title: Synthesis of [11C-methyl]-alpha-aminoisobutyric acid (AIB).
abstract: Alpha-aminoisobutyric acid (AIB) labeled with the cyclotron-produced, positron-emitting radionuclide 11C has been synthesized with the label in the alpha-methyl group. Our previously published synthesis of [11C] AIB in the carboxyl position from [11C] HCN requires a rigorous quality assurance program to ensure that the concentration of cyanide in the final product is below certain levels. This can be avoided using the method described here with [11C] CH3I. The radiochemical yield calculated to end of bombardment (EOB) was 45-55% from [11C] CO2 with radiochemical purity of [11C-methyl] AIB exceeding 99%. Synthesis times from [11C] CO2 were about 55 min. Specific activities of 1 Ci/mumol were achieved on average. It has been shown that [11C-carboxyl] AIB is a useful imaging agent in patients with soft tissue cancers and melanoma, and it demonstrates tumor uptake in a spectrum of other animal tumor models. Because AIB is a nonmetabolized amino acid, [11C-methyl] AIB should be equally as useful. Either agent can be employed for the quantification of the A-type amino acid transport system in vivo with PET.
authors.affiliation: Department of Nuclear Medicine, Warren G. Magnuson Clinical Center, National Institutes of Health, Bethesda, MD 20892, USA.
authors.forename: B
authors.initials: B
authors.lastname: Schmall
authors.forename: P S
authors.initials: PS
authors.lastname: Conti
authors.forename: M M
authors.initials: MM
authors.lastname: Alauddin
mesh_terms: D000621:Aminoisobutyric Acids / Q000138:chemical synthesis*; D000818:Animals; D002250:Carbon Radioisotopes; D002851:Chromatography, High Pressure Liquid; D002855:Chromatography, Thin Layer; D017357:Cyclotrons; D006801:Humans; D006847:Hydrocarbons, Iodinated; D007202:Indicators and Reagents; D007553:Isotope Labeling / Q000379:methods; D008545:Melanoma / Q000000981:diagnostic imaging; D009374:Neoplasms, Experimental; D011877:Radionuclide Imaging; D012983:Soft Tissue Neoplasms / Q000000981:diagnostic imaging
chemical_list: D000621:Aminoisobutyric Acids; D002250:Carbon Radioisotopes; D006847:Hydrocarbons, Iodinated; D007202:Indicators and Reagents; C100049:2-aminoisobutyric acid; C014055:methyl iodide