Syntheses of F-18 labeled fluoroalkyltyrosine derivatives and their biological evaluation in rat bearing 9L tumor.

Abstract

We hereby report the synthesis of four fluorine-18 labeled tyrosine derivatives, 3-(2-[(18)F]fluoroethyl)tyrosine ([(18)F]1, [(18)F]ortho-FET), 3-(3-[(18)F]fluoropropyl)tyrosine ([(18)F]2, [(18)F]ortho-FPT) O-methyl-[3-(2-[(18)F]fluoroethyl)]tyrosine ([(18)F]3, [(18)F]MFET), and O-methyl-[3-(3-[(18)F]fluoropropyl)]tyrosine ([(18)F]4, [(18)F]MFPT). The fluorine-18 labeled tyrosine derivatives were prepared by the displacement reaction of the ethyl and propyl tosylates with K[(18)F]/K2.2.2 in acetonitrile under no-carrier-added (NCA) conditions, followed by hydrolysis with 4N HCl. The biological properties of labeled compounds were evaluated in rats bearing 9L tumor after an intravenous injection and PET image was obtained. The tumor/blood and tumor/brain ratios were 2.06, 2.92 for [(18)F]1, 2.25, 4.05 for [(18)F]2, 2.88, 1.90 for [(18)F]3, and 2.00, 2.60 for [(18)F]4 at 60 min post injection, respectively. The PET image showed localized accumulation of PET tracers in 9L glioma of the rat.

• Authors: Byung Seok Moon, Tae Sup Lee, Kyo Chul Lee, Gwang Il An, Gi Jeong Cheon, Sang Moo Lim, Chang Woon Choi, Dae Yoon Chi, Kwon Soo Chun
• Journal: Bioorganic & medicinal chemistry letters (Bioorg Med Chem Lett) Vol. 17 Issue 1 Pg. 200-4 (Jan 01 2007) ISSN: 0960-894X [Print] England
• PMID: 17035015 (Publication Type: Journal Article, Research Support, Non-U.S. Gov't)

Chemical References

• Fluorine Radioisotopes
• Radiopharmaceuticals
• Tyrosine

Topics

• Animals
• Brain Neoplasms (metabolism)
• Fluorine Radioisotopes (chemistry)
• Glioma (metabolism)
• Radiopharmaceuticals (chemical synthesis, chemistry, pharmacokinetics)
• Rats
• Rats, Inbred F344
• Tissue Embedding
• Tyrosine (analogs & derivatives)