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

被引:9
作者
Gao Yun-Yan [1 ]
Liu Li-Hua [1 ]
Ou Zhi-Ze [1 ]
Li Yi [2 ]
Yang Guo-Qiang [3 ]
Wang Xue-Song [2 ]
机构
[1] Northwestern Polytech Univ, Dept Appl Chem, Sch Sci, Xian 710072, Peoples R China
[2] Chinese Acad Sci, Key Lab Photochem Convers & Optoelect Mat, Tech Inst Phys & Chem, Beijing 100190, Peoples R China
[3] Chinese Acad Sci, Key Lab Photochem, Inst Chem, Beijing 100190, Peoples R China
关键词
Fullerene; Cyclodextrin inclusion complex; Serum albumin; DNA cleavage; PHOTOINDUCED ELECTRON-TRANSFER; METHYLENE-COMPOUNDS; WATER; C-60; ALBUMIN; BINDING; PHOTOCLEAVAGE; FLUORESCENCE; HYPOCRELLIN; LIPOSOMES;
D O I
10.3866/PKU.WHXB20100238
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
A cholesterol modified fullerene (CHL-C-60) 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 spectrum and fluorescence spectrum indicate that CHL-C-60 forms an inclusion complex with gamma-cyclodextrin (gamma-CD) due to the strong interaction between gamma-cyclodextrin and the steroid ring. The water solubility of CHL-C-60 is enhanced significantly. CHL-C-60 can dissociate from cyclodextrin and subsequently bind to human serum albumin (HSA) and bovine serum albumin (BSA) with association constants of 5.73 x 10(4) and 7.05 x 10(4) L.moL(-1), respectively. The efficiency of desoxyribonucleic acid (DNA) photocleavage for CHL-C-omega/gamma-CD is as high as 60.5% under anaerobic conditions, which is caused by photoinduced electron transfer from pBR322 plasmid DNA to CHL-C-60.
引用
收藏
页码:495 / 501
页数:7
相关论文
共 54 条
[1]   Electrostatic assemblies of fullerene-porphyrin hybrids: Toward long-lived charge separation [J].
Balbinot, D ;
Atalick, S ;
Guldi, DM ;
Hatzimarinaki, M ;
Hirsch, A ;
Jux, N .
JOURNAL OF PHYSICAL CHEMISTRY B, 2003, 107 (48) :13273-13279
[2]   Synthesis and water solubility of adamantyl-OEG-fullerene hybrids [J].
Bar-Shir, A ;
Engel, Y ;
Gozin, M .
JOURNAL OF ORGANIC CHEMISTRY, 2005, 70 (07) :2660-2666
[3]   Formation and characterization of stable human serum albumin-tris-malonic acid [C60]fullerene complex [J].
Belgorodsky, B ;
Fadeev, L ;
Ittah, V ;
Benyamini, H ;
Zelner, S ;
Huppert, D ;
Kotlyar, AB ;
Gozin, M .
BIOCONJUGATE CHEMISTRY, 2005, 16 (05) :1058-1062
[4]   Interaction of C60-fullerene and carboxyfullerene with proteins:: Docking and binding site alignment [J].
Benyamini, H ;
Shulman-Peleg, A ;
Wolfson, HJ ;
Belgorodsky, B ;
Fadeev, L ;
Gozin, M .
BIOCONJUGATE CHEMISTRY, 2006, 17 (02) :378-386
[5]   Efficient cyclopropanation of C-60 starting from malonates [J].
Camps, X ;
Hirsch, A .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (11) :1595-1596
[6]  
Cataldo F, 2008, CARBON MATER-CHEM PH, V1, P317
[7]   2,6-Bis(porphyrin)-substituted pyrazine: a new class of supramolecular synthon binding to a transition-metal ion and fullerene (C60) [J].
Eda, Yusaku ;
Itoh, Kennosuke ;
Ito, Yoshio N. ;
Kawato, Toshio .
TETRAHEDRON, 2009, 65 (01) :282-288
[8]   Interactions in single wall carbon nanotubes/pyrene/porphyrin nanohybrids [J].
Ehli, Christian ;
Aminur Rahman, G. M. ;
Jux, Norbert ;
Balbinot, Domenico ;
Guldi, Dirk M. ;
Paolucci, Francesco ;
Marcaccio, Massimo ;
Paolucci, Demis ;
Melle-Franco, Manuel ;
Zerbetto, Francesco ;
Campidelli, Stephane ;
Prato, Maurizio .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (34) :11222-11231
[9]   Interfacial behavior and film-forming properties of an amphiphilic hexasubstituted [60]fullerene [J].
Felder-Flesch, D ;
Bourgogne, C ;
Gallani, JL ;
Guillon, D .
TETRAHEDRON LETTERS, 2005, 46 (38) :6507-6510
[10]   Liquid-crystalline cholesterol-based [60]fullerene hexaadducts [J].
Felder-Flesch, D ;
Rupnicki, L ;
Bourgogne, C ;
Donnio, B ;
Guillon, D .
JOURNAL OF MATERIALS CHEMISTRY, 2006, 16 (03) :304-309