Details

Autor(en) / Beteiligte

• Muñoz, Vanesa A.
• Dimarco Palencia, Frida C. D.
• Sancho, Matias I.
• Miskoski, Sandra
• García, Norman A.
• Ferrari, Gabriela V.
• Montaña, María Paulina

Titel

Experimental and Theoretical Study of the Stability of the Complex Fisetin–Cu(II) and A Comparative Study of Free Ligand and Complex Interaction with Molecular Singlet Oxygen

Ist Teil von

• Photochemistry and photobiology, 2020-07, Vol.96 (4), p.815-825

Ort / Verlag

United States: Blackwell Publishing Ltd

Erscheinungsjahr

2020

Link zum Volltext

Quelle

Alma/SFX Local Collection

Beschreibungen/Notizen

• In this work, the flavonol fisetin was selected in order to study its reactivity against Cu(II), a metal ion of interest in biological media and industry. The stoichiometry and apparent formation constant of the complex in ethanolic medium at 25°C were evaluated using spectrophotometric techniques. The resulting stoichiometry was a 1:1 ligand:metal complex, and a log K = 5.17 ± 0.12 was determined. Since two possible chelation sites can be proposed for the complex formation, quantum chemistry calculations were performed on these structures. Calculations suggest that the hydroxyl‐keto site is more stable for the complex formation than the catechol site. Flavonoids could exert protection against oxidative damage caused by reactive oxygen species, and this biological activity could be affected by chelation with metal ions. This led us to perform a study on the interaction of both, free flavonoid and complex, with reactive oxygen species. Our results showed both compounds quench molecular singlet oxygen photogenerated with visible light, mainly in a physical fashion. In order to analyze a possible protective effect of flavonoid and its complex against oxidative damage in biological environments, the amino acid tryptophan was selected as a model oxidation system. Free flavonoid does not have a marked protective effect, whereas its complex showed a relevant protective effect. Flavonoids can exert protection against oxidative damage caused by reactive oxygen species, and this biological activity could be affected by chelation with metallic ions. The stoichiometry and the apparent formation constant of the fisetin–Cu(II) complex were determined. The molecular structure of fisetin shows two possible chelation sites. A molecular modeling analysis of fisetin and its complex was performed to study spectroscopic properties and compared with experimental data.