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  1. Article ; Online: Oxygenation of Anandamide by Lipoxygenases.

    van Zadelhoff, Guus / van der Stelt, Mario

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

    2022  Volume 2576, Page(s) 307–316

    Abstract: The endocannabinoids anandamide and 2-arachidonoylglycerol are not only metabolized by serine hydrolases, such as fatty acid amide hydrolase, monoacylglycerol lipase, and α,β-hydrolases 6 and 12, but they also serve as substrates for cyclooxygenases, ... ...

    Abstract The endocannabinoids anandamide and 2-arachidonoylglycerol are not only metabolized by serine hydrolases, such as fatty acid amide hydrolase, monoacylglycerol lipase, and α,β-hydrolases 6 and 12, but they also serve as substrates for cyclooxygenases, cytochrome P450s, and lipoxygenases. These enzymes oxygenate the 1Z,4Z-pentadiene system of the arachidonic acid backbone of endocannabinoids, thereby giving rise to an entirely new array of bioactive lipids. Hereby, a protocol is provided for the enzymatic synthesis, purification, and characterization of various oxygenated metabolites of anandamide generated by lipoxygenases, which enables the biological study and detection of these metabolites.
    MeSH term(s) Alkadienes ; Arachidonic Acid ; Arachidonic Acids ; Cytochromes ; Endocannabinoids/metabolism ; Lipoxygenases ; Monoacylglycerol Lipases ; Polyunsaturated Alkamides ; Prostaglandin-Endoperoxide Synthases/metabolism ; Serine
    Chemical Substances Alkadienes ; Arachidonic Acids ; Cytochromes ; Endocannabinoids ; Polyunsaturated Alkamides ; Arachidonic Acid (27YG812J1I) ; Serine (452VLY9402) ; Lipoxygenases (EC 1.13.11.-) ; Prostaglandin-Endoperoxide Synthases (EC 1.14.99.1) ; Monoacylglycerol Lipases (EC 3.1.1.23) ; anandamide (UR5G69TJKH)
    Language English
    Publishing date 2022-09-24
    Publishing country United States
    Document type Journal Article
    ISSN 1940-6029
    ISSN (online) 1940-6029
    DOI 10.1007/978-1-0716-2728-0_26
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  2. Article ; Online: Anandamide and other N-acylethanolamines: A class of signaling lipids with therapeutic opportunities.

    Mock, Elliot D / Gagestein, Berend / van der Stelt, Mario

    Progress in lipid research

    2022  Volume 89, Page(s) 101194

    Abstract: N-acylethanolamines (NAEs), including N-palmitoylethanolamine (PEA), N-oleoylethanolamine (OEA), N-arachidonoylethanolamine (AEA, anandamide), N-docosahexaenoylethanolamine (DHEA, synaptamide) and their oxygenated metabolites are a lipid messenger family ...

    Abstract N-acylethanolamines (NAEs), including N-palmitoylethanolamine (PEA), N-oleoylethanolamine (OEA), N-arachidonoylethanolamine (AEA, anandamide), N-docosahexaenoylethanolamine (DHEA, synaptamide) and their oxygenated metabolites are a lipid messenger family with numerous functions in health and disease, including inflammation, anxiety and energy metabolism. The NAEs exert their signaling role through activation of various G protein-coupled receptors (cannabinoid CB
    MeSH term(s) Endocannabinoids/metabolism ; Peroxisome Proliferator-Activated Receptors ; Polyunsaturated Alkamides ; Dehydroepiandrosterone
    Chemical Substances anandamide (UR5G69TJKH) ; Endocannabinoids ; N-acylethanolamines ; Peroxisome Proliferator-Activated Receptors ; Polyunsaturated Alkamides ; synaptamide ; Dehydroepiandrosterone (459AG36T1B)
    Language English
    Publishing date 2022-09-20
    Publishing country England
    Document type Journal Article ; Review ; Research Support, Non-U.S. Gov't
    ZDB-ID 282560-0
    ISSN 1873-2194 ; 0079-6832 ; 0163-7827
    ISSN (online) 1873-2194
    ISSN 0079-6832 ; 0163-7827
    DOI 10.1016/j.plipres.2022.101194
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  3. Article ; Online: Fluorescence-Based NAPE-PLD Activity Assay.

    Mock, Elliot D / Driever, Wouter P F / van der Stelt, Mario

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

    2022  Volume 2576, Page(s) 233–240

    Abstract: N-Acylphosphatidylethanolamine phospholipase D (NAPE-PLD) is regarded as the principal enzyme that generates N-acylethanolamines (NAEs), a family of signaling lipids that includes the endocannabinoid anandamide. To investigate the biological function and ...

    Abstract N-Acylphosphatidylethanolamine phospholipase D (NAPE-PLD) is regarded as the principal enzyme that generates N-acylethanolamines (NAEs), a family of signaling lipids that includes the endocannabinoid anandamide. To investigate the biological function and biosynthesis of NAEs, we sought to develop potent NAPE-PLD inhibitors. To this aim, we utilized a high-throughput screening-compatible NAPE-PLD activity assay, which uses the fluorescence-quenched substrate PED6. This assay conveniently uses membrane fractions of NAPE-PLD overexpressing HEK293T cell lysates, thus avoiding the need for protein purification. Here, we give a detailed description of the NAPE-PLD PED6 fluorescence activity assay, which has increased throughput compared to previous radioactivity- or mass-spectrometry-based assays.
    MeSH term(s) Humans ; Endocannabinoids ; Fluorescence ; HEK293 Cells ; Phospholipase D/metabolism
    Chemical Substances Endocannabinoids ; Phospholipase D (EC 3.1.4.4)
    Language English
    Publishing date 2022-09-22
    Publishing country United States
    Document type Journal Article
    ISSN 1940-6029
    ISSN (online) 1940-6029
    DOI 10.1007/978-1-0716-2728-0_19
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  4. Article ; Online: Discovery of a Photoaffinity Probe that Captures the Active Conformation of the Cannabinoid CB

    De Paus, Laura V / An, Yu / Janssen, Antonius P A / van den Berg, Richard J B H N / Heitman, Laura H / van der Stelt, Mario

    Chembiochem : a European journal of chemical biology

    2024  Volume 25, Issue 7, Page(s) e202300785

    Abstract: The cannabinoid receptor type 2 ( ... ...

    Abstract The cannabinoid receptor type 2 (CB
    MeSH term(s) Receptors, Cannabinoid ; Fluorescent Dyes/chemistry ; Molecular Conformation ; Receptors, G-Protein-Coupled ; Cannabinoids
    Chemical Substances Receptors, Cannabinoid ; Fluorescent Dyes ; Receptors, G-Protein-Coupled ; Cannabinoids
    Language English
    Publishing date 2024-03-01
    Publishing country Germany
    Document type Journal Article
    ZDB-ID 2020469-3
    ISSN 1439-7633 ; 1439-4227
    ISSN (online) 1439-7633
    ISSN 1439-4227
    DOI 10.1002/cbic.202300785
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  5. Article ; Online: Dual allosteric and orthosteric pharmacology of synthetic analog cannabidiol-dimethylheptyl, but not cannabidiol, on the cannabinoid CB

    Bouma, Jara / Broekhuis, Jeremy D / van der Horst, Cas / Kumar, Poulami / Ligresti, Alessia / van der Stelt, Mario / Heitman, Laura H

    Biochemical pharmacology

    2023  Volume 218, Page(s) 115924

    Abstract: Cannabinoid ... ...

    Abstract Cannabinoid CB
    MeSH term(s) Cannabidiol/pharmacology ; Receptors, Cannabinoid/metabolism ; beta-Arrestin 1/metabolism ; GTP-Binding Proteins/metabolism ; Receptor, Cannabinoid, CB2/metabolism ; Dronabinol ; Receptor, Cannabinoid, CB1/metabolism ; Cannabinoid Receptor Agonists
    Chemical Substances cannabidiol-dimethylheptyl ; Cannabidiol (19GBJ60SN5) ; Receptors, Cannabinoid ; beta-Arrestin 1 ; GTP-Binding Proteins (EC 3.6.1.-) ; Receptor, Cannabinoid, CB2 ; Dronabinol (7J8897W37S) ; Receptor, Cannabinoid, CB1 ; Cannabinoid Receptor Agonists
    Language English
    Publishing date 2023-11-14
    Publishing country England
    Document type Journal Article ; Research Support, Non-U.S. Gov't
    ZDB-ID 208787-x
    ISSN 1873-2968 ; 0006-2952
    ISSN (online) 1873-2968
    ISSN 0006-2952
    DOI 10.1016/j.bcp.2023.115924
    Database MEDical Literature Analysis and Retrieval System OnLINE

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    Zs.A 19: Show issues Location:
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    Jg. 1995 - 2021: Lesesall (1.OG)
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  6. Article ; Online: P2X

    Singh, Simar / Sarroza, Dennis / English, Anthony / Whittington, Dale / Dong, Ao / Malamas, Michael / Makriyannis, Alexandros / van der Stelt, Mario / Li, Yulong / Zweifel, Larry / Bruchas, Michael R / Land, Benjamin B / Stella, Nephi

    British journal of pharmacology

    2024  

    Abstract: Background and purpose: Neurotransmission and neuroinflammation are controlled by local increases in both extracellular ATP and the endocannabinoid 2-arachidonoyl glycerol (2-AG). While it is known that extracellular ATP stimulates 2-AG production in ... ...

    Abstract Background and purpose: Neurotransmission and neuroinflammation are controlled by local increases in both extracellular ATP and the endocannabinoid 2-arachidonoyl glycerol (2-AG). While it is known that extracellular ATP stimulates 2-AG production in cells in culture, the dynamics and molecular mechanisms that underlie this response remain poorly understood. Detection of real-time changes in eCB levels with the genetically encoded sensor, GRAB
    Experimental approach: 2-AG and arachidonoylethanolamide (AEA) levels in Neuro2a (N2a) cells were measured by LC-MS, and GRAB
    Key results: 2-AG and AEA increased GRAB
    Conclusions and implications: Considering that P2X
    Language English
    Publishing date 2024-04-06
    Publishing country England
    Document type Journal Article
    ZDB-ID 80081-8
    ISSN 1476-5381 ; 0007-1188
    ISSN (online) 1476-5381
    ISSN 0007-1188
    DOI 10.1111/bph.16348
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  7. Article ; Online: Chemical Probes to Control and Visualize Lipid Metabolism in the Brain.

    Punt, Jeroen M / van der Vliet, Daan / van der Stelt, Mario

    Accounts of chemical research

    2022  Volume 55, Issue 22, Page(s) 3205–3217

    Abstract: ConspectusSignaling lipids, such as the endocannabinoids, play an important role in the brain. They regulate synaptic transmission and control various neurophysiological processes, including pain sensation, appetite, memory formation, stress, and anxiety. ...

    Abstract ConspectusSignaling lipids, such as the endocannabinoids, play an important role in the brain. They regulate synaptic transmission and control various neurophysiological processes, including pain sensation, appetite, memory formation, stress, and anxiety. Unlike classical neurotransmitters, lipid messengers are produced on demand and degraded by metabolic enzymes to control their lifespan and signaling actions. Chemical biology approaches have become one of the main driving forces to study and unravel the physiological role of lipid messengers in the brain. Here, we review how the development and use of chemical probes has allowed one to study endocannabinoid signaling by (i) inhibiting the biosynthetic and metabolic enzymes; (ii) visualizing the activity of these enzymes; and (iii) controlling the release and transport of the endocannabinoids. Activity-based probes were instrumental to guide the discovery of highly selective and in vivo active inhibitors of the biosynthetic (DAGL, NAPE-PLD) and metabolic (MAGL, FAAH) enzymes of endocannabinoids. These inhibitors allowed one to study the role of these enzymes in animal models of disease. For instance, the DAGL-MAGL axis was shown to control neuroinflammation and the NAPE-PLD-FAAH axis to regulate emotional behavior. Activity-based protein profiling and chemical proteomics were essential to guide the drug discovery and development of compounds targeting MAGL and FAAH, such as ABX-1431 (Lu AG06466) and PF-04457845, respectively. These experimental drugs are now in clinical trials for multiple indications, including multiple sclerosis and post-traumatic stress disorders. Activity-based probes have also been used to visualize the activity of these lipid metabolizing enzymes with high spatial resolution in brain slices, thereby showing the cell type-specific activity of these lipid metabolizing enzymes. The transport, release, and uptake of signaling lipids themselves cannot, however, be captured by activity-based probes in a spatiotemporal controlled manner. Therefore, bio-orthogonal lipids equipped with photoreactive, photoswitchable groups or photocages have been developed. These chemical probes were employed to investigate the protein interaction partners of the endocannabinoids, such as putative membrane transporters, as well as to study the functional cellular responses within milliseconds upon irradiation. Finally, genetically encoded sensors have recently been developed to monitor the real-time release of endocannabinoids with high spatiotemporal resolution in cultured neurons, acute brain slices, and in vivo mouse models. It is anticipated that the combination of chemical probes, highly selective inhibitors, and sensors with advanced (super resolution) imaging modalities, such as PharmacoSTORM and correlative light-electron microscopy, will uncover the fundamental basis of lipid signaling at nanoscale resolution in the brain. Furthermore, chemical biology approaches enable the translation of these fundamental discoveries into clinical solutions for brain diseases with aberrant lipid signaling.
    MeSH term(s) Animals ; Mice ; Endocannabinoids/metabolism ; Lipid Metabolism ; Brain/metabolism ; Neurons/metabolism ; Synaptic Transmission
    Chemical Substances Endocannabinoids
    Language English
    Publishing date 2022-10-25
    Publishing country United States
    Document type Review ; Journal Article
    ZDB-ID 1483291-4
    ISSN 1520-4898 ; 0001-4842
    ISSN (online) 1520-4898
    ISSN 0001-4842
    DOI 10.1021/acs.accounts.2c00521
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  8. Article ; Online: Targeting Endocannabinoid Signaling: FAAH and MAG Lipase Inhibitors.

    van Egmond, Noëlle / Straub, Verena M / van der Stelt, Mario

    Annual review of pharmacology and toxicology

    2020  Volume 61, Page(s) 441–463

    Abstract: Inspired by the medicinal properties of the ... ...

    Abstract Inspired by the medicinal properties of the plant
    MeSH term(s) Amidohydrolases ; Endocannabinoids ; Enzyme Inhibitors ; Humans ; Lipase
    Chemical Substances Endocannabinoids ; Enzyme Inhibitors ; Lipase (EC 3.1.1.3) ; Amidohydrolases (EC 3.5.-) ; fatty-acid amide hydrolase (EC 3.5.1.-)
    Language English
    Publishing date 2020-08-31
    Publishing country United States
    Document type Journal Article ; Research Support, Non-U.S. Gov't ; Review
    ZDB-ID 196587-6
    ISSN 1545-4304 ; 0362-1642
    ISSN (online) 1545-4304
    ISSN 0362-1642
    DOI 10.1146/annurev-pharmtox-030220-112741
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  9. Article ; Online: Cellular Assay to Study β-Arrestin Recruitment by the Cannabinoid Receptors 1 and 2.

    Bouma, Jara / Soethoudt, Marjolein / van Gils, Noortje / Xia, Lizi / van der Stelt, Mario / Heitman, Laura H

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

    2022  Volume 2576, Page(s) 189–199

    Abstract: Cannabinoid receptor 1 ( ... ...

    Abstract Cannabinoid receptor 1 (CB
    MeSH term(s) GTP-Binding Proteins/metabolism ; Humans ; Ligands ; Receptors, Cannabinoid/metabolism ; Receptors, G-Protein-Coupled/metabolism ; beta-Arrestin 1/metabolism ; beta-Arrestins/metabolism ; beta-Galactosidase/metabolism
    Chemical Substances Ligands ; Receptors, Cannabinoid ; Receptors, G-Protein-Coupled ; beta-Arrestin 1 ; beta-Arrestins ; beta-Galactosidase (EC 3.2.1.23) ; GTP-Binding Proteins (EC 3.6.1.-)
    Language English
    Publishing date 2022-09-24
    Publishing country United States
    Document type Journal Article
    ISSN 1940-6029
    ISSN (online) 1940-6029
    DOI 10.1007/978-1-0716-2728-0_15
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  10. Article ; Online: 2-AG-Mediated Control of GABAergic Signaling Is Impaired in a Model of Epilepsy.

    Colangeli, Roberto / Morena, Maria / Werner, Allison / Thompson, Roger J / van der Stelt, Mario / Pittman, Quentin J / Hill, Matthew N / Teskey, G Campbell

    The Journal of neuroscience : the official journal of the Society for Neuroscience

    2022  Volume 43, Issue 4, Page(s) 571–583

    Abstract: Repeated seizures result in a persistent maladaptation of endocannabinoid (eCB) signaling, mediated part by anandamide signaling deficiency in the basolateral amygdala (BLA) that manifests as aberrant synaptic function and altered emotional behavior. ... ...

    Abstract Repeated seizures result in a persistent maladaptation of endocannabinoid (eCB) signaling, mediated part by anandamide signaling deficiency in the basolateral amygdala (BLA) that manifests as aberrant synaptic function and altered emotional behavior. Here, we determined the effect of repeated seizures (kindling) on 2-arachidonoylglycerol (2-AG) signaling on GABA transmission by directly measuring tonic and phasic eCB-mediated retrograde signaling in an
    MeSH term(s) Rats ; Male ; Animals ; Endocannabinoids/pharmacology ; Drug Inverse Agonism ; Cannabinoid Receptor Agonists/pharmacology ; Epilepsy ; Receptors, Cannabinoid ; Enzyme Inhibitors/pharmacology ; Seizures ; gamma-Aminobutyric Acid ; Receptor, Cannabinoid, CB1
    Chemical Substances Endocannabinoids ; Cannabinoid Receptor Agonists ; Receptors, Cannabinoid ; Enzyme Inhibitors ; gamma-Aminobutyric Acid (56-12-2) ; Receptor, Cannabinoid, CB1
    Language English
    Publishing date 2022-12-02
    Publishing country United States
    Document type Journal Article ; Research Support, Non-U.S. Gov't
    ZDB-ID 604637-x
    ISSN 1529-2401 ; 0270-6474
    ISSN (online) 1529-2401
    ISSN 0270-6474
    DOI 10.1523/JNEUROSCI.0541-22.2022
    Database MEDical Literature Analysis and Retrieval System OnLINE

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