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 journalArticle

11 Citations (Scopus)

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

Fingerprint

Affinity Labels
Opioid Receptors
Opiate Alkaloids
Isoindoles
Fluorescence
Ligands
naphthalene

Cite this

Naphthalene dicarboxaldehyde as an electrophilic fluorogenic moiety for affinity labeling : Application to opioid receptor affinity labels with greatly improved fluorogenic properties. / McCurdy, Christopher R.; Le Bourdonnec, Bertrand; Metzger, Thomas G.; El Kouhen, Rachid; Zhang, Yan; Law, Ping-Yee; Portoghese, Philip S.

In: Journal of Medicinal Chemistry, Vol. 45, No. 14, 04.07.2002, p. 2887-2890.

Research output: Contribution to journalArticle

@article{86b64168ff1e4042a6a812273a872f87,
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 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.",
author = "McCurdy, {Christopher R.} and {Le Bourdonnec}, Bertrand and Metzger, {Thomas G.} and {El Kouhen}, Rachid and Yan Zhang and Ping-Yee Law and Portoghese, {Philip S}",
year = "2002",
month = "7",
day = "4",
doi = "10.1021/jm015586u",
language = "English (US)",
volume = "45",
pages = "2887--2890",
journal = "Journal of Medicinal Chemistry",
issn = "0022-2623",
publisher = "American Chemical Society",
number = "14",

}

TY - JOUR

T1 - Naphthalene dicarboxaldehyde as an electrophilic fluorogenic moiety for affinity labeling

T2 - Application to opioid receptor affinity labels with greatly improved fluorogenic properties

AU - McCurdy, Christopher R.

AU - Le Bourdonnec, Bertrand

AU - Metzger, Thomas G.

AU - El Kouhen, Rachid

AU - Zhang, Yan

AU - Law, Ping-Yee

AU - Portoghese, Philip S

PY - 2002/7/4

Y1 - 2002/7/4

N2 - 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.

AB - 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.

UR - http://www.scopus.com/inward/record.url?scp=0037019276&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0037019276&partnerID=8YFLogxK

U2 - 10.1021/jm015586u

DO - 10.1021/jm015586u

M3 - Article

VL - 45

SP - 2887

EP - 2890

JO - Journal of Medicinal Chemistry

JF - Journal of Medicinal Chemistry

SN - 0022-2623

IS - 14

ER -