Molecular encapsulation of 5-nitroindazole derivatives in 2,6-dimethyl-β-cyclodextrin: Electrochemical and spectroscopic studies

被引：16
|
作者：
Perez-Cruz, Fernanda [1 ]
Jullian, Carolina [1 ]
Rodriguez, Jorge [2 ,3 ]
Aran, Vicente J. [4 ]
Olea-Azar, Claudio [2 ]
机构：
[1] Univ Chile, Dept Quim Organ & Fisicoquim, Fac Ciencias Quim & Farmaceut, Santiago 1, Chile
[2] Univ Chile, Dept Quim Inorgan & Analit, Fac Ciencias Quim & Farmaceut, Santiago 1, Chile
[3] Univ Metropolitana Ciencias Educ, Dept Quim, Fac Ciencias Basicas, Santiago, Chile
[4] CSISC, Inst Quim Med, Madrid 28006, Spain
来源：
BIOORGANIC & MEDICINAL CHEMISTRY | 2009年 / 17卷 / 13期
关键词：
5-Nitroindazole; Cyclodextrin; Molecular modeling; NMR; ESR; AQUEOUS-SOLUTION; FLUORESCENCE ENHANCEMENT; BETA-CYCLODEXTRINS; PHASE-SOLUBILITY; AGGREGATION; INCLUSION; COMPLEX;
D O I：
10.1016/j.bmc.2009.04.067
中图分类号：
Q5 [生物化学]; Q7 [分子生物学];
学科分类号：
071010 ; 081704 ;
摘要：
Four different 5-nitroindazole derivatives (1-4) and its inclusion with Heptakis(2,6-di-O-methyl)-beta-cyclodextrin (DM beta CD) were investigated. The stoichiometric ratios and stability constants describing the extent of formation of the complexes were determined by phase-solubility measurements obtaining in all cases a type-A(L) diagram. Also electrochemical studies were carried out, where the observed change in the E-PC value indicated a lower feasibility of the nitro group reduction. The same behavior was observed in the ESR studies. The detailed spatial configuration is proposed based on 2D NMR methods. These results are further interpreted using molecular modeling studies. The latter results are in good agreement with the experimental data. (C) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码：4604 / 4611
页数：8
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