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

Research output: Contribution to journalArticle

7 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 languageEnglish
Pages (from-to)1416-1420
Number of pages5
JournalChemMedChem
Volume4
Issue number9
Early online date16 Jun 2009
DOIs
Publication statusPublished - 4 Sep 2009

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Enkephalins
Opioid Receptors
Display devices
Peptides
trifluoroethylamine
In Vitro Techniques

Keywords

  • amino acid sequence
  • analgesics
  • animals
  • enkephalins
  • ethylamines
  • mice
  • receptors, opioid

Cite this

Sinisi, R., Ghilardi, A., Ruiu, S., Lazzari, P., Malpezzi, L., Sani, M., ... Zanda, M. (2009). Synthesis and in vitro Evaluation of Trifluoroethylamine Analogues of Enkephalins. ChemMedChem, 4(9), 1416-1420. https://doi.org/10.1002/cmdc.200900158

Synthesis and in vitro Evaluation of Trifluoroethylamine Analogues of Enkephalins. / Sinisi, Roberta; Ghilardi, Alessandra; Ruiu, Stefania; Lazzari, Paolo; Malpezzi, Luciana; Sani, Monica; Pani, Luca; Zanda, Matteo.

In: ChemMedChem, Vol. 4, No. 9, 04.09.2009, p. 1416-1420.

Research output: Contribution to journalArticle

Sinisi, R, Ghilardi, A, Ruiu, S, Lazzari, P, Malpezzi, L, Sani, M, Pani, L & Zanda, M 2009, 'Synthesis and in vitro Evaluation of Trifluoroethylamine Analogues of Enkephalins', ChemMedChem, vol. 4, no. 9, pp. 1416-1420. https://doi.org/10.1002/cmdc.200900158
Sinisi R, Ghilardi A, Ruiu S, Lazzari P, Malpezzi L, Sani M et al. Synthesis and in vitro Evaluation of Trifluoroethylamine Analogues of Enkephalins. ChemMedChem. 2009 Sep 4;4(9):1416-1420. https://doi.org/10.1002/cmdc.200900158
Sinisi, Roberta ; Ghilardi, Alessandra ; Ruiu, Stefania ; Lazzari, Paolo ; Malpezzi, Luciana ; Sani, Monica ; Pani, Luca ; Zanda, Matteo. / Synthesis and in vitro Evaluation of Trifluoroethylamine Analogues of Enkephalins. In: ChemMedChem. 2009 ; Vol. 4, No. 9. pp. 1416-1420.
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