title: Naphthalene dicarboxaldehyde as an electrophilic fluorogenic moiety for affinity labeling: application to opioid receptor affinity labels with greatly improved fluorogenic properties.
abstract: To develop ligands with fluorogenic properties amenable for following the kinetics of cross-linking to receptors, a naphthalene dicarboxaldehyde moiety has been attached to an opiate pharmacophore 2 and evaluated in mu-opioid receptors. The fluorescence of the benzo[f]isoindole formed upon cross-linking of mu-opioid receptors by 2 permitted the time-course of covalent bonding to be followed. This demonstrated proof-of-concept suggests the usefulness of naphthalene dicarboxaldehyde-containing affinity labels as kinetic probes.
authors.affiliation: Department of Medicinal Chemistry, College of Pharmacy, School of Medicine, University of Minnesota, Minneapolis, MN 55455, USA.
authors.forename: Christopher R
authors.initials: CR
authors.lastname: McCurdy
authors.forename: Bertrand
authors.initials: B
authors.lastname: Le Bourdonnec
authors.forename: Thomas G
authors.initials: TG
authors.lastname: Metzger
authors.forename: Rachid
authors.initials: R
authors.lastname: El Kouhen
authors.forename: Yan
authors.initials: Y
authors.lastname: Zhang
authors.forename: Ping Y
authors.initials: PY
authors.lastname: Law
authors.forename: Philip S
authors.initials: PS
authors.lastname: Portoghese
mesh_terms: D000345:Affinity Labels / Q000138:chemical synthesis* / Q000494:pharmacology; D000447:Aldehydes / Q000138:chemical synthesis* / Q000494:pharmacology; D002460:Cell Line; D003432:Cross-Linking Reagents / Q000138:chemical synthesis / Q000494:pharmacology; D005453:Fluorescence; D006801:Humans; D009281:Naphthalenes / Q000138:chemical synthesis* / Q000494:pharmacology; D017450:Receptors, Opioid, mu / Q000037:antagonists & inhibitors / Q000378:metabolism*
chemical_list: D000345:Affinity Labels; D000447:Aldehydes; D003432:Cross-Linking Reagents; D009281:Naphthalenes; D017450:Receptors, Opioid, mu