{"database":"biostudies-literature","file_versions":[],"scores":null,"additional":{"submitter":["Karad SN"],"funding":["NIDA NIH HHS","National Institutes of Health","National Institute on Drug Abuse","National Institute of General Medical Sciences","NIGMS NIH HHS","NIH HHS"],"pagination":["571-576"],"full_dataset_link":["https://www.ebi.ac.uk/biostudies/studies/S-EPMC5486982"],"repository":["biostudies-literature"],"omics_type":["Unknown"],"volume":["12(8)"],"pubmed_abstract":["We describe the design, synthesis, and opioid activity of fluoroalkene (Tyr<sup>1</sup> -ψ[(Z)CF=CH]-Gly<sup>2</sup> ) and trifluoroethylamine (Tyr<sup>1</sup> -ψ[(S)/(R)-CF<sub>3</sub> CH-NH]-Gly<sup>2</sup> ) analogues of the endogenous opioid neuropeptide, Leu-enkephalin. The fluoroalkene peptidomimetic exhibited low nanomolar functional activity (5.0±2 nm and 60±15 nm for δ- and μ-opioid receptors, respectively) with a μ/δ-selectivity ratio that mimics that of the natural peptide. However, the trifluoroethylamine peptidomimetics, irrespective of stereochemistry, did not activate the opioid receptors, which suggest that bulky CF<sub>3</sub> substituents are not tolerated at this position."],"journal":["ChemMedChem"],"pubmed_title":["Synthesis and Opioid Activity of Tyr<sup>1</sup> -ψ[(Z)CF=CH]-Gly<sup>2</sup> and Tyr<sup>1</sup> -ψ[(S)/(R)-CF<sub>3</sub> CH-NH]-Gly<sup>2</sup> Leu-enkephalin Fluorinated Peptidomimetics."],"pmcid":["PMC5486982"],"funding_grant_id":["S10 OD016360","R33 DA036730","S10D016360","DA018151","R21 DA036730","DA036730","T32 GM008545","GM008545","R01 DA018151"],"pubmed_authors":["Prisinzano TE","Crowley RS","Altman RA","Karad SN","Pal M"],"additional_accession":[]},"is_claimable":false,"name":"Synthesis and Opioid Activity of Tyr<sup>1</sup> -ψ[(Z)CF=CH]-Gly<sup>2</sup> and Tyr<sup>1</sup> -ψ[(S)/(R)-CF<sub>3</sub> CH-NH]-Gly<sup>2</sup> Leu-enkephalin Fluorinated Peptidomimetics.","description":"We describe the design, synthesis, and opioid activity of fluoroalkene (Tyr<sup>1</sup> -ψ[(Z)CF=CH]-Gly<sup>2</sup> ) and trifluoroethylamine (Tyr<sup>1</sup> -ψ[(S)/(R)-CF<sub>3</sub> CH-NH]-Gly<sup>2</sup> ) analogues of the endogenous opioid neuropeptide, Leu-enkephalin. The fluoroalkene peptidomimetic exhibited low nanomolar functional activity (5.0±2 nm and 60±15 nm for δ- and μ-opioid receptors, respectively) with a μ/δ-selectivity ratio that mimics that of the natural peptide. However, the trifluoroethylamine peptidomimetics, irrespective of stereochemistry, did not activate the opioid receptors, which suggest that bulky CF<sub>3</sub> substituents are not tolerated at this position.","dates":{"release":"2017-01-01T00:00:00Z","publication":"2017 Apr","modification":"2024-11-19T14:41:41.382Z","creation":"2019-03-26T23:29:03Z"},"accession":"S-EPMC5486982","cross_references":{"pubmed":["28296145"],"doi":["10.1002/cmdc.201700103"]}}