title: Synthesis of tripeptides containing D-Trp substituted at the indole ring, assessment of opioid receptor binding and in vivo central antinociception.
abstract: The noncationizable tripeptide Ac-D-Trp-Phe-GlyNH2 was recently proposed as a novel minimal recognition motif for μ-opioid receptor. The introduction of different substituents (methyl, halogens, nitro, etc.) at the indole of D-Trp significantly influenced receptor affinities and resulted in serum stability and in a measurable effect on central antinociception in mice after ip administration.
authors: Department of Chemistry "G. Ciamician", University of Bologna , via Selmi 2, 40126 Bologna, Italy.
authors: Rossella
authors: R
authors: De Marco
authors: Andrea
authors: A
authors: Bedini
authors: Santi
authors: S
authors: Spampinato
authors: Luca
authors: L
authors: Gentilucci
mesh_terms: D000701:Analgesics, Opioid / Q000378:metabolism*; D000818:Animals; D057809:HEK293 Cells; D006801:Humans; D007211:Indoles / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D051379:Mice; D062105:Molecular Docking Simulation; D009842:Oligopeptides / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D010147:Pain Measurement; D011487:Protein Conformation; D011869:Radioligand Assay; D017465:Receptors, Opioid, delta / Q000819:agonists / Q000378:metabolism; D017473:Receptors, Opioid, kappa / Q000819:agonists / Q000378:metabolism; D017450:Receptors, Opioid, mu / Q000819:agonists / Q000378:metabolism; D013329:Structure-Activity Relationship; D014364:Tryptophan / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology
chemical_list: D000701:Analgesics, Opioid; D007211:Indoles; D009842:Oligopeptides; D017465:Receptors, Opioid, delta; D017473:Receptors, Opioid, kappa; D017450:Receptors, Opioid, mu; D014364:Tryptophan