Conversion of environmental pollutant to mutagens by visible light

doi:10.1016/0006-291X(79)90690-9

Biochemical and Biophysical Research Communications

Volume 89, Issue 2, 27 July 1979, Pages 729-734

https://doi.org/10.1016/0006-291X(79)90690-9 Get rights and content

Abstract

Illumination of DMBA, 3-methylcholanthrene, 2-aminoanthracene and chrysene with visible light resulted in the formation of direct-acting chemicals endowed with genotoxic and frameshift mutagenic activities. These findings may be of relevance in assessing the potential health hazards inherent in the planned conversion to diesel fuels which is expected to result in increased atmospheric levels of polycyclic aromatic hydrocarbons.

References (23)

A.W. Wood et al.
Biochem. Biophys. Res. Comm
(1977)
C. Malaveille et al.
Biochem. Biophys. Res. Comm
(1977)
H.S. Rosenkranz et al.
Mutation Res
(1976)
B.N. Ames et al.
Mutation Res
(1975)
M.W. Chou et al.
D.M. Jerina et al.
P.G. Wislocki et al.
Cancer Res
(1976)
A.W. Wood et al.
A.W. Wood et al.
Cancer Res
(1978)
A.W. Wood et al.
Cancer Res
(1978)

S.E. Hecht et al.

Cancer Res

(1978)

Cited by (28)

Mutation and DNA modification in Salmonella exposed to N-nitrosodimethylamine under UVA- and sunlight-irradiation
1999, Mutation Research - Genetic Toxicology and Environmental Mutagenesis
Previously, we reported that when Salmonella typhimurium and Escherichia coli were treated with N-nitrosodimethylamine (NDMA) under irradiation with ultraviolet-A (UVA), mutagenesis of the bacteria took place without externally added activation enzymes. We also observed the formation of O⁶-methylguanine (O⁶-meG), N⁷-methylguanine (N⁷-meG) and 7,8-dihydro-8-oxodeoxyguanosine (8-oxodG) in calf thymus DNA treated with NDMA plus UVA. In this study, we observed the mutagenicity of NDMA under irradiation of natural sunlight in S. typhimurium. Furthermore, we detected the formation of O⁶-meG, N⁷-meG and 8-oxodG in calf thymus DNA treated with NDMA plus simulated sunlight. Regarding the mutagenesis of S. typhimurium by NDMA plus UVA, we have now identified and quantified O⁶-meG formed in the genomic DNA of the bacteria under conditions of the mutagenesis.
Comparative investigations among meteorological conditions, air chemical-physical pollutants and airborne particulate mutagenicity: A long-term study (1990-1994) from a northern Italian town
1995, Chemosphere
The findings of a continuos monitoring (Apr90–Mar94) on urban air quality of a Po Valley town are reported. Chemical-physical and genotoxicity data were detected. The results show the presence of mutagenic agents during the whole investigated period.
Short term mutagenesis tests together with chemical-physical parameters analysis are able to better assess air quality and genotoxic risk for the population.
Photobiological activities of 1,6-dioxapyrene in pro- and eukaryotic cells
1993, Mutation Research - Fundamental and Molecular Mechanisms of Mutagenesis
The photobiological effect of a new pyrene derivative, 1,6-dioxapyrene (1,6,-DP), was studied in Salmonella typhimurium (strain TA100) and in the diploid strain D7 of the yeast Saccharomyces cerevisiae. In Salmonella, 1,6-DP shows little mutagenicity in the dark in comparison to benzo[a]pyrene (B[a]P). This mutagenic activity decreases in the presence of liver S9 homogenates from Aroclor induced XVIInc/Z mice. However, in combination with 365 nm (UVA) radiation and in the presence of S9 mix, 1,6-DP behaves as an effective photodynamic compound inducing lethal and mutagenic effects in both organisms. In yeast, its activity, like that of B[a]P, is highly dependent on the presence of oxygen. For the same incident dose of UVA, 1,6-DP is, however, at least 6 times more effective than B[a]P in inducing cytotoxic and mutagenic effects. At equitoxic doses, 1,6-DP is as photomutagemic as B[a]P, suggesting that in both cases mutagenicity is due to similar mechanisms.
Spectrophotometric measurements indicate physical interaction of 1,6-DP with DNA in the dark. Laser flash photolysis experiments show that 1,6-DP generates singlet oxygen with a quantum yield of 0.17. In vitro 1,6-DP produces oxidative damage to guanine bases specific for singlet oxygen mediated reactions. Alkaline step elution analysis of 1,6-DP plus UVA treated yeast cells indicates a decrease in average molecular weights in DNA and an induction of single strand breaks (ssb) originating from alkali labile sites. This effect is enhanced by D₂O and is thus likely to be due the production of singlet oxygen. The strand breaks appear to differ from those induced by γ-rays because little, if any, repair of these ssb occurs during 30 min of post-treatment incubation in complete growth medium. These results suggest that the photobiological effects of 1,6-DP are due to oxidative damage in DNA mostly induced by singlet oxygen.
Influence of lightning conditions on toxicity and genotoxicity of various PAH in the newt in vivo
1992, Mutation Research/Genetic Toxicology
We evaluated the influence of near-ultraviolet light (UVA) on the cytotoxicity and genotoxicity of 7 polycyclic aromatic hydrocarbons (PAH) in larvae of the amphibian Pleurodeles waltl. Benz[a]anthracene (BA), 7,12-benz[a]anthraquinone (BAQ) and anthracene (Ac) proved to be lethal at low doses (some ppb), and the following order of genotoxicity was observed: BA ≈ BAQ > DMBA > DMA (9,10-dimethylanthracene). Ac, AQ (9,10-anthraquinone) and DBA (dibenz[a,h]anthracene) were not found to be clastogenic.
In the larvae reared in normal conditions (subdued natural daylight/darkness alternation) or in continuous darkness, the BA derivatives were shown to be more genotoxic than BA itself: DMBA > BAQ > BA; BA (≥ 187.5 ppb) slightly increased the level of micronuclei in circulating erythrocytes, while DMBA was strongly clastogenic, in line with their reported carcinogenicity.
In other experiments, rearing media alone (i.e., water containing BA, BAQ or DMBA) were UVA-irradiated for 24 h, and then tested on larvae in the dark (‘IR-UV/dark’ conditions). Photodegradation of BA (50 and 100 ppb) gave rise to clastogenic products. By contrast, DMBA (12.5, 25 or 50 ppb) was destroyed by UVA, and we suggested that any potentially mutagenic photoproducts formed were not in sufficient amounts to yield a positive response in the newt micronucleus test.
Overview, conclusions, and recommendations of the IPCS collaborative study on complex mixtures
1992, Mutation Research/Reviews in Genetic Toxicology
The International Programme on Chemical Safety (IPCS) sponsored an international collaborative study to examine the variability associated with the extraction and bioassay of standard reference materials (SRMs) that are complex environmental mixtures provided by the U.S. National Institute of Standards and Technology (NIST). The study was also intended to evaluate the feasibility of establishing bioassay reference values and ranges for the SRMs. Twenty laboratories from North America, Europe, and Japan participated in the study. As part of the mandatory core protocol, each laboratory extracted the organic material from two particulate samples and bioassayed these extracts. A coal tar polycyclic aromatic hydrocarbon (PAH) solution and two mutagenic control compounds were also subjected to bioassay without prior extraction by the participating laboratories. The bioassay used was the Salmonella/ microsomal plate incorporation assay. For the optional portion of the study, a laboratory was free to use the SRMs for any type of exploratory research.
The primary purpose of the required portion of the study was to estimate the intra- and inter-laboratory variability in mutagenic potencies of the test materials and to determine whether or not the NIST mixtures could be used as reference materials by others performing the Salmonella assay. Repeatability (intra-laboratory variance) of the bioassay results ranged from 16% to 88% depending on the SRM and the bioassay conditions (tester strain and metabolic activation), whereas reproducibility (inter-laboratory variance) ranged from 33% to 152%. Between-laboratory variability was the main source of variation accounting for approximately 55–95% of the total variation for the three environmental samples. Variation in the mutagenic potency of the control compounds was comparable, with the exception of 1-nitropyrene for which the reproducibility ranged from 127% to 132%.
In summary, NIST SRMs provided useful materials for an international inter-laboratory study of complex mixtures. By establishing both intra-and inter-laboratory variance for the mutagenicity results for these materials, the usefulness of these SRMs as reference materials for the Salmonella bioassay was established, critical procedures within the bioassay protocol were identified, and recommendations for future efforts were delineated.
Structural requirements for the induction of the SOS repair in bacteria by nitrated polycyclic aromatic hydrocarbons and related chemicals
1992, Mutation Research - Fundamental and Molecular Mechanisms of Mutagenesis
The CASE (computer-automated structure evaluation) methodology was used to investigate the structural basis of the SOS-inducing activity of 56 nitrated polycyclic aromatic hydrocarbons (nitroarenes, nPAH) and the unsubstituted parent PAH molecules. Based upon the presence and/or absence of structural features, CASE identified 5 activating (biophores) and 4 inactivating (biophobes) fragments responsible for the SOS-inducing activity. Based upon these fragments, CASE correctly calculated the genotoxicity of 94.6% of the molecules in the training set (sensitivity = 0.85, specifity = 1.0). Disregarding the questionable experimental results of the unexpected very weak direct-acting activity of the unsubstituted benzo[a]pyrene, dibenzo[a,h]anthracene and 7,12-dimethylbenz[a]anthracene, the concordance of the prediction was 100%, i.e., sensitivity = 1.0, specifity = 1.0. Additionally, the quantitative analysis of the SOS-inducing potency showed a good correlation between the experimental and predicted results.
The present analyses indicate an identity in the structural determinants responsible for SOS induction in E. coli PQ37 (SOS chromotest) and mutagenicity in Salmonella typhimurium.

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^☆: This investigation was supported by the National Cancer Institute (CP 65855).

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Biochemical and Biophysical Research Communications

Conversion of environmental pollutant to mutagens by visible light☆

Abstract

Biochem. Biophys. Res. Comm

Biochem. Biophys. Res. Comm

Mutation Res

Mutation Res

Cancer Res

Cancer Res

Cancer Res

Cancer Res

Mutation and DNA modification in Salmonella exposed to N-nitrosodimethylamine under UVA- and sunlight-irradiation

Comparative investigations among meteorological conditions, air chemical-physical pollutants and airborne particulate mutagenicity: A long-term study (1990-1994) from a northern Italian town

Photobiological activities of 1,6-dioxapyrene in pro- and eukaryotic cells

Influence of lightning conditions on toxicity and genotoxicity of various PAH in the newt in vivo

Overview, conclusions, and recommendations of the IPCS collaborative study on complex mixtures

Structural requirements for the induction of the SOS repair in bacteria by nitrated polycyclic aromatic hydrocarbons and related chemicals