Object's details: Synthesis, Biological Activity, and NMR-Based Structural Studies of Deltorphin I Analogs Modified in Message Domain with a New a,a-Disubstituted Glycines

Provider:Repozytorium Instytutu Biochemii i Biofizyki Polskiej Akademii Nauk

Description

Title:
Synthesis, Biological Activity, and NMR-Based Structural Studies of Deltorphin I Analogs Modified in Message Domain with a New a,a-Disubstituted Glycines
Creator:
Lasota, Anika;
Frączak, Oliwia;
Muchowska, Adriana;
Nowakowski, Michał;
Maciejczyk, Maciej;
Ejchart, Andrzej;
Olma, Aleksandra
Description:
This article describes new deltorphin I analogs in which phenylalanine residues were replaced by the corresponding (R) or (S)-a-benzyl-b-azidoalanine, a-benzyl-b- (1-pyrrolidinyl)alanine, a-benzyl-b-(1-piperidinyl)alanine, and a-benzyl-b-(4-morpholinyl)-alanine residues. The potency and selectivity of the new analogs were evaluated by a competitive receptor binding assay in the rat brain using [3H]DAMGO (a l ligand) and [3H]DELT (a d ligand). The affinity of analogs containing (R) or (S)-abenzyl- b-azidoalanine in position 3 to d-receptors strongly depended on the chirality of the a,a-disubstituted residue. The conformational behavior of peptides modified with (R) or (S)-a-benzyl-b-(1-piperidinyl)Ala, which displays the opposite selectivity, was analyzed by 1H and 13C NMR. The l-selective Tyr-D-Ala-(R)- a-benzyl-b-(1-piperidinyl)Ala-Asp-Val-Val-Gly-NH2 lacks the helical conformation observed in the d-selective Tyr- D-Ala-(S)-a-benzyl-b-(1-piperidinyl)Ala-Asp-Val-Val-Gly- NH2. Our results support the proposal that differences between d- and l-selective opioid peptides are attributable to the presence or absence of a spatial overlap between the N-terminal message domain and the C-terminal address domain.
Object availability:
free access
Date:
2016.01.16
Type:
Article;
PeerReviewed
Language:
English
Format:
application/pdf
Publisher:
John Wiley & Sons Ltd
Relation: http://eprints.ibb.waw.pl/1278 ;http://onlinelibrary.wiley.com/doi/10.1111/cbdd.12730/abstract;jsessionid=29CEF2FB11C7D9F835E35C8937B0256E.f04t04 ;
10.1111/cbdd.12730
Subject:
QD Chemistry
Identifier: http://eprints.ibb.waw.pl/1278/7/CBDD-104.pdf ;
Lasota, Anika and Frączak, Oliwia and Muchowska, Adriana and Nowakowski, Michał and Maciejczyk, Maciej and Ejchart, Andrzej and Olma, Aleksandra (2016) Synthesis, Biological Activity, and NMR-Based Structural Studies of Deltorphin I Analogs Modified in Message Domain with a New a,a-Disubstituted Glycines. Chemical Biology & Drug Design, 87 (6). pp. 824-832. ISSN 1747-0285
Data provider:
Repozytorium Instytutu Biochemii i Biofizyki Polskiej Akademii Nauk

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Object's details: Synthesis, Biological Activity, and NMR-Based Structural Studies of Deltorphin I Analogs Modified in Message Domain with a New a,a-Disubstituted Glycines

Description

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