Synthesis and activity of endomorphin-2 and morphiceptin analogues with proline surrogates in position 2

被引：27

作者：

Giordano, Cesare ^{[1
]}

Sansone, Anna ^{[1
]}

Masi, Annalisa ^{[1
]}

Lucente, Gino ^{[1
]}

Punzi, Pasqualina ^{[2
]}

Mollica, Adriano ^{[3
]}

Pinnen, Francesco ^{[3
]}

Feliciani, Federica ^{[3
]}

Cacciatore, Ivana ^{[3
]}

Davis, Peg ^{[4
]}

Lai, Josephine ^{[4
]}

Ma, Shou-Wu ^{[4
]}

Porreca, Frank ^{[4
]}

Hruby, Victor ^{[5
]}

机构：

[1] Univ Roma La Sapienza, CNR, Ist Chim Biomol, Dipartimento Chim & Tecnol Farmaco, I-00185 Rome, Italy

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

[3] Univ Chieti Pescara G DAnnunzio, Dipartimento Sci Farmaco, I-00185 Rome, Italy

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

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

来源：

EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY | 2010年 / 45卷 / 10期

基金：

美国国家卫生研究院;

关键词：

Endomorphins; Opioid peptides; Peptide synthesis; beta-Sulphonamido peptides; Unusual amino acids; SOLID-PHASE SYNTHESIS; MU-OPIATE RECEPTOR; OPIOID RECEPTOR; BIOLOGICAL-ACTIVITY; CYCLIC PEPTIDOSULFONAMIDES; BIOACTIVE CONFORMATION; SULFONAMIDE JUNCTION; LEU-ENKEPHALIN; AMIDE BOND; PEPTIDES;

D O I：

10.1016/j.ejmech.2010.07.022

中图分类号：

R914 [药物化学];

学科分类号：

100701 ;

摘要：

The opioid agonists endomorphins (Tyr-Pro-Trp-Phe-NH(2); EM1 and Tyr-Pro-Phe-Phe-NH(2); EM2) and morphiceptin (Tyr-Pro-Phe-Pro-NH(2)) exhibit an extremely high selectivity for mu-opioid receptor. Here a series of novel EM2 and morphiceptin analogues containing in place of the proline at position 2 the S and R residues of beta-homologues of proline (HPro), of 2-pyrrolidinemethanesulphonic acid (HPrs) and of 3-pyrrolidinesulphonic acid (beta Prs) have been synthesized and their binding affinity and functional activity have been investigated. The highest p-receptor affinity is shown by [(S)beta Prs(2)]EM2 analogue (6e) which represents the first example of a beta-sulphonamido analogue in the field of mold peptides. (C) 2010 Elsevier Masson SAS. All rights reserved.

引用

页码：4594 / 4600

页数：7

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