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  1. Article ; Online: Utilization of LC-MS/MS and Drift Tube Ion Mobility for Characterizing Intact Oxidized Arachidonate-Containing Glycerophosphatidylethanolamine.

    Morel, Yulemni / Jones, Jace W

    Journal of the American Society for Mass Spectrometry

    2023  Volume 34, Issue 8, Page(s) 1609–1620

    Abstract: Lipid peroxidation is a key component in the pathogenesis of numerous disease states, where the oxidative damage of lipids frequently leads to membrane dysfunction and subsequent cellular death. Glycerophosphoethanolamine (PE) is the second most abundant ...

    Abstract Lipid peroxidation is a key component in the pathogenesis of numerous disease states, where the oxidative damage of lipids frequently leads to membrane dysfunction and subsequent cellular death. Glycerophosphoethanolamine (PE) is the second most abundant phospholipid found in cellular membranes and, when oxidized, has been identified as an executor of ferroptotic cell death. PE commonly exists in the plasmalogen form, where the presence of the vinyl ether bond and its enrichment in polyunsaturated fatty acids make it especially susceptible to oxidative degradation. This results in a multitude of oxidized products complicating identification and often requiring several analytical techniques for interpretation. In the present study, we outline an analytical approach for the structural characterization of intact oxidized products of arachidonate-containing diacyl and plasmalogen PE. Intact oxidized PE structures, including structural and positional isomers, were identified using complementary liquid chromatography techniques, drift tube ion mobility, and high-resolution tandem mass spectrometry. This work establishes a comprehensive method for the analysis of intact lipid peroxidation products and provides an important pathway to investigate how lipid peroxidation initially impacts glycerophospholipids and their role in redox biology.
    MeSH term(s) Chromatography, Liquid/methods ; Plasmalogens/chemistry ; Plasmalogens/metabolism ; Tandem Mass Spectrometry ; Oxidation-Reduction ; Glycerophospholipids
    Chemical Substances Plasmalogens ; Glycerophospholipids
    Language English
    Publishing date 2023-06-27
    Publishing country United States
    Document type Journal Article
    ZDB-ID 1073671-2
    ISSN 1879-1123 ; 1044-0305
    ISSN (online) 1879-1123
    ISSN 1044-0305
    DOI 10.1021/jasms.3c00083
    Database MEDical Literature Analysis and Retrieval System OnLINE

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    In stock of ZB MED Cologne/Königswinter

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    Zs.MO 241: Show issues

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  2. Article ; Online: Structure-specific, accurate quantitation of plasmalogen glycerophosphoethanolamine.

    Morel, Yulemni / Hegdekar, Nivedita / Sarkar, Chinmoy / Lipinski, Marta M / Kane, Maureen A / Jones, Jace W

    Analytica chimica acta

    2021  Volume 1186, Page(s) 339088

    Abstract: Changes in plasmalogen glycerophosphoethanolamine (PE-P) composition (structure and abundance) are a key indicator of altered lipid metabolism. Differential changes in the levels of PE-P have been reported in different disease states, including ... ...

    Abstract Changes in plasmalogen glycerophosphoethanolamine (PE-P) composition (structure and abundance) are a key indicator of altered lipid metabolism. Differential changes in the levels of PE-P have been reported in different disease states, including neurodegenerative diseases. Of particular interest, traumatic brain injury (TBI) has resulted in altered expression of glycerophospholipid profiles, including PE-P. To date, most analytical assays assessing PE-P have focused on general lipidomic workflows to evaluate the relative, semi-quantitative abundance of PE-P during disease progression. This approach provides a broad evaluation of PE-P, yet often lacks specificity and sensitivity for individual PE-P structures which is a necessity for robust quantitative data. The present study highlights the development of a targeted, quantitative method using a HILIC separation and selective reaction monitoring mass spectrometry for the confident identification and accurate quantitation of PE-P. Our innovative method incorporates both the sn-1 alkyl vinyl ether and sn-2 acyl chain as product ion transitions, for specific and sensitive quantitation of 100 PE-P structures. Our method also uniquely allowed for the unambiguous assignment and quantitation of di-unsaturated sn-1 PE-P structures, which to date have not been conclusively quantified. Application of this assay to a TBI mouse model resulted in distinct temporal profiles for plasma PE-P up to 28 days post injury. Plasma PE-P were significantly increased 24 h after induced TBI, followed by a gradual reduction to sham concentrations by day 28. Overall, we established a structure-specific, quantitative assay for identification and quantitation of a comprehensive set of PE-P structures with demonstrated relevance to brain injury.
    MeSH term(s) Animals ; Lipidomics ; Mass Spectrometry ; Mice ; Phosphatidylethanolamines ; Plasmalogens
    Chemical Substances Phosphatidylethanolamines ; Plasmalogens ; glycerophosphoethanolamine (1190-00-7)
    Language English
    Publishing date 2021-09-22
    Publishing country Netherlands
    Document type Journal Article
    ZDB-ID 1483436-4
    ISSN 1873-4324 ; 0003-2670
    ISSN (online) 1873-4324
    ISSN 0003-2670
    DOI 10.1016/j.aca.2021.339088
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  3. Article: Construction of 1H-indazoles from ortho-aminobenzoximes by the Mitsunobu reaction

    Conlon, Ivie L / Chan, Alexandria / Fletcher, Steven / Konsein, Katie / Morel, Yulemni

    Tetrahedron letters. 2019 July 08,

    2019  

    Abstract: Recently, there has been an upsurge in the occurrence of the indazole motif in drug discovery. Accordingly, newer, milder and more efficient routes towards their synthesis have emerged in the literature. We recently reported the Mitsunobu-triggered ... ...

    Abstract Recently, there has been an upsurge in the occurrence of the indazole motif in drug discovery. Accordingly, newer, milder and more efficient routes towards their synthesis have emerged in the literature. We recently reported the Mitsunobu-triggered cyclodehydration of salicylaldoximes to transient 1,2-benzisoxazoles, and salicylhydroxamic acids to their corresponding 3-hydroxybenzisoxazoles. We hypothesized subjecting ortho-aminobenzoximes to Mitsunobu conditions will likewise induce a cyclodehydration to deliver the corresponding 1H-indazoles. Indeed, secondary anilines afforded the predicted N1-substituted 1H-indazoles, and primary anilines, after activation with a Boc group, furnished the N1-Boc 1H-indazoles in good to excellent yields. This work further expands the chemical repertoire of the Mitsunobu reaction, representing its unprecedented use in the construction of the 1H-indazole nucleus.
    Keywords acids ; chemical reactions ; chemical structure ; drugs ; organic compounds
    Language English
    Dates of publication 2019-0708
    Publishing place Elsevier Ltd
    Document type Article
    Note Pre-press version
    ZDB-ID 204287-3
    ISSN 1873-3581 ; 0040-4039
    ISSN (online) 1873-3581
    ISSN 0040-4039
    DOI 10.1016/j.tetlet.2019.07.020
    Database NAL-Catalogue (AGRICOLA)

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    In stock of ZB MED Cologne/Königswinter

    Zs.A 2837: Show issues Location:
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  4. Article ; Online: Atp7b-dependent choroid plexus dysfunction causes transient copper deficit and metabolic changes in the developing mouse brain.

    Washington-Hughes, Clorissa L / Roy, Shubhrajit / Seneviratne, Herana Kamal / Karuppagounder, Senthilkumar S / Morel, Yulemni / Jones, Jace W / Zak, Alex / Xiao, Tong / Boronina, Tatiana N / Cole, Robert N / Bumpus, Namandjé N / Chang, Christopher J / Dawson, Ted M / Lutsenko, Svetlana

    PLoS genetics

    2023  Volume 19, Issue 1, Page(s) e1010558

    Abstract: Copper (Cu) has a multifaceted role in brain development, function, and metabolism. Two homologous Cu transporters, Atp7a (Menkes disease protein) and Atp7b (Wilson disease protein), maintain Cu homeostasis in the tissue. Atp7a mediates Cu entry into the ...

    Abstract Copper (Cu) has a multifaceted role in brain development, function, and metabolism. Two homologous Cu transporters, Atp7a (Menkes disease protein) and Atp7b (Wilson disease protein), maintain Cu homeostasis in the tissue. Atp7a mediates Cu entry into the brain and activates Cu-dependent enzymes, whereas the role of Atp7b is less clear. We show that during postnatal development Atp7b is necessary for normal morphology and function of choroid plexus (ChPl). Inactivation of Atp7b causes reorganization of ChPl' cytoskeleton and cell-cell contacts, loss of Slc31a1 from the apical membrane, and a decrease in the length and number of microvilli and cilia. In ChPl lacking Atp7b, Atp7a is upregulated but remains intracellular, which limits Cu transport into the brain and results in significant Cu deficit, which is reversed only in older animals. Cu deficiency is associated with down-regulation of Atp7a in locus coeruleus and catecholamine imbalance, despite normal expression of dopamine-β-hydroxylase. In addition, there are notable changes in the brain lipidome, which can be attributed to inhibition of diacylglyceride-to-phosphatidylethanolamine conversion. These results identify the new role for Atp7b in developing brain and identify metabolic changes that could be exacerbated by Cu chelation therapy.
    MeSH term(s) Mice ; Animals ; Copper-Transporting ATPases ; Copper/metabolism ; Choroid Plexus/metabolism ; Menkes Kinky Hair Syndrome/metabolism ; Brain/metabolism
    Chemical Substances Copper-Transporting ATPases (EC 7.2.2.8) ; Copper (789U1901C5) ; Atp7b protein, mouse (EC 7.2.2.8)
    Language English
    Publishing date 2023-01-10
    Publishing country United States
    Document type Journal Article
    ZDB-ID 2186725-2
    ISSN 1553-7404 ; 1553-7390
    ISSN (online) 1553-7404
    ISSN 1553-7390
    DOI 10.1371/journal.pgen.1010558
    Database MEDical Literature Analysis and Retrieval System OnLINE

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