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

Access to Document

10.1002/cmdc.200900158

Cite this

@article{0551fa71f37e4a1a827961535a5b4b9c,

title = "Synthesis and in vitro Evaluation of Trifluoroethylamine Analogues of Enkephalins",

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.",

keywords = "amino acid sequence, analgesics, animals, enkephalins, ethylamines, mice, receptors, opioid",

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

year = "2009",

month = sep,

day = "4",

doi = "10.1002/cmdc.200900158",

language = "English",

volume = "4",

pages = "1416--1420",

journal = "ChemMedChem",

issn = "1860-7187",

publisher = "John Wiley and Sons Ltd",

number = "9",

}

TY - JOUR

T1 - Synthesis and in vitro Evaluation of Trifluoroethylamine Analogues of Enkephalins

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

Y1 - 2009/9/4

N2 - 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.

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

C2 - 19533725

SN - 1860-7187

VL - 4

SP - 1416

EP - 1420

JO - ChemMedChem

JF - ChemMedChem

IS - 9

ER -

Synthesis and in vitro Evaluation of Trifluoroethylamine Analogues of Enkephalins

Abstract

Keywords

Access to Document

Fingerprint

Cite this