Open AccessDNA binding properties of 2ʹ-hydroxyflavanon and Schiff base derivative
Author(s) -
Violetta M Korolevich,
Paulina Błazińska,
Anna Sykuła,
Elżbieta Łodyga-Chruścińska
Publication year - 2019
Publication title -
vescì nacyânalʹnaj akadèmìì navuk belarusì. seryâ bìâlagìčnyh navuk
Language(s) - English
Resource type - Journals
eISSN - 2524-230X
pISSN - 1029-8940
DOI - 10.29235/1029-8940-2019-64-2-222-228
Subject(s) - chromone , intercalation (chemistry) , dna , flavanone , chemistry , derivative (finance) , molecule , stereochemistry , schiff base , combinatorial chemistry , biophysics , biochemistry , organic chemistry , biology , flavonoid , financial economics , economics , antioxidant
Flavanoids a class of plant and fungus secondary metabolites. 2ʹ-Hydroxyflavanone was previously isolated from Mimosa pudica (L.) whole plant and was found to exhibit anti-inflammatory effects in vitro and binding with calf timus DNA. There are also reports on anti-inflammatory properties of compounds bearing flavanone/chromone nucleus. The aim of this work was to develop a synthesis of new azomethine compounds derived from flavanones, to examine their spectroscopic properties and interaction with DNA. 2ʹ-Hydroxyflavanone and thiocarbohydrazide were used as substrates in the synthesis. The obtained products were analyzed by 1H NMR spectroscopy, UVVis. Ultraviolet spectroscopy was used to analyze the chemical-physical properties. Mechanism of interaction of bioactive 2ʹ-hydroxyflavanone with calf thymus deoxyribonucleic acid (DNA) was studied employing UV absorption. 2ʹ-Hydroxyflavanon and 2ʹHFTCH are photostable in DMSO. The interaction of 2ʹ-hydroxyflavanone and its derivative occurs by the mechanism of intercalation. The change in the structure of the 2ʹ-hydroxyflavanone molecule by Schiff base modification leads to an increase in DNA-binding properties. High binding ability of 2ʹ-hydroxyflavanone with DNA may be useful for development of new anti-inflammatory and antimicrobial remedies.