Nitropyrenes: Isolation, Identification, and Reduction of Mutagenic Impurities in Carbon Black and Toners

Rosenkranz, Herbert S.; McCoy, Elena C.; Sanders, Daniel R.; Butler, Marsha; Kiriazides, Demosthenes K.; Mermelstein, Robert

doi:10.1126/science.6996095

Cited by 339 publications

(115 citation statements)

References 14 publications

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“…Evidence for the mutagenicity of commercially available toner powder as DMSO and acetone extracts was found in two earlier studies employing the Salmonella assay with established S. typhimurium strains with and without S9-mix [Löfroth et al, 1980;Rosenkranz et al, 1980]. These findings were attributed to the content of the PAH nitropyrene as a contaminant in the CB.…”

Section: Discussionmentioning

confidence: 90%

“…CB-particles are known to be genotoxic in in vitro and in vivo assay systems [Totsuka et al, 2009]. According to the International Agency of Research on Cancer (IARC), there is sufficient evidence in experimental animals for the cancerogenicity of CB and its extracts [Rosenkranz et al, 1980], but there is inadequate evidence for carcinogenicity in humans [IARC, 1996].…”

Section: Introductionmentioning

confidence: 99%

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Genotoxic effects of three selected black toner powders and their dimethyl sulfoxide extracts in cultured human epithelial A549 lung cells in vitro

Gminski

Decker

Heinz

et al. 2010

Environ and Mol Mutagen

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Until now, the adverse effects of toner powders on humans have been considered to be minimal. However, several recent reports have suggested possible significant adverse health effects from toner dust inhalation. The aim of this study was to evaluate the genotoxic potential of black toner powders in vitro. For the study of DNA damage, A549 cells were exposed to toner-powder suspensions and to their DMSO extracts, and then subjected to the comet assay and to the in-vitro cytokinesis block micronucleus test (CB-MNvit). Cytotoxic effects of the toner samples were assessed by the erythrosin B assay. Furthermore, size, shape, and composition of the toner powders were investigated. None of the three toner powders or their DMSO extracts reduced cell viability; however, they did induce DNA damage and formed micronuclei at concentrations from 80 to 400 lg cm 22 , although to a varying extent. All toner powders contain considerable amounts of the pigments carbon black and magnetite (Fe 3 O 4 ) as well as small amounts of polycyclic aromatic hydrocarbons (PAHs). The overall results of our invitro study suggest that the investigated toner-powder samples are not cytotoxic but genotoxic. From the results of the physical and chemical characterization, we conclude that metals and metalloids as components of magnetite, or PAHs as components of the carbon-bearing material, are responsible for the genotoxic effects. Further research is necessary to determine the relevance of these in-vitro observations for private and occupational toner powder exposure.

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Section: Discussionmentioning

confidence: 90%

Section: Introductionmentioning

confidence: 99%

Genotoxic effects of three selected black toner powders and their dimethyl sulfoxide extracts in cultured human epithelial A549 lung cells in vitro

Gminski

Decker

Heinz

et al. 2010

Environ and Mol Mutagen

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“…1-Nitropyrene (1-NP) 1 , a representative of this class of compounds, is the most abundant nitroaromatic compound in the environment. 1-NP is mutagenic in many bacterial and mammalian assay systems and tumorigenic in experimental animals (5)(6)(7)(8).…”

Section: Introductionmentioning

confidence: 99%

Mutagenicity of the 1-Nitropyrene-DNA Adduct N-(Deoxyguanosin-8-yl)-1-aminopyrene in Mammalian Cells

Watt

Utzat

Hilario

et al. 2007

Chem. Res. Toxicol.

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The mutagenesis of the major DNA adduct N-(deoxyguanosin-8-yl)-1-aminopyrene (C8-AP-dG) formed by 1-nitropyrene was compared with the analogous C8-dG adducts of 2-aminofluorene (AF) and N-acetyl-2-aminofluorene (AAF) in simian kidney (COS-7) cells. The DNA sequence chosen for this comparison contained 5′-CCATCGCTACC-3′ that has been used for solution NMR investigations. The structural and conformational differences among these lesions are wellestablished (Patel et al., 1998). Accordingly, we found a notable difference in the viability of the progeny, which showed that the AAF adduct was most toxic and the AF adduct was least toxic with the AP adduct exhibiting intermediate toxicity. However, analysis of the progeny showed that translesion synthesis was predominantly error-free. Only low level mutations (<3%) were detected with G→T as the dominant type of mutation by all three DNA adducts. When C8-AP-dG was evaluated in a repetitive 5′-CGCGCG-3′ sequence, higher mutational frequency (~8%) was observed. Again, G→T was the major type of mutations in simian kidney cells, even though in bacteria CpG deletions predominate in this sequence (Hilario et al, 2002). Mutagenesis of C8-AP-dG in a 12-mer containing the local DNA sequence around codon 273 of the p53 tumor suppressor gene, where the adduct was located at the second base of this codon, was also investigated. In this 5′-GTGCGTGTTTGT-3′ site, the mutations were slightly lower but not very different from the progeny derived from the 5′-CGCGCG-3′ sequence. However, the mutational frequency increased by more than 50% when the 5′ C to the adduct was replaced with a 5-methylcytosine (5-MeC). With a 5-MeC, the most notable change in mutation was the enhancement of G→A, which occurred 2.5-times relative to a 5′ C. The C8-AP-dG adduct in codon 273 dodecamer sequence with a 5′ C or 5-MeC was also evaluated in human embryonic kidney (293T) cells. Similar to COS cells, targeted mutations doubled with a 5-MeC 5′ to the adduct. Except for an increase in G→C transversions, the results in 293T were similar to that in COS cells. We conclude that C8-AP-dG mutagenesis depends on the type of cell in which it is replicated, the neighboring DNA sequence, and the methylation status of the 5′ C.

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“…Nitropyrene, which is produced by diesel exhaust, coal fly ash, carbon black and toner, is a ubiquitous environmental pollutant (1,2). The pollutant is also detected in foods, such as grilled chicken (3,4).…”

Section: Introductionmentioning

confidence: 99%

“…1-Nitropyrene (1-NP), a representative of this class of compounds, and is the most abundant nitroaromatic compound in the environment. It has been well-established that 1-NP is mutagenic in bacteria, mammalian cells, and animals (1,(5)(6)(7)(8)(9). DNA sequence analysis of 1-NP-induced mutations in mice showed A → G transitions to be the most frequent mutations (5).…”

Section: Introductionmentioning

confidence: 99%

Mutation spectra induced by 1-nitropyrene 4,5-oxide and 1-nitropyrene 9,10-oxide in the supF gene of human XP-A fibroblasts

Kim

Kim²,

Cha³

et al. 2008

BMB Reports

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Nitropyrenes: Isolation, Identification, and Reduction of Mutagenic Impurities in Carbon Black and Toners

Cited by 339 publications

References 14 publications

Genotoxic effects of three selected black toner powders and their dimethyl sulfoxide extracts in cultured human epithelial A549 lung cells in vitro

Genotoxic effects of three selected black toner powders and their dimethyl sulfoxide extracts in cultured human epithelial A549 lung cells in vitro

Mutagenicity of the 1-Nitropyrene-DNA Adduct N-(Deoxyguanosin-8-yl)-1-aminopyrene in Mammalian Cells

Mutation spectra induced by 1-nitropyrene 4,5-oxide and 1-nitropyrene 9,10-oxide in the supF gene of human XP-A fibroblasts

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