9-[(3-[18F]-fluoro-1-hydroxy-2-propoxy)methyl]guanine ([18F]-FHPG): a potential imaging agent of viral infection and gene therapy using PET.
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.
Alauddin
M M
MM
PET Imaging Science Center, Department of Radiology, University of Southern California, Los Angeles 90033, USA.
Conti
P S
PS
Mazza
S M
SM
Hamzeh
F M
FM
Lever
J R
JR
D000998:Antiviral Agents / Q000737:chemistry* / Q000493:pharmacokinetics; D002851:Chromatography, High Pressure Liquid; D005462:Fluorine Radioisotopes / Q000737:chemistry*; D015774:Ganciclovir / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000493:pharmacokinetics; D015316:Genetic Therapy; D007553:Isotope Labeling; D011854:Radiochemistry / Q000379:methods; D014055:Tomography, Emission-Computed
C104325:9-((3-fluoro-1-hydroxy-2-propoxy)methyl)guanine; D000998:Antiviral Agents; D005462:Fluorine Radioisotopes; D015774:Ganciclovir