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

doi:10.1021/jm015586u

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 journal › Article › peer-review

15 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 language	English (US)
Pages (from-to)	2887-2890
Number of pages	4
Journal	Journal of medicinal chemistry
Volume	45
Issue number	14
DOIs	https://doi.org/10.1021/jm015586u
State	Published - Jul 4 2002

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McCurdy, C. R., Le Bourdonnec, B., Metzger, T. G., El Kouhen, R., Zhang, Y., Law, P.-Y., & Portoghese, P. S. (2002). Naphthalene dicarboxaldehyde as an electrophilic fluorogenic moiety for affinity labeling: Application to opioid receptor affinity labels with greatly improved fluorogenic properties. Journal of medicinal chemistry, 45(14), 2887-2890. https://doi.org/10.1021/jm015586u

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. et al.
In: Journal of medicinal chemistry, Vol. 45, No. 14, 04.07.2002, p. 2887-2890.

Research output: Contribution to journal › Article › peer-review

McCurdy, CR, Le Bourdonnec, B, Metzger, TG, El Kouhen, R, Zhang, Y, Law, P-Y & Portoghese, PS 2002, 'Naphthalene dicarboxaldehyde as an electrophilic fluorogenic moiety for affinity labeling: Application to opioid receptor affinity labels with greatly improved fluorogenic properties', Journal of medicinal chemistry, vol. 45, no. 14, pp. 2887-2890. https://doi.org/10.1021/jm015586u

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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.",

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AU - El Kouhen, Rachid

AU - Zhang, Yan

AU - Law, Ping-Yee

AU - Portoghese, Philip S

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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.

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

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