Labeling and evaluation of N-[11C]methylated quinoline-2-carboxamides as potential radioligands for visualization of peripheral benzodiazepine receptors. (Articolo in rivista)

Type
Label
  • Labeling and evaluation of N-[11C]methylated quinoline-2-carboxamides as potential radioligands for visualization of peripheral benzodiazepine receptors. (Articolo in rivista) (literal)
Anno
  • 2001-01-01T00:00:00+01:00 (literal)
Alternative label
  • Matarrese M. 1, Moresco R.M. 1, Cappelli A. 2, Anzini M. 3, Vomero S. 2, Simonelli P. 1, Verza E. 1, Magni F. 1, Sudati F. 1, Soloviev D. 1, Todde S. 1, Carpinelli A. 1, Kienle M.G. 1, Fazio F. 1 (2001)
    Labeling and evaluation of N-[11C]methylated quinoline-2-carboxamides as potential radioligands for visualization of peripheral benzodiazepine receptors.
    in Journal of medicinal chemistry
    (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#autori
  • Matarrese M. 1, Moresco R.M. 1, Cappelli A. 2, Anzini M. 3, Vomero S. 2, Simonelli P. 1, Verza E. 1, Magni F. 1, Sudati F. 1, Soloviev D. 1, Todde S. 1, Carpinelli A. 1, Kienle M.G. 1, Fazio F. 1 (literal)
Pagina inizio
  • 579 (literal)
Pagina fine
  • 585 (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#numeroVolume
  • 44 (literal)
Rivista
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#descrizioneSinteticaDelProdotto
  • Sono stati sintetizzati, marcati con carbonio-11 e valutati nell’animale da laboratorio (ratti) tre nuovi radiotraccianti, analoghi del PK11195, per lo studio in vivo dei recettori delle Benzodiazepine Periferiche (PBR), allo scopo di individuare nuovi radiotraccianti potenzialmente utilizzabili con la PET per lo studio delle patologie neurodegenerative. I risultati della ricerca hanno evidenziato che uno dei radiotraccianti sintetizzati ([11C]VC195) possiede caratteristiche farmacologiche simili allo standard di riferimento PK11195. Ulteriori sviluppi ddlla ricerca saranno rivolti al miglioramento, attraverso modifiche strutturali, del [11C]VC195 allo scopo di potenziarne le proprietà farmacologiche. (literal)
Note
  • ISI Web of Science (WOS) (literal)
Http://www.cnr.it/ontology/cnr/pubblicazioni.owl#affiliazioni
  • 1. INB-CNR, University of Milano/Bicocca, Institute H.S. Raffaele, Milan, Italy 2. Dipartimento Farmaco Chimico Tecnologico, Università di Siena, Italy 3. Dipartimento di Scienze Farmacobiologiche, Università di Catanzaro \"Magna Graecia\", Italy (literal)
Titolo
  • Labeling and evaluation of N-[11C]methylated quinoline-2-carboxamides as potential radioligands for visualization of peripheral benzodiazepine receptors. (literal)
Abstract
  • The novel quinoline-2-carboxamide derivatives N-[methyl-11C]-3-methyl-4-phenyl-N-(phenylmethyl)quinoline-2-carboxamide ([11C]4), (+/-)-N-[methyl-11C]-3-methyl-N-(1-methylpropyl)-4-phenylquinoline-2-carboxamide ([11C]5), and (+/-)-N-[methyl-11C]-3-methyl-4-(2-fluorophenyl)-N-(1-methylpropyl)quinoline-2-carboxamide ([11C]6) were labeled with carbon-11 (t1/2 = 20.4 min, beta+ = 99.8%) as potential radioligands for the noninvasive assessment of peripheral benzodiazepine type receptors (PBR) in vivo with positron emission tomography (PET). The radiosynthesis consisted of N-methylation of the desmethyl precursors 3-methyl-4-phenyl-N-(phenylmethyl)quinoline-2-carboxamide (4a), (+/-)-3-methyl-N-(1-methylpropyl)-4-phenylquinoline-2-carboxamide (5a), and (+/-)-4-(2-fluorophenyl)-3-methyl-N-(1-methylpropyl)quinoline-2-carboxamide (6a) with either [11C]methyl iodide or [11C]methyl triflate in the presence of tetrabutylammonium hydroxide or potassium hydroxide in dimethylformamide. The radioligands [11C]4, [11C]5, and [11C]6 were synthesized with over 99% radiochemical purity in 30 min, 30 +/- 5% radiochemical yield, calculated at the end of synthesis (EOS) non-decay-corrected, and 2.5 +/- 1.2 Ci/micromol of specific radioactivity. Inhibition studies in rats following intravenous pre-administration of 1-(2-chlorophenyl)-N-methyl-N-(1-methylpropyl)-3-isoquinolinecarboxamide (PK 11195, 1) showed high specific binding to PBR of [11C]4, [11C]5, and [11C]6 in heart, lung, kidney, adrenal gland, spleen, and brain. The biological data suggest that [11C]5, [11C]6, and particularly [11C]4 are promising radioligands for PBR imaging in vivo with PET. (literal)
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