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

Severo Salvadori, Stella Fiorini, Claudio Trapella, Frank Porreca, Peg Davis, Yusuke Sasaki, Akihiro Ambo, Ewa D. Marczak, Lawrence H. Lazarus, Gianfranco Balboni

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10 Scopus citations

Abstract

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.

Original languageEnglish (US)
Pages (from-to)3032-3038
Number of pages7
JournalBioorganic and Medicinal Chemistry
Volume16
Issue number6
DOIs
StatePublished - Mar 15 2008

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Keywords

  • Dmt-Tic pharmacophore
  • Opioid peptides
  • UFP-502
  • δ-Opioid receptors

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Molecular Biology
  • Pharmaceutical Science
  • Drug Discovery
  • Clinical Biochemistry
  • Organic Chemistry

Cite this

Salvadori, S., Fiorini, S., Trapella, C., Porreca, F., Davis, P., Sasaki, Y., Ambo, A., Marczak, E. D., Lazarus, L. H., & Balboni, G. (2008). Role of benzimidazole (Bid) in the δ-opioid agonist pseudopeptide H-Dmt-Tic-NH-CH2-Bid (UFP-502). Bioorganic and Medicinal Chemistry, 16(6), 3032-3038. https://doi.org/10.1016/j.bmc.2007.12.032