Design, synthesis and anti-oxidant activities of novel 1,2,3,4-tetrazine, 1,2,3-triazoles and coumarin derivatives and their nanoparticular encapsulation

• Published in: Nano express Vol. 5; no. 3; pp. 35008 - 35025
• Main Authors: Eyilcim, Oznur, Belmen, Burcu, Coksu, Irem, Acar, Serap, Yolacan, Cigdem, Gunkara, Omer Tahir
• Format: Journal Article
• Language: English
• Published: Bristol IOP Publishing 01-09-2024
• Subjects: 1,2,3,4-Tetrazines; 1,2,3-triazole; Analogs; Antidepressants; antioxidant activity; Antioxidants; Chemical synthesis; Coumarin; Functional groups; Heterocyclic compounds; Lactones; Nanoparticles; Nitrogen; NMR; Nuclear magnetic resonance; Oxidizing agents; Particle size; Triazoles; Zeta potential
• ISSN: 2632-959X; 2632-959X
• DOI: 10.1088/2632-959X/ad64f1

Abstract Nitrogen-containing heterocyclic compounds are currently used for a number of pharmaceutical and agricultural applications because they have biological activities such as antimicrobial, antiviral, antituberculosis, anticancer, analgesic, antioxidant, anti-inflammatory and antidepressant. 1,2,3,4-Tetrazines and 1,2,3-triazoles are examples of high-nitrogen heterocyclic compounds. Coumarins, on the other hand, are lactones that form a group of oxygenated heterocyclic compounds found in plants. In this article, two analogs of 1,2,3,4-tetrazine, two analogs of 1,2,3-triazole and five analogs of coumarin were designed and synthesized. Their chemical structures were characterized by detecting their FTIR, 1 H-NMR, and 13 C-NMR (APT) spectra. The antioxidant activities of all synthesized molecules were compared at a fixed concentration (0.25 mg ml −1 ) using the 1,1-diphenyl-2-picrylhydrazyl (DPPH) method. Molecules 9c and 9e , which showed the highest antioxidant activity, were loaded into PLGA (poly(lactic-co-glycolic) acid) nanoparticles using the oil in water (o/w) single emulsion solvent evaporation method as a model study. Synthesized nanoparticles characterized for particle size, zeta potential, functional groups, morphology, and release properties. Particle size and zeta potential of 9c /NP were determined as 216.1 ± 8.944 nm and −14.1 ± 2.40 mV, respectively. The particle size and zeta potential for 9e /NP were measured as 222.0 ± 12.490 nm and −12.4 ± 1.42 mV respectively. The study results obtained on model nanoparticle systems with elucidated physicochemical properties may have the potential to provide a promising basis for oxidative stress-related diseases in the future.