It’s amazing how the same molecule of a drug can show a profound effect when the only alteration is the spatial positioning of functional groups. In regards to Thalidomide, the sedative effects where exclusively reserved for the S-isomer. Conversely, the R-isomer was the culprit that impedes angiogenesis, consequently resulting in monstrous malformations. Unbeknownst at the time, the trade off for having a pleasant pregnancy was to have children born with anywhere from reduced or fused limbs to a Cyclops and Siamese twins.
It was also found that certain types of malformations where more prevalent in specific ethnicities due to the chirality. Different ethnicities of people metabolize chemicals at differing rates, so what may apply to one ethnic group may not apply to another. However it is still unclear what the exact mechanism of Thalidomide is. Nevertheless, what is known suggest that Thalidomide inserts into DNA at guanine sites accordingly changing the final proteins. The chirality of Thalidomide makes this molecule’s interaction with the enzymes very obnoxiously apparent in the many communities it encounters.
However, the S-isomer has a variety of other functions, many of which are still being explored. With the correct precautions, Thalidomide can be used therapeutically to treat the symptoms of other diseases. Thalidomide’s effective anti-inflammatory agent has made it a good contender in treating patients suffering from leprosy. In addition to treating leprosy, Thalidomide is also a known antiangiogenic and immunomodulatory mediator for cancer patients. It can also inhibit the growth of the HIV virus in vitro! Seemingly, from the S-isomer perspective, Thalidomide could function as a “wonder” drug.
Thalidomide has one chiral center and comes as a racemic mixture. Thalidomide’s two enantiomers can also undergo inversion into each other. It was seen that the rates of inversion increased with pH over the range of 7.0 - 7.5. In an in vitro experiment carried out by Eriksson, his findings supported the belief that chiral inversions take place primarily in the blood. Knowing the various affects that Thalidomide can have once taken it is important for drug companies to be able to distinguish between the two enantiomers.
From the perspective of the author who insists on manufacturing progeny one day, it is terrifying to consider the possibility of delivering an unhealthy child. It is emotionally taxing to know that your child may not have as high of a chance at survival outside the womb because of something you did. Since it seems that drugs have taken over
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