Affinity of fentanyl and its derivatives for the σ1-receptor

Piotr F. J. Lipiński; Edina Szűcs; Małgorzata Jarończyk; Piotr Kosson; Sándor Benyhe; Aleksandra Misicka; Ján Cz. Dobrowolski; Joanna Sadlej

doi:10.1039/C9MD00222G

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Affinity of fentanyl and its derivatives for the σ₁-receptor†‡

Piotr F. J. Lipiński,

*^a Edina Szűcs,^bc Małgorzata Jarończyk,^d Piotr Kosson,^e Sándor Benyhe,^b Aleksandra Misicka,

^af Ján Cz. Dobrowolski

^d and Joanna Sadlej^g

Author affiliations

* Corresponding authors

^a Department of Neuropeptides, Mossakowski Medical Research Centre, Polish Academy of Sciences, 02-106 Warsaw, Poland
E-mail: plipinski@imdik.pan.pl

^b Institute of Biochemistry, Biological Research Centre, Hungarian Academy of Sciences, Szeged, Hungary

^c Doctoral School of Theoretical Medicine, University of Szeged, Faculty of Medicine, Szeged, Hungary

^d National Medicines Institute, 00-725 Warsaw, Poland

^e Toxicology Research Laboratory, Mossakowski Medical Research Centre, Polish Academy of Sciences, 02-106 Warsaw, Poland

^f Faculty of Chemistry, University of Warsaw, 02-093 Warsaw, Poland

^g Faculty of Mathematics and Natural Sciences, Cardinal Stefan Wyszyński University in Warsaw, 1/3 Wóycickiego-Str., 01-938 Warsaw, Poland

Abstract

Fentanyl and its 11 commercially available derivatives were investigated as to their affinity for the σ₁ receptor. The parent compound is a rather poor binder (IC₅₀ = 4973 nM), but its close derivatives (benzylfentanyl or p-fluorofentanyl) have submicromolar affinities. Modelling provides a structural basis for the observed trends in activity.

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Article information

DOI: https://doi.org/10.1039/C9MD00222G
Article type: Research Article
Submitted: 16 Apr 2019
Accepted: 18 May 2019
First published: 13 Jun 2019

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Med. Chem. Commun., 2019,10, 1187-1191

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Affinity of fentanyl and its derivatives for the σ₁-receptor

P. F. J. Lipiński, E. Szűcs, M. Jarończyk, P. Kosson, S. Benyhe, A. Misicka, J. Cz. Dobrowolski and J. Sadlej, Med. Chem. Commun., 2019, 10, 1187 DOI: 10.1039/C9MD00222G

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