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2011 | 58 | 2 | 225-230
Article title

Cyclic enkephalin-deltorphin hybrids containing a carbonyl bridge: structure and opioid activity

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EN
Abstracts
EN
Six hybrid N-ureidoethylamides of octapeptides in which an N-terminal cyclic structure related to enkephalin was elongated by a C-terminal fragment of deltorphin were synthesized on MBHA resin. The synthetic procedure involved deprotection of Boc groups with HCl/dioxane and cleavage of the peptide resin with 45 % TFA in DCM. d-Lys and d-Orn were incorporated in position 2, and Lys, Orn, Dab, or Dap in position 5. The side chains of the dibasic amino function were protected with the Fmoc group. This protection was removed by treatment with 55 % piperidine in DMF, and cyclization was achieved by treatment with bis-(4-nitrophenyl)carbonate. Using various combinations of dibasic amino acids, peptides containing a 17-, 18-, 19- or 20-membered ring structure were obtained. The peptides were tested in the guinea-pig ileum (GPI) and mouse vas deferens (MVD) assays. Diverse opioid activities were observed, depending on the size of the ring. Extension of the enkephalin sequence at the C-terminus by a deltorphin fragment resulted in a change of receptor selectivity in favor of the δ receptor. The conformational propensities of selected peptides were determined using the EDMC method in conjunction with data derived from NMR experiments carried out in water. This approach allowed proper examination of the dynamical behavior of these small peptides. The results were compared with those obtained earlier with corresponding N-(ureidoethyl)pentapeptide amides.
Publisher

Year
Volume
58
Issue
2
Pages
225-230
Physical description
Dates
published
2011
received
2010-12-06
revised
2011-03-24
accepted
2011-05-08
(unknown)
2011-05-17
Contributors
  • Peptide Laboratory, Department of Chemistry, University of Warsaw, Warszawa, Poland
  • Laboratory of Biological NMR, Institute of Biochemistry and Biophysics, Polish Academy of Sciences, Warszawa, Poland
  • Department of Biochemistry, University of Alberta, Edmonton, Alberta, Canada
author
  • Laboratory of Chemical Biology and Peptide Research, Clinical Research Institute of Montreal, Montreal, Quebec H2W IR7, Canada
author
  • Peptide Laboratory, Department of Chemistry, University of Warsaw, Warszawa, Poland
  • Laboratory of Chemical Biology and Peptide Research, Clinical Research Institute of Montreal, Montreal, Quebec H2W IR7, Canada
author
  • Laboratory of Biological NMR, Institute of Biochemistry and Biophysics, Polish Academy of Sciences, Warszawa, Poland
author
  • Peptide Laboratory, Department of Chemistry, University of Warsaw, Warszawa, Poland
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Document Type
Publication order reference
Identifiers
YADDA identifier
bwmeta1.element.bwnjournal-article-abpv58p225kz
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