Novel TIPP (H-Tyr-Tic-Phe-Phe-OH) analogues displaying a wide range of efficacies at the δ opioid receptor. Discovery of two highly potent and selective δ opioid agonists

被引：3

作者：

Berezowska, Irena ^{[1
]}

Lemieux, Carole ^{[1
]}

Chung, Nga N. ^{[1
]}

Ding, Jinguo ^{[1
]}

Schiller, Peter W. ^{[1
,2
]}

机构：

[1] Clin Res Inst Montreal, Lab Chem Biol & Peptide Res, Montreal, PQ H2W 1R7, Canada

[2] Univ Montreal, Dept Pharmacol, Montreal, PQ H3C 3J7, Canada

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2012年 / 22卷 / 05期

基金：

美国国家卫生研究院; 加拿大健康研究院;

关键词：

Amino acid synthesis; Peptide synthesis; Opioid peptides; delta Opioid agonists; delta Partial opioid agonists; delta Opioid antagonist; ANTIDEPRESSANT-LIKE ACTIVITIES; CYCLIC ENKEPHALIN ANALOGS; DERIVATIVES; ANTAGONISTS; ACTIVATION; BINDING; LIGANDS; MODEL; PAIN;

D O I：

10.1016/j.bmcl.2012.01.063

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Analogues of the delta opioid antagonist peptide TIPP (H-Tyr-Tic-Phe-Phe-OH; Tic = 1,2,3,4-tetrahydroisoquinoline3-carboxylic acid) containing various 4 '-[N-(alkyl or aralkyl) carboxamido] phenylalanine analogues in place of Tyr(1) were synthesized. The compounds showed subnanomolar or low nanomolar delta opioid receptor binding affinity and various efficacy at the d receptor (antagonism, partial agonism, full agonism) in the [S-35] GTP gamma S binding assay. Two analogues, [1-Ncp(1)]TIPP (1- Ncp = 4 '-[N-(2-(naphthalene-1-yl)ethyl)carboxamido]phenylalanine) and [2-Ncp(1)]TIPP (2-Ncp = 4 '-[ N-(2-(naphthalene-2-yl) ethyl)carboxamido] phenylalanine), were identified as potent and selective delta opioid agonists. (c) 2012 Elsevier Ltd. All rights reserved.

引用

页码：1899 / 1902

页数：4

共 2 条

[1] Design, Synthesis, and Structure-Activity Relationship Exploration of Alkyl/Phenylalkyl Piperidine Analogues as Novel Highly Potent and Selective μ Opioid Receptor Agonists
Huang, Huoming
Li, Xinwei
Guo, Wei
Zhu, Chen
Qian, Yuanyuan
Shen, Qing
Xu, Xuejun
Li, Wei
Wang, Yujun
Fu, Wei
ACS CHEMICAL NEUROSCIENCE, 2021, 12 (02): : 285 - 299
[2] A comprehensive study on the putative δ-opioid receptor (sub)types using the highly selective δ-antagonist, Tyr-Tic-(2S,3R)-β-MePhe-Phe-OH
Birkas, Erika
Bakota, Lidia
Gulya, Karoly
Wen, Ting
Pintar, John
Toth, Geza
Szucs, Maria
NEUROCHEMISTRY INTERNATIONAL, 2011, 59 (02) : 192 - 201

← 1 →