物理化学学报 >> 2010, Vol. 26 >> Issue (02): 495-501.doi: 10.3866/PKU.WHXB20100238

生物物理化学 上一篇    下一篇

胆固醇修饰富勒烯/γ-环糊精包结复合物的生物活性

高云燕, 刘丽华, 欧植泽, 李嫕, 杨国强, 王雪松   

  1. 西北工业大学理学院应用化学系, 西安 710072; 中国科学院理化技术研究所, 光化学转换与功能材料重点实验室, 北京 100090; 中国科学院化学研究所, 光化学重点实验室, 北京 100190
  • 收稿日期:2009-08-28 修回日期:2009-11-12 发布日期:2010-01-26
  • 通讯作者: 高云燕, 欧植泽 E-mail:gaoyunyan@nwpu.edu.cn; ouzhize@nwpu.edu.cn

Biological Activity of a Cholesterol Modified Fullerene/γ-Cyclodextrin Inclusion Complex

GAO Yun-Yan, LIU Li-Hua, OU Zhi-Ze, LI Yi, YANG Guo-Qiang, WANG Xue-Song   

  1. Department of Applied Chemistry, School of Science, Northwestern Polytechnical University, Xi'an 710072, P. R. China; Key Laboratory of Photochemical Conversion and Optoelectronic Materials, Technical Institute of Physics and Chemistry, Chinese Academy of Sciences, Beijing 100190, P. R. China; Key Laboratory of Photochemistry, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, P. R. China
  • Received:2009-08-28 Revised:2009-11-12 Published:2010-01-26
  • Contact: GAO Yun-Yan, OU Zhi-Ze E-mail:gaoyunyan@nwpu.edu.cn; ouzhize@nwpu.edu.cn

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摘要：

采用Bingel-Hirsch反应合成了胆固醇修饰的富勒烯(CHL-C60), 通过核磁共振(NMR)、质谱(MS)、元素分析对CHL-C60的化学结构进行了表征. γ-环糊精(γ-CD)对甾环具有较强的包结能力, 能够与CHL-C60形成包结复合物(CHL-C60/γ-CD), 从而有效提高CHL-C60的水溶性. 紫外-可见吸收光谱和荧光光谱研究结果表明, CHL-C60能够从γ-CD的疏水空腔中解离出来, 与人血清白蛋白(HSA)及牛血清白蛋白(BSA)形成稳定的复合体, 其结合常数分别为5.73×104和7.05×104 L·moL-1. 无氧条件下, CHL-C60/γ-CD通过光诱导电子转移作用断裂pBR322质粒脱氧核糖核酸(DNA), 其效率可达60.5%.

关键词: 富勒烯, 环糊精包结物, 血清白蛋白, DNA断裂

Abstract:

A cholesterol modified fullerene (CHL-C60) was synthesized using the Bingel-Hirsch reaction and was characterized by nuclear magnetic resonance (NMR), mass spectra (MS), elemental analysis (EA). Results of UV-Vis spectrumand fluorescence spectrumindicate that CHL-C60 forms an inclusion complex with γ-cyclodextrin (γ-CD) due to the strong interaction between γ-cyclodextrin and the steroid ring. The water solubility of CHL-C60 is enhanced significantly. CHL-C60 can dissociate from cyclodextrin and subsequently bind to human serum albumin (HSA) and bovine serum albumin (BSA) with association constants of 5.73×104 and 7.05×104 L·moL-1, respectively. The efficiency of desoxyribonucleic acid (DNA) photocleavage for CHL-C60/γ-CD is as high as 60.5% under anaerobic conditions, which is caused by photoinduced electron transfer frompBR322 plasmid DNA to CHL-C60.

Key words: Fullerene, Cyclodextrin inclusion complex, Serumalbumin, DNA cleavage