Interaction of antidepressant drugs with lipid bilayers studied by high-resolution carbon-13(13C-) and high-power deuterium nuclear magnetic resonance (2H-NMR) spectroscopy: The manner of binding as deduced from the differential line-broadening of 13C-NMR signals.

Tabeta, Ryoko; Mahajan, Sudha; Maeda, Mitsuaki; Saitô, Hazime

doi:10.1248/cpb.33.1793

Cited by 11 publications

(9 citation statements)

References 1 publication

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“…Imipramine (1) was the first of the TCA's to be developed and it is still in widespread clinical use. 1 Its 13C-NMR spectrum in the aromatic region is shown in Fig. 1 with proposed assignments of Abraham et al2) and Saito and coworkers."…”

Section: Introductionsupporting

confidence: 52%

Two-dimensional nuclear magnetic resonance spectra of selected tricyclic antidepressants.

Craik¹,

Hall²,

Munro³

1987

CHEMICAL & PHARMACEUTICAL BULLETIN

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Two-dimensional nuclear magnetic resonance (2D NMR) spectroscopy has been used to assign 13C spectra of the tricyclic antidepressants imipramine and chlorimipramine . The 2D-INADEQUATE method was used to unambiguously assign the aromatic spectral region for the former compound. Errors in previous literature assignments based on 1D methods were corrected. For chlorimipramine the pitfalls of classical substituent chemical shift arguments for 13C assignments and the difficulties of 1D selective 1H irradiation in overlapped systems are contrasted with the power and relative simplicity of the 2D-13C, 1H-correlated and 13C, 1H RELAY methods.

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Section: Introductionsupporting

confidence: 52%

Two-dimensional nuclear magnetic resonance spectra of selected tricyclic antidepressants.

Craik¹,

Hall²,

Munro³

1987

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…Peaks in the center region could be due to residual HO 2 H or free [4-2 H]EGCg molecules in aqueous solution. [26] However it is improbable that this strong signal is due to a 2 H NMR peak from water because deuteriumdepleted water was used in these experiments. In addition, we previously showed that not all EGCg added is incorporated into liposomes.…”

Section: Resultsmentioning

confidence: 99%

Solid‐state NMR analysis of the orientation and dynamics of epigallocatechin gallate, a green tea polyphenol, incorporated into lipid bilayers

Kajiya

Kumazawa

Naito

et al. 2007

Magnetic Reson in Chemistry

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Catechins are the principle polyphenolic compounds in green tea; the four major compounds identified are epicatechin (EC), epigallocatechin (EGC), epicatechin gallate (ECg) and epigallocatechin gallate (EGCg). Tea catechins tend to attach externally to their targets, such as viral envelopes, cell membranes, or the surface of low-density lipoproteins. In order to further our understanding of the molecular mobility of these compounds in cells, we examined the interaction of tea catechins with lipid membranes using solid-state NMR techniques. Our previous work indicated that the EGCg molecule is incorporated into lipid bilayers in a unique orientation. However, the detailed configuration, orientation, and dynamics of EGCg in lipid bilayers have not been well-characterized. Here, we investigated the orientation and dynamics of EGCg incorporated into multi-lamellar vesicles (MLVs) and bicelles using solid-state NMR spectroscopy.

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“…It has also been proposed that locating desipramine or imipramine at the depth of carbon-6 would position the charged amine at a short distance from either the lipid O 22 32 or O 13 (Fig. 2) and a hydrogen bond forms between the charged drug acyl chain and these lipid oxygens, 45,46 also in agreement with 13 C and 1 H NMR results from studies on detergent micelles and liposomes that position the charged acyl chain of TCAs at the air-water interface. 47,48 Therefore, it is not surprising that both imipramine and desipramine interact with the lipid headgroups and that the extent of the drug-induced bilayer disordering effect is correlated with the effective charge of the drug.…”

Section: Discussionmentioning

confidence: 99%

Effects of antidepressants on the conformation of phospholipid headgroups studied by solid‐state NMR

Santos

Lee

Ramamoorthy

2004

Magnetic Reson in Chemistry

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The effect of tricyclic antidepressants (TCA) on phospholipid bilayer structure and dynamics was studied to provide insight into the mechanism of TCA-induced intracellular accumulation of lipids (known as lipidosis). Specifically we asked if the lipid-TCA interaction was TCA or lipid specific and if such physical interactions could contribute to lipidosis. These interactions were probed in multilamellar vesicles and mechanically oriented bilayers of mixed phosphatidylcholine-phosphatidylglycerol (PC-PG) phospholipids using (31)P and (14)N solid-state NMR techniques. Changes in bilayer architecture in the presence of TCAs were observed to be dependent on the TCA's effective charge and steric constraints. The results further show that desipramine and imipramine evoke distinguishable changes on the membrane surface, particularly on the headgroup order, conformation and dynamics of phospholipids. Desipramine increases the disorder of the choline site at the phosphatidylcholine headgroup while leaving the conformation and dynamics of the phosphate region largely unchanged. Incorporation of imipramine changes both lipid headgroup conformation and dynamics. Our results suggest that a correlation between TCA-induced changes in bilayer architecture and the ability of these compounds to induce lipidosis is, however, not straightforward as imipramine was shown to induce more dramatic changes in bilayer conformation and dynamics than desipramine. The use of (14)N as a probe was instrumental in arriving at the presented conclusions.

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Interaction of antidepressant drugs with lipid bilayers studied by high-resolution carbon-13(13C-) and high-power deuterium nuclear magnetic resonance (2H-NMR) spectroscopy: The manner of binding as deduced from the differential line-broadening of 13C-NMR signals.

Cited by 11 publications

References 1 publication

Two-dimensional nuclear magnetic resonance spectra of selected tricyclic antidepressants.

Two-dimensional nuclear magnetic resonance spectra of selected tricyclic antidepressants.

Solid‐state NMR analysis of the orientation and dynamics of epigallocatechin gallate, a green tea polyphenol, incorporated into lipid bilayers

Effects of antidepressants on the conformation of phospholipid headgroups studied by solid‐state NMR

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