Synthesis of chrysin derivatives and their interaction with DNA.
- Author:
Zun-Ting ZHANG
1
;
Li-Li CHEN
Author Information
1. School of Chemistry and Materials Science, Shaanxi Normal University, Xi'an 710062, China. zhangzt@snnu.edu.cn
- Publication Type:Journal Article
- MeSH:
Animals;
Crystallography;
DNA;
metabolism;
Drug Interactions;
Flavones;
chemical synthesis;
chemistry;
Flavonoids;
chemical synthesis;
chemistry;
metabolism;
Magnetic Resonance Spectroscopy;
Molecular Structure;
X-Ray Diffraction
- From:
Acta Pharmaceutica Sinica
2007;42(5):492-496
- CountryChina
- Language:Chinese
-
Abstract:
Using chrysin as a leading compound, intermediate 5, 7-dihydroxy-6, 8-bis (hydroxymethyl) flavone (1) was synthesized by hydroxymethylation. The intermediate reacted with different alcohols to afford 5, 7-dihydroxy-6, 8-bis ( methoxymethyl) flavone (2), 6, 8-bis (ethoxymethyl) -5, 7dihydroxyflavone (3), 6, 8-bis-(butoxymethyl)-5, 7-dihydroxyflavone (4), 6, 8-bis (pentyloxymethyl) -5,7-dihydroxy flavone (5) and 6, 8-bis-(ethoxymethyl) -5-hydroxy-7-methoxyflavone (6). These compounds were characterized by IR, 1H NMR, 13C NMR and element analysis. The crystal structure of 6 was determined by X-ray crystal diffraction. The interaction of the derivatives with CT-DNA was studied by fluorescent spectroscopy. According to the Stern-Volmer equation, the quenching constants of the compounds 1 - 4 were measured, separately, they were K(q1) = 9.71 x 10(3) L x mol(-1), K(q2) = 2.25 x 10(4) L x mol(-1), K(q3) = 1.03 x 10(4) L x mol(-1) and K(q4) = 7.96 x 10(3) L x mol(-1). Compounds 1-4 showed higher binding affinity with DNA than chrysin did. The results provided the experimental basis for developing a more effective flavonoid and worthing further thoroughly study.
