Host-guest inclusion systems of daidzein with 2-hydroxypropy1-β-cyclodextrin (HP-β-CD) and sulfobutyl ether-β-cyclodextrin (SBE-β-CD): Preparation, binding behaviors and water solubility

被引:38
作者
Deng, Yinghui [1 ,2 ]
Pang, Yanhua [3 ]
Guo, Yafei [1 ]
Ren, Yufeng [1 ]
Wang, Fen [1 ]
Liao, Xiali [1 ]
Yang, Bo [1 ]
机构
[1] Kunming Univ Sci & Technol, Fac Life Sci & Technol, Kunming 650500, Peoples R China
[2] Qujing Med Coll, Qujing 655000, Peoples R China
[3] Armed Police Yunnan Corps & Qujing Detachment, Qujing 655000, Peoples R China
基金
中国国家自然科学基金;
关键词
Daidzein; 2-Hydroxypropyl-beta-cyclodextrin (HP-beta-CD); Sulfobutyl ether-beta-cyclodextrin (SBE-beta-CD); Inclusion complex; Water solubility; CANCER-CELLS; HUMAN-ERYTHROCYTES; SOY ISOFLAVONE; DERIVATIVES; GENISTEIN; COMPLEXES; ANTIOXIDANT; CHEMISTRY; METHODOLOGY; STABILITY;
D O I
10.1016/j.molstruc.2016.04.040
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
Daidzein is an isoflavone of naturally abundance existing in plants and foods which has attracted much attention for its significant benefits on human health. However, its application was severely limited by its poor solubilities, instability and low bioavailability. To overcome these drawbacks, inclusion complexes of daidzein with two cyclodextrin (CD) derivatives, i.e., 2-hydropropy1-beta-cyclodextrin (HP-beta-CD) and sulfobutyl ether-beta-cyclodextrin (SBE-beta-CD) were prepared and characterized both in solution and solid state by 1D and 2D NMR, XRD, SEM and elemental analyses. Fluorescence spectroscopy and the Job plot were used to demonstrate a mainly 1:1 inclusion mode between daidzein and CDs. Their thermal stabilities were evaluated with TG and DSC experiments. Moreover, water solubility of daidzein was significantly improved by inclusion complexation with CDs. These results might suggest valuable approaches to developments of new pharmaceutical formulations of daidzein. (C) 2016 Elsevier B.V. All rights reserved.
引用
收藏
页码:307 / 315
页数:9
相关论文
共 48 条
[1]   Cyclodextrin derivatives in pharmaceutics [J].
Albers, E ;
Muller, BW .
CRITICAL REVIEWS IN THERAPEUTIC DRUG CARRIER SYSTEMS, 1995, 12 (04) :311-337
[2]   Pesticides microencapsulation. A safe and sustainable industrial process [J].
Alonso, Mariluz L. ;
Laza, Jose M. ;
Alonso, Rosa M. ;
Jimenez, Rosa M. ;
Vilas, Jose L. ;
Fananas, Roberto .
JOURNAL OF CHEMICAL TECHNOLOGY AND BIOTECHNOLOGY, 2014, 89 (07) :1077-1085
[3]   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
[4]   Daidzein/cyclodextrin/hydrophilic polymer ternary systems [J].
Borghetti, Greice Stefani ;
Pinto, Angela Pinheiro ;
Lula, Ivana Silva ;
Sinisterra, Ruben Dario ;
Teixeira, Helder Ferreira ;
Bassani, Valquiria Linck .
DRUG DEVELOPMENT AND INDUSTRIAL PHARMACY, 2011, 37 (08) :886-893
[5]   A NEW PH-METRIC METHODOLOGY FOR THE DETERMINATION OF THERMODYNAMIC INCLUSION CONSTANTS OF GUEST CYCLODEXTRIN COMPLEXES [J].
BOUDEVILLE, P ;
BURGOT, JL .
JOURNAL OF PHARMACEUTICAL SCIENCES, 1995, 84 (09) :1083-1089
[6]   SOLUBILITY BEHAVIOR OF BETA-CYCLODEXTRIN IN WATER COSOLVENT MIXTURES [J].
CHATJIGAKIS, AK ;
DONZE, C ;
COLEMAN, AW ;
CARDOT, P .
ANALYTICAL CHEMISTRY, 1992, 64 (14) :1632-1634
[7]   Daidzein promotes glucose uptake through glucose transporter 4 translocation to plasma membrane in L6 myocytes and improves glucose homeostasis in Type 2 diabetic model mice [J].
Cheong, Sun Hee ;
Furuhashi, Keisuke ;
Ito, Katsuki ;
Nagaoka, Masato ;
Yonezawa, Takayuki ;
Miura, Yutaka ;
Yagasaki, Kazumi .
JOURNAL OF NUTRITIONAL BIOCHEMISTRY, 2014, 25 (02) :136-143
[8]   Review: A History of Cyclodextrins [J].
Crini, Gregorio .
CHEMICAL REVIEWS, 2014, 114 (21) :10940-10975
[9]   Investigation of transport of genistein, daidzein and their inclusion complexes prepared with different cyclodextrins on Caco-2 cell line [J].
Daruhazi, Agnes Emma ;
Kiss, Timea ;
Vecsernyes, Miklos ;
Szente, Lajos ;
Szoke, Eva ;
Lemberkovics, Eva .
JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS, 2013, 84 :112-116
[10]   Combination of low dose of genistein and daidzein has synergistic preventive effects on isogenic human prostate cancer cells when compared with individual soy isoflavone [J].
Dong, Xin ;
Xu, Wenqing ;
Sikes, Robert A. ;
Wu, Changqing .
FOOD CHEMISTRY, 2013, 141 (03) :1923-1933