INCLUSION COMPLEX-FORMATION OF ANTHRACYCLINE ANTIBIOTICS WITH CYCLODEXTRINS - A PROTON NUCLEAR-MAGNETIC-RESONANCE AND MOLECULAR MODELING STUDY

被引:29
作者
BEKERS, O
KETTENESVANDENBOSCH, JJ
VANHELDEN, SP
SEIJKENS, D
BEIJNEN, JH
BULT, A
UNDERBERG, WJM
机构
[1] NETHERLANDS CANC INST,1066 CX AMSTERDAM,NETHERLANDS
[2] STATE UNIV UTRECHT,FAC CHEM,3584 CH UTRECHT,NETHERLANDS
来源
JOURNAL OF INCLUSION PHENOMENA AND MOLECULAR RECOGNITION IN CHEMISTRY | 1991年 / 11卷 / 02期
关键词
ANTHRACYCLINES; CYCLODEXTRINS; COMPLEX FORMATION; COMPLEX STRUCTURE; H-1-NMR; MOLECULAR MODELING;
D O I
10.1007/BF01153301
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
The inclusion complexation of the anthracyline antibiotics doxorubicin and daunorubicin with cyclodextrins has been studied by proton NMR and molecular modelling. The anthracyclines were found to complex with gamma-cyclodextrin, whereby the aglyconic part of the molecule is included in the cyclodextrin cavity. Job ratio plots based on NMR data indicate that the complex has a stoichiometry of 1:1. Complex constant values of 345 M-1 and 323 M-1 (at pH 3) were found for doxorubicin and daunorubicin, respectively.
引用
收藏
页码:185 / 193
页数:9
相关论文
共 22 条
[1]   ANTITUMOR ANTHRACYCLINES - RECENT DEVELOPMENTS [J].
ARCAMONE, F .
MEDICINAL RESEARCH REVIEWS, 1984, 4 (02) :153-188
[2]  
ARCAMONE F, 1968, TETRAHEDRON LETT, V30, P3353
[3]   ASPECTS OF THE CHEMICAL-STABILITY OF DOXORUBICIN AND 7 OTHER ANTHRACYCLINES IN ACIDIC SOLUTION [J].
BEIJNEN, JH ;
WIESE, G ;
UNDERBERG, WJM .
PHARMACEUTISCH WEEKBLAD-SCIENTIFIC EDITION, 1985, 7 (03) :109-116
[4]   ASPECTS OF THE DEGRADATION KINETICS OF DAUNORUBICIN IN AQUEOUS-SOLUTION [J].
BEIJNEN, JH ;
VANDERHOUWEN, OAGJ ;
VOSKUILEN, MCH ;
UNDERBERG, WJM .
INTERNATIONAL JOURNAL OF PHARMACEUTICS, 1986, 31 (1-2) :75-82
[5]   ASPECTS OF THE DEGRADATION KINETICS OF DOXORUBICIN IN AQUEOUS-SOLUTION [J].
BEIJNEN, JH ;
VANDERHOUWEN, OAGJ ;
UNDERBERG, WJM .
INTERNATIONAL JOURNAL OF PHARMACEUTICS, 1986, 32 (2-3) :123-131
[6]   STABILIZATION OF MITOMYCINS ON COMPLEXATION WITH CYCLODEXTRINS IN AQUEOUS ACIDIC MEDIA [J].
BEKERS, O ;
BEIJNEN, JH ;
BRAMEL, EHG ;
OTAGIRI, M ;
BULT, A ;
UNDERBERG, WJM .
INTERNATIONAL JOURNAL OF PHARMACEUTICS, 1989, 52 (03) :239-248
[7]   INCLUSION COMPLEXATION OF DOXORUBICIN AND DAUNORUBICIN WITH CYCLODEXTRINS [J].
BEKERS, O ;
BEIJNEN, JH ;
OTAGIRI, M ;
BULT, A ;
UNDERBERG, WJM .
JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS, 1990, 8 (8-12) :671-674
[8]   EFFECT OF CYCLODEXTRINS ON ANTHRACYCLINE STABILITY IN ACIDIC AQUEOUS-MEDIA [J].
BEKERS, O ;
BEIJNEN, JH ;
BRAMEL, EHG ;
OTAGIRI, M ;
UNDERBERG, WJM .
PHARMACEUTISCH WEEKBLAD-SCIENTIFIC EDITION, 1988, 10 (05) :207-212
[9]   A SPECTROPHOTOMETRIC INVESTIGATION OF THE INTERACTION OF IODINE WITH AROMATIC HYDROCARBONS [J].
BENESI, HA ;
HILDEBRAND, JH .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1949, 71 (08) :2703-2707
[10]  
Crooke S.T., 1980, ANTHRACYCLINES CURRE