title: The use of [18F]4-fluorobenzyl iodide (FBI) in PET radiotracer synthesis: model alkylation studies and its application in the design of dopamine D1 and D2 receptor-based imaging agents.
abstract: [18F]4-Fluorobenzyl iodide ([18F]FBI) was prepared, and a series of model alkylation studies were conducted to determine its chemical reactivity toward nitrogen and sulfur nucleophiles of varying nucleophilicities. [18F]FBI was found to react rapidly with secondary amines and anilines to give the corresponding N-[18F]4-fluorobenzyl analogue in high yield. Amides and thiol groups required the use of a base catalyst. The utility of [18F]FBI was documented by investigation of dopamine D1 and D2 receptor-based radiotracers.
authors.affiliation: Cerebrovascular Research Center, University of Pennsylvania, Philadelphia 19104-6063.
authors.forename: R H
authors.initials: RH
authors.lastname: Mach
authors.forename: S T
authors.initials: ST
authors.lastname: Elder
authors.forename: T E
authors.initials: TE
authors.lastname: Morton
authors.forename: P A
authors.initials: PA
authors.lastname: Nowak
authors.forename: P H
authors.initials: PH
authors.lastname: Evora
authors.forename: J G
authors.initials: JG
authors.lastname: Scripko
authors.forename: R R
authors.initials: RR
authors.lastname: Luedtke
authors.forename: C D
authors.initials: CD
authors.lastname: Unsworth
authors.forename: T
authors.initials: T
authors.lastname: Filtz
authors.forename: A V
authors.initials: AV
authors.lastname: Rao
mesh_terms: D000478:Alkylation; D000818:Animals; D001549:Benzamides / Q000138:chemical synthesis; D001552:Benzazepines / Q000138:chemical synthesis; D005462:Fluorine Radioisotopes; D005464:Fluorobenzenes / Q000138:chemical synthesis / Q000737:chemistry*; D007553:Isotope Labeling / Q000379:methods; D007700:Kinetics; D008956:Models, Chemical; D009584:Nitrogen / Q000737:chemistry; D010880:Piperidines / Q000138:chemical synthesis; D051381:Rats; D017207:Rats, Sprague-Dawley; D017447:Receptors, Dopamine D1 / Q000032:analysis* / Q000378:metabolism; D017448:Receptors, Dopamine D2 / Q000032:analysis* / Q000378:metabolism; D013455:Sulfur / Q000737:chemistry; D014055:Tomography, Emission-Computed
chemical_list: D001549:Benzamides; D001552:Benzazepines; D005462:Fluorine Radioisotopes; D005464:Fluorobenzenes; D010880:Piperidines; D017447:Receptors, Dopamine D1; D017448:Receptors, Dopamine D2; C083673:fluoroclebopride; C083674:7-chloro-8-hydroxy-1-(4'-(4-fluorobenzyl)thiophenyl)-3-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine; C083672:4-fluorobenzyl iodide; D013455:Sulfur; D009584:Nitrogen