Effect of anchoring 4-anilidopiperidines to opioid peptides

Ravil R. Petrov; Yeon Sun Lee; Ruben S Vardanyan; Lu Liu; Shou Wu Ma; Peg Davis; Josephine Lai; Frank Porreca; Todd W. Vanderah; Victor J Hruby

doi:10.1016/j.bmcl.2013.03.065

Effect of anchoring 4-anilidopiperidines to opioid peptides

Ravil R. Petrov, Yeon Sun Lee, Ruben S Vardanyan, Lu Liu, Shou Wu Ma, Peg Davis, Josephine Lai, Frank Porreca, Todd W. Vanderah, Victor J Hruby

Research output: Contribution to journal › Article › peer-review

8 Scopus citations

Abstract

We report here the design, synthesis, and in vitro characterization of new opioid peptides featuring a 4-anilidopiperidine moiety. Despite the fact that the chemical structures of fentanyl surrogates have been found suboptimal per se for the opioid activity, the corresponding conjugates with opioid peptides displayed potent opioid activity. These studies shed an instructive light on the strategies and potential therapeutic values of anchoring the 4-anilidopiperidine scaffold to different classes of opioid peptides.

Original language	English (US)
Pages (from-to)	3434-3437
Number of pages	4
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	23
Issue number	11
DOIs	https://doi.org/10.1016/j.bmcl.2013.03.065
State	Published - Jun 1 2013

Keywords

Analgesic
Bivalent ligand
Dynorphine analog
Fentanyl
Opioid peptide

ASJC Scopus subject areas

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

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10.1016/j.bmcl.2013.03.065

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title = "Effect of anchoring 4-anilidopiperidines to opioid peptides",

abstract = "We report here the design, synthesis, and in vitro characterization of new opioid peptides featuring a 4-anilidopiperidine moiety. Despite the fact that the chemical structures of fentanyl surrogates have been found suboptimal per se for the opioid activity, the corresponding conjugates with opioid peptides displayed potent opioid activity. These studies shed an instructive light on the strategies and potential therapeutic values of anchoring the 4-anilidopiperidine scaffold to different classes of opioid peptides.",

keywords = "Analgesic, Bivalent ligand, Dynorphine analog, Fentanyl, Opioid peptide",

author = "Petrov, {Ravil R.} and Lee, {Yeon Sun} and Vardanyan, {Ruben S} and Lu Liu and Ma, {Shou Wu} and Peg Davis and Josephine Lai and Frank Porreca and Vanderah, {Todd W.} and Hruby, {Victor J}",

note = "Funding Information: The work was supported by Grants from the USDHS, National Institute on Drug Abuse ( DA-12394 and DA-06284 ). ",

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doi = "10.1016/j.bmcl.2013.03.065",

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T1 - Effect of anchoring 4-anilidopiperidines to opioid peptides

AU - Petrov, Ravil R.

AU - Lee, Yeon Sun

AU - Vardanyan, Ruben S

AU - Liu, Lu

AU - Ma, Shou Wu

AU - Davis, Peg

AU - Lai, Josephine

AU - Porreca, Frank

AU - Vanderah, Todd W.

AU - Hruby, Victor J

N1 - Funding Information: The work was supported by Grants from the USDHS, National Institute on Drug Abuse ( DA-12394 and DA-06284 ).

PY - 2013/6/1

Y1 - 2013/6/1

N2 - We report here the design, synthesis, and in vitro characterization of new opioid peptides featuring a 4-anilidopiperidine moiety. Despite the fact that the chemical structures of fentanyl surrogates have been found suboptimal per se for the opioid activity, the corresponding conjugates with opioid peptides displayed potent opioid activity. These studies shed an instructive light on the strategies and potential therapeutic values of anchoring the 4-anilidopiperidine scaffold to different classes of opioid peptides.

AB - We report here the design, synthesis, and in vitro characterization of new opioid peptides featuring a 4-anilidopiperidine moiety. Despite the fact that the chemical structures of fentanyl surrogates have been found suboptimal per se for the opioid activity, the corresponding conjugates with opioid peptides displayed potent opioid activity. These studies shed an instructive light on the strategies and potential therapeutic values of anchoring the 4-anilidopiperidine scaffold to different classes of opioid peptides.

KW - Analgesic

KW - Bivalent ligand

KW - Dynorphine analog

KW - Fentanyl

KW - Opioid peptide

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JO - Bioorganic and Medicinal Chemistry Letters

JF - Bioorganic and Medicinal Chemistry Letters

IS - 11

ER -

Effect of anchoring 4-anilidopiperidines to opioid peptides

Abstract

Keywords

ASJC Scopus subject areas

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