Researchers at Dartmouth College have developed a technique to produce synthetic steroids. The process, published in Nature Chemistry yesterday, facilitates access to rare, mirror-image isomers of naturally occurring steroid structures, they report.
"This is a fundamentally new molecular strategy for steroid construction," said Glenn Micalizio, the New Hampshire Professor of Chemistry at Dartmouth. "This technology allows the preparation of either mirror-image isomer with equal ease, but with unprecedented efficiency."
According to researchers, molecules based on the unnatural mirror image isomer of steroids form the foundation of a vast collection of underexplored potential medicines. While these compounds share the basic drug-like physical properties of the natural class, they boast complementary 3D structures with broad potential in the clinic.
The new process, developed in the Micalizio Laboratory at Dartmouth, produces steroidal structures of either enantiomer. Using inexpensive and abundant starting materials, the new class of synthetics can be produced in as few as five chemical steps.
The advance is based on a chemical reaction discovered in 2014 by Micalizio that forges half of the steroid structure.
To show the value of the streamline process, the research team demonstrated that one of the molecules prepared in their initial study has potent and selective growth inhibitory properties against three different human cancer cell lines.
"We're not just saying these things have potential," said Micalizio, "here is one example from the relatively small number of compounds that we produced that proves their potential value as anti-cancer agents."