Molecules: You'd better learn to live with them.
As I mentioned in the previous entries on HF, mercury fulminate, and phosphine, I really like Breaking Bad.
As an astute commenter noted yesterday, they sometimes make some mistakes:
Like pentavalent carbon (green dots).
But they usually do a pretty good job and even sneak in some real chemistry:
See Walter fill orbitals!
During Walter's chemo last week, you saw some red stuff flowing into his IV. This was likely doxorubicin:
Doxorubicin is a DNA-binding molecule, like proflavine, ethidium, or paraquat.
Proflavine and ethidium are intercalators - they slip between the bases in DNA. Paraquat is a groove binder - it nestles itself in the crevice between the two strands of DNA. Doxorubicin is a little bit of both. The central aromatic bit intercalates a base pair, and the amino sugar hits the groove.
DNA-binding drugs are common in cancer chemotherapy: Cisplatin is yet another. The general toxicity of these compounds is why chemo is such a miserable experience, and medchem is always on the lookout for new targets. Another class of ligands targets DNA, but only a special structure that plays some roles in cancer called a quadruplex. The hope is that such strategies will make for less-toxic treatments.
Interestingly, that positively charged sugar on doxorubicin binds in the same places metal ions bind in the groove.
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Comments
I'll be a tad bit more forgiving towards "Breaking Bad" for the pentavalent carbons than I was towards the ACS brochure cover that was making the rounds awhile back. :)
Posted by: benji | March 7, 2008 6:18 PM
There seems to be a green spot next to every instance of a pentavalent carbon, so maybe that's meant to represent the charge?
Anyway, cracking show and the fact that the main character has been doing reactions that I've been doing a lot of recently (woo! reductive aminations!) only adds to the fun.
Posted by: Michemal | March 11, 2008 11:40 AM