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

共 50 条

[1] Design, Synthesis and Antinociceptive Activity of Novel Endomorphin-2 and Morphiceptin Analogues
Georgiev, K.
Dzimbova, T.
Nocheva, H.
Bocheva, A.
Pajpanova, T.
JOURNAL OF PEPTIDE SCIENCE, 2012, 18 : S120 - S120
[2] Synthesis and antinociceptive activity of cyclic endomorphin-2 and morphiceptin analogs
Janecka, A
Fichna, J
Kruszynski, R
Sasaki, Y
Ambo, A
Costentin, J
do-Rego, JC
BIOCHEMICAL PHARMACOLOGY, 2005, 71 (1-2) : 188 - 195
[3] Antinociceptive and antidepressant-like action of endomorphin-2 analogs with proline surrogates in position 2
Perlikowska, Renata
Piekielna, Justyna
Mazur, Marzena
Koralewski, Robert
Olczak, Jacek
do Rego, Jean-Claude
Fichna, Jakub
Modranka, Jakub
Janecki, Tomasz
Janecka, Anna
BIOORGANIC & MEDICINAL CHEMISTRY, 2014, 22 (17) : 4803 - 4809
[4] Opioid receptor binding and antinociceptive activity of the analogues of endomorphin-2 and morphiceptin with phenylalanine mimics in the position 3 or 4
Gao, Yanfeng
Liu, Xin
Liu, Weixia
Qi, Yuanming
Liu, Xuefeng
Zhou, Yifeng
Wang, Rui
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2006, 16 (14) : 3688 - 3692
[5] Characterization of antinociceptive activity of novel endomorphin-2 and morphiceptin analogs modified in the third position
Fichna, J
do-Rego, JC
Kosson, P
Costentin, J
Janecka, A
BIOCHEMICAL PHARMACOLOGY, 2005, 69 (01) : 179 - 185
[6] Synthesis and biological activity of endomorphin-2 analogues containing isoproline, oxopiperadine or oxopyrrolidine ring in position 2
Ambo, A.
Tanaka, M.
Minamizawa, M.
Sasaki, Y.
JOURNAL OF PEPTIDE SCIENCE, 2012, 18 : S110 - S110
[7] ANALOGUES OF ENDOMORPHIN-2 MODIFIED WITH 4-ALKYLPSEUDOPROLINES IN POSITION 2
Katarzynska, J.
Chung, N. N.
Schiller, P. W.
Leplawy, M. T.
Zabrocki, J.
JOURNAL OF PEPTIDE SCIENCE, 2004, 10 : 266 - 266
[8] Analogues of endomorphin-2 modified with 4-methylpseudoproline in position 2
Katarzynska, Joanna
Chung, Nga N.
Schiller, Peter W.
Leplawy, Miroslaw T.
Zabrocki, Janusz
Peptides 2004, Proceedings: BRIDGES BETWEEN DISCIPLINES, 2005, : 982 - 983
[9] Characterization of [35s] GTPγs binding stimulated by endomorphin-2 and morphiceptin analogues
Janecka, A.
Fichna, J.
Piestrzeniewicz, M.
Costentin, J.
do-Rego, J-C.
FEBS JOURNAL, 2006, 273 : 96 - 97
[10] Synthesis and analgesic activities of endomorphin-2 and its analogues
Shi, Zhi-Hao
Wei, Yun-Yang
Wang, Chuan-Jin
Yu, Li
CHEMISTRY & BIODIVERSITY, 2007, 4 (03) : 458 - 467

← 1 2 3 4 5 →