TY - JOUR
T1 - o-naphthalenedicarboxaldehyde derivative of 7′-aminonaltrindole as a selective δ-opioid receptor affinity label
AU - Haris, Sarika Prabhu
AU - Zhang, Yan
AU - Le Bourdonnec, Bertrand
AU - McCurdy, Christopher R.
AU - Portoghese, Philip S.
PY - 2007/7/12
Y1 - 2007/7/12
N2 - Incorporation of a naphthalene-dialdehyde moiety into the δ antagonist, 6′-aminonaltrindole afforded a potent, selective, irreversible δ-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 ε-amino group of Lys214, which could explain its irreversibility and transformation into a δ-agonist through a conformational change of TM5.
AB - Incorporation of a naphthalene-dialdehyde moiety into the δ antagonist, 6′-aminonaltrindole afforded a potent, selective, irreversible δ-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 ε-amino group of Lys214, which could explain its irreversibility and transformation into a δ-agonist through a conformational change of TM5.
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U2 - 10.1021/jm061194h
DO - 10.1021/jm061194h
M3 - Article
C2 - 17555306
AN - SCOPUS:34447540010
SN - 0022-2623
VL - 50
SP - 3392
EP - 3396
JO - Journal of medicinal chemistry
JF - Journal of medicinal chemistry
IS - 14
ER -
