Photoaffinity labelling of the mu-opioid receptor is dependent on the nature of the photosensitive group of carfentanil derivatives.
Arylazido and aryldiazonium derivatives of carfentanil, bearing their photoactivatable function at the same position on the molecule, were synthesized. In the dark both of them exhibited similar binding affinity profiles and behaved as mu-selective and reversible ligands of the opioid receptor sites. Following irradiation, only the azido analog displayed the properties of an efficient, irreversible and selective label of the mu-opioid receptor, allowing physicochemical requirements for alkylation of this receptor subtype to be examined. Evidence is presented to consider this azido compound a promising tool for characterizing the mu-opioid receptor protein.
Galzi
J L
JL
Laboratoire de Chimie Bio-Organique, C.N.R.S. (U.R.A. 1386), Faculté de Pharmacie, Université Louis Pasteur-Strasbourg, Illkirch, France.
Mejean
A
A
Goeldner
M
M
Hirth
C
C
Ilien
B
B
D000345:Affinity Labels; D000818:Animals; D002498:Centrifugation; D055598:Chemical Phenomena; D002627:Chemistry, Physical; D005283:Fentanyl / Q000031:analogs & derivatives*; D005374:Filtration; D008297:Male; D010777:Photochemistry; D051381:Rats; D011919:Rats, Inbred Strains; D011957:Receptors, Opioid / Q000378:metabolism*; D017450:Receptors, Opioid, mu; D013056:Spectrophotometry, Ultraviolet
D000345:Affinity Labels; D011957:Receptors, Opioid; D017450:Receptors, Opioid, mu; C017114:carfentanil; D005283:Fentanyl