Radiosynthesis and biological evaluation of L and D S-(3-[18F]Fluoropropyl)-homocysteine for tumor imaging using positron emission tomography

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dc.contributor.authorBourdier, Ten_AU
dc.contributor.authorShepherd, Ren_AU
dc.contributor.authorBerghofer, PJen_AU
dc.contributor.authorJackson, TWen_AU
dc.contributor.authorFookes, CJRen_AU
dc.contributor.authorDenoyer, Den_AU
dc.contributor.authorDorow, DSen_AU
dc.contributor.authorGreguric, Ien_AU
dc.contributor.authorGrégoire, MCen_AU
dc.contributor.authorHicks, RJen_AU
dc.contributor.authorKatsifis, Aen_AU
dc.date.accessioned2014-01-22T23:57:53Zen_AU
dc.date.available2014-01-22T23:57:53Zen_AU
dc.date.issued2011-03-24en_AU
dc.date.statistics2014-01-23en_AU
dc.description.abstractInterest 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.en_AU
dc.identifier.citationBourdier, T., Shepherd, R., Berghofer, P., Jackson, T., Fookes, C. J. R., Denoyer, D., Dorow, D. S., Greguric, I., Grégoire, 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. doi:10.1021/jm101513qen_AU
dc.identifier.govdoc5280en_AU
dc.identifier.issn0022-2623en_AU
dc.identifier.issue6en_AU
dc.identifier.journaltitleJournal of Medicinal Chemistryen_AU
dc.identifier.pagination1860-1870en_AU
dc.identifier.urihttp://dx.doi.org/10.1021/jm101513qen_AU
dc.identifier.urihttp://apo.ansto.gov.au/dspace/handle/10238/5178en_AU
dc.identifier.volume54en_AU
dc.language.isoenen_AU
dc.publisherAmericam Chemical Societyen_AU
dc.subjectHomocysteineen_AU
dc.subjectProteinsen_AU
dc.subjectPositron computed tomographyen_AU
dc.subjectIn vivoen_AU
dc.subjectTyrosineen_AU
dc.subjectImpuritiesen_AU
dc.titleRadiosynthesis and biological evaluation of L and D S-(3-[18F]Fluoropropyl)-homocysteine for tumor imaging using positron emission tomographyen_AU
dc.typeJournal Articleen_AU
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