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Please use this identifier to cite or link to this item: http://apo.ansto.gov.au/dspace/handle/10238/5178

Title: Radiosynthesis and biological evaluation of L and D S-(3-[18F]Fluoropropyl)-homocysteine for tumor imaging using positron emission tomography.
Authors: Bourdier, T
Shepherd, R
Berghofer, P
Jackson, T
Fookes, C J
Denoyer, D
Dorow, D
Greguric, I
Gregoire, M-C
Hicks, R J
Katsifis, A
Keywords: HOMOCYSTEINE
PROTEINS
POSITRON COMPUTED TOMOGRAPHY
IN VIVO
TYROSINE
IMPURITIES
Issue Date: 24-Mar-2011
Publisher: Americam Chemical Society
Citation: Bourdier, T., Shepherd, R., Berghofer, P., Jackson, T., Fookes, C. J., Denoyer, D., Dorow, D., Greguric, I., Gregoire, M-C., Hicks, R. J., & Katsifis, A. Radiosynthesis and biological evaluation of L and D S-(3-[18F]Fluoropropyl)-homocysteine for tumor imaging using positron emission tomography. (2011). Journal of Medicinal Chemistry, 54 (6), 1860-1870.
Abstract: Interest in radiolabeled amino acids for metabolic imaging of cancer and limitations with [11C]methionine has prompted the development of a new 18F-labeled methionine derivative S-(3-[18F]fluoropropyl)homocysteine ([18F]FPHCys). The L and D enantiomers of [18F]FPHCys were prepared from their respective protected S-(3-tosyloxypropyl)homocysteine precursors 1 by [18F]fluoride substitution using K2.2.2 and potassium oxalate, followed by acid hydrolysis on a Tracerlab FXFN synthesis module. [18F]-L-FPHCys and [18F]-D-FPHCys were isolated in 20 ( 5% radiochemical yield and >98% radiochemical and enantiomeric purity in 65 min. Competitive uptake studies in A375 and HT29 tumor cells suggest that L- and D-[18F]FPHCys are taken up by the L-transporter system. [18F]-L-FPHCys and [18F]-D-FPHCys displayed good stability In Vivo without incorporation into protein at least 2 h postinjection. Biodistribution studies demonstrate good uptake in A375 tumor-bearing rodents with tumor to blood ratios of 3.5 and 5.0 for [18F]-L-FPHCys and [18F]-D-FPHCys, respectively, at 2 h postinjection. © 2011, American Chemical Society.
URI: http://dx.doi.org/10.1021/jm101513q
http://apo.ansto.gov.au/dspace/handle/10238/5178
ISSN: 0022-2623
Appears in Collections:Journal Articles

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