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A Transmetalation Reaction Enables the Synthesis of [(18)F]5-Fluorouracil from [(18)F]Fluoride for Human PET Imaging.

Hoover AJ, Lazari M, Ren H, Narayanam MK, Murphy JM, van Dam RM, Hooker JM, Ritter T - Organometallics (2016)

Bottom Line: The application of transition metal mediators has enabled impactful (18)F-fluorination methods, but to date none of these reactions have been applied to produce a human-injectable PET tracer.The first preparation of nickel σ-aryl complexes by transmetalation from arylboronic acids or esters was developed and enabled the synthesis of the [(18)F]5-fluorouracil precursor.Routine production of >10 mCi doses of [(18)F]5-fluorouracil was accomplished with a new instrument for azeotrope-free [(18)F]fluoride concentration in a process that leverages the tolerance of water in nickel-mediated (18)F-fluorination.

View Article: PubMed Central - PubMed

Affiliation: Department of Chemistry and Chemical Biology, Harvard University , 12 Oxford Street, Cambridge, Massachusetts 02138, United States.

ABSTRACT

Translation of new (18)F-fluorination reactions to produce radiotracers for human positron emission tomography (PET) imaging is rare because the chemistry must have useful scope and the process for (18)F-labeled tracer production must be robust and simple to execute. The application of transition metal mediators has enabled impactful (18)F-fluorination methods, but to date none of these reactions have been applied to produce a human-injectable PET tracer. In this article we present chemistry and process innovations that culminate in the first production from [(18)F]fluoride of human doses of [(18)F]5-fluorouracil, a PET tracer for cancer imaging in humans. The first preparation of nickel σ-aryl complexes by transmetalation from arylboronic acids or esters was developed and enabled the synthesis of the [(18)F]5-fluorouracil precursor. Routine production of >10 mCi doses of [(18)F]5-fluorouracil was accomplished with a new instrument for azeotrope-free [(18)F]fluoride concentration in a process that leverages the tolerance of water in nickel-mediated (18)F-fluorination.

No MeSH data available.


Related in: MedlinePlus

Synthesisof Nickel(II) σ-Aryl Complexes by Transmetalationfrom Boronic Acids and EstersYields of isolatedproducts aregiven.Synthesized fromarylboronic acid.Synthesizedfrom the arylboronic ester of 2,2-dimethyl-1,3-propanediol.
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sch4: Synthesisof Nickel(II) σ-Aryl Complexes by Transmetalationfrom Boronic Acids and EstersYields of isolatedproducts aregiven.Synthesized fromarylboronic acid.Synthesizedfrom the arylboronic ester of 2,2-dimethyl-1,3-propanediol.


A Transmetalation Reaction Enables the Synthesis of [(18)F]5-Fluorouracil from [(18)F]Fluoride for Human PET Imaging.

Hoover AJ, Lazari M, Ren H, Narayanam MK, Murphy JM, van Dam RM, Hooker JM, Ritter T - Organometallics (2016)

Synthesisof Nickel(II) σ-Aryl Complexes by Transmetalationfrom Boronic Acids and EstersYields of isolatedproducts aregiven.Synthesized fromarylboronic acid.Synthesizedfrom the arylboronic ester of 2,2-dimethyl-1,3-propanediol.
© Copyright Policy - editor-choice
Related In: Results  -  Collection

License
Show All Figures
getmorefigures.php?uid=PMC4829938&req=5

sch4: Synthesisof Nickel(II) σ-Aryl Complexes by Transmetalationfrom Boronic Acids and EstersYields of isolatedproducts aregiven.Synthesized fromarylboronic acid.Synthesizedfrom the arylboronic ester of 2,2-dimethyl-1,3-propanediol.
Bottom Line: The application of transition metal mediators has enabled impactful (18)F-fluorination methods, but to date none of these reactions have been applied to produce a human-injectable PET tracer.The first preparation of nickel σ-aryl complexes by transmetalation from arylboronic acids or esters was developed and enabled the synthesis of the [(18)F]5-fluorouracil precursor.Routine production of >10 mCi doses of [(18)F]5-fluorouracil was accomplished with a new instrument for azeotrope-free [(18)F]fluoride concentration in a process that leverages the tolerance of water in nickel-mediated (18)F-fluorination.

View Article: PubMed Central - PubMed

Affiliation: Department of Chemistry and Chemical Biology, Harvard University , 12 Oxford Street, Cambridge, Massachusetts 02138, United States.

ABSTRACT

Translation of new (18)F-fluorination reactions to produce radiotracers for human positron emission tomography (PET) imaging is rare because the chemistry must have useful scope and the process for (18)F-labeled tracer production must be robust and simple to execute. The application of transition metal mediators has enabled impactful (18)F-fluorination methods, but to date none of these reactions have been applied to produce a human-injectable PET tracer. In this article we present chemistry and process innovations that culminate in the first production from [(18)F]fluoride of human doses of [(18)F]5-fluorouracil, a PET tracer for cancer imaging in humans. The first preparation of nickel σ-aryl complexes by transmetalation from arylboronic acids or esters was developed and enabled the synthesis of the [(18)F]5-fluorouracil precursor. Routine production of >10 mCi doses of [(18)F]5-fluorouracil was accomplished with a new instrument for azeotrope-free [(18)F]fluoride concentration in a process that leverages the tolerance of water in nickel-mediated (18)F-fluorination.

No MeSH data available.


Related in: MedlinePlus