Question

Does anyone happen to have any good resources for the metabolism of polycyclic aromatic hydrocarbons? Specifically benzo[b]fluoranthene? I'm having issues finding good information about the metabolites of BbF.

Answer 1

Thanks, the wiki pages aren't particularly useful- the EPA one, I've read, same with the pubmed abstract. There are a few papers based on the pub med one that I've read as well--most everything seems to be conjecture as to the specific metabolism, though.

Answer 2

have you been checking Reaxys for the specific molecule?

Answer 3

I've actually never heard of Reaxys, I should have access through my school though--I'll have to look in to that, thanks.

Answer 4

Can also suggest SciFinder, as reaxys is a bit more for chemists...

Answer 5

As a matter of fact I just list the databases I use:
Reaxys, SciFinder and Web of Science.
(Citation Databases so no need to worry :) )

Answer 6

Polycyclic aromatic hydrocarbons require a multistep metabolic activation by specific enzymes. The enzyme system primarily responsible for PAH metabolism is the mixed-function oxidase system, which requires NADH or NADPH and molecular oxygen to convert the nonpolar PAHs into the polar hydroxy derivatives and arene oxides. The first reaction is an epoxidation. With benzo(a)pyrene, the product is the corresponding 7,8-epoxide that , in turn, is subject of epoxide hydrolases to form stereoisomeric dihydrodiols. These are converted further to the 7,8-dihydrodiol-9,10-epoxide. The terminal oxidase is cytochrome P-450 (CYP1A1). The diol epoxide can exist in four stereoisomeric forms of which the key carcinogenic product is benzo(a)pyrene-r-7,t-8-diol-t-9,10-epoxide. PAH epoxides can then be conjugated with glutathione. This conjugation is regarded as a true detoxification reaction and is mediated by glutathione transferase (GSTM1). The epoxides that are not conjugated with glutathione are converted into phenols and diols as mentioned above. These PAH metabolites, however, are sometimes not sufficiently polar to be excreted and are therefore conjugated with glucuronic or sulfuric acids to enable excretion to occur. In addition to conjugation, the hydroxylated derivatives of PAHs may undergo a number of oxidation and hydroxylation reactions. These include the conversion of phenols to phenol-epoxides and subsequently to diphenols and triols, diols to tetrols and diol-epoxides, and triols to triol-epoxides and pentols

Answer 7

v http://cancerres.aacrjournals.org/content/42/4/1479.full.pdf

Answer 8

i use reaxys too !

Answer 9

@shawn123 : thanks on the link, but I had already read it and some of the newer things based on that paper.

For anyone else who might be interested in such things, this has been my best find thus far: For anyone else interested in such things--thus far this is the best resource i've found on the subject: http://monographs.iarc.fr/ENG/Monographs/vol92/
section 4, specifically.