Biological active analogues of the opioid peptide biphalin: Mixed α/β3-peptides

Adriano Mollica; Francesco Pinnen; Roberto Costante; Marcello Locatelli; Azzurra Stefanucci; Stefano Pieretti; Peg Davis; Josephine Lai; David Rankin; Frank Porreca; Victor J. Hruby

doi:10.1021/jm301456c

Biological active analogues of the opioid peptide biphalin: Mixed α/β³-peptides

Adriano Mollica, Francesco Pinnen, Roberto Costante, Marcello Locatelli, Azzurra Stefanucci, Stefano Pieretti, Peg Davis, Josephine Lai, David Rankin, Frank Porreca, Victor J. Hruby

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

38 Scopus citations

Abstract

Natural residues of the dimeric opioid peptide Biphalin were replaced by the corresponding homo-β³ amino acids. The derivative 1 containing hβ³ Phe in place of Phe showed good μ- and δ-receptor affinities (K_i^δ = 0.72 nM; K _i^μ = 1.1 nM) and antinociceptive activity in vivo together with an increased enzymatic stability in human plasma.

Original language	English (US)
Pages (from-to)	3419-3423
Number of pages	5
Journal	Journal of Medicinal Chemistry
Volume	56
Issue number	8
DOIs	https://doi.org/10.1021/jm301456c
State	Published - Apr 25 2013

ASJC Scopus subject areas

Molecular Medicine
Drug Discovery

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10.1021/jm301456c

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abstract = "Natural residues of the dimeric opioid peptide Biphalin were replaced by the corresponding homo-β3 amino acids. The derivative 1 containing hβ3 Phe in place of Phe showed good μ- and δ-receptor affinities (Kiδ = 0.72 nM; K iμ = 1.1 nM) and antinociceptive activity in vivo together with an increased enzymatic stability in human plasma.",

author = "Adriano Mollica and Francesco Pinnen and Roberto Costante and Marcello Locatelli and Azzurra Stefanucci and Stefano Pieretti and Peg Davis and Josephine Lai and David Rankin and Frank Porreca and Hruby, {Victor J.}",

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T1 - Biological active analogues of the opioid peptide biphalin

T2 - Mixed α/β3-peptides

AU - Mollica, Adriano

AU - Pinnen, Francesco

AU - Costante, Roberto

AU - Locatelli, Marcello

AU - Stefanucci, Azzurra

AU - Pieretti, Stefano

AU - Davis, Peg

AU - Lai, Josephine

AU - Rankin, David

AU - Porreca, Frank

AU - Hruby, Victor J.

PY - 2013/4/25

Y1 - 2013/4/25

N2 - Natural residues of the dimeric opioid peptide Biphalin were replaced by the corresponding homo-β3 amino acids. The derivative 1 containing hβ3 Phe in place of Phe showed good μ- and δ-receptor affinities (Kiδ = 0.72 nM; K iμ = 1.1 nM) and antinociceptive activity in vivo together with an increased enzymatic stability in human plasma.

AB - Natural residues of the dimeric opioid peptide Biphalin were replaced by the corresponding homo-β3 amino acids. The derivative 1 containing hβ3 Phe in place of Phe showed good μ- and δ-receptor affinities (Kiδ = 0.72 nM; K iμ = 1.1 nM) and antinociceptive activity in vivo together with an increased enzymatic stability in human plasma.

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JO - Journal of Medicinal Chemistry

JF - Journal of Medicinal Chemistry

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ER -

Biological active analogues of the opioid peptide biphalin: Mixed α/β³-peptides

Abstract

ASJC Scopus subject areas

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