Synthesis and evaluation of new endomorphin-2 analogues containing (Z)-α,β-didehydrophenylalanine (δZPhe) residues

Domenica Torino, Adriano Mollica, Francesco Pinnen, Federica Feliciani, Gino Lucente, Giancarlo Fabrizi, Gustavo Portalone, Peg Davis, Josephine Lai, Shou Wu Ma, Frank Porreca, Victor J. Hruby

Research output: Contribution to journalArticlepeer-review

36 Scopus citations


New endomorphin-2 (EM-2) analogues incorporating (Z)-α,β- didehydrophenylalanine (δZPhe) in place of the native phenylalanine in EM-2 are reported. Tyr-Pro-δZPhe-Phe-NH 2 {[δZPhe3]EM-2} (1), Tyr-Pro-Phe-δZPhe-NH2 {[δZPhe 4]EM-2} (2), and Tyr-Pro-δZPhe- δZPhe-NH2 {[δZPhe 3,4]EM-2}(3) have been synthesized, their opioid receptor binding affinities and tissue bioassay activities were determined, and their conformational properties were examined. Compound 2 shows high μ opioid receptor selectivity and μ agonist activity comparable to those of the native peptide. The conformation adopted in solution and in the crystal by N-Boc-Tyr-Pro-δZPhe-Phe-NH2 (8) is reported.

Original languageEnglish (US)
Pages (from-to)4550-4554
Number of pages5
JournalJournal of Medicinal Chemistry
Issue number11
StatePublished - Jun 10 2010

ASJC Scopus subject areas

  • Molecular Medicine
  • Drug Discovery


Dive into the research topics of 'Synthesis and evaluation of new endomorphin-2 analogues containing (Z)-α,β-didehydrophenylalanine (δZPhe) residues'. Together they form a unique fingerprint.

Cite this