Synthesis and in vitro binding of N,N-Dialkyl-2-phenylindol-3-yl-glyoxylamides for the peripheral benzodiazepine binding sites

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dc.contributor.authorHomes, TPen_AU
dc.contributor.authorMattner, Fen_AU
dc.contributor.authorKeller, PAen_AU
dc.contributor.authorKatsifis, Aen_AU
dc.date.accessioned2014-10-09T23:24:30Zen_AU
dc.date.available2014-10-09T23:24:30Zen_AU
dc.date.issued2006-06-01en_AU
dc.date.statistics2014-10-10en_AU
dc.description.abstractA series of NN-dialkyl-2-phenylindol-3-glyoxylamides bearing the halogens iodine and bromine were synthesised and their binding affinity for the peripheral benzodiazepine binding sites (PBBS) in rat kidney mitochondrial membranes was evaluated Using [H-3]PK11195. Central benzodiazepine receptor (CBR) affinities were also evaluated in rat cortices using [H-3]flumazenil to determine their selectivity for PBBS over CBR. The tested compounds had PBBS binding affinities (IC50) ranging from 7.86 to 618 nM, with all compounds showing high selectivity over the CBR (CBR IC50 > 5000 nM). Among the 12 compounds tested, those with a diethylamide group were the most potent. The highest affinity iodinated PBBS ligand, N,N-diethyl-[5-chloro-2-(4-iodophenyl)indol-3-yl]glyoxylamide (4c), was radiolabelled with iodine-123. This high affinity and selective radioligand may be useful for imaging neurodegencration, inflammation and tumours using single photon emission computed tomography. © 2006, Elsevier Ltd.en_AU
dc.identifier.citationHomes, T. P., Mattner, F., Keller, P. A., & Katsifis, A. (2006). Synthesis and in vitro binding of N,N-Dialkyl-2-phenylindol-3-yl-glyoxylamides for the peripheral benzodiazepine binding sites. Bioorganic & Medicinal Chemistry, 14(11), 3938-3946. doi:10.1016/j.bmc.2006.01.039en_AU
dc.identifier.govdoc4522en_AU
dc.identifier.issn0968-0896en_AU
dc.identifier.issue11en_AU
dc.identifier.journaltitleBioorganic & Medicinal Chemistryen_AU
dc.identifier.pagination3938-3946en_AU
dc.identifier.urihttp://dx.doi.org/10.1016/j.bmc.2006.01.039en_AU
dc.identifier.urihttp://apo.ansto.gov.au/dspace/handle/10238/5907en_AU
dc.identifier.volume14en_AU
dc.language.isoenen_AU
dc.publisherPergamon-Elsevier Science Ltden_AU
dc.subjectCentral nervous systemen_AU
dc.subjectNervous systemen_AU
dc.subjectIronen_AU
dc.subjectIodinationen_AU
dc.subjectBrainen_AU
dc.subjectInflammationen_AU
dc.titleSynthesis and in vitro binding of N,N-Dialkyl-2-phenylindol-3-yl-glyoxylamides for the peripheral benzodiazepine binding sitesen_AU
dc.typeJournal Articleen_AU
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