Synthesis, Characterization, and Biomedical Applications of an Alkylated Quercetin–Gadolinium Complex

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–1 s–1 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.