Probes for narcotic receptor mediated phenomena. 10. Irreversible ligands to opioid receptors based on biologically potent endoethenooripavines. Reversible binding of fit to mu and delta opioid receptors.
A p-isothiocyanatophenylacetylamino moiety at the C7alpha position on an endoethenooripavine (NIH 10358) was found to irreversibly bind to both the mu and delta opioid receptors in rat brain membrane preparations. However, the same endoethenooripavine nucleus with a p-methylfumaroylaminophenylacetylamino moiety at that position (NIH 10364) binds specifically and irreversibly to only mu opioid receptors. Hypotheses are being developed concerning receptor subclass alkylation specificity. For example, it has now been found that the delta receptor irreversible agonist, FIT, can interact with both mu and delta receptors in a reversible manner.
D000477:Alkylating Agents / Q000378:metabolism; D000818:Animals; D001562:Benzimidazoles / Q000378:metabolism; D001667:Binding, Competitive; D001921:Brain / Q000378:metabolism; D005283:Fentanyl / Q000031:analogs & derivatives* / Q000378:metabolism; D066298:In Vitro Techniques; D017879:Isothiocyanates; D008566:Membranes / Q000378:metabolism; D009022:Morphine Derivatives; D051381:Rats; D011957:Receptors, Opioid / Q000378:metabolism*; D017465:Receptors, Opioid, delta; D017450:Receptors, Opioid, mu; D013797:Thebaine / Q000031:analogs & derivatives / Q000378:metabolism
D000477:Alkylating Agents; D001562:Benzimidazoles; D017879:Isothiocyanates; D009022:Morphine Derivatives; D011957:Receptors, Opioid; D017465:Receptors, Opioid, delta; D017450:Receptors, Opioid, mu; D013797:Thebaine; C037091:fentanyl isothiocyanate; C044631:NIH 10358; C044628:NIH 10364; D005283:Fentanyl