Synthesis and in vitro Evaluation of Trifluoroethylamine Analogues of Enkephalins

Roberta Sinisi; Alessandra Ghilardi; Stefania Ruiu; Paolo Lazzari; Luciana Malpezzi; Monica Sani; Luca Pani; Matteo Zanda

doi:10.1002/cmdc.200900158

Synthesis and in vitro Evaluation of Trifluoroethylamine Analogues of Enkephalins

Roberta Sinisi, Alessandra Ghilardi, Stefania Ruiu, Paolo Lazzari, Luciana Malpezzi, Monica Sani, Luca Pani, Matteo Zanda

Medical Sciences

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

10 Citations (Scopus)

Abstract

Here we show that enkephalin analogues with the Gly 3–Phe 4 peptide bond replaced by a stereochemically defined trifluoroethylamine function display binding affinities in the nanomolar range for the μ- and δ-opioid receptors, only 30- to 80-fold lower than those of the natural compounds, whereas the Gly 2–Gly 3 trifluoroethylamine analogues have lower affinity.

Original language	English
Pages (from-to)	1416-1420
Number of pages	5
Journal	ChemMedChem
Volume	4
Issue number	9
Early online date	16 Jun 2009
DOIs	https://doi.org/10.1002/cmdc.200900158
Publication status	Published - 4 Sept 2009

Keywords

amino acid sequence
analgesics
animals
enkephalins
ethylamines
mice
receptors, opioid

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10.1002/cmdc.200900158

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abstract = "Here we show that enkephalin analogues with the Gly 3–Phe 4 peptide bond replaced by a stereochemically defined trifluoroethylamine function display binding affinities in the nanomolar range for the μ- and δ-opioid receptors, only 30- to 80-fold lower than those of the natural compounds, whereas the Gly 2–Gly 3 trifluoroethylamine analogues have lower affinity.",

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AU - Sinisi, Roberta

AU - Ghilardi, Alessandra

AU - Ruiu, Stefania

AU - Lazzari, Paolo

AU - Malpezzi, Luciana

AU - Sani, Monica

AU - Pani, Luca

AU - Zanda, Matteo

PY - 2009/9/4

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AB - Here we show that enkephalin analogues with the Gly 3–Phe 4 peptide bond replaced by a stereochemically defined trifluoroethylamine function display binding affinities in the nanomolar range for the μ- and δ-opioid receptors, only 30- to 80-fold lower than those of the natural compounds, whereas the Gly 2–Gly 3 trifluoroethylamine analogues have lower affinity.

KW - amino acid sequence

KW - analgesics

KW - animals

KW - enkephalins

KW - ethylamines

KW - mice

KW - receptors, opioid

U2 - 10.1002/cmdc.200900158

DO - 10.1002/cmdc.200900158

M3 - Article

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JO - ChemMedChem

JF - ChemMedChem

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ER -

Synthesis and in vitro Evaluation of Trifluoroethylamine Analogues of Enkephalins

Abstract

Keywords

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