Synthesis of mixed MOR/KOR efficacy cyclic opioid peptide analogs with antinociceptive activity after systemic administration

R Perlikowska, J Piekielna, L Gentilucci… - European journal of …, 2016 - Elsevier
Cyclic pentapeptide Tyr-c [D-Lys-Phe-Phe-Asp] NH 2, based on the structure of
endomorphin-2 (EM-2), which shows high affinity to the μ-opioid receptor (MOR) and a very …

Pharmacological properties of novel cyclic pentapeptides with μ-opioid receptor agonist activity

R Perlikowska, J Piekielna, J Fichna… - Medicinal …, 2014 - ingentaconnect.com
In our previous paper we have reported the synthesis and biological activity of a cyclic
analog, Tyr-c (D-Lys-Phe-Phe-Asp)-NH2, based on endomorphin-2 (EM-2) structure. This …

Pharmacological characterization of endomorphin-2-based cyclic pentapeptides with methylated phenylalanine residues

R Perlikowska, D Malfacini, MC Cerlesi, J Piekielna… - Peptides, 2014 - Elsevier
As part of our continuing studies on the structure–activity relationships of cyclic
pentapeptides based on the structure of endomorphin-2, we report here the synthesis and …

Effect of 2′, 6′-dimethyl-L-tyrosine (Dmt) on pharmacological activity of cyclic endomorphin-2 and morphiceptin analogs

J Fichna, R Perlikowska, A Wyrębska, K Gach… - Bioorganic & medicinal …, 2011 - Elsevier
This study reports the synthesis and biological evaluation of a series of new side-chain-to-
side-chain cyclized endomorphin-2 (EM-2) and morphiceptin analogs of a general structure …

Redoubling the ring size of an endomorphin‐2 analog transforms a centrally acting mu‐opioid receptor agonist into a pure peripheral analgesic

J Piekielna, R De Marco, L Gentilucci… - Peptide …, 2016 - Wiley Online Library
The study reports the synthesis and biological evaluation of two opioid analogs, a monomer
and a dimer, obtained as products of the solid‐phase, side‐chain to side‐chain cyclization of …

Synthesis and antinociceptive activity of cyclic endomorphin-2 and morphiceptin analogs

A Janecka, J Fichna, R Kruszynski, Y Sasaki… - Biochemical …, 2005 - Elsevier
Cyclic analogs of the opioid peptides endomorphin-2 and morphiceptin of the type Tyr-X-
Phe-Phe-Y-NH2 and Tyr-X-Phe-d-Pro-Y-NH2 (X= Lys or Asp and Y= Lys or Asp) …

Ring size in cyclic endomorphin-2 analogs modulates receptor binding affinity and selectivity

J Piekielna, A Kluczyk, L Gentilucci… - Organic & …, 2015 - pubs.rsc.org
The study reports the solid-phase synthesis and biological evaluation of a series of new side
chain-to-side chain cyclized opioid peptide analogs of the general structure Tyr-[D-Xaa-Phe …

Synthesis and Evaluation of the Affinity toward μ-Opioid Receptors of Atypical, Lipophilic Ligands Based on the Sequence c[-Tyr-Pro-Trp-Phe-Gly-]

G Cardillo, L Gentilucci, A Tolomelli… - Journal of medicinal …, 2004 - ACS Publications
An ultimate and general model describing the interaction between opioid ligands and μ-
opioid receptors is not available yet, so the mode of action of atypical peptide analogues or …

Novel endomorphin‐2 analogs with μ‐opioid receptor antagonist activity

R Kruszynski, J Fichna, JC Do‐Rego… - The Journal of …, 2005 - Wiley Online Library
A series of position 4‐substituted endomorphin‐2 (Tyr‐Pro‐Phe‐Phe‐NH2) analogs
containing 3‐(1‐naphthyl)‐alanine (1‐Nal) or 3‐(2‐naphthyl)‐alanine (2‐Nal) in l‐or d …

Biological activity of endomorphin and [Dmt1] endomorphin analogs with six-membered proline surrogates in position 2

R Perlikowska, K Gach, J Fichna, G Toth… - Bioorganic & medicinal …, 2009 - Elsevier
Endogenous μ-opioid receptor (MOR) selective peptides, endomorphin-1 (EM-1) and
endomorphin-2 (EM-2), unlike so called 'typical opioids', are characterized by the presence …