Unknown

Dataset Information

0

The biological activity and metabolic stability of peptidic bifunctional compounds that are opioid receptor agonists and neurokinin-1 receptor antagonists with a cystine moiety.

ABSTRACT: In order to improve metabolic stability, a ring structure with a cystine moiety was introduced into TY027 (Tyr-D-Ala-Gly-Phe-Met-Pro-Leu-Trp-NH-[3',5'-(CF(3))(2)Bzl]), which is a lead compound of our developing bifunctional peptide possessing opioid agonist and NK1 antagonist activities. TY038 (Tyr-cyclo[D-Cys-Gly-Phe-Met-Pro-D-Cys]-Trp-NH-[3',5'-(CF(3))(2)Bzl]) was found as a highly selective delta opioid agonist over mu receptor in conventional tissue-based assays, together with an effective NK1 antagonist activity and good metabolic stability with more than 24h half life in rat plasma.

SUBMITTER: Yamamoto T 

PROVIDER: S-EPMC2775479 | biostudies-literature | 2009 Oct

REPOSITORIES: biostudies-literature

Json Xml
altmetric image

Publications

The biological activity and metabolic stability of peptidic bifunctional compounds that are opioid receptor agonists and neurokinin-1 receptor antagonists with a cystine moiety.

Yamamoto Takashi T   Nair Padma P   Ma Shou-wu SW   Davis Peg P   Yamamura Henry I HI   Vanderah Todd W TW   Porreca Frank F   Lai Josephine J   Hruby Victor J VJ  

Bioorganic & medicinal chemistry 20090821 20

In order to improve metabolic stability, a ring structure with a cystine moiety was introduced into TY027 (Tyr-D-Ala-Gly-Phe-Met-Pro-Leu-Trp-NH-[3',5'-(CF(3))(2)Bzl]), which is a lead compound of our developing bifunctional peptide possessing opioid agonist and NK1 antagonist activities. TY038 (Tyr-cyclo[D-Cys-Gly-Phe-Met-Pro-D-Cys]-Trp-NH-[3',5'-(CF(3))(2)Bzl]) was found as a highly selective delta opioid agonist over mu receptor in conventional tissue-based assays, together with an effective N  ...[more]

Similar Datasets

Unknown Biological and conformational evaluation of bifunctional compounds for opioid receptor agonists and neurokinin 1 receptor antagonists possessing two penicillamines.
| S-EPMC2943425 | biostudies-literature
Unknown Improving metabolic stability by glycosylation: bifunctional peptide derivatives that are opioid receptor agonists and neurokinin 1 receptor antagonists.
| S-EPMC3521585 | biostudies-literature
Unknown Design, synthesis, and biological evaluation of novel bifunctional C-terminal-modified peptides for delta/mu opioid receptor agonists and neurokinin-1 receptor antagonists.
| S-EPMC2365895 | biostudies-literature
Unknown The importance of micelle-bound states for the bioactivities of bifunctional peptide derivatives for delta/mu opioid receptor agonists and neurokinin 1 receptor antagonists.
| S-EPMC2675940 | biostudies-literature
Unknown A structure-activity relationship study and combinatorial synthetic approach of C-terminal modified bifunctional peptides that are delta/mu opioid receptor agonists and neurokinin 1 receptor antagonists.
| S-EPMC2737825 | biostudies-literature
Unknown Design and synthesis of novel hydrazide-linked bifunctional peptides as delta/mu opioid receptor agonists and CCK-1/CCK-2 receptor antagonists.
| S-EPMC1614704 | biostudies-literature
Unknown Repurposing of a Nucleoside Scaffold from Adenosine Receptor Agonists to Opioid Receptor Antagonists.
| S-EPMC6210068 | biostudies-literature
Unknown Pyrrolo- and pyridomorphinans: non-selective opioid antagonists and delta opioid agonists/mu opioid partial agonists.
| S-EPMC4112151 | biostudies-literature
Unknown Design of novel neurokinin 1 receptor antagonists based on conformationally constrained aromatic amino acids and discovery of a potent chimeric opioid agonist-neurokinin 1 receptor antagonist.
| S-EPMC3096782 | biostudies-literature
Unknown Further Optimization and Evaluation of Bioavailable, Mixed-Efficacy ?-Opioid Receptor (MOR) Agonists/?-Opioid Receptor (DOR) Antagonists: Balancing MOR and DOR Affinities.
| S-EPMC4772774 | biostudies-literature