Novel molecular drug carrier: encapsulation of oxaliplatin in cucurbit[7]uril and its effects on stability and reactivity of the drug

被引:266
作者
Jeon, YJ
Kim, SY
Ko, YH
Sakamoto, S
Yamaguchi, K
Kim, K
机构
[1] Pohang Univ Sci & Technol, Natl Creat Res Initiat Ctr Smart Supramol, Pohang 790784, South Korea
[2] Pohang Univ Sci & Technol, Dept Chem, Div Mol & Life Sci, Pohang 790784, South Korea
[3] Tokushima Bunri Univ, Analyt Chem Lab, Dept Pharmaceut Technol, Fac Pharmaceut Sci, Sanuki City 7692193, Japan
关键词
D O I
10.1039/b504487a
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Oxaliplatin forms a stable 1 : 1 inclusion complex with cucurbit[7] uril as indicated by NMR, mass spectrometry, isothermal titration calorimetry and X-ray crystallography. The encapsulation of the drug results in a large enhancement in stability, a moderate decrease in reactivity toward guanosine but a much larger decrease in reactivity toward L-methionine, which suggests the encapsulation not only increases the stability of the drug but also may reduce unwanted side effects caused by protein binding of the platinum drug. A preliminary in vitro assay using various tumor cell lines reveals that the encapsulation results in a decrease in the antitumor activity of oxaliplatin.
引用
收藏
页码:2122 / 2125
页数:4
相关论文
共 49 条
[1]   THE X-RAY CRYSTAL-STRUCTURE OF A 1-1 ADDUCT BETWEEN ALPHA-CYCLODEXTRIN AND CYCLOBUTANE-1,1-DICARBOXYLATODIAMMINEPLATINUM(II) [J].
ALSTON, DR ;
SLAWIN, AMZ ;
STODDART, JF ;
WILLIAMS, DJ .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (22) :1602-1604
[2]   THE BINDING OF CYCLOBUTANE-1,1-DICARBOXYLATODIAMMINEPLATINUM(II) BY ALPHA-CYCLODEXTRIN IN AQUEOUS-SOLUTION [J].
ALSTON, DR ;
LILLEY, TH ;
STODDART, JF .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1985, (22) :1600-1602
[3]  
[Anonymous], 2004, ENCY SUPRAMOLECULAR
[4]  
ATWOOD JL, 1996, COMPREHENSIVE SUPRAM, V3
[5]   Cucurbit[7]uril and o-carborane self-assemble to form a molecular ball bearing [J].
Blanch, RJ ;
Sleeman, AJ ;
White, TJ ;
Arnold, AP ;
Day, AI .
NANO LETTERS, 2002, 2 (02) :147-149
[6]   CUCURBITURIL AS A LIGAND FOR THE COMPLEXATION OF CATIONS IN AQUEOUS-SOLUTIONS [J].
BUSCHMANN, HJ ;
CLEVE, E ;
SCHOLLMEYER, E .
INORGANICA CHIMICA ACTA, 1992, 193 (01) :93-97
[7]  
Cram D.J., 1994, CONTAINER MOL THEIR
[8]   MOLECULAR CONTAINER COMPOUNDS [J].
CRAM, DJ .
NATURE, 1992, 356 (6364) :29-36
[9]   Controlling factors in the synthesis of cucurbituril and its homologues [J].
Day, A ;
Arnold, AP ;
Blanch, RJ ;
Snushall, B .
JOURNAL OF ORGANIC CHEMISTRY, 2001, 66 (24) :8094-8100
[10]  
Day AI, 2002, ANGEW CHEM INT EDIT, V41, P275, DOI 10.1002/1521-3773(20020118)41:2<275::AID-ANIE275>3.0.CO