title: Design and evaluation of naphthol- and carbazole-containing fluorescent sigma ligands as potential probes for receptor binding studies.
abstract: Some 3,3-dimethyl-1-(3-naphthylpropyl)piperidine and 1-cyclohexyl-4-(3-naphthylpropyl)piperazine derivatives, structurally containing naphthol as a fluorescent moiety, were prepared for being potentially used as fluorescent sigma ligands. Structurally related analogs were also prepared, where the naphthalene nucleus was replaced by the fluorescent carbazole moiety and chain length was varied. For all compounds the in vitro affinities toward sigma receptors and Delta8-Delta7 sterol isomerase site were measured, and the fluorescent properties were determined. Compound 19 gave the best results both for sigma receptor affinities (sigma1, Ki = 6.78 nM and sigma2, Ki = 26.4 nM) and fluorescence features; thus, it was chosen for in vitro saturation binding analysis at sigma receptors. The good results obtained in such assay suggested that the fluorescent compound 19 could be used instead of a radioligand in "green" binding assays.
authors: Dipartimento Farmacochimico, Università di Bari, via Orabona 4, 70125 Bari, Italy.
authors: Savina
authors: S
authors: Ferorelli
authors: Carmen
authors: C
authors: Abate
authors: Nicola Antonio
authors: NA
authors: Colabufo
authors: Mauro
authors: M
authors: Niso
authors: Carmela
authors: C
authors: Inglese
authors: Francesco
authors: F
authors: Berardi
authors: Roberto
authors: R
authors: Perrone
mesh_terms: D000818:Animals; D002227:Carbazoles / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D003164:Competitive Bidding; D005456:Fluorescent Dyes / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D066298:In Vitro Techniques; D008024:Ligands; D008099:Liver / Q000378:metabolism; D009284:Naphthols / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D010879:Piperazines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D010880:Piperidines / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D011869:Radioligand Assay; D051381:Rats; D017465:Receptors, Opioid, delta / Q000378:metabolism*; D013329:Structure-Activity Relationship
chemical_list: C523625:1-cyclohexyl-4-(3-(6-hydroxynaphthalen-1-yl)propyl)piperazine; D002227:Carbazoles; D005456:Fluorescent Dyes; D008024:Ligands; D009284:Naphthols; D010879:Piperazines; D010880:Piperidines; D017465:Receptors, Opioid, delta