Naphthalene dicarboxaldehyde as an electrophilic fluorogenic moiety for affinity labeling: Application to opioid receptor affinity labels with greatly improved fluorogenic properties

Christopher R. McCurdy, Bertrand Le Bourdonnec, Thomas G. Metzger, Rachid El Kouhen, Yan Zhang, Ping-Yee Law, Philip S Portoghese

Research output: Contribution to journalArticlepeer-review

14 Scopus citations

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 μ opioid receptors. The fluorescence of the benzo[f]isoindole formed upon cross-linking of μ 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.

Original languageEnglish (US)
Pages (from-to)2887-2890
Number of pages4
JournalJournal of medicinal chemistry
Volume45
Issue number14
DOIs
StatePublished - Jul 4 2002

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