of Health Sciences, Ankara University, Ankara, Turkey.

出版信息

Pharmacol Res Perspect. 2025 Feb;13(1):e70044. doi: 10.1002/prp2.70044.

Abstract

In this study, the structure of a new boron compound obtained using 3-methoxy catechol and 4-methoxy phenyl boronic acid was characterized by H, C NMR, LC-MS-IT-TOF, UV-Vis and FTIR spectroscopy. The antioxidant activities of the newly synthesized compound were evaluated by DPPH free radical scavenging, ABTS quation radical scavenging and CUPRAC copper reducing capacity methods. Anticholinesterase activities were determined by acetylcholinesterase and butyrylcholinesterase enzyme inhibitor assays. Antiurease and antithyrosinase enzyme inhibition activities were also examined. Cytotoxic effects were evaluated on healthy cell lines and breast and colon cancer cell lines using MTT method. The results showed that the synthesized compound has high antioxidant activity. Especially the average antioxidant activity values obtained at 10 μg/mL concentration were found to be statistically significantly (p < 0.05) higher than the reference values of α-TOC and BHT. When the antioxidant activity data (IC) were compared separately with α-TOC and BHT reference values, the new compound was found to be more effective. In acetylcholinesterase enzyme inhibition, the average activity values were found to be statistically significantly (p < 0.05) higher than the galantamine reference value. However, no statistically significant difference was observed at BChE (% inhibition) level with galantamine reference value. In terms of urease and tyrosinase enzyme inhibition activities, the urease activity of the synthesized compound was statistically significantly (p < 0.05) lower than the thiurea reference value. Tyrosinase activity was statistically significantly (p < 0.05) lower than kojic acid reference values. The synthesized and characterized compound was found to have no toxic effect on healthy cell lines and did not show any cytotoxic effect on breast cancer (MCF-7) and colon cancer (HT-29) cell lines.

摘要

在本研究中,使用3-甲氧基儿茶酚和4-甲氧基苯硼酸获得的一种新型硼化合物的结构通过氢谱、碳谱、液相色谱-质谱联用仪-离子阱-飞行时间质谱、紫外可见光谱和傅里叶变换红外光谱进行了表征。通过二苯基苦味酰基自由基清除法、ABTS阳离子自由基清除法和铜离子还原抗氧化能力法评估了新合成化合物的抗氧化活性。通过乙酰胆碱酯酶和丁酰胆碱酯酶抑制剂试验测定了抗胆碱酯酶活性。还检测了抗脲酶和抗酪氨酸酶的酶抑制活性。使用MTT法评估了对健康细胞系以及乳腺癌和结肠癌细胞系的细胞毒性作用。结果表明,合成的化合物具有高抗氧化活性。特别是在10μg/mL浓度下获得的平均抗氧化活性值在统计学上显著高于α-生育酚和丁基羟基甲苯的参考值(p < 0.05)。当将抗氧化活性数据(IC)分别与α-生育酚和丁基羟基甲苯参考值进行比较时,发现新化合物更有效。在乙酰胆碱酯酶抑制方面,发现平均活性值在统计学上显著高于加兰他敏参考值(p < 0.05)。然而,在丁酰胆碱酯酶(抑制率)水平上与加兰他敏参考值未观察到统计学上的显著差异。就脲酶和酪氨酸酶抑制活性而言,合成化合物的脲酶活性在统计学上显著低于硫脲参考值(p < 0.05)。酪氨酸酶活性在统计学上显著低于曲酸参考值(p < 0.05)。发现合成并表征的化合物对健康细胞系没有毒性作用,并且对乳腺癌(MCF-7)和结肠癌(HT-29)细胞系没有显示出任何细胞毒性作用。

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