skip to main content
OSTI.GOV title logo U.S. Department of Energy
Office of Scientific and Technical Information

Title: Synthesis of 2'-deoxy-2'-[.sup.18F]fluoro-5-methyl-1-B-D-arabinofuranosyluracil (.sup.18F-FMAU)

Patent ·
OSTI ID:1165432

The present invention relates to methods of synthesizing .sup.18F-FMAU. In particular, .sup.18F-FMAU is synthesized using one-pot reaction conditions in the presence of Friedel-Crafts catalysts. The one-pot reaction conditions are incorporated into a fully automated cGMP-compliant radiosynthesis module, which results in a reduction in synthesis time and simplifies reaction conditions. The one-pot reaction conditions are also suitable for the production of 5-substituted thymidine or cytidine analogs. The products from the one-pot reaction (e.g. the labeled thymidine or cytidine analogs) can be used as probes for imaging tumor proliferative activity. More specifically, these [.sup.18F]-labeled thymidine or cytidine analogs can be used as a PET tracer for certain medical conditions, including, but not limited to, cancer disease, autoimmunity inflammation, and bone marrow transplant.

Research Organization:
Univ. of Southern California, Los Angeles, CA (United States)
Sponsoring Organization:
USDOE
DOE Contract Number:
SC0002353
Assignee:
University of Southern California (Los Angeles, CA)
Patent Number(s):
8,912,319
Application Number:
13/183,924
OSTI ID:
1165432
Resource Relation:
Patent File Date: 2011 Jul 15
Country of Publication:
United States
Language:
English

References (14)

Imaging agents and methods for the preparation and use thereof patent March 1999
2'-deoxy-2'-fluoro-d-arabinofuranosyl pyrimidine nucleoside patent December 2001
Nucleosides for imaging and treatment applications patent January 2004
Improved synthesis of 2′-deoxy-2′-[18F]-fluoro-1-β-d-arabinofuranosyl-5-iodouracil ([18F]-FIAU) journal May 2010
The improved syntheses of 5-substituted 2′-[18F]fluoro-2′-deoxy-arabinofuranosyluracil derivatives ([18F]FAU, [18F]FEAU, [18F]FFAU, [18F]FCAU, [18F]FBAU and [18F]FIAU) using a multistep one-pot strategy journal July 2011
Automated synthesis of 2′-deoxy-2′-[18F]fluoro-5-methyl-1-β-d-arabinofuranosyluracil ([18F]-FMAU) using a one reactor radiosynthesis module journal February 2011
A fully automated synthesis of [ 18 F]-FEAU and [ 18 F]-FMAU using a novel dual reactor radiosynthesis module journal November 2009
Synthesis of 2′-deoxy-2′-[18F]fluoro-β-D-arabinofuranosyl nucleosides, [18F]FAU, [18F]FMAU, [18F]FBAU and [18F]FIAU, as potential PET agents for imaging cellular proliferation: synthesis of [18F]labelled FAU, FMAU, FBAU, FIAU journal April 2003
Synthesis of [18F]-labeled 2?-deoxy-2?-fluoro-5-methyl-1-?-D-arabinofuranosyluracil ([18F]-FMAU)
  • Alauddin, Mian M.; Conti, Peter S.; Fissekis, John D.
  • Journal of Labelled Compounds and Radiopharmaceuticals, Vol. 45, Issue 7 https://doi.org/10.1002/jlcr.549
journal January 2002
A general synthesis of 2?-deoxy-2?-[18F]fluoro-1-?-D-arabinofuranosyluracil and its 5-substituted nucleosides
  • Alauddin, Mian M.; Conti, Peter S.; Fissekis, John D.
  • Journal of Labelled Compounds and Radiopharmaceuticals, Vol. 46, Issue 4 https://doi.org/10.1002/jlcr.637
journal January 2003
Controlled microwave heating in modern organic synthesis: highlights from the 2004–2008 literature journal April 2009
Microwaving in F-18 Chemistry: Quirks and Tweaks book January 2006
Design and Optimization of Coin-Shaped Microreactor Chips for PET Radiopharmaceutical Synthesis journal February 2010
Rapid Prototyping of Microfluidic Systems in Poly(dimethylsiloxane) journal October 1998