Utility of nuclear magnetic resonance spectroscopy to characterize the structure of dexamethasone sodium phosphate inclusion complexes with cyclodextrins in solution and to analyze potential competitive effects

Echezarreta-Lopez, M.; Perdomo-López, Iliana; Estrada, Ernesto; Vila-Jato, J. L.; Torres‐Labandeira, Juan J.

doi:10.1002/jps.10145

Cited by 11 publications

(3 citation statements)

References 24 publications

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“…Similar ROESY cross peaks have been observed for the inclusion complexes formed between salbutamol and β-CD and for dexamethasone sodium phosphate and γ -CD. [31,32] The doxepin H-6, H-α, H-β, and H-γ resonances also have cross peaks only to the cyclodextrin H-3 proton that is located near the mouth of the cyclodextrin cavity. The cross peak between cyclodextrin H-3 and doxepin H-α is strongest of the nonaromatic protons followed by H-6, and then H-β, and H-γ .…”

Section: (A) For the B Ring H-b1 And H-b3 Resonancesmentioning

confidence: 97%

NMR characterization of the host–guest inclusion complex between β‐cyclodextrin and doxepin

Cruz

Becker

Morris

et al. 2008

Magnetic Reson in Chemistry

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The interaction between doxepin, a member of the tricyclic antidepressant (TCA) class of drugs, with beta-cyclodextrin (beta-CD) was investigated using NMR. Several TCAs have been reported to form a complex with beta-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-beta-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 beta-CD cavity. Changes in the doxepin (1)H NMR spectrum and the behavior of ROESY exchange cross peaks suggest that inclusion complex formation decreases the rate of internal motions of doxepin.

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Section: (A) For the B Ring H-b1 And H-b3 Resonancesmentioning

confidence: 97%

NMR characterization of the host–guest inclusion complex between β‐cyclodextrin and doxepin

Cruz

Becker

Morris

et al. 2008

Magnetic Reson in Chemistry

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“…Inclusion complex formation was confirmed by Differential Scanning Calorimetry (DSC), Infrared (IR) spectroscopy (data not shown) and proton nuclear magnetic resonance ( 1 H NMR) spectroscopy adapting previously reported protocols (Echezarreta-Lopez et al, 2002;Sousa et al, 2005) using methodology similar to that described by (Win et al, 2010).…”

Section: Characterisation Of the Inclusion Complexesmentioning

confidence: 61%

Antibacterial Activity of β-Cyclodextrin and 2-Hydroxypropyl-β-Cyclodextrin Trimethoprim Complexes

M.¹

2011

American Journal of Microbiology

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“…The γ-CD is a cyclic molecule composed of glucopyranose monomers, featuring a hydrophilic surface and a lipophilic central cavity (Saokham and Loftsson, 2017). It includes the liposoluble components within its central cavity, thereby enhancing the solubility in a water-soluble environment (Echezarreta-Lopez et al, 2002;Uekama et al, 1982;Vianna et al, 1998). Research results have demonstrated that the γ-CD is suitable when used in the model of the C. elegans (Kashima et al, 2012).…”

Section: Introductionmentioning

confidence: 99%

Sesamolin has the ability to induce longevity effects on the Caenorhabditis elegans, and the mechanism depends on the SIR-2.1 and AAK-2 proteins

Chin,

Lee,

Yang

2024

Journal of Food Bioactives

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Sesamolin, one of the prominent lignans in sesame seeds, offers diverse physiological benefits. However, the longevity effects and mechanisms of sesamolin remain unclear. We hypothesized that sesamolin can exert the longevity effects in the Caenorhabditis (C.) elegans when prepared with the γ-cyclodextrin to form an inclusion complex (named γCD-SM). In this study, the γCD-SM was prepared, and the lifespan assays, health indexes, and loss-of-function assays in the C. elegans or mutants were conducted. The results demonstrated that the γCD-SM significantly extended the C. elegans’ lifespan and improved the health indexes, such as the pharyngeal pumping and body bends. The longevity effects of the γCD-SM were found to depend on the signaling of the SIR-2.1 and AAK-2. In conclusion, the γ-CD inclusion is a crucial step for assessing the sesamolin's longevity effects in the C. elegans. This study confirms that sesamolin exhibits the longevity effects, and its mechanism relies on the signaling of the SIR-2.1 and the AAK-2 proteins, suggesting its potential as a health-promoting ingredient.

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Utility of nuclear magnetic resonance spectroscopy to characterize the structure of dexamethasone sodium phosphate inclusion complexes with cyclodextrins in solution and to analyze potential competitive effects

Cited by 11 publications

References 24 publications

NMR characterization of the host–guest inclusion complex between β‐cyclodextrin and doxepin

NMR characterization of the host–guest inclusion complex between β‐cyclodextrin and doxepin

Antibacterial Activity of β-Cyclodextrin and 2-Hydroxypropyl-β-Cyclodextrin Trimethoprim Complexes

Sesamolin has the ability to induce longevity effects on the Caenorhabditis elegans, and the mechanism depends on the SIR-2.1 and AAK-2 proteins

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Utility of nuclear magnetic resonance spectroscopy to characterize the structure of dexamethasone sodium phosphate inclusion complexes with cyclodextrins in solution and to analyze potential competitive effects

Cited by 11 publications

References 24 publications

NMR characterization of the host–guest inclusion complex between β‐cyclodextrin and doxepin

NMR characterization of the host–guest inclusion complex between β‐cyclodextrin and doxepin

Antibacterial Activity of &beta;-Cyclodextrin and 2-Hydroxypropyl-&beta;-Cyclodextrin Trimethoprim Complexes

Sesamolin has the ability to induce longevity effects on the Caenorhabditis elegans, and the mechanism depends on the SIR-2.1 and AAK-2 proteins

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Antibacterial Activity of β-Cyclodextrin and 2-Hydroxypropyl-β-Cyclodextrin Trimethoprim Complexes