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 have shown promising anticancer results

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

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

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About ChemistDan

A second year PhD student based in Sheffield researching the reasons behind the molecular blinking phenomenon that allowed for the development of super-resolution optical microscopy.
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2 Responses to Teaching old drugs new tricks

  1. Hey Dan! It’s Al, enjoyed the fusion of medicine and chemistry! Lenalidomide (derived from Thalidomide) is currently in use as a treatment for Multiple Myeloma in the UK – don’t know if this is the one you are talking about but is interesting none the less. Need to meet up next time we are back home – hope you are well 🙂

  2. ChemistDan says:

    Hey! Did not know about Lenalidomide (should have researched more haha), but since it is so close in structure to thalidomide I guess it would have a similar problem in that it would be broken down in the body fairly quickly, so joining it to a curcumin fragment might make it even more effective? Just a guess! Definitely keen for another meet up but might not be home now until Christmas! Will let you know though

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