title: Development of endocannabinoid-based chemical probes for the study of cannabinoid receptors.
abstract: We report the synthesis of new chemical probes (1a,b, 2a-c, 3a-c) based on the structure of the main endocannabinoids for their use in biological systems directly or via click chemistry. As proof of concept, 2-arachidonyl glyceryl ether based biotinylated 3b enables direct visualization of CB(1) receptor in cells. These results represent the starting point for the development of advanced small molecule chemical probes able to generate valuable information about the cannabinoid receptors.
authors.affiliation: Departamento de Química Orgánica I, Facultad de Ciencias Químicas, Universidad Complutense de Madrid, E-28040 Madrid, Spain.
authors.forename: Lidia
authors.initials: L
authors.lastname: Martín-Couce
authors.forename: Mar
authors.initials: M
authors.lastname: Martín-Fontecha
authors.forename: Samanta
authors.initials: S
authors.lastname: Capolicchio
authors.forename: María L
authors.initials: ML
authors.lastname: López-Rodríguez
authors.forename: Silvia
authors.initials: S
authors.lastname: Ortega-Gutiérrez
mesh_terms: D000475:Alkenes / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D001095:Arachidonic Acids / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D001577:Benzophenones / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D001667:Binding, Competitive; D001710:Biotin / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D063385:Cannabinoid Receptor Modulators / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D002460:Cell Line; D057930:Click Chemistry; D063388:Endocannabinoids; D005989:Glycerides / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D006801:Humans; D008024:Ligands; D015335:Molecular Probes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D053284:Polyunsaturated Alkamides / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D011869:Radioligand Assay; D043884:Receptor, Cannabinoid, CB1 / Q000378:metabolism*; D043885:Receptor, Cannabinoid, CB2 / Q000378:metabolism*; D013329:Structure-Activity Relationship
chemical_list: D000475:Alkenes; D001095:Arachidonic Acids; D001577:Benzophenones; D063385:Cannabinoid Receptor Modulators; D063388:Endocannabinoids; D005989:Glycerides; D008024:Ligands; D015335:Molecular Probes; D053284:Polyunsaturated Alkamides; D043884:Receptor, Cannabinoid, CB1; D043885:Receptor, Cannabinoid, CB2; C424442:noladin ether; D001710:Biotin; C094503:glyceryl 2-arachidonate; C078814:anandamide