Celebrate Princeton Invention 2016: Selective fluorination of drug and PET imaging molecules

Invention Selective fluorination of drug and PET imaging molecules

Inventor John Groves, the Hugh Stott Taylor Chair of Chemistry

What it does The invention is a method of adding fluorine to molecules for use in imaging and therapeutics. Fluorinated molecules are used as tracers that can detect cancer during positron emission tomography (PET) scans. Fluorine also can be added to drugs where the replacement of select hydrogen atoms with fluorine atoms can improve a drug’s potency and potentially reduce side effects. Until now, however, fluorination involved using toxic and complicated fluorinating agents and a multistep process.

Groves and his collaborators invented new catalysts that fluorinate molecules using safe-to-handle fluoride salts in a single step. The technique is clean, fast and inexpensive, and can be used to generate imaging molecules, drug candidates and new agricultural chemicals.

The method involves the use of a manganese-based catalyst that adds fluorine to sites on molecules that previously were inaccessible by other techniques. The catalyst adds fluorine in place of hydrogen in benzylic carbon-hydrogen bonds.

The new technique can be used to produce radioactive 18F isotopes for use as tracer molecules — which emit particles called positrons — that are detectable using PET scanning and can pinpoint the locations of cancer in the body. The method could also be used to add 18F to various molecules and then test to see if certain attributes — such as specificity for cancer or half-life — are improved.

Contributors Wei Liu, who earned his Ph.D. in chemistry in 2014 and is now a research associate at the University of California-Berkeley, and Xiongyi Huang, who earned his Ph.D. in chemistry in 2016 and is now a research associate at the California Institute of Technology.

Development status Patent protection is pending. Princeton is seeking outside interest for further development of this technology.

Funding sources U.S. Department of Energy and the National Science Foundation