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• W2005497400 abstract "The interaction between doxepin, a member of the tricyclic antidepressant (TCA) class of drugs, with β-cyclodextrin (β-CD) was investigated using NMR. Several TCAs have been reported to form a complex with β-CD having 1:1 stoichiometry. Previous results from UV-visible spectroscopy, fluorescence measurements, and molecular modeling indicated that for imipramine, desipramine, and amitriptyline, the TCA aliphatic tail is included in the cyclodextrin cavity with apparently no interaction of the tricyclic ring. An alternative view of the doxepin–β-CD complex is presented in this work using analysis of complexation-induced chemical shifts (CICSs), the method of continuous variation (Job's analysis), and analysis of ROESY spectra. The Job's plot derived from the NMR spectral data confirms that the complex formed has 1:1 stoichiometry. The largest changes in the CICS data were observed for the aromatic protons of one of the doxepin rings, with much smaller chemical shift changes observed for the protons of the other aromatic ring and the doxepin tail. Perhaps the most significant evidence for inclusion of the doxepin tricyclic ring is the strong ROESY cross peaks between the doxepin aromatic resonances and the protons located inside the β-CD cavity. Changes in the doxepin 1H NMR spectrum and the behavior of ROESY exchange cross peaks suggest that inclusion complex formation decreases the rate of internal motions of doxepin. Copyright © 2008 John Wiley & Sons, Ltd." @default.
• W2005497400 created "2016-06-24" @default.
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• W2005497400 date "2008-09-01" @default.
• W2005497400 modified "2023-10-14" @default.
• W2005497400 title "NMR characterization of the host-guest inclusion complex between β-cyclodextrin and doxepin" @default.
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• W2005497400 doi "https://doi.org/10.1002/mrc.2267" @default.
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