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A faster track to the tools that track disease
Date:5/21/2014

Radioactivity is usually associated with nuclear fallout or comic-book spider bites, but in very small amounts it can be a useful tool for diagnosing diseases.

Small molecules containing a radioactive isotope of fluorine called "18F radiotracers" are used to detect and track certain diseases in patients. Once injected into the body, these molecules accumulate in specific targets, such as tumors, and can be visualized by their radioactive tag on a positron emission tomography (PET) scan. The 18F tags quickly decay so no radioactivity remains after about a day.

But there are only a few methods available for making 18F radiotracers. And existing methods tend to require harsh conditions that scramble the placement of a radiotracer's more delicate chemical bonds. Now, researchers at Princeton University report a route to 18F radiotracers that avoids that problem.

"It's the first method to do enantioselective carbon-18F bond formation," said principal investigator Abigail Doyle, a Princeton associate professor of chemistry.

Up to this point, radiotracers have mostly been evaluated as mixtures of enantiomers. Enantiomers are molecules that are completely identical in composition but the arrangement of atoms at the chiral center are mirror images, like how a person's left and right hands are similar, but oppositely oriented. A chiral center is an atom, usually carbon, which is connected to four different groups.

"We know in biology, small molecule interactions with enzymes often depend on the 3D properties of the molecule. Being able to prepare the enantiomers of a given chiral tracer, in order to optimize which tracer has the best binding and imaging properties could be really useful," Doyle said.

Doyle's research team developed a cobalt fluoride catalyst[18F](salen)CoFto install the radioactive fluoride through the ring-opening reaction of epoxides. Their method demonstrated excellent enantioselectivity for
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Contact: Tien Nguyen
tienn@princeton.edu
609-258-6523
Princeton University
Source:Eurekalert  

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