Synthesis of 8-[(18)F]fluoroguanine derivatives: in vivo probes for imaging gene expression with positron emission tomography.
A new method for the preparation of 8-[(18)F]fluoroguanine derivatives based on a direct radiofluorination reaction has been developed. The radiofluorination of ganciclovir (1a) with [(18)F]F(2) was carried out in absolute ethanol in the presence of tetraethylammonium hydroxide at room temperature to give 8-[(18)F]fluoroganciclovir (3a) in an approximately 1% radiochemical yield. Similarly, 8-[(18)F]fluoropenciclovir (3b), 8-[(18)F]fluoroacyclovir (3c), and 8-[(18)F]fluoroguanosine (3d) were synthesized from penciclovir (1b), acyclovir (1c), and guanosine (1d), respectively, using [(18)F]F(2). The structural analyses of the final products (3a, 3b, 3c, and 3d) were carried out after (18)F decay by (1)H, (13)C, and (19)F nuclear magnetic resonance and high resolution mass spectroscopy.
Namavari
M
M
Division of Nuclear Medicine, Department of Molecular and Medical Pharmacology, UCLA School of Medicine, Los Angeles, California 90095-6948, USA.
Barrio
J R
JR
Toyokuni
T
T
Gambhir
S S
SS
Cherry
S R
SR
Herschman
H R
HR
Phelps
M E
ME
Satyamurthy1
N
N
D000212:Acyclovir / Q000031:analogs & derivatives / Q000737:chemistry; D015774:Ganciclovir / Q000737:chemistry; D015870:Gene Expression; D006147:Guanine / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D006151:Guanosine / Q000737:chemistry; D007553:Isotope Labeling; D009682:Magnetic Resonance Spectroscopy; D019275:Radiopharmaceuticals / Q000138:chemical synthesis*; D014055:Tomography, Emission-Computed / Q000379:methods*
D019275:Radiopharmaceuticals; D006151:Guanosine; C053539:penciclovir; D006147:Guanine; D015774:Ganciclovir; D000212:Acyclovir