9-[(3-[18F]-fluoro-1-hydroxy-2-propoxy)methyl]guanine ([18F]-FHPG): a potential imaging agent of viral infection and gene therapy using PET.

Abstract

A no-carrier-added synthesis of 9-[(3-[18F]-fluoro-1-hydroxy-2-propoxy)methyl]-guanine ([18F]-FHPG) is reported. The 9-[(1,3-dihydroxy-2-propoxy)methyl)guanine (DHPG) was converted to 9-[N2,O-bis(methoxytrityl)-3-(tosyl)-2-propoxy-methyl]guanine by treatment with methoxytrityl chloride followed by tosylation. The tosylate was reacted with [18F]-KF in the presence of kryptofix 2.2.2. to produce the 3-fluoro-N2-O-bis-(methoxytrityl) derivative. Removal of the methoxytrityl protecting groups by acid hydrolysis produced [18F]-FHPG. The labeled product was purified by HPLC on a reverse-phase C18 column, and eluted in 9 min with a mobile phase of 5% acetonitrile in water. The radiochemical yield was 7-17%, with an average of 10% in 10 runs (corrected for decay to EOB). The radiochemical purity was > 99%, and specific activities with an average of 526 mCi/mumol were obtained. The synthesis time was 70-80 min, including HPLC purification and determination of radiochemical purity and specific activity.

• Authors: M M Alauddin, P S Conti, S M Mazza, F M Hamzeh, J R Lever
• Journal: Nuclear medicine and biology (Nucl Med Biol) Vol. 23 Issue 6 Pg. 787-92 (Aug 1996) ISSN: 0969-8051 [Print] United States
• PMID: 8940722 (Publication Type: Journal Article)

Chemical References

• 9-((3-fluoro-1-hydroxy-2-propoxy)methyl)guanine
• Antiviral Agents
• Fluorine Radioisotopes
• Ganciclovir

Topics

• Antiviral Agents (chemistry, pharmacokinetics)
• Chromatography, High Pressure Liquid
• Fluorine Radioisotopes (chemistry)
• Ganciclovir (analogs & derivatives, chemical synthesis, pharmacokinetics)
• Genetic Therapy
• Isotope Labeling
• Radiochemistry (methods)
• Tomography, Emission-Computed