Bacterial and Human Cell Mutagenicity Study of Some C 18 H 10 Cyclopenta-Fused Polycyclic Aromatic Hydrocarbons Associated with Fossil Fuels Combustion

Lafleur, Arthur L.; Longwell, John P.; Marr, Joseph A.; Monchamp, Peter A.; Plummer, Elaine F.; Thilly, William G.; Mulder, Patrick P. Y.; Boere, Ben B.; Cornelisse, J.; Lugtenburg, J.

doi:10.2307/3431424

Cited by 17 publications

(10 citation statements)

References 23 publications

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“…In addition to the nine PAH identified in the Report, 20 this chromatogram displays 41 other PAH -some of which have greater than five rings, partially hydrogenated rings, alkyl substituents, carbonyl groups, or cyclopenta-fused rings. It should be noted that some of the species identified in Figure 3- 21,22 conclusions about health effects. The fact that the Report gives measurements of only nine PAH-none of which have greater than six rings, substituent groups, or cyclopenta-fused rings -is most probably a consequence of the GC-MS analytical methods used.…”

Section: Methods Of Analysismentioning

confidence: 99%

Toxic substances form coal combustion--a co prehemsice assessment

Huggins¹,

Huffman²,

Shah³

1997

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The Clean Air Act Amendments of 1990 identify a number of hazardous air pollutants (HAPs) as candidates for regulation. Should regulations be imposed on HAP emissions from coal-fired power plants, a sound understanding of the fundamental principles controlling the formation and partitioning of toxic species during coal combustion will be needed. With support from the Federal Energy Technology Center (FETC), the Electric Power Research Institute, and VTT (Finland), Physical Sciences Inc. (PSI) has teamed with researchers from USGS, MIT, the University of Arizona (UA), the University of Kentucky (UKy), the University of Connecticut, and Princeton University to develop a broadly applicable emissions model useful to regulators and utility planners. The new Toxics Partitioning Engineering Model (ToPEM) will be applicable to all combustion conditions including new fuels and coal blends, low-NO combustion systems, x and new power generation plants. Development of ToPEM will be based on PSI's existing Engineering Model for Ash Formation (EMAF). During the last quarter coal analysis was completed on the final program coal, from the Wyodak Seam of the Powder River Basin. Combustion testing continued, including data collected on the self-sustained combustor at UA. Data from PSI and MIT were used to identify the governing mechanisms for trace element vaporization from the program coals. Mercury speciation and measurements were continued. Review of the existing trace element and organics emissions literature was completed. And, model development was begun.iv A description of the work plan for accomplishing these objectives is presented in Section 2.1 of this report.The work discussed in this report highlights the accomplishments of the sixth quarter of this program. These accomplishments include completion of standard coal analysis on the final Phase I program coal. The selective leaching work, to determine the forms of occurrence of various trace elements, was completed for the three bituminous coals. Data from the combustion zone experiments at PSI and MIT were analyzed to explore the observed differences between the two facilities and to determine the dominant mechanisms for trace element vaporization. The review of the existing trace element and organics emissions data from power plants was completed. Two major combustion experiments were completed on the self-sustained reactor at UA. Finally, work was begun to identify the models, and model parameters, required for ToPEM development, and how these models can be incorporated into the existing Engineering Model for Ash Formation (EMAF) Specifically, in the last quarter the trace element concentration analysis was completed for the Wyodak coal. This analysis indicated that the concentrations of trace elements in this coal are within the range of the bituminous coals in this program, with the exception of arsenic. The concentration of this element, and that of chromium, is much lower than was found in the other program coals. The CCSEM analysis of this coal are ...

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Section: Methods Of Analysismentioning

confidence: 99%

Toxic substances form coal combustion--a co prehemsice assessment

Huggins¹,

Huffman²,

Shah³

1997

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“…One of the best studied representatives is cyclopenta[cd]pyrene (1). It exhibits a high metabolismdependent mutagenic response in bacterial [3,6] and human cell bioassays [7,8]. In addition, 1 also possesses tumour-initiating and moderate carcinogenic potential [9][10][11].…”

Section: Introductionmentioning

confidence: 99%

“…The facile formation of epoxides at the five-membered ring is supported in the case of 1 by the isolation of dihydrodiols (derived from the action of the epoxide-hydrolase on the epoxide) in metabolic studies with liver microsomes ( [15], see however also references [16,17] in which bio-activation of PAH dihydro-diols by sulfonation is reported), as well as the reaction of the epoxides with DNA in vitro (isolation of DNA-adducts) [18][19][20][21][22]. The importance of the olefinic bond in the five-membered ring is substantiated by the observation that dihydro-CP-PAH derivatives, which contain a saturated five-membered ring, generally exhibit no mutagenic activity in bacterial bioassays [7,23,24]. Interestingly, tentative results indicate that epoxidation of the olefinic bond in the cyclopenta moiety in contrast to the parent bioactive CP-PAH, leads to direct-acting bacterial mutagens (without the need for an exogenous metabolic activation mixture, −S9-mix, see below) that exert cytotoxicity at high concentrations [25,26].…”

Section: Introductionmentioning

confidence: 99%

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CP-arene oxides: the ultimate, active mutagenic forms of cyclopenta-fused polycyclic aromatic hydrocarbons (CP-PAHs)

Otero-Lobato

Kaats-Richters

Koper

et al. 2005

Mutation Research/Genetic Toxicology and Environmental Mutagene

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The bacterial mutagenic response (Ames-assay, Salmonella typhimurium strain TA98 ± S9-mix) of a series of monocyclopentafused polycyclic aromatic hydrocarbons (CP-PAHs) identified in combustion exhausts, viz. cyclopenta[cd]pyrene (1), acephenanthrylene (2), aceanthrylene (3) and cyclopenta[hi]chrysene (4), is re-evaluated. The mutagenic effects are compared with those exerted by the corresponding partially hydrogenated derivatives, 3,4-dihydrocyclopenta[cd]pyrene (5), 4,5-dihydroacephenanthrylene (6), 1,2-dihydroaceanthrylene (7) and 4,5-dihydrocyclopenta[hi]chrysene (8). It is shown that the olefinic bond of the externally fused five-membered ring of 1, 3 and 4 is of importance for a positive mutagenic response. In contrast, whilst CP-PAH 2 is found inactive, its dihydro analogue (6) shows a weak metabolism-dependent response. The importance of epoxide formation at the external olefinic bond in the five-membered ring is substantiated by the bacterial mutagenic response of independently synthesized cyclopenta[cd]pyrene-3,4-epoxide (9), acephenanthrylene-4,5-epoxide (10), aceanthrylene-1,2-epoxide (11) and cyclopenta[hi]chrysene-4,5-epoxide (12). Their role as ultimate, active mutagenic forms, when CP-PAHs 1, 3 and 4 exhibit a positive mutagenic response, is confirmed. Semi-empirical Austin Model 1 (AM1) calculations on the formation of the CP-arene oxides (9-12) and their conversion into the monohydroxy-carbocations (9a-12a and 9b-12b) via epoxide-ring opening support our results. For 2 and 4, which also possess a bay-region besides an annelated cyclopenta moiety, the calculations rationalize that epoxidation at the olefinic bond of the cyclopenta moiety is favoured.

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“…CP-PAHs are also of interest because they generally exhibit unusual physicochemical properties [Koper et al, 2004] and, more important, they possess enhanced genotoxic properties when compared to their parent PAHs lacking the cyclopenta moiety. For example, one of the most studied CP-PAHs, cyclopenta[cd]pyrene, is a bacterial and mammalian cell mutagen, tumor promoter, and (co)carcinogen Wood et al, 1980;Cavalieri et al, 1983;Lafleur et al, 1993;Busby et al, 1997]. In contrast, its parent PAH, pyrene, is biologically inactive [Matijasevic and Zeiger, 1985].…”

Section: Introductionmentioning

confidence: 99%

Cyclopenta[cd]fluoranthene and its precursors in combustion exhausts: A survey of their bacterial mutagenic activity

Otero-Lobato

Jenneskens

Seinen

2004

Environ and Mol Mutagen

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Cyclopenta [cd]fluoranthene (1) and 3-ethynylfluoranthene (2) have both recently been identified in combustion exhausts. In this study, their mutagenic activities were compared to that of fluoranthene (3), one of the most abundant polycyclic aromatic hydrocarbons (PAHs) in combustion exhausts, in the Salmonella/microsome reversion assay (Ames assay) using S. typhimurium strain TA98. The mutagenicity of 1 was modest in comparison to other active cyclopenta PAHs. Unexpectedly, 2 was mutagenic both with and without exogenous metabolic activation (rat liver S9). Furthermore, cyclopenta[cd]fluoranthene-3,4-epoxide (6) was synthesized in order to evaluate its role as the ultimate mutagenic active form of 1. The epoxide 6 was a direct-acting mutagen. In addition, a pyrolysate containing a mixture of 1 (85%), 2 (2%), and 3 (13%) obtained by flash vacuum thermolysis of 3-(1-chloroethenyl)fluoranthene (2a) at 1,050°C was also mutagenic, but a significant mutagenic response was detected only in the presence of S9 activation. The results of this study indicate that 1 and 2 can contribute to the mutagenic activity of combustion exhausts. Environ. Mol. Mutagen. 44: 304 -312, 2004.

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Bacterial and Human Cell Mutagenicity Study of Some C 18 H 10 Cyclopenta-Fused Polycyclic Aromatic Hydrocarbons Associated with Fossil Fuels Combustion

Cited by 17 publications

References 23 publications

Toxic substances form coal combustion--a co prehemsice assessment

Toxic substances form coal combustion--a co prehemsice assessment

CP-arene oxides: the ultimate, active mutagenic forms of cyclopenta-fused polycyclic aromatic hydrocarbons (CP-PAHs)

Cyclopenta[cd]fluoranthene and its precursors in combustion exhausts: A survey of their bacterial mutagenic activity

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