Berczyński Paweł, Kładna Aleksandra, Kruk Irena, Sarı Elmas, Murat Hatice Nehir, Bozdağ Dündar Oya, Aboul-Enein Hassan Y
Institute of Physics, Faculty of Mechanical Engineering and Mechatronics, West Pomeranian University of Technology in Szczecin, Szczecin, Poland.
Department of History of Medicine and Medical Ethics, Pomeranian Medical University, Szczecin, Poland.
Luminescence. 2017 Dec;32(8):1431-1441. doi: 10.1002/bio.3342. Epub 2017 Jun 1.
Flavones exhibit a variety of beneficial effects and are well known for their medicinal importance in several diseases, including cardiovascular, neurodegenerative and cancer. The inclusion of the piperazine ring to the flavone backbone is an important strategy in drug discovery but only a few studies have synthesized piperazinyl flavone compounds to test their biological activity. While there is a major focus on the antioxidant properties of drugs in therapy of several diseases of inflammatory origin, we synthesized a series of the novel piperazinyl flavone analogues bearing the phenyl ring with different substituents. The analogues were evaluated for in vitro antioxidant activity against superoxide anion radical, hydroxyl radical, 2,2-diphenyl-1-picrylhydrazyl radical, and hydrogen peroxide scavenging properties. The total antioxidant status based on the absorbance of the 2,2'-azino-bis(3-ethylbenzothiazoline-6-sulphonic acid) radical cation (ABTS ) and total antioxidant capacity using the Fe(III)-ferrozine complex were also monitored. The results of the above studies showed that the compounds synthesized were found possessed moderate radical scavenging potential, and that their interaction with reactive oxygen species is complex and depends on their structural conformation and the type of substituent R in the piperazine ring being attached. Best antiradical activity were found for the compounds with methoxy groups on the phenyl ring of substituent R, whereas the presence of methoxy or trifluoromethyl groups in substituent R resulted in higher ABTS and ion Fe(III) reduction. These compounds are promising molecules to be used for their antioxidant properties and may be regarded, after improvement of the antioxidant potential, to control diseases of free radical etiology.
黄酮类化合物具有多种有益作用，并且因其在包括心血管疾病、神经退行性疾病和癌症在内的多种疾病中的药用价值而广为人知。在黄酮骨架中引入哌嗪环是药物发现中的一项重要策略，但只有少数研究合成了哌嗪基黄酮化合物以测试其生物活性。虽然在几种炎症性疾病的治疗中主要关注药物的抗氧化特性，但我们合成了一系列带有不同取代基苯环的新型哌嗪基黄酮类似物。对这些类似物针对超氧阴离子自由基、羟基自由基、2,2-二苯基-1-苦基肼自由基的体外抗氧化活性以及过氧化氢清除特性进行了评估。还监测了基于2,2'-偶氮双(3-乙基苯并噻唑啉-6-磺酸)自由基阳离子(ABTS )吸光度的总抗氧化状态以及使用Fe(III)-亚铁嗪络合物的总抗氧化能力。上述研究结果表明，合成的化合物具有中等程度的自由基清除潜力，并且它们与活性氧的相互作用很复杂，取决于它们的结构构象以及连接的哌嗪环中取代基R的类型。发现取代基R的苯环上带有甲氧基的化合物具有最佳的抗自由基活性，而取代基R中存在甲氧基或三氟甲基会导致更高的ABTS和离子Fe(III)还原。这些化合物因其抗氧化特性而有望成为有应用价值的分子，并且在抗氧化潜力得到改善后，可被视为用于控制自由基病因引起的疾病。
