P polycyclic aromatic hydrocarbons

DE VOS R H, VAN DOKKUM W, SCHOUTEN A and DE JONG-BERKHOUT P Polycyclic aromatic hydrocarbons in Dutch total diet samples (1984-1986) , Food and Chemical Toxicology, 1990 28 263-268. 

Woodhead, R. J., Law, R. J., and Matthiessen, P., Polycyclic aromatic hydrocarbons in surface sediments around England and Wales, and their possible biological significance. Mar. Pollut. Bull, 38, 773-790, 1999. 

Carcinogens Cancer-producing agents Skin Respiratory Bladder/urinary tract Liver Nasal Bone marrow Coal tar pitch dust crude anthracene dust mineral oil mist arsenic. Asbestos polycyclic aromatic hydrocarbons nickel ore arsenic bis-(chloromethyl) ether mustard gas. p-naphthylamine benzidine 4-am i nodi pheny lam ine. Vinyl chloride monomer. Mustard gas nickel ore. Benzene. 

In fused ring systems, the positions are not equivalent and there is usually a preferred orientation even in the unsubstituted hydrocarbon. The preferred positions may often by predicted as for benzene rings. Thus it is possible to draw more canonical forms for the arenium ion when naphthalene is attacked at the a position than when it is attacked at the p position, and the a position is the preferred site of attack,though, as previously mentioned (p. 682), the isomer formed by substitution at the p position is thermodynamically more stable and is the product if the reaction is reversible and equilibrium is reached. Because of the more extensive delocalization of charges in the corresponding arenium ions, naphthalene is more reactive than benzene and substitution is faster at both positions. Similarly, anthracene, phenanthrene, and other fused polycyclic aromatic hydrocarbons are also substituted faster than benzene. 

The phosphorescence lifetimes for the p-aminobenzoic acid anion adsorbed on sodium acetate as a function of temperature were evaluated in a manner similar to the one discussed by Oelkrug and coworkers (,28-30) for polycyclic aromatic hydrocarbons adsorbed on y-alumina. In general, the solid-surface phosphorescence lifetime cutrves for the anion of p-aminobenzoic acid followed Equation 2. 

Monteiro, P.R.R., Reis-Henriques, M.A., and Coimbra, J. (2000a). Plasma steroid levels in female flounder (Platichthys flesus) after chronic dietary exposure to single polycyclic aromatic hydrocarbons. Marine Environmental Research 49, 453 67. 

KAYALI-SAYADI M N, RUBIO-BARROSO S, CUESTA-JIMENEZ M P and PALO-DIEZ L M (1998) Rapid determination of polycyclic aromatic hydrocarbons in tea infusion samples by high-performance liquid chromatography and fluorimetric detection based on solid-phase extraction , 123, 2145-8. 

Hammel KE, B Kalyanaraman, TK Kirk (1986) Oxidation of polycyclic aromatic hydrocarbons and dibenzo(p)dioxins by Phanerochaete chrysosporium ligninase. J Biol Chem 261 16948-16952. 

Richnow HH, A Eschenbach, B Mahro, R Seifert, P Wehrnng, P Albrecht, W Michaelis (1998) The nse of Relabelled polycyclic aromatic hydrocarbons for the analysis of their transformation in soil. Chemosphere 36 2211-2224. 

Bastiaens L, D Springael, P Wattiau, H Harms, R deWachter, H Verachtert, L Diels (2000) Isolation of adherent polycyclic aromatic hydrocarbons (PAH)-degrading bacteria using PAH-sorbing carriers. Appl Environ Microbiol 66 1834-1843. 

Coates JD, J Woodward, J Allen, P Philip, DR Lovley (1997) Anaerobic degradation of polycyclic aromatic hydrocarbons and alkanes in petroleum-contaminated marine harbor sediments. Appl Environ Microbiol 63 3589-3593. 

Arino S, R Marchal, J-P Vandecasteele (1998) Involvement of a rhamnolipid-producing strain of Pseudomonas aeruginosa in the degradation of polycyclic aromatic hydrocarbons by a bacterial community. J Appl Microbiol 84 769-776. 

Madsen T, P Kristensen (1997) Effects of bacterial inoculation and nonionic surfactants on degradation of polycyclic aromatic hydrocarbons in soil. Environ Toxicol Chem 16 631-637. 

Tiehm A, M Stieber, P Werner, FM Frimmel (1997) Surfactant-enhanced mobilization and biodegradation of polycyclic aromatic hydrocarbons in manufactured gas plant soil. Environ Sci Technol 31 2570-2576. 

Spectra at p (=20) wavelengths. Because of the Lambert-Beer law, all measured spectra are linear combinations of the two pure spectra. Together they form a 15x20 data matrix. For example the UV-visible spectra of mixtures of two polycyclic aromatic hydrocarbons (PAH) given in Fig. 34.2 are linear combinations of the pure spectra shown in Fig. 34.3. These mixture spectra define a data matrix X, which can be written as the product of a 15x2 concentration matrix C with the 2x20 matrix of the pure spectra ... 

CRMs for Contaminants in Environmental Matrices For nearly two decades NIST has been involved in the development of SRMs for the determination of organic contaminants such as polycyclic aromatic hydrocarbons (PAHs), polychlorinated biphenyls (PCBs), and chlorinated pesticides in natural environmental matrices such as fossil fuels (Hertz et al.1980 Kline et al. 1985), air and diesel particulate material (May and Wise 1984 Wise et al. 2000), coal tar (Wise et al. 1988a), sediment (Schantz et al. 1990, 1995a Wise et al. 1995), mussel tissue (Wise et al. 1991 Schantz et al. 1997a), fish oil, and whale blubber (Schantz et al. 1995b). Several papers have reviewed and summarized the development of these environmental matrix SRMs (Wise et al. 1988b Wise 1993 Wise and Schantz 1997 Wise et al. 2000). Seventeen natural matrix SRMs for the determination of organic contaminants are currently available from NIST with certified and reference concentrations primarily for PAHs, PCBs, chlorinated pesticides, polychlorinated dibenzo-p-dioxins (PCDDs), and polychlorinated dibenzofiirans (PCDFs) see Table 3.11. 

Hulbert, P. B. Grover, P. L. Chemical rearrangement of phenol-epoxide metabolites of polycyclic aromatic hydrocarbons to quinone-methides. Biochem. Biophys. Res. Commun. 1983, 117, 129-134. 

Baldrian, P., der Wiesche, C., Gabriel, J., Nerud, E, and Zadrazil, F., Influence of cadmium and mercury on activities of ligninolytic enzymes and degradation of polycyclic aromatic hydrocarbons by Pleurotus ostreatus in soil, Appl Environ Microbiol, 66 (6), 2471-2478, 2000. 

Table 1 Concentrations of chlorinated polycyclic aromatic hydrocarbons (CIPAHs), polybrominated diphenyl ethers (PBDEs), polychlorinated biphenyls (PCBs), polybrominated biphenyls (PBBs), polychlorinated dibenzo-p-dioxins and dibenzofurans (PCDD/Fs), and polybrominated dibenzo-p-dioxins and dibenzofurans (PBDD/Fs) in ambient air, soil, and human samples collected from e-waste recycling and reference sites in China... 

Jacinto, M.J., Santos, O., Landers, R., Kiyohara, P.K. and Rossi, L.M. (2009) On the catalytic hydrogenation of polycyclic aromatic hydrocarbons into less toxic compounds by a facile recoverable catalyst. Applied Catalysis B Environmental, 90 (3-4), 688-692. 

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.

Oxidation is intimately linked to the activation of polycyclic aromatic hydrocarbons (PAH) to carcinogens (1-3). Oxidation of PAH in animals and man is enzyme-catalyzed and is a response to the introduction of foreign compounds into the cellular environment. The most intensively studied enzyme of PAH oxidation is cytochrome P-450, which is a mixed-function oxidase that receives its electrons from NADPH via a one or two component electron transport chain (10. Some forms of this enzyme play a major role in systemic metabolism of PAH (4 ). However, there are numerous examples of carcinogens that require metabolic activation, including PAH, that induce cancer in tissues with low mixed-function oxidase activity ( 5). In order to comprehensively evaluate the metabolic activation of PAH, one must consider all cellular pathways for their oxidative activation. 

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