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Titolo:
Synthesis of [C-11]2 beta-carbomethoxy-3 beta-(3 '-iodo-4 '-methyl, -ethyland isopropyl phenyl)nortropane as potential radiotracers for examination of the serotonin transporter with positron emission tomography
Autore:
Sandell, J; Halldin, C; Helfenbein, J; Chou, YH; Vercouillie, J; Emond, P; Swahn, CG; Guilloteau, D; Farde, L;
Indirizzi:
Karolinska Hosp, Karolinska Inst, Dept Clin Neurosci, Psychiat Sect, S-17176 Stockholm, Sweden Karolinska Hosp Stockholm Sweden S-17176 Sect, S-17176 Stockholm, Sweden Univ Tours, Fac Pharmaceut Sci, Lab Biophys Med & Pharmaceut, INSERM U316,F-37200 Tours, France Univ Tours Tours France F-37200 aceut, INSERM U316,F-37200 Tours, France
Titolo Testata:
JOURNAL OF LABELLED COMPOUNDS & RADIOPHARMACEUTICALS
fascicolo: 10, volume: 43, anno: 2000,
pagine: 1033 - 1046
SICI:
0362-4803(200009)43:10<1033:SO[BB'>2.0.ZU;2-0
Fonte:
ISI
Lingua:
ENG
Soggetto:
NOR-BETA-CIT; HUMAN BRAIN; HIGH-AFFINITY; C-11 (+)MCN5652; PET EXAMINATION; UPTAKE SITES; BINDING; DOPAMINE; LIGAND; RADIOLIGANDS;
Keywords:
positron emission tomography; EINT; LBT-14; LBT-44; serotonin transporter; carbon-11;
Tipo documento:
Article
Natura:
Periodico
Settore Disciplinare:
Life Sciences
Physical, Chemical & Earth Sciences
Citazioni:
19
Recensione:
Indirizzi per estratti:
Indirizzo: Sandell, J Karolinska Hosp, Karolinska Inst, Dept Clin Neurosci, Psychiat Sect, S-17176 Stockholm, Sweden Karolinska Hosp Stockholm Sweden S-17176 76 Stockholm, Sweden
Citazione:
J. Sandell et al., "Synthesis of [C-11]2 beta-carbomethoxy-3 beta-(3 '-iodo-4 '-methyl, -ethyland isopropyl phenyl)nortropane as potential radiotracers for examination of the serotonin transporter with positron emission tomography", J LABEL C R, 43(10), 2000, pp. 1033-1046

Abstract

Research on depression and anxiety disorders would benefit from the development of suitable radioligands for PET-imaging of the serotonin transporter. Three cocaine analogues, 2 beta-carbomethoxy-3 beta-(3'-iodo-4'-methyl, -ethyl and isopropyl phenyl)nortropane (LBT-14, EINT and LBT-44), were prepared in a three-step synthesis by 1-4 addition of the appropriate Grignard reagent to anhydroecgonine methyl ester as first step. Iodination of the phenyl ring was accomplished with a mixture of yellow mercuric oxide, perchloric acid and acetic acid followed by a solution of iodine in dichloromethane. N-desmethylation was performed by using 2,2,2-trichloroethylchloroformiate followed by treatment of zinc in acetic acid. Acidic hydrolysis of the ester functions gave the carboxylic acid analogues of LBT-14, EINT and LBT-44. The precursors were labelled with C-11 using [C-11]methyl iodide or [C-11]methyl triflate in dimethyl formamide (DMF) and tetrabutyl ammonmium hydroxide (TBAH) as base. [C-11]LBT-14, [C-11]EINT and [C-11]LBT-44 were all examined in Cynomolgus monkey with PET. All three compounds entered the monkeybrain to a high degree (similar to 5-10% of injected dose). There was a marked uptake of radioactivity in the thalamus and the brainstem, regions known to contain serotonin transporters. Pre-treatment with the selective serotonin transporter inhibitor citalopram had minor effect on the binding ratios, suggesting that none of the three examined radioligands are preferable to the previously examined non-iodinated 4'-isopropenyl analogue [C-11]RTI-357 for the study of the serotonin reuptake system with PET.

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Documento generato il 22/01/20 alle ore 21:39:43