Kaviarasi Sathyasivam, Shalini Devi K S, Vinoth Perumal, Sridharan Vellaisamy, Yuba Eiji, Harada Atsushi, Krishnan Uma Maheswari
Centre for Nanotechnology & Advanced Biomaterials, SASTRA Deemed University, Thanjavur 613401, India.
School of Chemical & Biotechnology, SASTRA Deemed University, Thanjavur 613401, India.
ACS Biomater Sci Eng. 2019 Mar 11;5(3):1215-1227. doi: 10.1021/acsbiomaterials.8b01254. Epub 2019 Feb 14.
Flavonoids and their derivatives have been extensively studied for their pharmaceutical applications due to their antioxidant and anti-inflammatory properties. The coordination complexes of several flavonoids have demonstrated DNA binding ability that can confer anticancer properties. The structure of the flavonoid has a pronounced influence on its pharmacological properties. Herein we report the synthesis and characterization of alkylated quercetin and its complex with gadolinium. The structure of the complex was confirmed using spectroscopic techniques. The ability of the gadolinium-alkylated quercetin complex to serve as a magnetic contrast agent was compared with gadolinium-quercetin complex. The quercetin-gadolinium complex was found to exhibit better contrast property with a relaxivity of 0.2952 μg mL s when compared to the gadolinium complex of alkylated quercetin. This difference primarily arises due to the greater hydrophobicity of the alkylated quercetin complex that restricts access of water. However, the alkylated quercetin was found to exhibit better enzyme mimic activity as the metal ion served as a redox center that enabled quantification of hydrogen peroxide in the concentration range 50-450 μM within 5 s with a sensitivity of 64 nA/μM and limit of detection of 7.3 μM. The better sensing performance of the alkylated quercetin-gadolinium complex, reported here for the first time, when compared to quercetin-gadolinium complex can be attributed to the enhanced electroactive area on the working electrode.
由于黄酮类化合物及其衍生物具有抗氧化和抗炎特性，因此已对其在药物应用方面进行了广泛研究。几种黄酮类化合物的配位络合物已证明具有DNA结合能力，可赋予抗癌特性。黄酮类化合物的结构对其药理特性有显著影响。在此，我们报告了烷基化槲皮素及其与钆络合物的合成与表征。使用光谱技术确认了该络合物的结构。将钆 - 烷基化槲皮素络合物用作磁性造影剂的能力与钆 - 槲皮素络合物进行了比较。与烷基化槲皮素的钆络合物相比，发现槲皮素 - 钆络合物具有更好的造影特性，弛豫率为0.2952 μg mL s。这种差异主要是由于烷基化槲皮素络合物的疏水性更强，限制了水的进入。然而，发现烷基化槲皮素表现出更好的酶模拟活性，因为金属离子作为氧化还原中心，能够在5秒内对浓度范围为50 - 450 μM的过氧化氢进行定量，灵敏度为64 nA/μM，检测限为7.3 μM。本文首次报道的烷基化槲皮素 - 钆络合物与槲皮素 - 钆络合物相比具有更好的传感性能，这可归因于工作电极上增强的电活性面积。
