title: o-Naphthalenedicarboxaldehyde derivative of 7'-aminonaltrindole as a selective delta-opioid receptor affinity label.
abstract: Incorporation of a naphthalene-dialdehyde moiety into the delta antagonist, 6'-aminonaltrindole afforded a potent, selective, irreversible delta-agonist 1. However, flow cytometry studies revealed no time-dependent specific fluorescence, suggesting that both Lys214 and Cys216 at the recognition site are not involved in covalent binding. Molecular simulation studies suggest that compound 1 may form a Schiff base with the epsilon-amino group of Lys214, which could explain its irreversibility and transformation into a delta-agonist through a conformational change of TM5.
authors.affiliation: Department of Medicinal Chemistry, College of Pharmacy, University of Minnesota, Minneapolis, Minnesota 55455, USA.
authors.forename: Sarika Prabhu
authors.initials: SP
authors.lastname: Haris
authors.forename: Yan
authors.initials: Y
authors.lastname: Zhang
authors.forename: Bertrand
authors.initials: B
authors.lastname: Le Bourdonnec
authors.forename: Christopher R
authors.initials: CR
authors.lastname: McCurdy
authors.forename: Philip S
authors.initials: PS
authors.lastname: Portoghese
mesh_terms: D000345:Affinity Labels; D009682:Magnetic Resonance Spectroscopy; D009271:Naltrexone / Q000031:analogs & derivatives* / Q000737:chemistry; D009292:Narcotic Antagonists / Q000737:chemistry*; D017465:Receptors, Opioid, delta / Q000378:metabolism*; D016339:Spectrometry, Mass, Fast Atom Bombardment
chemical_list: D000345:Affinity Labels; D009292:Narcotic Antagonists; D017465:Receptors, Opioid, delta; D009271:Naltrexone; C055382:naltrindole