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镇痛药异恶唑酮及其铜配合物与不同环糊精形成包合物的研究:荧光、傅里叶变换红外光谱和核磁共振。

Painkiller Isoxicam and Its Copper Complex Can Form Inclusion Complexes with Different Cyclodextrins: A Fluorescence, Fourier Transform Infrared Spectroscopy, and Nuclear Magnetic Resonance Study.

机构信息

Chemical Sciences Division, Saha Institute of Nuclear Physics , 1/AF Bidhannagar, Kolkata - 700064, India.

出版信息

J Phys Chem B. 2017 Sep 14;121(36):8454-8466. doi: 10.1021/acs.jpcb.7b05649. Epub 2017 Aug 29.

DOI:10.1021/acs.jpcb.7b05649
PMID:28806512
Abstract

The interaction of a painkiller Isoxicam, belonging to the oxicam group of nonsteroidal anti-inflammatory drugs (NSAIDs) and its copper complex with different cyclodextrins (β-CD, γ-CD, HPβCD, and HPγCD), has been investigated in both solution and the solid state. Steady state and time-resolved fluorescence spectroscopy, fluorescence anisotropy, H NMR, and FTIR spectroscopy are used. Both the drug and its copper complex form a host-guest inclusion complex with all CDs. Fluorescence spectroscopy is used to determine binding constants and stoichiometries of the host-guest complex. The strongest binding is seen for γ-CD. H NMR study showed that Isoxicam penetrates into the CD cavity from the more accessible wider side. For β- and γ-CD, Isoxicam showed one type of binding, i.e., formation of an inclusion complex, whereas, for HPβCD and HPγCD, it showed two types of binding, i.e., inclusion in the CD cavities and interaction with the outer surface of the CD molecules mainly near the hydroxy propyl group. Deeper penetration occurred into the larger diameter cavity of γ-CD and HPγCD compared to β-CD and HPβCD. From FTIR and H NMR study, it is seen that predominantly the π-electron-rich benzene part of the drug and its complex penetrate into the host cavity.

摘要

已在溶液和固态中研究了属于非甾体抗炎药(NSAIDs)氧杂蒽类的止痛药异丁酮和其铜配合物与不同环糊精(β-CD、γ-CD、HPβCD 和 HPγCD)的相互作用。使用稳态和时间分辨荧光光谱法、荧光各向异性、H NMR 和傅里叶变换红外光谱法。药物及其铜配合物均与所有 CD 形成主客体包络复合物。荧光光谱用于确定主客体配合物的结合常数和化学计量比。与 γ-CD 的结合最强。NMR 研究表明,异丁酮从更易接近的宽侧进入 CD 腔。对于β-CD 和γ-CD,异丁酮显示出一种结合方式,即形成包络复合物,而对于 HPβCD 和 HPγCD,它显示出两种结合方式,即包埋在 CD 腔中和与 CD 分子的外表面相互作用,主要是在羟丙基附近。与β-CD 和 HPβCD 相比,异丁酮及其复合物更深地进入了较大直径的γ-CD 和 HPγCD 腔。从 FTIR 和 H NMR 研究中可以看出,药物及其配合物的π-富电子苯部分主要进入主体腔。

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