polycyclic aromatic hydrocarbons l.
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  2. What Are They? • PAHs are a group of chemicals that are formed during the incomplete burning of coal, oil and gas, garbage, or other organic substances. • PAHs can be formed through natural processes or those related to human activities. • There are more than 100 different PAHs. Most PAHs do not occur alone in the environment. Rather they are found as mixtures of two or more PAHs.

  3. What Are They? (Continued) • PAHs can occur in the air attached to organic particles, in the soil, or in the sediments as solids. • They can also be found in substances such as crude oil, coal, creosote, and road / roofing tar. • Evaporation into air does occur very easily. Global transport occurs.

  4. What Are They? (Continued) • Examples of Polycyclic Aromatic Hydrocarbons are on overhead. • Examples: Acenaphthene, Anthracene, Benz[a]anthracene, Benzo[a]pyrene, Benzo[b]fluoranthene, Benzo[ghi]pyrene, Benzo[k]fluoranthene, Chrysene, Dibenz[a,h]anthracene, Fluoranthene, Fluorene, Indeno[1,2,3-cd]pyrene, Phenanthrene, and Pyrene

  5. Toxicity • Although unmetabolized PAHs can have toxic effects, the major concern in animals is the ability of reactive metabolites to bind to proteins and DNA. • Four, five and six ring PAHs have greater carcinogenic potential than do two, three or seven ring PAHs. • The addition of alkyl groups to PAHs enhances the carcinogenic potential of these compounds.

  6. Exposure • Some exposure to PAHs comes through inhalation: • In the environment you are exposed to PAH vapors or PAHs attached to dust and other particles in the air. These can come from vehicle exhausts, coal burning, wildfires, agricultural burning, and hazardous waste sites. • Other inhalation exposures come from PAHs present in tobacco smoke, smoke from wood burning fireplaces, and creosote-treated wood products.

  7. Exposure (Continued) • Some exposure to PAHs by ingestion: • Cooking meat or other foods at high temperatures that results in charring of the food increases the amount of PAHs in the food.

  8. Animal Exposure • Exposures to animals are: • Fish - from light MW forms in the water; from higher MW forms in the sediment. • Birds - mainly through the exposure of birds to oil spills. • Mammals - also through oil spills.

  9. Absorption, Distribution, Excretion • These are highly lipophilic compounds so they are absorbed quickly by all routes of exposure. • Storage is mostly in kidneys, liver and fat tissue. • PAHs do not have long half-lives. Usually measured in days. Excretion is primarily by urine and feces.

  10. Metabolism • Important regions of PAH molecules are: • Bay Region - there is a terminal ring on one side of the bay region • L Region - this is a site between two ring fusion points, it is alpha to two fusion points. • K Region - this is a region of high electron density in all resonance structures. • All of these regions are highly reactive. Epoxides can be formed at all three regions.

  11. Metabolism (Continued) • Bay region dihydrodiol epoxides are the main carcinogenic species. • Bay region metabolites represent only a small fraction of the total metabolism of the parent hydrocarbon since metabolism occurs at many sites on the molecule.

  12. Metabolism (Continued) • What makes the bay region metabolite unusual and the most carcinogenic? • Bay region dihydrodiol epoxides are particularly resistant to enzymatic detoxification. The bay region epoxides are not good substrates for epoxide hydrolase or for glutathione conjugation. • The resistance is presumably due to the steric inaccessibility of the bay region.

  13. Benzo[a]pyrene • Benzo[a]pyrene diol epoxides show a strong preference for reaction with purine residues, particularly guanine. • B(a)P is one of the most intensely studied PAHs as it is an extremely potent carcinogen. • Metabolic transformations catalyzed by the CYPs are mainly hydroxylations occurring at the various available sites on the aromatic rings (phase I reactions), and conjugations of the hydroxyl groups with glucuronic acid, sulphate, or glutathione (phase II reactions).

  14. Benzo[a]pyrene • It now seems that the ultimate carcinogen is an epoxide of a dihydrodiol metabolite where the epoxide is adjacent to the bay region. Although a number of the epoxides are mutagenic, the 7,8-dihydrodiol, 9,10 epoxide is believed to be the ultimate carcinogen. • The diasteroisomer believed to be the ultimate carcinogen is shown next.

  15. Benzo[a]pyrene • Other metabolites are B(a)P known to be produced are the 3,6-quinone and semiquinone. • These metabolites are cytotoxic and cause DNA strand breaks. They are also mutagenic.