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Take Three Buckeyballs Before Meals

a tiny little pill
Blacksburg - Apr 10, 2002
Virginia Tech Ph.D. student Erick B. Iezzi has developed the first organic derivative of a metallofullerene. He has figured out how to make the metal-filled buckeyballs soluble, bringing them a step closer to biological applications, such as the delivery of medicine or radioactive material to a disease site.

The work was presented at the 223nd national meeting of the American Chemical Society, April 7-11 in Orlando.

Iezzi is working with chemistry professor Harry Dorn, known for having developed a method for inserting metal atoms inside of fullerenes, creating a novel family of molecules and the architecture for a new field of chemistry. These filled fullerenes (metallofullerenes) are now being developed as improved MRI reagents, and other non-medical applications.

But the idea of using the 60 to 80-atom hollow carbon molecules for drug delivery is what fired Iezzi's imagination. Thus, he has added biological functionality to a buckeyball. Iezzi has attached a chemical group known as "13C labeled 6,7-dimethoxyisochroman-3-one" to an 80-atom fullerene containing three scandium atoms anchored by a nitrogen atom (Sc3N@C80). That is, he attached an isochromanone derivative to a buckeyball.

"You heat the isochromanone until it loses carbon dioxide and attaches to the fullerene," Iezzi explains, as if he's making a sandwich instead of working with invisible molecules.

"These molecules are so novel that no one knew how they would react or where we would attach other molecules," he says. The aim is to attach water-soluble groups "such as peptides or hydrophilic chains, so we can get these molecules into the blood stream."

"It is a first step in making drugs," says Dorn.

Iezzi and Dorn presented their paper, "Novel derivatives of trimetallic nitride endohedral metallofullerenes for biological applications", April 9, as part of the Symposium on Biological Applications of Carbon Fullerenes and Nanotubes.

Dorn's research group has published two articles on organic funtionalization in the Journal of the American Chemical Society since December 2001, with Iezzi being the lead author on the first.

At the ACS, Iezzi will also discuss work pertaining to functionalizing nanotubes, which has not previously been reported. (Nanotubes are fullerenes that have been opened on two sides with additional atom groups added in the characteristic hexagon shape to form a hollow carbon tube.)

Iezzi did his undergraduate work at Duquesne University in Pittsburgh. He is from Jeannette, Pa.

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