光谱学与光谱分析 |
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Research on the Interactions between Genistein and Its Glucosides with DNA |
LI Hua1,YU Yan-ying1*,HU Xin1,CAO Shu-wen1,2 |
1.Department of Chemistry, Nanchang University, Nanchang 330031, China 2.State Key Laboratory of Food Science and Technology, Nanchang University, Nanchang 330047, China |
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Abstract The interactions of genistein(GEN), genistein glucoside(GENG) and genistein 7,4’-di-O-β- D- glucoside(GEND) with calf thymus DNA(ctDNA) in Tris (pH 7.2) buffer were investigated by UV spectra, fluorescence spectra and viscosity.From the absorption titration experiments, no obvious red shifts were found, but the notable hypochromicities were observed.The π→π* transitions of GEN at 262 nm showed a 10% decrease in intensity at [GEN]/[DNA]=2, and for the GENG and GEND, the decreases were 24.8% and 18% at 260 and 258 nm, respectively.These results indicated that there were intercalations between these compounds and ctDNA, involving a strong π-stacking interacting.The hypochromism of the two glucosides was bigger than that of GEN, which suggested that the two glucosides intercalated deeply into the DNA base pairs.The emission intensity of DNA-EB system at 600 nm decreased remarkably with increasing the three compounds, indicating that these compounds could intercalate into DNA and replace EB from the DNA-EB system.And at 25 and 37 ℃, the fluorescence quenching curves of these compounds with DNA-EB system were not linear curves.According to the classical Stern-Volmer equation, it was not single static or dynamic quenching model, so there would be hydrogen bonding besides intercalation.Viscosity experiments were carried out by an Ubbelodhe viscometer at (20.0±0.1)℃.The relative viscosity of ctDNA increased steadily with increasing these compounds.The results clearly showed that these compounds could intercalate between DNA base pairs, causing an extension of the helix, and thus increased the viscosity of DNA.And because of the greatest increase in viscosity of the DNA, the interaction of GENG with DNA was the strongest, followed by GEND, and then GEN.The results were consistent with the above spectral results.These results suggested that genistein and its glucosides could bind to ctDNA partly by intercalation and hydrogen bonding mode, and the binding ability to ctDNA followed the order of GENG>GEND>GEN from which, the authors speculated that 7 or 4’-O-glycosylation modification maybe an effective way to improve medicinal activity of genistein, and its glucoside modified derivatives may be a promising candidate for anticancer drug, which deserves further research.
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Received: 2007-03-02
Accepted: 2007-06-08
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Corresponding Authors:
YU Yan-ying
E-mail: yuyanying@ncu.edu.cn
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[1] CHI Yan-hua, ZHUANG Jia, XUE Qi-bin, et al(迟燕华, 庄 稼, 薛其彬, 等).Spectroscopy and Spectral Analysis(光谱学与光谱分析), 2006, 26(1):97. [2] JI Liang-nian(计亮年).World Sci-tech R & D(世界科技研究与发展), 2004, 26(6):1. [3] Richard A Dixon, Daneel Ferreira.Phytochemistry, 2002, 60(3):205. [4] JIN Yong-sheng, LIU Chao-mei, WU Qiu-ye, et al(金永生, 刘超美, 吴秋业, 等).Academic Journal of Second Military University(第二军医大学学报), 2005, 26(2):182. [5] Alessandra Russo, Venera Cardile, Laura Lombarbo, et al.J.Nutr.Biochem., 2006, 17(2):103. [6] TANG Yu-ping, LOU Feng-chang, MA Wen, et al(唐于平, 楼凤昌, 马 雯, 等).Journal of China Pharmaceutical University(中国药科大学学报), 2001, 32(3):187. [7] Joanna Popiolkiewicz, Krzysztof Polkowski, Janusz S Skierski.Cancer Letters, 2005, 229:67. [8] WANG Ping-hong, ZHANG Qi, YUAN Wen-bing, et al(王平红, 张 岐, 袁文兵, 等).Spectroscopy and Spectral Analysis(光谱学与光谱分析), 2006, 26(7):1298. [9] GUO Yu-hua, CHEN Xiao-lan, ZHANG Ting, et al(郭玉华, 陈晓岚, 张 婷, 等).Spectroscopy and Spectral Analysis(光谱学与光谱分析), 2006, 26(3):475. [10] WU Bao-yan, GAO Li-hua, WANG Ke-zhi(吴宝燕, 高丽华, 王科志).Chemical Journal of Chinese Universities(高等学校化学学报), 2005, 26:1206. [11] Zhou Q H, Yang P.Inorganica Chimica Acta, 2006, 359:1200. [12] LI Zhi-liang, CHEN Jian-hua, ZHANG Kai-cheng, et al(李志良, 陈建华, 章开诚, 等).Science in China (Series B)(中国科学, B辑), 1991, 21:1193. [13] Usha S, Johnson I M, Malathi R.Mol.and Cellular Biochemistry, 2006, 284:57. [14] LI Lai-sheng, HUANG Wei-dong, WANG Rui-qiong, et al(李来生, 黄伟东, 王瑞琼, 等).Acta Chimica Sinica(化学学报), 1999, 57:572. [15] Sigma D S, Mazuder A, Perrin D M.Chem.Rev., 1993, 93:2295. [16] Satyanarayana S, Daborusak J C, Chaires J B.Biochemistry, 1992, 31:9319. [17] LEI Ying-jie, YANG Yi-cheng, SHI Xiao-feng(雷英杰, 杨易成, 史小凤).Journal of Tianjin University of Technology(天津理工大学学报), 2006, 22(3):52. [18] Usha S, Johnson I M, Malathi R.J.Biochem.Mol.Biol., 2005, 38(2):198. [19] ZHANG Jian, ZHANG Gao-yong, XIE Ke-chang, et al(张 剑, 张高勇, 谢克昌, 等).Acta Chimica Sinica(化学学报), 2003, 61(10):1658. |
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