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

Mian M. Alauddin, Peter S. Conti, Samuel M. Mazza, Fayez M. Hamzeh, John R. Lever

Research output: Contribution to journalArticle

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/μmol were obtained. The synthesis time was 70-80 min, including HPLC purification and determination of radiochemical purity and specific activity.

Original languageEnglish (US)
Pages (from-to)787-792
Number of pages6
JournalNuclear Medicine and Biology
Volume23
Issue number6
DOIs
StatePublished - Aug 1996

Fingerprint

Viral Genes
Guanine
Virus Diseases
Genetic Therapy
High Pressure Liquid Chromatography
Chlorides
Hydrolysis
Acids
Water
9-((3-fluoro-1-hydroxy-2-propoxy)methyl)guanine
Therapeutics
acetonitrile

Keywords

  • DHPG
  • ganciclovir
  • gene therapy
  • viral infection

ASJC Scopus subject areas

  • Cancer Research
  • Molecular Medicine
  • Radiology Nuclear Medicine and imaging

Cite this

Synthesis of 9-[(3-[18F]-fluoro-1-hydroxy-2-propoxy)methyl]guanine ([18F]-FHPG) : A potential imaging agent of viral infection and gene therapy using PET. / Alauddin, Mian M.; Conti, Peter S.; Mazza, Samuel M.; Hamzeh, Fayez M.; Lever, John R.

In: Nuclear Medicine and Biology, Vol. 23, No. 6, 08.1996, p. 787-792.

Research output: Contribution to journalArticle

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