Mutagenic activity of methyl-substituted tri-and tetracyclic aromatic sulfur heterocycles

McFall, Teri; Booth, Gary M.; Lee, Milton L.; Tominaga, Yoshinori; Pratap, Ramendra; Tedjamulia, Marvin L.; Castle, Raymond N.

doi:10.1016/0165-1218(84)90161-7

Cited by 80 publications

(27 citation statements)

References 14 publications

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“…Many researchers have reported the toxic and mutagenic potential of PASHs (Eastmond et al, 1984;Karcher et al, 1981;Pelroy et al, 1983;McFall et al, 1984). PASHs have been found in the effluents of wastewater treatment plants of many fossil fuel processing sites.…”

Section: Introductionmentioning

confidence: 97%

Sonochemical degradation of polycyclic aromatic sulfur hydrocarbons (PASHs) in aqueous solutions exemplified by benzothiophene

Kim

Huang²

2005

Journal of the Chinese Institute of Engineers

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The degradation of polycyclic aromatic sulfur hydrocarbons (PASHs) in aqueous solutions due to sonochemical processes was studied. Benzothiophene (BT), and dibenzothiophene (DBT) in addition to two polycyclic aromatic hydrocarbons, namely phenanthrene (Phe) and naphthalene (Nap) were compared. Results showed that all polycyclic aromatic compounds were decomposed rapidly following a pseudo-first-order kinetics upon ultrasonic irradiation in aqueous solutions. The rate constant increased with increasing pH and decreased with increasing initial benzothiophene concentration. Whereas, for temperature, the rate increased with temperature up to 50°C then decreased upon further increase in temperature above 50°C. Hydroxybenzothiophenes, dihydroxybenzothiophenes, and benzothiophene-dione were identified as major intermediates. Also evolution of carbon dioxide and sulfite was observed. Hydroxyl radicals play the major role in the decomposition of PASHs. The toxicity of sonochemically treated solutions was evaluated by monitoring the respiration rate of E. coli. Results indicate that a sonochemically treated benzothiophene sample improved the respiration rate of E. coli compared to an untreated sample.

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Section: Introductionmentioning

confidence: 97%

Sonochemical degradation of polycyclic aromatic sulfur hydrocarbons (PASHs) in aqueous solutions exemplified by benzothiophene

Kim

Huang²

2005

Journal of the Chinese Institute of Engineers

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“…However, their sulfur analogues, polycyclic aromatic sulfur heterocycles (PASHs), have received far less attention although their presence has been confirmed in air particulate matter [5, 6], sediments [7–9], coal liquids [10], diesel [9], heavy oil [11], crude oil [9, 11–17], shale oil [10, 12, 15, 18], coal tar [12–15, 19–21], mussels [7, 8], and fish [7, 8]. In addition, their carcinogenic and mutagenic potential have been reported [22, 23]. PASHs exist in an even greater variety of structures compared to PAHs due to the presence of the sulfur atom.…”

Section: Introductionmentioning

confidence: 99%

Retention behavior of isomeric polycyclic aromatic sulfur heterocycles in reversed-phase liquid chromatography

Wilson

Sander

Alda

et al. 2016

Journal of Chromatography A

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Retention indices for 70 polycyclic aromatic sulfur heterocycles (PASHs) were determined using reversed-phase liquid chromatography (LC) on a monomeric and a polymeric C18 stationary phase. Molecular shape parameters [length, breadth, thickness (T), and length-to-breadth ratio (L/B)] were calculated for all the compounds studied. Correlations between the retention on the polymeric C18 phase and PASH geometry (L/B and T) were investigated for six specific PASH isomer groups with molecular mass (MM) 184 Da, 234 Da, 258 Da, 284 Da, 334 Da, and 384 Da. Similar to previous studies for polycyclic aromatic hydrocarbons (PAHs), PASH elution order on the polymeric C18 phase was generally found to follow increasing L/B values. Correlation coefficients for retention vs L/B ranged from r = 0.45 (MM 184 Da) to r = 0.89 (MM 284 Da). In the case of smaller PASHs (MM ≤ 234 Da), the location of the sulfur atom in the bay-region of the structure resulted in later than expected elution of these isomers based on L/B. In the case of the larger PASHs (MM ≥ 284 Da), nonplanarity had a significant influence on earlier than predicted elution based on L/B values.

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“…A number of un-substituted 3-and 4-ring thiophenes were tested by Pelroy and co-workers (1983) and McFall et al (1984, cited in Jacob, 1990 for mutagenic activity in S. typhimurium strains TA 98 and TA100. Of the 3-ring thiophenes only naphtho [1,2-b]thiophene was mutagenic whereas its isomers naphtho[2,1-b]thiophene and naphtho [2,3-b]thiophene and dibenzothiophene were not.…”

Section: Sulfur-containing Aromatics (Condensed Thiophenes)mentioning

confidence: 99%

Scientific Opinion on Mineral Oil Hydrocarbons in Food

2012

EFS2

103

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Consumers are exposed to a range of mineral oil hydrocarbons (MOH) via food. Mineral oil saturated hydrocarbons (MOSH) consist of linear and branched alkanes, and alkyl-substituted cyclo-alkanes, whilst mineral oil aromatic hydrocarbons (MOAH) include mainly alkyl-substituted polyaromatic hydrocarbons. Products, commonly specified according to their physico-chemical properties, may differ in chemical composition depending on the oil source. Technical grade MOH contain 15 -35 % MOAH, which is minimised in food grade MOSH (white oils). Major sources of MOH in food are food packaging and additives, processing aids, and lubricants. Estimated MOSH exposure ranged from 0.03 to 0.3 mg/kg b.w. per day, with higher exposure in children. Specific production practices of bread and grains may provide additional MOSH exposure. Except for white oils, exposure to MOAH is about 20 % of that of MOSH. Absorption of alkanes with carbon number above C 35 is negligible. Branched and cyclic alkanes are less efficiently oxidised than n-alkanes. MOSH from C 16 to C 35 may accumulate and cause microgranulomas in several tissues including lymph nodes, spleen and liver. Hepatic microgranulomas associated with inflammation in Fischer 344 rats were considered the critical effect. The no-observed-adverse-effect level for induction of liver microgranulomas by the most potent MOSH, 19 mg/kg b.w. per day, was used as a Reference Point for calculating margins of exposure (MOEs) for background MOSH exposure. MOEs ranged from 59 to 680. Hence, background exposure to MOSH via food in 1 On request from the European Commission, Question No EFSA-Q-2010-00170, adopted on 3 May 2012. 2 SUMMARYFollowing a request from the European Commission, the EFSA Panel on Contaminants in the Food Chain (CONTAM Panel) was asked to deliver a scientific opinion on mineral oil hydrocarbons (MOH) in Food. Mineral oil hydrocarbons occur in food both as a result of contamination and from various intentional uses in food production. In order to assess the need for possible regulatory measures as regards MOH in food, EFSA was requested to assess the risks related to their occurrence in food. More specifically, the opinion should evaluate whether new toxicity data are available and whether the current acceptable daily intakes (ADIs) are still applicable, explore whether certain classes (or subclasses) of MOH are more relevant due to their toxicity or to differences in the way they are metabolised by the human body, and identify the different background sources, other than from adulteration or misuse, of MOH occurrence in food. In addition a dietary exposure assessment was requested for the general population and for specific subgroups of the population (e.g. infants, children and people following specific diets), by taking into account the background occurrence of MOH in food. Included in the request was also to advise on MOH and food classes to be included if monitoring were to be set up for their presence in food.The scientific literature and other sources were s...

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Mutagenic activity of methyl-substituted tri-and tetracyclic aromatic sulfur heterocycles

Cited by 80 publications

References 14 publications

Sonochemical degradation of polycyclic aromatic sulfur hydrocarbons (PASHs) in aqueous solutions exemplified by benzothiophene

Sonochemical degradation of polycyclic aromatic sulfur hydrocarbons (PASHs) in aqueous solutions exemplified by benzothiophene

Retention behavior of isomeric polycyclic aromatic sulfur heterocycles in reversed-phase liquid chromatography

Scientific Opinion on Mineral Oil Hydrocarbons in Food

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