Position Impact of Hydroxy Groups on Spectral, Acid–Base Profiles and DNA Interactions of Several Monohydroxy Flavanones

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-hydroxyflavanone, 6-hydroxyflavanone and 7-hydroxyflavanone and linking them to their biological activity. Potentiometric titration, UV–Vis spectroscopy were used to investigate influence of pH on acid–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 affnities 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–activity relationships observed for antioxidant activity and DNA interactions suggest that 6-hydroxyflavanone can protect DNA against oxidative damage most effectively than flavanone, 2-hydroxyflavanone or 7-hydroxyflavanone

In vitrostudy of hesperetin Schiff bases antioxidant activity on rat liver mitochondria

Three hesperetin Schiff bases: hesperetin thiosemicarbazone (HTSC), hesperetin isoniazone (HIN) and hesperetin benzhydrazone (HHSB) have been synthesized and characterized by using analytical and spectral techniques. The influence of substituents on hesperetin antioxidant activity has been studied in vitro using mitochondrial assays. The studied compounds have been found to exhibit both antioxidant and pro-oxidant activity

Schiff bases – interesting range of applications in various fields of science

Kompleksy metali odgrywają istotną rolę zarówno w rolnictwie, jak również chemii farmaceutycznej i przemysłowej. Zasady Schiffa są produktami kondensacji pierwszorzędowych amin i związków karbonylowych. Związki te oraz ich kompleksy z metalami są coraz częściej stosowane jako katalizatory, polimery i barwniki. W artykule przedstawiono właściwości zasad Schiffa oraz korzyści wynikające z ich stosowania w różnych gałęziach przemysłu.Metal complexes play an important role in agriculture as well as industrial and pharmaceutical chemistry. Schiff bases are the condensation products of primary amines and carbonyl compounds. Schiff bases and their metal complexes are increasingly being used as catalysts, polymers and dyes. This paper reviews the properties of Schiff bases and benefits of their use in various branches of industry

Регуляция активности белков множественной лекарственной устойчивости основаниями Шиффа гесперетина

In this study, we considered the effect of hesperetin, its Schiff base with isoniazid (HIN) and the complex with copper ions (II) (CuHIN) on MDR activity in cells lines, as well as their antioxidant activity. The Schiff base of hesperetin (HIN) had a strong inhibitory effect on MDR activity at a concentration of 5 μM and possessed a strong antioxidant activity with respect to free radical DPPH• compared with hesperetin. The introduction of copper ions into the Schiff base structure led to a less stimulating effect on the activity of MDR proteins in the cell lines. The ability of Schiff base of hesperetin (HIN) to inhibit MDR proteins may have the potential to develop low-toxicity antitumor and antimicrobial drugs.В данной работе исследованы антиоксидантная активность и рассмотрены эффекты гесперетина, его основания Шиффа с изониазидом (HIN) и комплекса с ионами меди (II) (CuHIN) на активность белков множественной лекарственной устойчивости (МЛУ) в клеточных линиях, а также выявлена их антиоксидантная активность. Производное гесперетина (HIN) оказывает сильный игибирующий эффект на активность МЛУ белков при концентрации 5 мкМ и обладает значительной антиоксидантной активностью в отношении к свободному радикалу DPPH• по сравнению с гесперетином. Введение в структуру основания Шиффа ионов меди приводит к незначительному стимулирующему действию на активность МЛУ белков в клеточных линиях. Способность основания Шиффа гесперетина (HIN) ингибировать активность МЛУ белков может иметь потенциал в разработке противоопухолевых и антимикробных лекарств низкой токсичности