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

Research output: Contribution to journalArticle

10 Citations (Scopus)

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

Fingerprint

Opioid Analgesics
Brain-Derived Neurotrophic Factor
Substitution reactions
Pharmacology
Messenger RNA
2',6'-dimethyltyrosyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid 1H-benzimidazol-2-ylmethylamide
benzimidazole
2',6'-dimethyltyrosyl-1,2,3,4-tetrahydroisoquinoline-3-carboxylic acid
imidazole

Keywords

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

ASJC Scopus subject areas

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

Cite this

Role of benzimidazole (Bid) in the δ-opioid agonist pseudopeptide H-Dmt-Tic-NH-CH2-Bid (UFP-502). / Salvadori, Severo; Fiorini, Stella; Trapella, Claudio; Porreca, Frank; Davis, Peg; Sasaki, Yusuke; Ambo, Akihiro; Marczak, Ewa D.; Lazarus, Lawrence H.; Balboni, Gianfranco.

In: Bioorganic and Medicinal Chemistry, Vol. 16, No. 6, 15.03.2008, p. 3032-3038.

Research output: Contribution to journalArticle

Salvadori, S, Fiorini, S, Trapella, C, Porreca, F, Davis, P, Sasaki, Y, Ambo, A, Marczak, ED, Lazarus, LH & 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, vol. 16, no. 6, pp. 3032-3038. https://doi.org/10.1016/j.bmc.2007.12.032
Salvadori, Severo ; Fiorini, Stella ; Trapella, Claudio ; Porreca, Frank ; Davis, Peg ; Sasaki, Yusuke ; Ambo, Akihiro ; Marczak, Ewa D. ; Lazarus, Lawrence H. ; Balboni, Gianfranco. / Role of benzimidazole (Bid) in the δ-opioid agonist pseudopeptide H-Dmt-Tic-NH-CH2-Bid (UFP-502). In: Bioorganic and Medicinal Chemistry. 2008 ; Vol. 16, No. 6. pp. 3032-3038.
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