BIOMAT Database Logo BIOMAT Database Logo

Radiosynthesis of 2'-deoxy-2'-[18F]-fluoro-5-methyl-1-beta-L-arabinofuranosyluracil ([18F]-L-FMAU) for PET. 2007

Uday Mukhopadhyay, and Ashutosh Pal, and Juri G Gelovani, and William Bornmann, and Mian M Alauddin
Department of Experimental Diagnostic Imaging, University of Texas M D Anderson Cancer Center, Houston, TX, USA.

Radiosynthesis of 2'-deoxy-2'-[(18)F]-fluoro-5-methyl-1-beta-L-arabinofuranosyluracil ([(18)F]-L-FMAU) is reported. Compound 1 was synthesized and converted to 2-triflate 2. Compound 3 was prepared from 2 using tetrabutylammonium[(18)F]fluoride, converted to 4, and then coupled with 5. The crude product was hydrolyzed, and purified by HPLC to obtain 7a. The radiochemical yield of [(18)F]-L-FMAU was 26% decay corrected (d.c.) in four runs with radiochemical purity >99% and specific activity 2200 mCi/micromol. The synthesis time was 3.3-3.5h from the end of bombardment (EOB).

UI MeSH Term Description Entries
D007553 Isotope Labeling Techniques for labeling a substance with a stable or radioactive isotope. It is not used for articles involving labeled substances unless the methods of labeling are substantively discussed. Tracers that may be labeled include chemical substances, cells, or microorganisms. Isotope Labeling, Stable,Isotope-Coded Affinity Tagging,Isotopically-Coded Affinity Tagging,Affinity Tagging, Isotope-Coded,Affinity Tagging, Isotopically-Coded,Isotope Coded Affinity Tagging,Labeling, Isotope,Labeling, Stable Isotope,Stable Isotope Labeling,Tagging, Isotope-Coded Affinity,Tagging, Isotopically-Coded Affinity
D005462 Fluorine Radioisotopes Unstable isotopes of fluorine that decay or disintegrate emitting radiation. F atoms with atomic weights 17, 18, and 20-22 are radioactive fluorine isotopes. Radioisotopes, Fluorine
D001086 Arabinofuranosyluracil A pyrimidine nucleoside formed in the body by the deamination of CYTARABINE. Ara-U,Arabinosyluracil,Arauridine,Sponguridine,Uracil Arabinofuranoside,Uracil Arabinoside,1-beta-D-Arabinofuranosyl Uracil,NSC 68928,1 beta D Arabinofuranosyl Uracil,Ara U,Arabinofuranoside, Uracil,Arabinoside, Uracil,Uracil, 1-beta-D-Arabinofuranosyl
D049268 Positron-Emission Tomography An imaging technique using compounds labelled with short-lived positron-emitting radionuclides (such as carbon-11, nitrogen-13, oxygen-15 and fluorine-18) to measure cell metabolism. It has been useful in study of soft tissues such as CANCER; CARDIOVASCULAR SYSTEM; and brain. SINGLE-PHOTON EMISSION-COMPUTED TOMOGRAPHY is closely related to positron emission tomography, but uses isotopes with longer half-lives and resolution is lower. PET Imaging,PET Scan,Positron-Emission Tomography Imaging,Tomography, Positron-Emission,Imaging, PET,Imaging, Positron-Emission Tomography,PET Imagings,PET Scans,Positron Emission Tomography,Positron Emission Tomography Imaging,Positron-Emission Tomography Imagings,Scan, PET,Tomography Imaging, Positron-Emission,Tomography, Positron Emission
D019275 Radiopharmaceuticals Compounds that are used in medicine as sources of radiation for radiotherapy and for diagnostic purposes. They have numerous uses in research and industry. (Martindale, The Extra Pharmacopoeia, 30th ed, p1161) Radiopharmaceutical

Related Publications

Uday Mukhopadhyay, and Ashutosh Pal, and Juri G Gelovani, and William Bornmann, and Mian M Alauddin
Microwave-assisted one-pot radiosynthesis of 2'-deoxy-2'-[18F]fluoro-5-methyl-1-β-d-arabinofuranosyluracil ([18F]-FMAU).
October 2012, Nuclear medicine and biology,
Uday Mukhopadhyay, and Ashutosh Pal, and Juri G Gelovani, and William Bornmann, and Mian M Alauddin
Improved synthesis of 2'-deoxy-2'-[18F]fluoro-5-methyl-1-β-D-arabinofuranosyluracil ([18F]FMAU).
January 2011, Current radiopharmaceuticals,
Uday Mukhopadhyay, and Ashutosh Pal, and Juri G Gelovani, and William Bornmann, and Mian M Alauddin
Automated synthesis of 2'-deoxy-2'-[18F]fluoro-5-methyl-1-β-D-arabinofuranosyluracil ([18F]-FMAU) using a one reactor radiosynthesis module.
February 2011, Nuclear medicine and biology,
Uday Mukhopadhyay, and Ashutosh Pal, and Juri G Gelovani, and William Bornmann, and Mian M Alauddin
[18F]-2'-Fluoro-5-methyl-1-beta-D-arabinofuranosyluracil (18F-FMAU) in prostate cancer: initial preclinical observations.
January 2012, Molecular imaging,
Uday Mukhopadhyay, and Ashutosh Pal, and Juri G Gelovani, and William Bornmann, and Mian M Alauddin
Journey of 2'-deoxy-2'-fluoro-5-methyl-1-β-D-arabinofuranosyluracil (FMAU): from Antiviral Drug to PET Imaging Agent.
January 2018, Current medicinal chemistry,
Uday Mukhopadhyay, and Ashutosh Pal, and Juri G Gelovani, and William Bornmann, and Mian M Alauddin
In vivo evaluation of 2'-deoxy-2'-[(18)F]fluoro-5-iodo-1-beta-D-arabinofuranosyluracil ([18F]FIAU) and 2'-deoxy-2'-[18F]fluoro-5-ethyl-1-beta-D-arabinofuranosyluracil ([18F]FEAU) as markers for suicide gene expression.
June 2007, European journal of nuclear medicine and molecular imaging,
Uday Mukhopadhyay, and Ashutosh Pal, and Juri G Gelovani, and William Bornmann, and Mian M Alauddin
Pharmacokinetics of 1-(2-deoxy-2-fluoro-beta-L-arabinofuranosyl)-5-methyluracil (L-FMAU) in rats.
September 1995, Pharmaceutical research,
Uday Mukhopadhyay, and Ashutosh Pal, and Juri G Gelovani, and William Bornmann, and Mian M Alauddin
Effect of Androgen on Normal Biodistribution of [18F]-2'-Fluoro-5-methyl-1-beta-D-arabinofuranosyluracil (18F-FMAU) in Athymic Non-tumor-bearing Male Mice.
February 2017, Anticancer research,
Uday Mukhopadhyay, and Ashutosh Pal, and Juri G Gelovani, and William Bornmann, and Mian M Alauddin
Pharmacokinetics of the thymidine analog 2'-fluoro-5-methyl-1-beta-D-arabinofuranosyluracil (FMAU) in tumor-bearing rats.
May 2004, Nuclear medicine and biology,
Uday Mukhopadhyay, and Ashutosh Pal, and Juri G Gelovani, and William Bornmann, and Mian M Alauddin
Synthesis and evaluation of 2'-deoxy-2'-18F-fluoro-5-fluoro-1-beta-D-arabinofuranosyluracil as a potential PET imaging agent for suicide gene expression.
December 2004, Journal of nuclear medicine : official publication, Society of Nuclear Medicine,
Copied contents to your clipboard!