Structure-activity relationships of novel endomorphin-2 analogues with N-O turns induced by alpha-aminoxy acids

Jie Wei; Xuan Shao; Maozhen Gong; Beibei Zhu; Yuxin Cui; Yanfeng Gao; Rui Wang

doi:10.1016/j.bmcl.2005.04.050

Structure-activity relationships of novel endomorphin-2 analogues with N-O turns induced by alpha-aminoxy acids

Bioorg Med Chem Lett. 2005 Jun 15;15(12):2986-9. doi: 10.1016/j.bmcl.2005.04.050.

Authors

Jie Wei¹, Xuan Shao, Maozhen Gong, Beibei Zhu, Yuxin Cui, Yanfeng Gao, Rui Wang

Affiliation

¹ Department of Biochemistry and Molecular Biology, School of Life Sciences, Lanzhou University, Lanzhou 730000, China.

PMID: 15984054
DOI: 10.1016/j.bmcl.2005.04.050

Abstract

Endomorphin-2 (H-Tyr-Pro-Phe-Phe-NH2, EM-2) is a putative endogenous mu-opioid receptor ligand. To study the structure-activity relationship against its receptor, we introduced N-O turns into EM-2 and got the analogues with potent affinities for mu-opioid receptor. Our results indicated that N-O turn structures at the Pro2-aminoxy-Phe3 position of EM-2 analogues played important roles for their affinities. These novel analogues with N-O turns provided a new approach to develop potent analgesics related to EM-2.

Publication types

Comparative Study
Research Support, Non-U.S. Gov't

MeSH terms

Amino Acids / chemistry*
Amino Acids, Cyclic
Analgesics, Opioid / chemical synthesis
Analgesics, Opioid / chemistry
Analgesics, Opioid / pharmacology*
Animals
Brain / drug effects
Brain / metabolism
Ileum / drug effects
Ileum / metabolism
Ligands
Male
Mice
Molecular Structure
Oligopeptides / chemical synthesis
Oligopeptides / chemistry
Oligopeptides / pharmacology*
Rats
Rats, Wistar
Receptors, Opioid, delta / agonists*
Receptors, Opioid, mu / agonists*
Structure-Activity Relationship
Swine
Vas Deferens / drug effects
Vas Deferens / metabolism

Substances

Amino Acids
Amino Acids, Cyclic
Analgesics, Opioid
Ligands
Oligopeptides
Receptors, Opioid, delta
Receptors, Opioid, mu
endomorphin 2