Teaching old drugs new tricks

Thalidomide. If you studied chemistry to A level you will know that this is the name of a drug which was once prescribed as a sedative and to pregnant women to prevent morning sickness in the 1950s. It was, however, banned for use because of a property of thalidomide that was, at the time, overlooked – its stereochemistry (the way its atoms are arranged in 3D space).

The chemical structure of Thalidomide. For those unfamiliar with stick drawings, every corner is a carbon.

 

The image above shows thalidomide’s structure. The wiggly line between the carbon on the 6-membered ring and the nitrogen on the 5-membered ring indicates that there are two ways to arrange the molecule in 3D space, i.e. if the 5-membered ring is in the plane of your computer screen, the 6-membered ring could either be seen to be angled into or out of the screen. It was discovered that one of these arrangements was responsible for birth defects amongst children whose mother had taken the drug during pregnancy.

BUT it has recently been discovered that combining thalidomide with a yellow pigment from turmeric (curcumin) produces a molecule which can kill multiple myeloma cells – the second most common blood cancer! The curcumin section (which also shows anti-cancer properties) ensures that the thalidomide section doesn’t degrade in the body, and the thalidomide section makes the curcumin section more water soluble. The hybrid compound has higher toxicity against cancer cells than thalidomide or curcumin alone or any combination of the two.

The new hybrid compounds have not yet reached human clinical trials,  but have shown promising activity against myeloma and prostate cancer in animal models.

One of the cucumin-thalidomide hybrids which has shown promising anticancer results

Reference: Org. Biomol. Chem., 2013, 11, 4757-4763. DOI: 10.1039/C3OB40595H

For more of my chemistry based articles, here is a link to my personal blog: http://danthechemist.wordpress.com/

Dan Jenkinson

Final year chemistry student at the University of Sheffield, wanting to share my love for science with the world.

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