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Pyrene

About: Pyrene is a research topic. Over the lifetime, 12465 publications have been published within this topic receiving 358896 citations.


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Journal ArticleDOI
TL;DR: It appears that physical binding of polycyclic aromatic hydrocarbons consists of intercalation into these sites, and increasing salt concentration increases the duplex content of denatured DNA.
Abstract: We have investigated the physical binding of pyrene and benzo[a]pyrene derivatives to denatured DNA. These compounds exhibit a red shift in their absorbance spectra of 9 nm when bound to denatured calf thymus DNA, compared to a shift of 10 nm when binding occurs to native DNA. Fluorescence from the hydrocarbons is severely quenched when bound to both native and denatured DNA. Increasing sodium ion concentration decreases binding of neutral polycyclic aromatic hydrocarbons to native DNA and increases binding to denatured DNA. The direct relationship between binding to denatured DNA and salt concentration appears to be a general property of neutral polycyclic aromatic hydrocarbons. Absorption measurements at 260 nm were used to determine the duplex content of denatured DNA. When calculated on the basis of duplex binding sites, equilibrium constants for binding of 7,8,9,10-tetrahydroxy-7,8,9,10-tetrahydro-benzo[a]pyrene to denatured DNA are an order of magnitude larger than for binding to native DNA. The effect of salt on the binding constant was used to calculate the sodium ion release per bound ligand, which was 0.36 for both native and denatured DNA. Increasing salt concentration increases the duplex content of denatured DNA, and it appears that physical binding of polycyclic aromatic hydrocarbons consists of intercalation into these sites.

1,808 citations

Journal ArticleDOI
TL;DR: The carcinogenicity of polycyclic aromatic hydrocarbons (PAHs) is associated with the complexity of the molecule, and with metabolic activation to reactive diol epoxide intermediates and their subsequent covalent binding to critical targets in DNA.
Abstract: Polycyclic aromatic hydrocarbons (PAHs) are formed during incomplete combustion. Domestic wood burning and road traffic are the major sources of PAHs in Sweden. In Stockholm, the sum of 14 different PAHs is 100-200 ng/m(3) at the street-level site, the most abundant being phenanthrene. Benzo[a]pyrene (B[a]P) varies between 1 and 2 ng/m(3). Exposure to PAH-containing substances increases the risk of cancer in humans. The carcinogenicity of PAHs is associated with the complexity of the molecule, i.e., increasing number of benzenoid rings, and with metabolic activation to reactive diol epoxide intermediates and their subsequent covalent binding to critical targets in DNA. B[a]P is the main indicator of carcinogenic PAHs. Fluoranthene is an important volatile PAH because it occurs at high concentrations in ambient air and because it is an experimental carcinogen in certain test systems. Thus, fluoranthene is suggested as a complementary indicator to B[a]P. The most carcinogenic PAH identified, dibenzo[a,l]pyrene, is also suggested as an indicator, although it occurs at very low concentrations. Quantitative cancer risk estimates of PAHs as air pollutants are very uncertain because of the lack of useful, good-quality data. According to the World Health Organization Air Quality Guidelines for Europe, the unit risk is 9 X 10(-5) per ng/m(3) of B[a]P as indicator of the total PAH content, namely, lifetime exposure to 0.1 ng/m(3) would theoretically lead to one extra cancer case in 100,000 exposed individuals. This concentration of 0.1 ng/m(3) of B[a]P is suggested as a health-based guideline. Because the carcinogenic potency of fluoranthene has been estimated to be approximately 20 times less than that of B[a]P, a tentative guideline value of 2 ng/m(3) is suggested for fluoranthene. Other significant PAHs are phenanthrene, methylated phenanthrenes/anthracenes and pyrene (high air concentrations), and large-molecule PAHs such as dibenz[a,h]anthracene, benzo[b]fluoranthene, benzo[k]fluoranthene, and indeno[1,2,3-cd]pyrene (high carcinogenicity). Additional source-specific indicators are benzo[ghi]perylene for gasoline vehicles, retene for wood combustion, and dibenzothiophene and benzonaphthothiophene for sulfur-containing fuels.

1,433 citations

Journal ArticleDOI
22 Nov 1974-Nature
TL;DR: It is suggested that epoxides are the important reactive metabolites responsible for the biological effects of these carcinogens4.
Abstract: CARCINOGENIC polycyclic hydrocarbons such as the widespread environmental contaminant, benzo(a)pyrene (Fig. 1a), undoubtedly require metabolic activitation. Boyland1 proposed that epoxides, whose formation is catalysed by the NADPH-dependent microsomal mono-oxygenases2,3, are the initial products of double-bond oxidation and we have suggested that epoxides are the important reactive metabolites responsible for the biological effects of these carcinogens4.

1,127 citations

Journal ArticleDOI
Hélène Budzinski1, I. Jones1, J. Bellocq1, C. Pierard1, Ph. Garrigues1 
TL;DR: In this paper, surface sediments, collected in the Gironde estuary during February and October 1993, were analysed for polycyclic aromatic hydrocarbons (PAHs) and the aromatic fractions were separated by liquid chromatography of the extracts and analysed by gas chromatography/mass spectrometry (GC/MS).

1,085 citations


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Performance
Metrics
No. of papers in the topic in previous years
YearPapers
2023495
2022942
2021364
2020345
2019371
2018386