Comment · Thu, September 18, 2014 · Ceretropic
Can 9-fluorenol/hydrafinil possibly intercalate/damage DNA?
Original post in this thread
inquilinekea · 6 points
It is a PAH that's not too distantly related from http://en.wikipedia.org/wiki/2-Acetylaminofluorene, which is a huge mutagen.
I'm currently trying to go through papers right now. The only real one I could find so far is http://www.sciencedirect.com/science/article/pii/S0300483X09003370# . It indicates that 9-fluorenol has some ability to interact with DNA, compared with the other PAHs (it's smaller than the others, but that doesn't say much since the others are really potent intercalating agents). But the research is early, so anything is still possible.
In atomic force microscopy, a clear morphological change of calf thymus DNA from linear type to condensation form was observed after binding with 9-hydroxyfluorene. The change is similar to the one observed with the DNA-intercalating electrochemical indicator, suggesting that 9-hydroxyfluorene binds with DNA also by intercalation
There's also this: http://www.ncbi.nlm.nih.gov/pubmed/23254141
9-fluorenol is used as a precursor for some intercalating agents (http://www.ncbi.nlm.nih.gov/pubmed/15028268 ) though this might not say much about its own potential
What they were answering
sowhatquestion · 1 points
This is good to know. My first thought when I read OP's post: if fluorenol could readily damage DNA, wouldn't it have manifested some symptoms in the rats it was given to? Since the chemical structure of DNA is either very similar or identical (?) across species.
u/MisterYouAreSoDumb · Ceretropic
Yes, it certainly would have. Also, Cephalon would not look at a substance that damages DNA. Minor structural changes to a molecule make drastic differences in toxicity. The one he posted is not even a minor change, but a major one. And it is metabolites of that other compound that cause the damage. The inability for 9-fluorenol to convert to anything close to those damaging compounds, means the equivocation is not warranted. The only similarity is the fluorene base structure.
Just look at the difference between amphetamine and 4-chloroamphetamine. One is safely used by people everywhere for ADHD, while the other is a potent neurotoxin. That is just the difference of a single chlorine.