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新型 TIPP（H-Tyr-Tic-Phe-Phe-OH）类似物在 δ 阿片受体上显示出广泛的疗效。发现两种高效和选择性的 δ 阿片受体激动剂。

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.

机构信息

Laboratory of Chemical Biology and Peptide Research, Clinical Research Institute of Montreal, 110 Pine Avenue West, Montreal, QC, Canada H2W 1R7.

出版信息

Bioorg Med Chem Lett. 2012 Mar 1;22(5):1899-902. doi: 10.1016/j.bmcl.2012.01.063. Epub 2012 Jan 28.

DOI:10.1016/j.bmcl.2012.01.063
PMID:22325949
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC3288262/
Abstract

Analogues of the δ 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 δ opioid receptor binding affinity and various efficacy at the δ receptor (antagonism, partial agonism, full agonism) in the [(35)S]GTPγS 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 δ opioid agonists.

摘要

合成了含有各种 4'-[N-(烷基或芳基)羧酰胺基]苯丙氨酸类似物代替 Tyr(1)的 δ 阿片样肽 TIPP( H-Tyr-Tic-Phe-Phe-OH; Tic=1,2,3,4-四氢异喹啉 3-羧酸)类似物。这些化合物在[(35)S]GTPγS 结合测定中表现出亚纳摩尔或低纳摩尔的 δ 阿片受体结合亲和力和不同的 δ 受体效力(拮抗、部分激动、完全激动)。两种类似物，[1-Ncp(1)]TIPP(1-Ncp=4'-[N-(2-(萘-1-基)乙基)羧酰胺基]苯丙氨酸)和[2-Ncp(1)]TIPP(2-Ncp=4'-[N-(2-(萘-2-基)乙基)羧酰胺基]苯丙氨酸)，被鉴定为强效和选择性的 δ 阿片样激动剂。

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Cyclic opioid peptide agonists and antagonists obtained via ring-closing metathesis.通过闭环复分解反应获得的环状阿片肽激动剂和拮抗剂。
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