Evaluation of the metabolic chiral inversion of d-selenomethionine in rats by stable isotope dilution gas chromatography–mass spectrometry

Matsukawa, Tetsuya; Hasegawa, Hiroshi; Goto, Hidenori; Shinohara, Yoshihiko; Shinohara, Atsuko; Omori, Yuki; Ichida, Kimiyoshi; Yokoyama, Kazuhito

doi:10.1016/j.jpba.2015.04.014

Cited by 5 publications

(3 citation statements)

References 22 publications

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“…Overall, the significant improvement in delivery of SeMet from the NP could be explained by the protection of the nanoparticle provided by zein, along with the sustained release close to the epithelium. Endogenous SeMet was not detected in rat plasma prior to administration and was also not detected at any time point in the saline group, which is consistent with previous studies in both rats and humans [ 54 , 55 ]. Jejunal instillations give the best chance of absorption and are a benchmark for further in vivo work with SeMet-NPs.…”

Section: Discussionsupporting

confidence: 91%

Evaluation of Selenomethionine Entrapped in Nanoparticles for Oral Supplementation Using In Vitro, Ex Vivo and In Vivo Models

et al. 2023

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Selenium methionine (SeMet) is an essential micronutrient required for normal body function and is associated with additional health benefits. However, oral administration of SeMet can be challenging due to its purported narrow therapeutic index, low oral bioavailability, and high susceptibility to oxidation. To address these issues, SeMet was entrapped in zein-coated nanoparticles made from chitosan using an ionic gelation formulation. The high stability of both the SeMet and selenomethionine nanoparticles (SeMet-NPs) was established using cultured human intestinal and liver epithelial cells, rat liver homogenates, and rat intestinal homogenates and lumen washes. Minimal cytotoxicity to Caco-2 and HepG2 cells was observed for SeMet and SeMet-NPs. Antioxidant properties of SeMet were revealed using a Reactive Oxygen Species (ROS) assay, based on the observation of a concentration-dependent reduction in the build-up of peroxides, hydroxides and hydroxyl radicals in Caco-2 cells exposed to SeMet (6.25–100 μM). The basal apparent permeability coefficient (Papp) of SeMet across isolated rat jejunal mucosae mounted in Ussing chambers was low, but the Papp was increased when presented in NP. SeMet had minimal effects on the electrogenic ion secretion of rat jejunal and colonic mucosae in Ussing chambers. Intra-jejunal injections of SeMet-NPs to rats yielded increased plasma levels of SeMet after 3 h for the SeMet-NPs compared to free SeMet. Overall, there is potential to further develop SeMet-NPs for oral supplementation due to the increased intestinal permeability, versus free SeMet, and the low potential for toxicity.

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Section: Discussionsupporting

confidence: 91%

Evaluation of Selenomethionine Entrapped in Nanoparticles for Oral Supplementation Using In Vitro, Ex Vivo and In Vivo Models

et al. 2023

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“…Like HPLC, GC/MS is widely used in studies on chiral drug metabolism and the advantages of GC/MS coupled with stable isotope labeling technology have been increasingly recognized [94] .…”

Section: Stereoselective Analytical Methodsmentioning

confidence: 99%

Significance and challenges of stereoselectivity assessing methods in drug metabolism

Shen

Zeng

2016

Journal of Pharmaceutical Analysis

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Stereoselectivity in drug metabolism can not only influence the pharmacological activities, tolerability, safety, and bioavailability of drugs directly, but also cause different kinds of drug–drug interactions. Thus, assessing stereoselectivity in drug metabolism is of great significance for pharmaceutical research and development (R&D) and rational use in clinic. Although there are various methods available for assessing stereoselectivity in drug metabolism, many of them have shortcomings. The indirect method of chromatographic methods can only be applicable to specific samples with functional groups to be derivatized or form complex with a chiral selector, while the direct method achieved by chiral stationary phases (CSPs) is expensive. As a detector of chromatographic methods, mass spectrometry (MS) is highly sensitive and specific, whereas the matrix interference is still a challenge to overcome. In addition, the use of nuclear magnetic resonance (NMR) and immunoassay in chiral analysis are worth noting. This review presents several typical examples of drug stereoselective metabolism and provides a literature-based evaluation on current chiral analytical techniques to show the significance and challenges of stereoselectivity assessing methods in drug metabolism.

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“…The enantioselective separation of SeMet has been carried out by HPLC and GC . Some of these methods were applied to the enantiomeric determination of SeMet in different food products (food supplements, yeast, breast milk, and infant formulas) .…”

Section: Introductionmentioning

confidence: 99%

A micellar electrokinetic chromatography approach using diastereomeric derivatization and a volatile surfactant for the enantioselective separation of selenomethionine

2019

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A MEKC methodology with UV detection was developed for the enantioselective separation of selenomethionine (SeMet). The use of (+)‐1‐(9‐fluorenyl)ethyl chloroformate (FLEC) as chiral derivatization reagent to form SeMet diastereomers enabled their subsequent separation using ammonium perfluorooctanoate (APFO) as a volatile pseudostationary phase. The effect of APFO concentration and pH, temperature, injection volume, and derivatization conditions (time and FLEC/SeMet ratio) were evaluated in order to select the best separation conditions. A chiral resolution of 4.4 for DL‐SeMet was achieved in less than 6 min using 100 mM APFO at pH 8.5 as electrophoretic buffer. Satisfactory results were obtained in terms of linearity, precision (RSD from 3.4 to 5.1% for migration times and from 1.8 to 4.6% for corrected peak areas), accuracy, and LODs (3.1 × 10−6 M and 3.7 × 10−6 M for d and l enantiomers, respectively). The method was successfully applied to the determination of l‐SeMet in food supplements.

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Evaluation of the metabolic chiral inversion of d-selenomethionine in rats by stable isotope dilution gas chromatography–mass spectrometry

Cited by 5 publications

References 22 publications

Evaluation of Selenomethionine Entrapped in Nanoparticles for Oral Supplementation Using In Vitro, Ex Vivo and In Vivo Models

Evaluation of Selenomethionine Entrapped in Nanoparticles for Oral Supplementation Using In Vitro, Ex Vivo and In Vivo Models

Significance and challenges of stereoselectivity assessing methods in drug metabolism

A micellar electrokinetic chromatography approach using diastereomeric derivatization and a volatile surfactant for the enantioselective separation of selenomethionine

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