Synthesis and evaluation of new endomorphin analogues modified at the Pro2 residue

被引：35

作者：

Torino, Domenica ^{[2
,3
]}

Mollica, Adriano ^{[4
]}

Pinnen, Francesco ^{[4
]}

Lucente, Gino ^{[2
,3
]}

Feliciani, Federica ^{[4
]}

Davis, Peg ^{[5
]}

Lai, Josephine ^{[5
]}

Ma, Shou-Wu ^{[5
]}

Porreca, Frank ^{[5
]}

Hruby, Victor J. ^{[1
]}

机构：

[1] Univ Arizona, Dept Chem, Tucson, AZ 85721 USA

[2] Univ Roma La Sapienza, Dipartimento Chim & Tecnol Farmaco, I-00185 Rome, Italy

[3] Univ Roma La Sapienza, Ist Chim Biomol, CNR, Sez Roma, I-00185 Rome, Italy

[4] Univ G dAnnunzio, Dipartimento Sci Farmaco, I-66100 Chieti, Italy

[5] Univ Arizona, Dept Pharmacol, Tucson, AZ 85719 USA

来源：

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS | 2009年 / 19卷 / 15期

关键词：

Azetidine carboxylic acids; 3,4-Didehydro-(S)-proline; Didehydro-alanine; Endomorphins; mu-Receptors; MU-OPIOID-RECEPTOR; BETA-AMINO ACIDS; BIOACTIVE CONFORMATION; ENZYMATIC-HYDROLYSIS; PROLINE ANALOGS; AGONIST; DEGRADATION; INHIBITORS; PEPTIDES; L-3,4-DEHYDROPROLINE;

D O I：

10.1016/j.bmcl.2009.06.008

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

Six new endomorphin analogues, incorporating constrained amino acids in place of native proline have been synthesized. Residues of (S)-azetidine-2-carboxylic acid (Aze), 3,4-dehydro-(S)-proline (Delta(3)Pro), azetidine-3-carboxylic acid (3Aze) and dehydro-alanine (Delta Ala) have been used to prepare [Delta(3)Pro(2)]EM-2 (1), [Aze(2)]EM-1 (2), [Aze(2)]EM-2 (3), [3Aze(2)]EM-1 (4), [3Aze(2)]EM-2 (5) and [Delta Ala(2)]EM-2 (6). Binding assays and functional bioactivities for mu-and delta-receptors are reported. The highest affinity, bioactivity and selectivity are shown by peptides 2 and 3 containing the Aze residue. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：4115 / 4118

页数：4

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