In lieu of H-Dmt-Tic-OH, H-Dmt-analogues included 2-amino-3(1H-benzoimidazol-2-yl)-propionic acid, N(Bzl)Gly, l-octahydroindole-2-carboxylic acid, [3S-(3α,4aβ,8aβ)]-decahydro-3-isoquinoline carboxylic acid, benzimidazole-, pyridoindole- or spiroinden-derivatives, or C-terminally modified. l- or d-Ala, Sar, or Pro were spacers between aromatic nuclei. Only H-Dmt-(Xaa-)-pyridoindole exhibited high affinities with δ and μ antagonism. The peptides competed equally against [3H]DPDPE (δ agonist) or [3H]N,N(CH3)2-Dmt-Tic-OH (δ antagonist) signaling a single δ binding site. The data confirm the importance of Tic for δ affinity and antagonism, while heterocyclic or heteroaliphatic nuclei, or spacer exert effects on μ- and δ-receptor properties.

Opioid pseudopeptides containing heteroaromatic or heteroaliphatic nuclei

BALBONI, Gianfranco
Primo
;
SALVADORI, Severo
Secondo
;
GUERRINI, Remo;
2000

Abstract

In lieu of H-Dmt-Tic-OH, H-Dmt-analogues included 2-amino-3(1H-benzoimidazol-2-yl)-propionic acid, N(Bzl)Gly, l-octahydroindole-2-carboxylic acid, [3S-(3α,4aβ,8aβ)]-decahydro-3-isoquinoline carboxylic acid, benzimidazole-, pyridoindole- or spiroinden-derivatives, or C-terminally modified. l- or d-Ala, Sar, or Pro were spacers between aromatic nuclei. Only H-Dmt-(Xaa-)-pyridoindole exhibited high affinities with δ and μ antagonism. The peptides competed equally against [3H]DPDPE (δ agonist) or [3H]N,N(CH3)2-Dmt-Tic-OH (δ antagonist) signaling a single δ binding site. The data confirm the importance of Tic for δ affinity and antagonism, while heterocyclic or heteroaliphatic nuclei, or spacer exert effects on μ- and δ-receptor properties.
Balboni, Gianfranco; Salvadori, Severo; Guerrini, Remo; Bianchi, C; Santagada, V; Calliendo, G; Bryant, Sd; Lazarus, Lh
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Utilizza questo identificativo per citare o creare un link a questo documento: http://hdl.handle.net/11392/470841
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