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Synthesis and in vitro Evaluation of Trifluoroethylamine Analogues of Enkephalins
Author(s) -
Sinisi Roberta,
Ghilardi Alessandra,
Ruiu Stefania,
Lazzari Paolo,
Malpezzi Luciana,
Sani Monica,
Pani Luca,
Zanda Matteo
Publication year - 2009
Publication title -
chemmedchem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.817
H-Index - 100
eISSN - 1860-7187
pISSN - 1860-7179
DOI - 10.1002/cmdc.200900158
Subject(s) - enkephalin , affinities , chemistry , stereochemistry , in vitro , binding affinities , peptide , receptor , opioid peptide , opioid , biochemistry
No gain with pain : At least when it comes to analgesics! 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.