Polycyclic aromatic hydrocarbons metabolism

McElroy AE (1990) Polycyclic aromatic hydrocarbon metabolism in the polychaete. Nereis virens Aquat Toxicol 18 35-50. 

Pickard, M. A. Roman, R. Tinoco, R., and Vazquez-Duhalt, R., Polycyclic aromatic hydrocarbon metabolism by white rot fungi and oxidation by Coriolopsis gallica UAMH 8260 laccase. Applied and Environmental Microbiology, 1999. 65(9) pp. 3805-3809. 

Thakker DR, Yagi H, Levin W, et al. Polycyclic aromatic hydrocarbons metabolic activation to ultimate carcinogens. In Anders MW, ed. Bioactivation of Foreign Compounds. Orlando, FL Academic Press 1985 177-242. 

D. R. Thakker, H. Yagi, W. Levin, A. W. Wood, A. H. Conney, D. M. Jerina, Polycyclic Aromatic Hydrocarbons Metabolic Activation to Ultimate Carcinogens , in Bioactivation of Foreign Compounds , Ed. M. W. Anders, Academic Press, Orlando, 1985, p. 177 - 242. 

Table 5.1. Representative polycyclic aromatic hydrocarbons metabolized by different species of bacteria... 

HALL, M, and grover p l, (1990). Polycyclic aromatic hydrocarbons metabolism, activation, and tumor initiation , pp. 327-372. In c s cooper... 

Khan, A.A., R.-F. Wang, W.-W. Cao, W. Franklin, and C.E. Cerniglia. 1996. Reclassification of a polycyclic aromatic hydrocarbon-metabolizing bacterium, Beijerinckia sp. strain B1 as Sphingomonas yanoikuyae by fatty acid analysis, protein pattern analysis, DNA-DNA hybridization, and 16S ribosomal DNA sequencing. Int.. ... 

Sims, P. and Grover, P.L. (1974) Epoxides in polycyclic aromatic hydrocarbon metabolism and carcinogenesis. Adv. Cancer Res., 20, 165-274. 

Otto, S., C. Marcus, C. Pidgeon, and C. Jefcoate (1991). A novel adrenooorticotropin-inducible cytochrome P450 from rat adrenal microsomes catalyzes polycyclic aromatic hydrocarbon metabolism. Endocrinology 129, 970-982. 

Mann, K. K., Matulka, R. A., Hahn, M. E., Trombino, A. F., Lawrence, B. P., Kerkvliet, N. 1. Sherr, D. H. (1999). The role of polycyclic aromatic hydrocarbon metabolism in dimethylbenz[a] anthracene induced pre-B lymphocyte apoptosis. Toxicology and Applied Pharmacology, 161, 10-22. 

Epoxides are often encountered in nature, both as intermediates in key biosynthetic pathways and as secondary metabolites. The selective epoxidation of squa-lene, resulting in 2,3-squalene oxide, for example, is the prelude to the remarkable olefin oligomerization cascade that creates the steroid nucleus [7]. Tetrahydrodiols, the ultimate products of metabolism of polycyclic aromatic hydrocarbons, bind to the nucleic acids of mammalian cells and are implicated in carcinogenesis [8], In organic synthesis, epoxides are invaluable building blocks for introduction of diverse functionality into the hydrocarbon backbone in a 1,2-fashion. It is therefore not surprising that chemistry of epoxides has received much attention [9]. 

The metabolic activity of other white-rot fungi including Phanerochaete chrysosporium and Pleurotus ostreacus has been discussed in the context of polycyclic aromatic hydrocarbons. For example, the mineralization potential of the manganese peroxide system fmmNematolomafrowardii for a number of substrates has been demonstrated (Hofrichter et al. 1998) the formation of CO2 from labeled substrates ranged from 7% (pyrene) to 36% (pentachlorophenol), 42% (2-amino-4, 6-dinitrotoluene), and 49% (catechol). 

Heitkamp MA, W Franklin, CE Cerniglia (1988b) Microbial metabolism of polycyclic aromatic hydrocarbons isolation and characterization of a pyrene-degrading bacterium. Appl Environ Microbiol 54 2549-2555. 

Kazunga C, MD Aitken (2000) Products from the incomplete metabolism of pyrene by polycyclic aromatic hydrocarbon-degrading bacteria. Appl Environ Microbiol 66 1917-1922. 

Many process mixtures, notably fermentations, require sample preconcentration, microdialysis, microfiltration, or ultrafiltration prior to analysis. A capillary mixer has been used as a sample preparation and enrichment technique in microchromatography of polycyclic aromatic hydrocarbons in water.8 Microdialysis to remove protein has been coupled to reversed phase chromatography to follow the pharmacokinetics of the metabolism of acetaminophen into acetaminophen-4-O-sulfate and acetaminophen-4-O-glucu-ronide.9 On-line ultrafiltration was used in a process monitor for Aspergillus niger fermentation.10... 

Stereoselective Metabolism and Activations of Polycyclic Aromatic Hydrocarbons... 

Figure 7. Steric model proposed by Jerina, et al. for the catalytic binding site of cytochrome P-450c (P-448) to account for the stereoselective metabolism of polycyclic aromatic hydrocarbons (48). The boundary should be enlarged in the directions shown to accommodate substrates whose mechanism of stereoselective oxygenation does not fit the steric model originally proposed.

Effects of Methyl and Fluorine Substitution on the Metabolic Activation and Tumorigenicity of Polycyclic Aromatic Hydrocarbons... 

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