Synthesis, structural characterization, DNA binding and antioxidant studies of 4,4′-Nitrophenoxyaniline derived azo dyes
| Autor: | Samina Qamar, Fouzia Perveen, Huma Bano, Zareen Akhter, Sammer Yousuf |
|---|---|
| Rok vydání: | 2019 |
| Předmět: |
010405 organic chemistry
Chemistry DPPH Organic Chemistry Crystal structure Resorcinol 010402 general chemistry 01 natural sciences 0104 chemical sciences Analytical Chemistry Inorganic Chemistry Bond length chemistry.chemical_compound Phenol Spectroscopy Single crystal Nuclear chemistry Monoclinic crystal system |
| Zdroj: | Journal of Molecular Structure. 1197:345-353 |
| ISSN: | 0022-2860 |
| Popis: | Evaluation of DNA sensing and antioxidant potential has always been an open field of interest for pharmacists and other researchers. This paper presents a study on the synthesis, DNA sensing, and free radical scavenging potential of a series of new azo dyes derived from 4,4-nitrophenoxyaniline. The dyes were synthesized by classical diazotization-coupling method involving phenol, naphthol, and resorcinol as coupling component. Structural characterization of the synthesized dyes was done by Fourier transform infrared (FT-IR), Nuclear magnetic resonance (NMR), Ultraviolet–visible (UV/VIS) spectroscopy and single crystal XRD techniques. X-ray diffractions results revealed that dye 1a, 2 b, and 3c crystallized in the monoclinic system with P21/c, P21/n, and P21/c space groups respectively. Furthermore, for the dye 2 b, the single crystal X-ray data revealed a shorter N N bond length confirming predomination of hydrazo-keto form as compared to 1a and 3c dyes. The mode of interaction of these dyes with Salmon Sperm (SS) DNA was investigated using UV/VIS spectroscopy, viscosity, and molecular docking techniques. These results showed that synthesized dyes bind to the SS-DNA in a mixed binding mode with the dominant partial intercalative mode. Furthermore, the antioxidant potential of these dyes was also evaluated using 2,2-diphenyl-1-picrylhydrazyl (DPPH) and H2O2 antioxidant assays. |
| Databáze: | OpenAIRE |
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