Role of benzimidazole (Bid) in the δ-opioid agonist pseudopeptide H-Dmt-Tic-NH-CH2-Bid (UFP-502)

H-Dmt-Tic-NH-CH 2 -Bid (UFP-502) was the first δ opioid agonist prepared from the Dmt-Tic pharmacophore. It showed interesting pharmacological properties, such as stimulation of mRNA BDNF expression, and antidepression. To evaluate the importance of 1 H -benzimidazol-2-yl (Bid) in the induction of δ...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry 2008-03, Vol.16 (6), p.3032-3038
Main Authors: SALVADORI, Severo, FIORINI, Stella, TRAPELLA, Claudio, PORRECA, Frank, DAVIS, Peg, SASAKI, Yusuke, AMBO, Akihiro, MARCZAK, Ewa D, LAZARUS, Lawrence H, BALBONI, Gianfranco
Format: Article
Language:English
Subjects:
Biological and medical sciences
Medical sciences
Neuropharmacology
Neurotransmitters. Neurotransmission. Receptors
Peptidergic system (neuropeptide, opioid peptide, opiates...). Adenosinergic and purinergic systems
Pharmacology. Drug treatments
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Summary:H-Dmt-Tic-NH-CH 2 -Bid (UFP-502) was the first δ opioid agonist prepared from the Dmt-Tic pharmacophore. It showed interesting pharmacological properties, such as stimulation of mRNA BDNF expression, and antidepression. To evaluate the importance of 1 H -benzimidazol-2-yl (Bid) in the induction of δ agonism, it was substituted by similar heterocycles: The substitution of NH(1) by O or S, transforms the reference δ agonist into δ antagonists. Phenyl ring of benzimidazole is not important for δ agonism; in fact 1 H -imidazole-2-yl retains δ agonist activity.
ISSN:0968-0896
1464-3391
DOI:10.1016/j.bmc.2007.12.032