Bioorganic & Medicinal Chemistry Letters 2011-04-15

An efficient and expedient method for the synthesis of 11C-labeled α-aminoisobutyric acid: a tumor imaging agent potentially useful for cancer diagnosis.

Koichi Kato, Atsushi B Tsuji, Tsuneo Saga, Ming-Rong Zhang

Index: Bioorg. Med. Chem. Lett. 21 , 2437-2440, (2011)

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Abstract

We describe the synthesis of (11)C-labeled α-aminoisobutyric acid 2 from iodo[(11)C]methane and methyl N-(diphenylmethylen)-d,l-alaniate (5). The tetrabutylammonium fluoride (TBAF)-promoted α-[(11)C]methylation of sterically hindered analog 5 was a key step in our synthesis process. Total radiochemical conversion of 2 was high and a remote-controlled synthesis was carried out. A comparative tumor positron emission tomography (PET) imaging study using the same model mouse showed higher uptake of 2 than with (11)C-labeled methionine and [(18)F] fluorodeoxyglucose (FDG).Copyright © 2011 Elsevier Ltd. All rights reserved.