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

Nucl Med Biol. 1996 Aug;23(6):787-92. doi: 10.1016/0969-8051(96)00075-3.

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.

MeSH terms

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

Substances

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