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

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• 作者：Severo Salvadori ; Stella Fiorini ; Claudio Trapella ; Frank Porreca ; Peg Davis ; Yusuke Sasaki ; Akihiro Ambo ; Ewa D. Marczak ; Lawrence H. Lazarus ; Gianfranco Balboni
• 关键词：Dmt-Tic pharmacophore ; δ ; -Opioid receptors ; Opioid peptides ; UFP-502
• 刊名：Bioorganic and Medicinal Chemistry
• 出版年：2008
• 期刊代码：9_09680896
• 类别：ch
• 出版时间：15 March 2008
• 卷：16
• 期：6
• 页码：3032-3038
• 文件大小：171 K

摘要

H-Dmt-Tic-NH-CH₂-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 1H-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 1H-imidazole-2-yl retains δ-agonist activity.