Position Impact of Hydroxy Groups on Spectral, Acid–Base Profiles and DNA Interactions of Several Monohydroxy Flavanones
| Autor: | Antonio Zucca, Vitali T. Cheshchevik, Violetta M Korolevich, Elżbieta Łodyga-Chruścińska, Maria Itria Pilo, Agnieszka Kowalska-Baron, Paulina Błazińska |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2019 |
| Předmět: |
Models
Molecular structure–activity relationship Chemical structure Potentiometric titration Molecular Conformation Pharmaceutical Science Protonation Article Analytical Chemistry monohydroxy flavanones lcsh:QD241-441 Structure-Activity Relationship chemistry.chemical_compound Deprotonation lcsh:Organic chemistry Computational chemistry Drug Discovery Animals Structure–activity relationship Physical and Theoretical Chemistry dissociation constants Molecular Structure Organic Chemistry Biological activity DNA Models Theoretical chemistry Chemistry (miscellaneous) Flavanones Molecular Medicine Cattle Cyclic voltammetry DNA interactions Flavanone Algorithms |
| Zdroj: | Molecules Volume 24 Issue 17 Molecules, Vol 24, Iss 17, p 3049 (2019) |
| ISSN: | 1420-3049 |
| DOI: | 10.3390/molecules24173049 |
| Popis: | Structure-related biological activities of flavanones are still considered largely unexplored. Since they exhibit various medicinal activities, it is intriguing to enter deeper into their chemical structures, electronic transitions or interactions with some biomolecules in order to find properties that allow us to better understand their effects. Little information is available on biological activity of flavanone and its monohydroxy derivatives in relation to their physicochemical properties as spectral profiles, existence of protonated/deprotonated species under pH changes or interaction with Calf Thymus DNA. We devoted this work to research demonstrating differences in the physicochemical properties of the four flavanones: flavanone, 2&prime hydroxyflavanone, 6-hydroxyflavanone and 7-hydroxyflavanone and linking them to their biological activity. Potentiometric titration, UV&ndash Vis spectroscopy were used to investigate influence of pH on acid&ndash base and spectral profiles and to propose the mode of interaction with DNA. Cyclic voltammetry was applied to evaluate antioxidant potentiality and additionally, theoretical DFT(B3LYP) method to disclose electronic structure and properties of the compounds. Molecular geometries, proton affinities and pKa values have been determined. According to computational and cyclic voltammetry results we could predict higher antioxidant activity of 6-hydroxyflavanone with respect to other compounds. The values of Kb intrinsic binding constants of the flavanones indicated weak interactions with DNA. Structure&ndash activity relationships observed for antioxidant activity and DNA interactions suggest that 6-hydroxyflavanone can protect DNA against oxidative damage most effectively than flavanone, 2&prime hydroxyflavanone or 7-hydroxyflavanone. |
| Databáze: | OpenAIRE |
| Externí odkaz: |
|
| Nepřihlášeným uživatelům se plný text nezobrazuje | K zobrazení výsledku je třeba se přihlásit. |