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Turkman, Nashaat; Pal, Ashutosh; Tong, William P.; Gelovani, Juri G.; Alauddin, Mian M.
Journal of labelled compounds & radiopharmaceuticals, 15 May 2011, Letnik: 54, Številka: 5Journal Article
Introduction: The hepatocellular carcinoma–intestine–pancreas and pancreatitis‐associated proteins, also known as lactose‐binding protein, is upregulated in peritumoral pancreatic tissue. Previously, we reported ethyl‐β‐D‐galactopyranosyl‐(1,4′)‐2′‐deoxy‐2′‐18Ffluoro‐β‐D‐glucopyranoside (Et‐18F‐FDL), a radiofluorinated lactose analog for positron emission tomography (PET) of small pancreatic carcinomas in mice. However, synthesis of the precursor for Et‐18F‐FDL involves 11 steps, which is quite lengthy, and produces overall low yields. Here, we report on synthesis and radiolabeling of another analog of lactose, the 1′‐18Ffluoroethyl‐β‐D‐lactose for PET imaging of pancreatic carcinomas. Methods: Two precursor compounds, 1′‐bromoethyl‐2′,3′,6′,2,3,4,6‐hepta‐O‐acetyl‐β‐D‐lactose 4, and 1′‐p‐toluenesulfonylethyl‐2′,3′,6′,2,3,4,6‐hepta‐O‐acetyl‐β‐D‐lactose 5, were synthesized in two and three steps, respectively; then, cold fluorination and radiofluorination of these precursors were performed. The reaction mixture was passed through a silica gel Sep‐pack cartridge, eluted with EtOAc, and the 1′‐18Ffluoroethyl‐2′,3′,6′,2,3,4,6‐hepta‐O‐acetyl‐β‐D‐lactose (18F‐6) purified by HPLC. After hydrolysis of the protecting groups, the 1′‐18Ffluoroethyl‐β‐D‐lactose 18F‐7 was neutralized, diluted with saline, filtered through a sterile Millipore filter, and analyzed by radio‐TLC. Results: The average decay‐corrected radiochemical yield was 9% (n = 7) with>99% radiochemical purity and specific activity of 55.5 GBq/µmol. Conclusion: A new analog of lactose, 1′‐18Ffluoroethyl‐β‐D‐lactose, has been synthesized in good yields, with high purity and high specific activity suitable for PET imaging of early pancreatic carcinomas. Copyright © 2011 John Wiley & Sons, Ltd. We reported Et‐18FFDL for PET imaging of small pancreatic carcinomas in mice. Synthesis of the precursor for Et‐18FFDL involves 11 steps, which is quite lengthy. We report now radiosynthesis of another analog of lactose for PET. Two precursors were synthesized in two and three steps, respectively. Radiofluorination of these precursors produced an intermediate product, which was purified and hydrolyzed to obtain the final product. The newly synthesized analog may be suitable for PET imaging of early pancreatic carcinomas. Copyright © 2011 John Wiley & Sons, Ltd.
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