Synthesis and plasma stability of disulfide-bridged cyclic endomorphin-1 derivatives

Mansfeld, Friederike M. and Toth, Istvan (2012) Synthesis and plasma stability of disulfide-bridged cyclic endomorphin-1 derivatives. International Journal of Organic Chemistry, 2 1: 1-6. doi:10.4236/ijoc.2012.21001

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Author Mansfeld, Friederike M.
Toth, Istvan
Title Synthesis and plasma stability of disulfide-bridged cyclic endomorphin-1 derivatives
Journal name International Journal of Organic Chemistry   Check publisher's open access policy
ISSN 2161-4687
Publication date 2012-03
Sub-type Article (original research)
DOI 10.4236/ijoc.2012.21001
Open Access Status DOI
Volume 2
Issue 1
Start page 1
End page 6
Total pages 6
Editor Bouzid Menaa
Place of publication Irvine, CA, U.S.A.
Publisher Scientific Research Publishing
Collection year 2013
Language eng
Formatted abstract
Endomorphin-1 is an endogenous opioid peptide that mediates pain relief through interaction with the µ-opioid receptor in the central nervous system. To enhance the metabolic stability of this tetrapeptide, cyclisation through the formation of a disulfide bridge between the side chains of cysteine residues added to the sequence was explored. A further increase in stability was achieved through N-terminal modification with lipoamino acid and lactose succinamic acid, and the inclusion of D-amino acids. The latter also provided an alternative spatial arrangement of the aromatic side chains. The lipidated cyclic derivatives were insoluble in aqueous buffer, however, the cyclic peptides and glycopeptides showed greatly improved stability towards enzymatic degradation in human plasma.
Keyword Endomorphin-1
Opioid Peptide
Q-Index Code C1
Q-Index Status Confirmed Code
Institutional Status UQ

Document type: Journal Article
Sub-type: Article (original research)
Collections: Official 2013 Collection
School of Chemistry and Molecular Biosciences
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Created: Mon, 26 Mar 2012, 08:44:43 EST by Lucy O'Brien on behalf of School of Chemistry & Molecular Biosciences