{"database":"biostudies-literature","file_versions":[],"scores":null,"additional":{"submitter":["Rodriguez-Soacha DA"],"funding":["Elitenetzwerk Bayern","Deutscher Akademischer Austauschdienst","National Institute on Alcohol Abuse and Alcoholism","Deutsche Forschungsgemeinschaft","National Institute of Diabetes and Digestive and Kidney Diseases","NIDDK NIH HHS","NIDA NIH HHS","NIAAA NIH HHS","European Cooperation in Science and Technology","National Institute on Drug Abuse"],"pagination":["1632-1647"],"full_dataset_link":["https://www.ebi.ac.uk/biostudies/studies/S-EPMC9016771"],"repository":["biostudies-literature"],"omics_type":["Unknown"],"volume":["12(9)"],"pubmed_abstract":["Human cannabinoid receptor type 1 (<i>h</i>CB<sub>1</sub>R) plays important roles in the regulation of appetite and development of addictive behaviors. Herein, we describe the design, synthesis, photocharacterization, molecular docking, and <i>in vitro</i> characterization of \"photo-rimonabant\", i.e., azo-derivatives of the selective <i>h</i>CB<sub>1</sub>R antagonist SR1411716A (rimonabant). By applying azo-extension strategies, we yielded compound <b>16a</b>, which shows marked affinity for CB<sub>1</sub>R (<i>K</i><sub>i (<i>cis</i> form)</sub> = 29 nM), whose potency increases by illumination with ultraviolet light (CB<sub>1</sub>R K<sub>i</sub><i>trans</i>/<i>cis</i> ratio = 15.3). Through radioligand binding, calcium mobilization, and cell luminescence assays, we established that <b>"],"journal":["ACS chemical neuroscience"],"pubmed_title":["\"Photo-Rimonabant\": Synthesis and Biological Evaluation of Novel Photoswitchable Molecules Derived from Rimonabant Lead to a Highly Selective and Nanomolar \"<i>Cis</i>-On\" CB<sub>1</sub>R Antagonist."],"pmcid":["PMC9016771"],"funding_grant_id":["AA023256","DFG DE1546/10-1","CA15135 (MuTaLiG)","U18 DA052495","R01 DK124615","R01 AA022235","DK124615","R01 DK100414","R01 DK103625","PhD scholarship","DA052495","International Doctoral Program &quot;Receptor Dynamics&quot;"],"pubmed_authors":["Sotriffer C","Fender J","Lorenz K","Collado JA","Rodriguez-Soacha DA","Maitra R","Decker M","Ramirez YA","Munoz E"],"additional_accession":[]},"is_claimable":false,"name":"\"Photo-Rimonabant\": Synthesis and Biological Evaluation of Novel Photoswitchable Molecules Derived from Rimonabant Lead to a Highly Selective and Nanomolar \"<i>Cis</i>-On\" CB<sub>1</sub>R Antagonist.","description":"Human cannabinoid receptor type 1 (<i>h</i>CB<sub>1</sub>R) plays important roles in the regulation of appetite and development of addictive behaviors. Herein, we describe the design, synthesis, photocharacterization, molecular docking, and <i>in vitro</i> characterization of \"photo-rimonabant\", i.e., azo-derivatives of the selective <i>h</i>CB<sub>1</sub>R antagonist SR1411716A (rimonabant). By applying azo-extension strategies, we yielded compound <b>16a</b>, which shows marked affinity for CB<sub>1</sub>R (<i>K</i><sub>i (<i>cis</i> form)</sub> = 29 nM), whose potency increases by illumination with ultraviolet light (CB<sub>1</sub>R K<sub>i</sub><i>trans</i>/<i>cis</i> ratio = 15.3). Through radioligand binding, calcium mobilization, and cell luminescence assays, we established that <b>","dates":{"release":"2021-01-01T00:00:00Z","publication":"2021 May","modification":"2026-05-09T17:31:25.887Z","creation":"2024-11-15T12:40:07.105Z"},"accession":"S-EPMC9016771","cross_references":{"pubmed":["33856764"],"doi":["10.1021/acschemneuro.1c00086"]}}