Opis

• Tytuł:
  Synthesis, Biological Activity, and NMR-Based Structural Studies of Deltorphin I Analogs Modified in Message Domain with a New a,a-Disubstituted Glycines
• Twórca:
  Lasota, Anika;
  Frączak, Oliwia;
  Muchowska, Adriana;
  Nowakowski, Michał;
  Maciejczyk, Maciej;
  Ejchart, Andrzej;
  Olma, Aleksandra
• Opis:
  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.
• Dostępność obiektu:
  Dostęp otwarty
• Data:
  2016.01.16
• Typ:
  Article;
  PeerReviewed
• Język:
  angielski;
  eng
• Format:
  application/pdf
• Wydawca:
  John Wiley & Sons Ltd
• Relacja: http://eprints.ibb.waw.pl/1278 ;http://onlinelibrary.wiley.com/doi/10.1111/cbdd.12730/abstract;jsessionid=29CEF2FB11C7D9F835E35C8937B0256E.f04t04 ;
  10.1111/cbdd.12730
• Temat i słowa kluczowe:
  QD Chemistry
• Identyfikator: 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
• Dostawca danych:
  Repozytorium Instytutu Biochemii i Biofizyki Polskiej Akademii Nauk
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