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

doi:10.1016/j.bmcl.2011.02.065

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

Bioorg Med Chem Lett. 2011 Apr 15;21(8):2437-40. doi: 10.1016/j.bmcl.2011.02.065. Epub 2011 Feb 18.

Authors

Koichi Kato¹, Atsushi B Tsuji, Tsuneo Saga, Ming-Rong Zhang

Affiliation

¹ Department of Molecular Probes, National Institute of Radiological Sciences, 4-9-1 Anagawa, Inage-ku, Chiba 263-8555, Japan. katok@nirs.go.jp

PMID: 21392981
DOI: 10.1016/j.bmcl.2011.02.065

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).

MeSH terms

Aminoisobutyric Acids / chemical synthesis
Aminoisobutyric Acids / chemistry*
Animals
Carbon Radioisotopes / chemistry
Disease Models, Animal
Mice
Neoplasms / diagnostic imaging*
Positron-Emission Tomography
Radiopharmaceuticals / chemical synthesis
Radiopharmaceuticals / chemistry*

Substances

Aminoisobutyric Acids
Carbon Radioisotopes
Radiopharmaceuticals
2-aminoisobutyric acid