o-Naphthalenedicarboxaldehyde Derivative of 7‘-Aminonaltrindole as a Selective δ-Opioid Receptor Affinity Label

2007 ◽  
Vol 50 (14) ◽  
pp. 3392-3396 ◽  
Author(s):  
Sarika Prabhu Haris ◽  
Yan Zhang ◽  
Bertrand Le Bourdonnec ◽  
Christopher R. McCurdy ◽  
Philip S. Portoghese
Keyword(s):  
Opioid Receptor ◽  
Receptor Affinity ◽  
Affinity Label ◽  
Δ Opioid Receptor

Cyclic deltorphin analogues with high δ opioid receptor affinity and selectivity

Peptides ◽  
1994 ◽  
pp. 514-516 ◽  
Author(s):  
H. I. Mosberg ◽  
H. B. Kroona ◽  
J. R. Omnaas ◽  
K. Sobczyk-Kojiro ◽  
P. Bush ◽  
...  
Keyword(s):  
Opioid Receptor ◽  
Receptor Affinity ◽  
Δ Opioid Receptor

scholarly journals β2-Homo-Amino Acid Scan of µ-Selective Opioid Tetrapeptide TAPP

Molecules ◽  
2020 ◽  
Vol 25 (10) ◽  
pp. 2461 ◽  
Author(s):  
Dagmara Tymecka ◽  
Piotr F. J. Lipiński ◽  
Piotr Kosson ◽  
Aleksandra Misicka
Keyword(s):  
Amino Acids ◽  
Amino Acid ◽  
Human Plasma ◽  
Opioid Receptor ◽  
Molecular Modelling ◽  
Parent Compound ◽  
Common Element ◽  
Ionic Interaction ◽  
Receptor Affinity ◽  
Δ Opioid Receptor

TAPP (H-Tyr-d-Ala-Phe-Phe-NH2) is a potent, µ-selective opioid ligand. In order to gain further insights into pharmacophoric features of this tetrapeptide, we have performed a β2-Homo-amino acid (β2hAA) scan of the TAPP sequence. To this aim, 10 novel analogues have been synthesized and evaluated for µ-opioid and δ-opioid receptor affinity as well as for stability in human plasma. The derivatives included compounds in which a (R)- or (S)-β2-Homo-Homologue replaced the amino acids in the TAPP sequence. The derivatives with (R)- or (S)-β2hPhe4 turned out to bind µOR with affinities equal to that of the parent. β2hAAs in position 1 and 3 resulted in rather large affinity decreases, but the change differed depending on the stereochemistry. β2-Homologation in the second position gave derivatives with very poor µOR binding. According to molecular modelling, the presented α/β-peptides adopt a variety of binding poses with their common element being an ionic interaction between a protonable amine of the first residue and Asp147. A feature required for high µOR affinity seems the ability to accommodate the ring in the fourth residue in a manner similar to that found for TAPP. Contrary to what might be expected, several compounds were significantly less stable in human plasma than the parent compound.

Relationship between receptor affinity and topography of N-terminally extended and bridged [Tyr1 → Asp4]deltorphin C analogues: Novel probes for the δ-opioid receptor

1993 ◽  
Vol 230 (3) ◽  
pp. 357-361 ◽  
Author(s):  
Severo Salvadori ◽  
Sharon D. Bryant ◽  
Piero A. Temussi ◽  
Dayne M. Bundy ◽  
Martti Attila ◽  
...  
Keyword(s):  
Opioid Receptor ◽  
Receptor Affinity ◽  
Δ Opioid Receptor

Covalently Induced Activation of the δ Opioid Receptor by a Fluorogenic Affinity Label, 7‘-(Phthalaldehydecarboxamido)naltrindole (PNTI)

2001 ◽  
Vol 44 (7) ◽  
pp. 1017-1020 ◽  
Author(s):  
Bertrand Le Bourdonnec ◽  
Rachid El Kouhen ◽  
Gennady Poda ◽  
Ping Y. Law ◽  
Horace H. Loh ◽  
...  
Keyword(s):  
Opioid Receptor ◽  
Affinity Label ◽  
Δ Opioid Receptor

DIPPA: An opioid receptor affinity label that produces selective and long-lasting κ antagonism in mice

1994 ◽  
Vol 54 (1) ◽  
pp. 49-50
Author(s):  
An-Chih Chang ◽  
Akira E. Takemori ◽  
Philip S. Portoghese
Keyword(s):  
Opioid Receptor ◽  
Receptor Affinity ◽  
Affinity Label

ENKEPHALIN-INDUCED DESENSITIZATION OF ADENYLATE CYCLASE IN RECOMBINANT CV CELLS EXPRESSING A MOUSE δ-OPIOID RECEPTOR

Analgesia ◽  
1995 ◽  
Vol 1 (4) ◽  
pp. 603-606
Author(s):  
Vincent Nappey ◽  
Jean-luc Butour ◽  
Christiane Moisand ◽  
Claire Gaveriaux-Ruff ◽  
Brigitte Kieffer ◽  
...  
Keyword(s):  
Adenylate Cyclase ◽  
Opioid Receptor ◽  
Δ Opioid Receptor
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