skip to main content
DOE Patents 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)

Abstract

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.

Inventors:
; ;
Issue Date:
Research Org.:
Univ. of Southern California, Los Angeles, CA (United States)
Sponsoring Org.:
USDOE
OSTI Identifier:
1165432
Patent Number(s):
8912319
Application Number:
13/183,924
Assignee:
University of Southern California (Los Angeles, CA)
Patent Classifications (CPCs):
C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07H - SUGARS
C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07B - GENERAL METHODS OF ORGANIC CHEMISTRY
DOE Contract Number:  
SC0002353
Resource Type:
Patent
Resource Relation:
Patent File Date: 2011 Jul 15
Country of Publication:
United States
Language:
English
Subject:
60 APPLIED LIFE SCIENCES; 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats

Li, Zibo, Cai, Hancheng, and Conti, Peter S. Synthesis of 2'-deoxy-2'-[.sup.18F]fluoro-5-methyl-1-B-D-arabinofuranosyluracil (.sup.18F-FMAU). United States: N. p., 2014. Web.
Li, Zibo, Cai, Hancheng, & Conti, Peter S. Synthesis of 2'-deoxy-2'-[.sup.18F]fluoro-5-methyl-1-B-D-arabinofuranosyluracil (.sup.18F-FMAU). United States.
Li, Zibo, Cai, Hancheng, and Conti, Peter S. Tue . "Synthesis of 2'-deoxy-2'-[.sup.18F]fluoro-5-methyl-1-B-D-arabinofuranosyluracil (.sup.18F-FMAU)". United States. https://www.osti.gov/servlets/purl/1165432.
@article{osti_1165432,
title = {Synthesis of 2'-deoxy-2'-[.sup.18F]fluoro-5-methyl-1-B-D-arabinofuranosyluracil (.sup.18F-FMAU)},
author = {Li, Zibo and Cai, Hancheng and Conti, Peter S},
abstractNote = {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.},
doi = {},
journal = {},
number = ,
volume = ,
place = {United States},
year = {2014},
month = {12}
}

Patent:

Save / Share:

Works referenced in this record:

Improved synthesis of 2′-deoxy-2′-[18F]-fluoro-1-β-d-arabinofuranosyl-5-iodouracil ([18F]-FIAU)
journal, May 2010


A fully automated synthesis of [ 18 F]-FEAU and [ 18 F]-FMAU using a novel dual reactor radiosynthesis module
journal, November 2009


Synthesis of [18F]-labeled 2?-deoxy-2?-fluoro-5-methyl-1-?-D-arabinofuranosyluracil ([18F]-FMAU)
journal, January 2002

  • 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

A general synthesis of 2?-deoxy-2?-[18F]fluoro-1-?-D-arabinofuranosyluracil and its 5-substituted nucleosides
journal, January 2003

  • 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

Controlled microwave heating in modern organic synthesis: highlights from the 2004–2008 literature
journal, April 2009


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