Synthesis of biflavones and their interaction with DNA.
- Author:
Zun-Ting ZHANG
1
;
Run-Li GAO
;
Su-Kai ZHUANG
Author Information
1. Key Laboratory of Ministry of Education for Medicinal Resource and Natural Pharmaceutical Chemistry, National Engineering Laboratory for Resource Development of Endangered Crude Drug in Northwest of China, School of Chemistry and Materials Science, Shaanxi Normal University, Xi'an, China. zhangzt@snnu.edu.cn
- Publication Type:Journal Article
- MeSH:
Biflavonoids;
chemical synthesis;
chemistry;
DNA;
chemistry;
Flavonoids;
chemical synthesis;
chemistry;
Molecular Structure
- From:
Acta Pharmaceutica Sinica
2009;44(8):873-878
- CountryChina
- Language:Chinese
-
Abstract:
To explore new biflavones, 7-hydroxy-8-hydroxymethyl-4'-methoxyisoflavone (1), (5, 7-dihydroxyflavone-8-yl)-(7'-hydroxy-4"-methoxyisoflavone-8'-yl)methane (2), bis(7-hydroxy-4'-methoxyflavone-8-yl) methane (3), bis(3', 5'-diisopropyl-7, 4'-dihydroxy-isoflavone-8-yl)methane (4), and bis(7-hydroxy-isoflavone-8-yl) methane (5) were designed and synthesized from chrysin, formononetin, 7, 4'-dihydroxy-3', 5'-diisopropyl-isoflavone and 7-hydroxy-isoflavone. Their structures were identified with IR, 1H NMR, 13C NMR and elemental analysis. The binding of 1-5 with DNA was studied with fluorescent spectroscopy. Compounds 2-5 showed higher binding affinity with DNA than 1. According to the Stern-Volmer equation, the binding constants of 2, 3 were determined at 35 degrees C and 25 degrees C respectively, they were Kq2 (25 degrees C) = 1.95 x 10(4) Lx mol(-1) and Kq2 (35 degrees C) = 1.67 x 10(4) L x mol(-1); Kq3 (25 degrees C) = 1.89 x 10(4) L x mol(-1) and Kq3 (35 degrees C) = 1.58 x 10(4) L x mol(-1). The quenching mechanism of 2, 3 was suggested as static quenching.
