Article

Novel multiple opioid ligands based on 4-aminobenzazepinone (Aba), azepinoindole (Aia) and tetrahydroisoquinoline (Tic) scaffolds.

Department of Organic Chemistry, Vrije Universiteit Brussel, B-1050 Brussels, Belgium.
Bioorganic & medicinal chemistry letters (impact factor: 2.65). 03/2010; 20(5):1610-3. DOI:10.1016/j.bmcl.2010.01.055 pp.1610-3
Source: PubMed

ABSTRACT The dimerization and trimerization of the Dmt-Tic, Dmt-Aia and Dmt-Aba pharmacophores provided multiple ligands which were evaluated in vitro for opioid receptor binding and functional activity. Whereas the Tic- and Aba multimers proved to be dual and balanced delta/mu antagonists, as determined by the functional [S(35)]GTPgammaS binding assay, the dimerization of potent Aia-based 'parent' ligands unexpectedly resulted in substantial less efficient receptor binding and non-active dimeric compounds.

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Keywords

balanced delta/mu antagonists
 
dimerization
 
Dmt-Tic
 
functional [S(35)]GTPgammaS binding assay
 
multiple ligands
 
non-active dimeric compounds
 
opioid receptor binding
 
potent Aia-based 'parent' ligands
 
Tic-