Understanding the structural requirements of 4-anilidopiperidine analogues for biological activities at μ and δ opioid receptors

Yeon Sun Lee; Joel Nyberg; Sharif Moye; Richard S. Agnes; Peg Davis; Shou wu Ma; Josephine Lai; Frank Porreca; Ruben Vardanyan; Victor J. Hruby

doi:10.1016/j.bmcl.2007.01.114

Understanding the structural requirements of 4-anilidopiperidine analogues for biological activities at μ and δ opioid receptors

Yeon Sun Lee, Joel Nyberg, Sharif Moye, Richard S. Agnes, Peg Davis, Shou wu Ma, Josephine Lai, Frank Porreca, Ruben Vardanyan, Victor J. Hruby

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

26 Scopus citations

Abstract

New 4-anilidopiperidine analogues in which the phenethyl group of fentanyl was replaced by several aromatic ring-contained amino acids (or acids) were synthesized to study the biological effect of the substituents on μ and δ opioid receptor interactions. These analogues showed broad (47 nM-76 μM) but selective (up to 17-fold) binding affinities at the μ opioid receptor over the δ opioid receptor, as predicted from the message-address concept.

Original language	English (US)
Pages (from-to)	2161-2165
Number of pages	5
Journal	Bioorganic and Medicinal Chemistry Letters
Volume	17
Issue number	8
DOIs	https://doi.org/10.1016/j.bmcl.2007.01.114
State	Published - Apr 15 2007

Keywords

4-Anilidopiperidine analogues
Analgesic effects
Dmt-Tic
Fentanyl
Opioid receptors

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.2007.01.114

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title = "Understanding the structural requirements of 4-anilidopiperidine analogues for biological activities at μ and δ opioid receptors",

abstract = "New 4-anilidopiperidine analogues in which the phenethyl group of fentanyl was replaced by several aromatic ring-contained amino acids (or acids) were synthesized to study the biological effect of the substituents on μ and δ opioid receptor interactions. These analogues showed broad (47 nM-76 μM) but selective (up to 17-fold) binding affinities at the μ opioid receptor over the δ opioid receptor, as predicted from the message-address concept.",

keywords = "4-Anilidopiperidine analogues, Analgesic effects, Dmt-Tic, Fentanyl, Opioid receptors",

author = "Lee, {Yeon Sun} and Joel Nyberg and Sharif Moye and Agnes, {Richard S.} and Peg Davis and Ma, {Shou wu} and Josephine Lai and Frank Porreca and Ruben Vardanyan 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). We thank Margie Colie for assistance with the manuscript.",

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doi = "10.1016/j.bmcl.2007.01.114",

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AU - Lee, Yeon Sun

AU - Nyberg, Joel

AU - Moye, Sharif

AU - Agnes, Richard S.

AU - Davis, Peg

AU - Ma, Shou wu

AU - Lai, Josephine

AU - Porreca, Frank

AU - Vardanyan, Ruben

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). We thank Margie Colie for assistance with the manuscript.

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Y1 - 2007/4/15

N2 - New 4-anilidopiperidine analogues in which the phenethyl group of fentanyl was replaced by several aromatic ring-contained amino acids (or acids) were synthesized to study the biological effect of the substituents on μ and δ opioid receptor interactions. These analogues showed broad (47 nM-76 μM) but selective (up to 17-fold) binding affinities at the μ opioid receptor over the δ opioid receptor, as predicted from the message-address concept.

AB - New 4-anilidopiperidine analogues in which the phenethyl group of fentanyl was replaced by several aromatic ring-contained amino acids (or acids) were synthesized to study the biological effect of the substituents on μ and δ opioid receptor interactions. These analogues showed broad (47 nM-76 μM) but selective (up to 17-fold) binding affinities at the μ opioid receptor over the δ opioid receptor, as predicted from the message-address concept.

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KW - Dmt-Tic

KW - Fentanyl

KW - Opioid receptors

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Understanding the structural requirements of 4-anilidopiperidine analogues for biological activities at μ and δ opioid receptors

Abstract

Keywords

ASJC Scopus subject areas

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