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

doi:10.1016/j.bmc.2007.12.032

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 journal › Article › peer-review

11 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 language	English (US)
Pages (from-to)	3032-3038
Number of pages	7
Journal	Bioorganic and Medicinal Chemistry
Volume	16
Issue number	6
DOIs	https://doi.org/10.1016/j.bmc.2007.12.032
State	Published - Mar 15 2008

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

Access to Document

10.1016/j.bmc.2007.12.032

Cite this

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

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.",

keywords = "Dmt-Tic pharmacophore, Opioid peptides, UFP-502, δ-Opioid receptors",

author = "Severo Salvadori and Stella Fiorini and Claudio Trapella and Frank Porreca and Peg Davis and Yusuke Sasaki and Akihiro Ambo and Marczak, \{Ewa D.\} and Lazarus, \{Lawrence H.\} and Gianfranco Balboni",

year = "2008",

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doi = "10.1016/j.bmc.2007.12.032",

language = "English (US)",

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journal = "Bioorganic and Medicinal Chemistry",

issn = "0968-0896",

publisher = "Elsevier Ltd",

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T1 - Role of benzimidazole (Bid) in the δ-opioid agonist pseudopeptide H-Dmt-Tic-NH-CH2-Bid (UFP-502)

AU - Salvadori, Severo

AU - Fiorini, Stella

AU - Trapella, Claudio

AU - Porreca, Frank

AU - Davis, Peg

AU - Sasaki, Yusuke

AU - Ambo, Akihiro

AU - Marczak, Ewa D.

AU - Lazarus, Lawrence H.

AU - Balboni, Gianfranco

PY - 2008/3/15

Y1 - 2008/3/15

N2 - 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.

AB - 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.

KW - Dmt-Tic pharmacophore

KW - Opioid peptides

KW - UFP-502

KW - δ-Opioid receptors

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DO - 10.1016/j.bmc.2007.12.032

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VL - 16

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JO - Bioorganic and Medicinal Chemistry

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