Utility of cyclodextrins in the formulation of genistein Part 1. Preparation and physicochemical properties of genistein complexes with native cyclodextrins

被引:38
作者
Daruhazi, Agnes Emma [1 ]
Szente, Lajos [2 ]
Balogh, Balazs [3 ]
Matyus, Peter [3 ]
Beni, Szabolcs [4 ]
Takacs, Maria [4 ]
Gergely, Andras [4 ]
Horvath, Peter [4 ]
Szoke, Eva [1 ]
Lemberkovics, Eva [1 ]
机构
[1] Semmelweis Univ, Dept Pharmacognosy, H-1085 Budapest, Hungary
[2] CycloLab Ltd, H-1097 Budapest, Hungary
[3] Semmelweis Univ, Dept Organ Chem, H-1092 Budapest, Hungary
[4] Semmelweis Univ, Dept Pharmaceut Chem, H-1092 Budapest, Hungary
关键词
Ononis; Genistein; Solubility; Parent cyclodextrins; Circular dichroism; ROESY;
D O I
10.1016/j.jpba.2008.06.007
中图分类号
O65 [分析化学];
学科分类号
070302 ; 081704 ;
摘要
Isoflavones are suitable guest molecules for inclusion complex formation with cyclodextrins (CDs). The molecular encapsulation with CDs results in a solid, molecularly dispersed form and in a significantly improved aqueous solubility of isoflavones. Genistein, a key isoflavone constituent of Ononidis spinosae radix was found to form a supramolecular, non-covalent inclusion complex with both beta-cyclodextrin (beta-CD) and gamma-cyclodextrin (gamma-CD), while it did not form a stable complex with alpha-CD. The guest genistein was found to spatially located in the less polar cavity of cyclodextrin. The isolated binary genistein/CD complexes appeared novel crystalline lattices. The in vitro dissolution of genistein entrapped into both beta- and gamma-CD, significantly surpassed that of the plain isoflavone. (C) 2008 Elsevier B.V. All rights reserved.
引用
收藏
页码:636 / 640
页数:5
相关论文
共 23 条
[1]   URINARY-EXCRETION OF LIGNANS AND ISOFLAVONOID PHYTOESTROGENS IN JAPANESE MEN AND WOMEN CONSUMING A TRADITIONAL JAPANESE DIET [J].
ADLERCREUTZ, H ;
HONJO, H ;
HIGASHI, A ;
FOTSIS, T ;
HAMALAINEN, E ;
HASEGAWA, T ;
OKADA, H .
AMERICAN JOURNAL OF CLINICAL NUTRITION, 1991, 54 (06) :1093-1100
[2]   Gut bacterial metabolism of the soy isoflavone daidzein: Exploring the relevance to human health [J].
Atkinson, C ;
Frankenfeld, CL ;
Lampe, JW .
EXPERIMENTAL BIOLOGY AND MEDICINE, 2005, 230 (03) :155-170
[3]   Phytoestrogens derived from red clover: An alternative to estrogen replacement therapy? [J].
Beck, VB ;
Rohr, U ;
Jungbauer, A .
JOURNAL OF STEROID BIOCHEMISTRY AND MOLECULAR BIOLOGY, 2005, 94 (05) :499-518
[4]   Cyclodextrin/imatinib complexation:: Binding mode and charge dependent stabilities [J].
Beni, Szabolcs ;
Szakacs, Zoltan ;
Csernak, Orsolya ;
Barcza, Lajos ;
Noszal, Bela .
EUROPEAN JOURNAL OF PHARMACEUTICAL SCIENCES, 2007, 30 (02) :167-174
[5]   Hydroxypropyl-beta-cyclodextrins: Induced circular dichroism spectra of included phenolphthalein as a function of the degree of substitution [J].
BuvariBarcza, A ;
Kajtar, J ;
Szente, L ;
Barcza, L .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1996, (04) :489-491
[6]   The rutin/β-cyclodextrin interactions in fully aqueous solution:: spectroscopic studies and biological assays [J].
Calabrò, ML ;
Tommasini, S ;
Donato, P ;
Stancanelli, R ;
Raneri, D ;
Catania, S ;
Costa, C ;
Villari, V ;
Ficarra, P ;
Ficarra, R .
JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS, 2005, 36 (05) :1019-1027
[7]   UV-vis and FTIR-ATR spectroscopic techniques to study the inclusion complexes of genistein with β-cyclodextrins [J].
Crupi, V. ;
Ficarra, R. ;
Guardo, M. ;
Majolino, D. ;
Stancanelli, R. ;
Venuti, V. .
JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS, 2007, 44 (01) :110-117
[8]   Inactivation of thyroid peroxidase by soy isoflavones, in vitro and in vivo [J].
Doerge, DR ;
Chang, HC .
JOURNAL OF CHROMATOGRAPHY B-ANALYTICAL TECHNOLOGIES IN THE BIOMEDICAL AND LIFE SCIENCES, 2002, 777 (1-2) :269-279
[10]  
HIGUCHI WT, 1965, ADV ANAL METHODS INS, P123