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  1. Article ; Online: Analysis of Surface Expression of NMDAR Subunits in Primary Hippocampal Neurons.

    Kuchtiak, Viktor / Smejkalova, Tereza / Horak, Martin / Vyklicky, Ladislav / Balik, Ales

    Methods in molecular biology (Clifton, N.J.)

    2024  Volume 2799, Page(s) 29–46

    Abstract: The expression and activity of ionotropic glutamate receptors control signal transduction at the excitatory synapses in the CNS. The NMDAR comprises two obligatory GluN1 subunits and two GluN2 or GluN3 subunits in different combinations. Each GluN ... ...

    Abstract The expression and activity of ionotropic glutamate receptors control signal transduction at the excitatory synapses in the CNS. The NMDAR comprises two obligatory GluN1 subunits and two GluN2 or GluN3 subunits in different combinations. Each GluN subunit consists of four domains: the extracellular amino-terminal and agonist-binding domains, the transmembrane domain, and the intracellular C-terminal domain (CTD). The CTD interaction with various classes of intracellular proteins is critical for trafficking and synaptic localization of NMDARs. Amino acid mutations or the inclusion of premature stop codons in the CTD could contribute to the emergence of neurodevelopmental and neuropsychiatric disorders. Here, we describe the method of preparing primary hippocampal neurons and lentiviral particles expressing GluN subunits that can be used as a model to study cell surface expression and synaptic localization of NMDARs. We also show a simple method of fluorescence immunostaining of eGFP-tagged GluN2 subunits and subsequent microscopy technique and image analysis to study the effects of disease-associated mutations in the CTDs of GluN2A and GluN2B subunits.
    MeSH term(s) Receptors, N-Methyl-D-Aspartate/metabolism ; Receptors, N-Methyl-D-Aspartate/genetics ; Hippocampus/metabolism ; Hippocampus/cytology ; Neurons/metabolism ; Animals ; Protein Subunits/metabolism ; Protein Subunits/genetics ; Cells, Cultured ; Rats ; Humans ; Lentivirus/genetics ; Primary Cell Culture/methods ; Gene Expression
    Chemical Substances Receptors, N-Methyl-D-Aspartate ; Protein Subunits ; N-methyl D-aspartate receptor subtype 2A (VH92ICR8HX)
    Language English
    Publishing date 2024-05-10
    Publishing country United States
    Document type Journal Article ; Research Support, Non-U.S. Gov't ; Research Support, N.I.H., Extramural
    ISSN 1940-6029
    ISSN (online) 1940-6029
    DOI 10.1007/978-1-0716-3830-9_3
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  2. Article ; Online: Synthesis of deuterium labeled NMDA receptor inhibitor - 20-Oxo-5β-[9,12,12-(2)H(3)]pregnan-3α-yl-L-glutamyl 1-ester.

    Kapras, Vojtech / Slavickova, Alena / Stastna, Eva / Vyklicky, Ladislav / Vales, Karel / Chodounska, Hana

    Steroids

    2012  Volume 77, Issue 3, Page(s) 282–287

    Abstract: 20-Oxo-5β-[9,12,12-(2)H(3)]pregnan-3α-yl-l-glutamyl 1-ester 11 was synthesized as an internal ... standard for quantification of a neuroprotective NMDA receptor ligand, 20-oxo-5β-pregnan-3α-yl-l-glutamyl 1 ...

    Abstract 20-Oxo-5β-[9,12,12-(2)H(3)]pregnan-3α-yl-l-glutamyl 1-ester 11 was synthesized as an internal standard for quantification of a neuroprotective NMDA receptor ligand, 20-oxo-5β-pregnan-3α-yl-l-glutamyl 1-ester 18 and its metabolites, in plasma and tissue. 11α-Hydroxy-progesterone (1) was reduced under basic conditions to yield the corresponding 5β-steroid. Protection of the 3- and 20-oxo groups and oxidation of the 11α-hydroxy group was then followed by a deuterium exchange, conducted under basic conditions using deuterated methanol. Next, the carbonyl moiety at C-11 was reduced and the 11α-hydroxyl group removed through utilization of the Barton-McCombie reaction. Subsequent deprotection of the 3- and 20-acetals and stereoselective reduction of the 3-oxo group gave the desired trideuterated pregnanolone (8). This was coupled with protected glutamic acid, which was then deprotected to yield [9,12,12-(2)H(3)]-pregnanolone glutamate (11) with >99% isotopic purity.
    MeSH term(s) Chromatography, Thin Layer ; Deuterium/chemistry ; Glutamates/chemistry ; Hydroxyprogesterones/chemistry ; Isotope Labeling/methods ; Magnetic Resonance Spectroscopy ; Molecular Structure ; Oxidation-Reduction ; Pregnanolone/analogs & derivatives ; Pregnanolone/chemical synthesis ; Pregnanolone/chemistry ; Receptors, N-Methyl-D-Aspartate/antagonists & inhibitors ; Solvents/chemistry
    Chemical Substances 20-oxo-5-pregnan-3-yl-glutamyl 1-ester ; Glutamates ; Hydroxyprogesterones ; Receptors, N-Methyl-D-Aspartate ; Solvents ; 11-hydroxyprogesterone (312-90-3) ; Deuterium (AR09D82C7G) ; Pregnanolone (BXO86P3XXW)
    Language English
    Publishing date 2012-02
    Publishing country United States
    Document type Journal Article ; Research Support, Non-U.S. Gov't
    ZDB-ID 80312-1
    ISSN 1878-5867 ; 0039-128X
    ISSN (online) 1878-5867
    ISSN 0039-128X
    DOI 10.1016/j.steroids.2011.12.019
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  3. Article: Membrane currents induced by L-homocysteic acid in mouse cultured hippocampal neurons.

    Vyklický, L / Vlachová, V

    Neuroscience

    1992  Volume 48, Issue 4, Page(s) 813–819

    Abstract: The concentration-response relationship of membrane currents induced by L-homocysteic acid was ... in the dose-response relationship could be distinguished. The first was characterized by responses to 3-100 microM L ... were antagonized by 30 microM D-L-2-amino-5-phosphonovaleric acid indicating activation of the N-methyl ...

    Abstract The concentration-response relationship of membrane currents induced by L-homocysteic acid was studied on mouse embryonic hippocampal neurons in culture (n = 56). In the majority of neurons two phases in the dose-response relationship could be distinguished. The first was characterized by responses to 3-100 microM L-homocysteic acid which desensitized with a time-constant greater than 1 s in a concentration-dependent manner and were antagonized by 30 microM D-L-2-amino-5-phosphonovaleric acid indicating activation of the N-methyl-D-aspartate receptors. At higher concentrations of L-homocysteic acid this component was strongly depressed. The second phase was characterized by sustained responses that were concentration-dependent (1 mM L-homocysteic acid maximum concentration tested) and were not blocked by D-L-2-amino-5-phosphonovaleric acid indicating activation of non-N-methyl-D-aspartate receptors. Eight neurons did not exhibit these two-phase characteristics in the concentration-response relationship at the beginning of the recording. The magnitude of responses to L-homocysteic acid was positively related to concentration and the responses were partially blocked by D-L-2-amino-5-phosphonovaleric acid. In these neurons, however, repeated applications of L-homocysteic acid at concentrations 30 microM up to 300 microM resulted in a long-lasting, three- to four-fold increase of the membrane current. This increase was completely blocked by D-L-2-amino-5-phosphonovaleric acid (50-100 microM) suggesting that it was produced by activation of receptors.(ABSTRACT TRUNCATED AT 250 WORDS)
    MeSH term(s) 2-Amino-5-phosphonovalerate/pharmacology ; Animals ; Cells, Cultured ; Dose-Response Relationship, Drug ; Embryo, Mammalian ; Hippocampus/physiology ; Homocysteine/analogs & derivatives ; Homocysteine/pharmacology ; Magnesium/pharmacology ; Membrane Potentials/drug effects ; Mice ; Mice, Inbred BALB C ; Neurons/drug effects ; Neurons/physiology
    Chemical Substances Homocysteine (0LVT1QZ0BA) ; homocysteic acid (1001-13-4) ; 2-Amino-5-phosphonovalerate (76726-92-6) ; Magnesium (I38ZP9992A)
    Language English
    Publishing date 1992-06
    Publishing country United States
    Document type Journal Article ; Research Support, Non-U.S. Gov't
    ZDB-ID 196739-3
    ISSN 1873-7544 ; 0306-4522
    ISSN (online) 1873-7544
    ISSN 0306-4522
    DOI 10.1016/0306-4522(92)90269-8
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  4. Article ; Online: Pitfalls of NMDA Receptor Modulation by Neuroactive Steroids. The Effect of Positive and Negative Modulation of NMDA Receptors in an Animal Model of Schizophrenia.

    Holubova, Kristina / Chvojkova, Marketa / Hrcka Krausova, Barbora / Vyklicky, Vojtech / Kudova, Eva / Chodounska, Hana / Vyklicky, Ladislav / Vales, Karel

    Biomolecules

    2021  Volume 11, Issue 7

    Abstract: Evidence from clinical and preclinical studies implicates dysfunction ... ...

    Abstract Evidence from clinical and preclinical studies implicates dysfunction of
    MeSH term(s) Animals ; Antipsychotic Agents/pharmacology ; Behavior, Animal/drug effects ; Bridged Bicyclo Compounds, Heterocyclic/metabolism ; Disease Models, Animal ; Dizocilpine Maleate/pharmacology ; Elevated Plus Maze Test ; HEK293 Cells ; Humans ; Male ; Pregnenolone/metabolism ; Pregnenolone/pharmacology ; Rats, Long-Evans ; Rats, Wistar ; Receptors, N-Methyl-D-Aspartate/antagonists & inhibitors ; Receptors, N-Methyl-D-Aspartate/metabolism ; Reflex, Startle/drug effects ; Schizophrenia/drug therapy ; Schizophrenia/metabolism ; Steroids/pharmacology ; Rats
    Chemical Substances Antipsychotic Agents ; Bridged Bicyclo Compounds, Heterocyclic ; Receptors, N-Methyl-D-Aspartate ; Steroids ; pregnenolone sulfate (04Y4D91RG0) ; Dizocilpine Maleate (6LR8C1B66Q) ; tert-butylbicyclophosphorothionate (70636-86-1) ; Pregnenolone (73R90F7MQ8)
    Language English
    Publishing date 2021-07-14
    Publishing country Switzerland
    Document type Journal Article ; Research Support, Non-U.S. Gov't
    ZDB-ID 2701262-1
    ISSN 2218-273X ; 2218-273X
    ISSN (online) 2218-273X
    ISSN 2218-273X
    DOI 10.3390/biom11071026
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  5. Article: Cobalt ions block L-glutamate and L-aspartate-induced currents in cultured neurons from embryonic chick spinal cord.

    Vyklický, L / Vyklický, L / Vlachová, V / Michl, J / Vyskocil, F

    Neuroscience letters

    1985  Volume 61, Issue 3, Page(s) 345–350

    Abstract: The effects of Co2+ on L-glutamate and L-aspartate responses wee studied in cultured spinal cord ...

    Abstract The effects of Co2+ on L-glutamate and L-aspartate responses wee studied in cultured spinal cord neurons of the embryonic spinal cord of the chick by employing the patch-clamp technique in whole cell mode [9]. It was found that Co2+ blocks the responses at negative membrane potentials for both amino acids, while only partial inhibition was observed at positive membrane potentials. Co2+ alone decreases the resting membrane current which exhibits reversal close to zero. It is suggested that the effects of Co2+ are produced by non-specific interaction with negative charges on the outer side of the membrane.
    MeSH term(s) Animals ; Aspartic Acid/antagonists & inhibitors ; Cell Membrane Permeability/drug effects ; Cells, Cultured ; Chick Embryo ; Cobalt/pharmacology ; Embryo, Mammalian ; Embryo, Nonmammalian ; Excitatory Amino Acid Antagonists ; Glutamates/metabolism ; Glutamic Acid ; Ion Channels/drug effects ; Membrane Potentials/drug effects ; Spinal Cord/drug effects
    Chemical Substances Excitatory Amino Acid Antagonists ; Glutamates ; Ion Channels ; Aspartic Acid (30KYC7MIAI) ; Cobalt (3G0H8C9362) ; Glutamic Acid (3KX376GY7L)
    Language English
    Publishing date 1985-11-11
    Publishing country Ireland
    Document type Comparative Study ; Journal Article
    ZDB-ID 194929-9
    ISSN 1872-7972 ; 0304-3940
    ISSN (online) 1872-7972
    ISSN 0304-3940
    DOI 10.1016/0304-3940(85)90488-4
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  6. Article: Synthesis of deuterium labeled NMDA receptor inhibitor – 20-Oxo-5β-[9,12,12-²H₃]pregnan-3α-yl-l-glutamyl 1-ester

    Kapras, Vojtech / Slavickova, Alena / Stastna, Eva / Vyklicky, Ladislav, Jr / Vales, Karel / Chodounska, Hana

    Steroids. 2012 Feb., v. 77, no. 3

    2012  

    Abstract: 20-Oxo-5β-[9,12,12-²H₃]pregnan-3α-yl-l-glutamyl 1-ester 11 was synthesized as an internal standard ... for quantification of a neuroprotective NMDA receptor ligand, 20-oxo-5β-pregnan-3α-yl-l-glutamyl 1-ester 18 and ...

    Abstract 20-Oxo-5β-[9,12,12-²H₃]pregnan-3α-yl-l-glutamyl 1-ester 11 was synthesized as an internal standard for quantification of a neuroprotective NMDA receptor ligand, 20-oxo-5β-pregnan-3α-yl-l-glutamyl 1-ester 18 and its metabolites, in plasma and tissue. 11α-Hydroxy-progesterone (1) was reduced under basic conditions to yield the corresponding 5β-steroid. Protection of the 3- and 20-oxo groups and oxidation of the 11α-hydroxy group was then followed by a deuterium exchange, conducted under basic conditions using deuterated methanol. Next, the carbonyl moiety at C-11 was reduced and the 11α-hydroxyl group removed through utilization of the Barton–McCombie reaction. Subsequent deprotection of the 3- and 20-acetals and stereoselective reduction of the 3-oxo group gave the desired trideuterated pregnanolone (8). This was coupled with protected glutamic acid, which was then deprotected to yield [9,12,12-²H₃]-pregnanolone glutamate (11) with >99% isotopic purity.
    Keywords deuterium ; glutamic acid ; metabolites ; methanol ; oxidation
    Language English
    Dates of publication 2012-02
    Size p. 282-287.
    Publishing place Elsevier Inc.
    Document type Article
    ZDB-ID 80312-1
    ISSN 1878-5867 ; 0039-128X
    ISSN (online) 1878-5867
    ISSN 0039-128X
    DOI 10.1016/j.steroids.2011.12.019
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  7. Article ; Online: Pregnane-based steroids are novel positive NMDA receptor modulators that may compensate for the effect of loss-of-function disease-associated GRIN mutations.

    Kysilov, Bohdan / Hrcka Krausova, Barbora / Vyklicky, Vojtech / Smejkalova, Tereza / Korinek, Miloslav / Horak, Martin / Chodounska, Hana / Kudova, Eva / Cerny, Jiri / Vyklicky, Ladislav

    British journal of pharmacology

    2022  Volume 179, Issue 15, Page(s) 3970–3990

    Abstract: Background and purpose: N-methyl-D-aspartate receptors (NMDARs) play a critical role in synaptic plasticity, and mutations in human genes encoding NMDAR subunits have been described in individuals with various neuropsychiatric disorders. Compounds with ... ...

    Abstract Background and purpose: N-methyl-D-aspartate receptors (NMDARs) play a critical role in synaptic plasticity, and mutations in human genes encoding NMDAR subunits have been described in individuals with various neuropsychiatric disorders. Compounds with a positive allosteric effect are thought to compensate for reduced receptor function.
    Experimental approach: We have used whole-cell patch-clamp electrophysiology on recombinant rat NMDARs and human variants found in individuals with neuropsychiatric disorders, in combination with in silico modelling, to explore the site of action of novel epipregnanolone-based NMDAR modulators.
    Key results: Analysis of the action of 4-(20-oxo-5β-pregnan-3β-yl) butanoic acid (EPA-But) at the NMDAR indicates that the effect of this steroid with a "bent" structure is different from that of cholesterol and oxysterols and shares a disuse-dependent mechanism of NMDAR potentiation with the "planar" steroid 20-oxo-pregn-5-en-3β-yl sulfate (PE-S). The potentiating effects of EPA-But and PE-S are additive. Alanine scan mutagenesis identified residues that reduce the potentiating effect of EPA-But. No correlation was found between the effects of EPA-But and PE-S at mutated receptors that were less sensitive to either steroid. The relative degree of potentiation induced by the two steroids also differed in human NMDARs carrying rare variants of hGluN1 or hGluN2B subunits found in individuals with neuropsychiatric disorders, including intellectual disability, epilepsy, developmental delay, and autism spectrum disorder.
    Conclusion and implications: Our results show novel sites of action for pregnanolones at the NMDAR and provide an opportunity for the development of new therapeutic neurosteroid-based ligands to treat diseases associated with glutamatergic system hypofunction.
    MeSH term(s) Animals ; Autism Spectrum Disorder ; Mutation ; Pregnanes/pharmacology ; Rats ; Receptors, N-Methyl-D-Aspartate/genetics ; Steroids
    Chemical Substances Pregnanes ; Receptors, N-Methyl-D-Aspartate ; Steroids
    Language English
    Publishing date 2022-04-08
    Publishing country England
    Document type Journal Article ; Research Support, Non-U.S. Gov't
    ZDB-ID 80081-8
    ISSN 1476-5381 ; 0007-1188
    ISSN (online) 1476-5381
    ISSN 0007-1188
    DOI 10.1111/bph.15841
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  8. Article ; Online: Disease-associated nonsense and frame-shift variants resulting in the truncation of the GluN2A or GluN2B C-terminal domain decrease NMDAR surface expression and reduce potentiating effects of neurosteroids.

    Kysilov, Bohdan / Kuchtiak, Viktor / Hrcka Krausova, Barbora / Balik, Ales / Korinek, Miloslav / Fili, Klevinda / Dobrovolski, Mark / Abramova, Vera / Chodounska, Hana / Kudova, Eva / Bozikova, Paulina / Cerny, Jiri / Smejkalova, Tereza / Vyklicky, Ladislav

    Cellular and molecular life sciences : CMLS

    2024  Volume 81, Issue 1, Page(s) 36

    Abstract: N-methyl-D-aspartate receptors (NMDARs) play a critical role in normal brain function, and variants in genes encoding NMDAR subunits have been described in individuals with various neuropsychiatric disorders. We have used whole-cell patch-clamp ... ...

    Abstract N-methyl-D-aspartate receptors (NMDARs) play a critical role in normal brain function, and variants in genes encoding NMDAR subunits have been described in individuals with various neuropsychiatric disorders. We have used whole-cell patch-clamp electrophysiology, fluorescence microscopy and in-silico modeling to explore the functional consequences of disease-associated nonsense and frame-shift variants resulting in the truncation of GluN2A or GluN2B C-terminal domain (CTD). This study characterizes variant NMDARs and shows their reduced surface expression and synaptic localization, altered agonist affinity, increased desensitization, and reduced probability of channel opening. We also show that naturally occurring and synthetic steroids pregnenolone sulfate and epipregnanolone butanoic acid, respectively, enhance NMDAR function in a way that is dependent on the length of the truncated CTD and, further, is steroid-specific, GluN2A/B subunit-specific, and GluN1 splice variant-specific. Adding to the previously described effects of disease-associated NMDAR variants on the receptor biogenesis and function, our results improve the understanding of the molecular consequences of NMDAR CTD truncations and provide an opportunity for the development of new therapeutic neurosteroid-based ligands.
    MeSH term(s) Humans ; Electrophysiological Phenomena ; Neurosteroids ; Receptors, N-Methyl-D-Aspartate/genetics ; Receptors, N-Methyl-D-Aspartate/metabolism
    Chemical Substances Neurosteroids ; Receptors, N-Methyl-D-Aspartate ; N-methyl D-aspartate receptor subtype 2A (VH92ICR8HX) ; NR2B NMDA receptor
    Language English
    Publishing date 2024-01-12
    Publishing country Switzerland
    Document type Journal Article
    ZDB-ID 1358415-7
    ISSN 1420-9071 ; 1420-682X
    ISSN (online) 1420-9071
    ISSN 1420-682X
    DOI 10.1007/s00018-023-05062-6
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  9. Article ; Online: Total Synthesis of ent-Pregnanolone Sulfate and Its Biological Investigation at the NMDA Receptor.

    Kapras, Vojtech / Vyklicky, Vojtech / Budesinsky, Milos / Cisarova, Ivana / Vyklicky, Ladislav / Chodounska, Hana / Jahn, Ullrich

    Organic letters

    2018  Volume 20, Issue 4, Page(s) 946–949

    Abstract: A unique asymmetric total synthesis of the unnatural enantiomer of pregnanolone, as well as a study of its biological activity at the NMDA receptor, is reported. The asymmetry is introduced by a highly atom-economic organocatalytic Robinson annulation. A ...

    Abstract A unique asymmetric total synthesis of the unnatural enantiomer of pregnanolone, as well as a study of its biological activity at the NMDA receptor, is reported. The asymmetry is introduced by a highly atom-economic organocatalytic Robinson annulation. A new method for the construction of the cyclopentane D-ring consisting of Cu
    MeSH term(s) Cyclization ; Molecular Structure ; Pregnanolone/chemical synthesis ; Receptors, N-Methyl-D-Aspartate ; Stereoisomerism ; Sulfates
    Chemical Substances Receptors, N-Methyl-D-Aspartate ; Sulfates ; Pregnanolone (BXO86P3XXW)
    Language English
    Publishing date 2018-01-24
    Publishing country United States
    Document type Journal Article ; Research Support, Non-U.S. Gov't
    ISSN 1523-7052
    ISSN (online) 1523-7052
    DOI 10.1021/acs.orglett.7b03838
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  10. Article ; Online: Effects of Pregnanolone Glutamate and Its Metabolites on GABA

    Abramova, Vera / Leal Alvarado, Vanessa / Hill, Martin / Smejkalova, Tereza / Maly, Michal / Vales, Karel / Dittert, Ivan / Bozikova, Paulina / Kysilov, Bohdan / Hrcka Krausova, Barbora / Vyklicky, Vojtech / Balik, Ales / Fili, Klevinda / Korinek, Miloslav / Chodounska, Hana / Kudova, Eva / Ciz, David / Martinovic, Jan / Cerny, Jiri /
    Bartunek, Petr / Vyklicky, Ladislav

    ACS chemical neuroscience

    2023  Volume 14, Issue 10, Page(s) 1870–1883

    Abstract: ... metabolites of a neuroprotective synthetic steroid 20-oxo-5β-pregnan-3α-yl l-glutamyl 1-ester (pregnanolone ...

    Abstract Multiple molecular targets have been identified to mediate membrane-delimited and nongenomic effects of natural and synthetic steroids, but the influence of steroid metabolism on neuroactive steroid signaling is not well understood. To begin to address this question, we set out to identify major metabolites of a neuroprotective synthetic steroid 20-oxo-5β-pregnan-3α-yl l-glutamyl 1-ester (pregnanolone glutamate, PAG) and characterize their effects on GABA
    MeSH term(s) Rats ; Animals ; Pregnanolone/pharmacology ; Pregnanolone/chemistry ; Receptors, N-Methyl-D-Aspartate ; Zebrafish ; Glutamic Acid ; Esters ; gamma-Aminobutyric Acid ; Receptors, GABA-A
    Chemical Substances Pregnanolone (BXO86P3XXW) ; Receptors, N-Methyl-D-Aspartate ; Glutamic Acid (3KX376GY7L) ; Esters ; gamma-Aminobutyric Acid (56-12-2) ; Receptors, GABA-A
    Language English
    Publishing date 2023-05-01
    Publishing country United States
    Document type Journal Article ; Research Support, Non-U.S. Gov't
    ISSN 1948-7193
    ISSN (online) 1948-7193
    DOI 10.1021/acschemneuro.3c00131
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