Microbial mutagenicity of 3- and 4-ring polycyclic aromatic sulfur heterocycles

Pelroy, R.A.; Stewart, Donald C.; Tominaga, Yoshinori; Iwao, Masatomo; Castle, Raymond N.; Lee, Milton L.

doi:10.1016/0165-1218(83)90150-7

Cited by 89 publications

(49 citation statements)

References 5 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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“…Investigators target polycyclic aromatic hydrocarbons (PAH) to assess risk because these compounds bioaccumulate (4,5), are toxic (6,7), mutagenic (8), and carcinogenic (9)(10)(11)(12)(13)(14). Despite knowing many polycyclic aromatic sulfur heterocycles (PASH), condensed ring aromatic thiophenes, exhibit mutagenic (15,16) and carcinogenic (17)(18)(19) activity, they are generally ignored in risk assessments (20). A comprehensive study of their gas chromatographic retention times and mass spectral patterns is needed to accurately quantify them in the environment should these compounds become regulated.…”

Section: Introductionmentioning

confidence: 99%

Mass Spectra and Retention Indexes for Polycyclic Aromatic Sulfur Heterocycles and Some Alkylated Analogs

Zeigler

Schantz

Wise

et al. 2012

Polycyclic Aromatic Compounds

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Polycyclic aromatic sulfur heterocycles (PASH) are ubiquitous in fossil fuels and pose risk to the environment due to their toxicity. Some PASH, resistant to degradation in the environment, are used to differentiate pollutant source and weathering. Although retention data exist for some PASH, few mass spectra are available, so misidentification often occurs between isomers in the same family. In this study, the retention behavior of 119 PASH on 14%-cyanopropyl/86%-polydimethylsiloxane (DB-1701ms), trifluoropropylmethylpolysiloxane (Rtx-200ms), 5%-phenyl/95%-dimethyl (Rxi-5ms), and 50%-diphenyl/50%-dimethyl (Rxi-17Sil-ms) are reported along with their mass spectra. This data is guiding on-going research aimed at identifying PASH in coal tar by multidimensional GC-GC/MS for compounds where standards are not available.

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“…Both aand P-thienylketene precursors are commercially available and such transformations would constitute a general synthetic route to PAH's incorporating a terminal thiophene nucleus. A number of these compounds are of interest in environmental chemistry and toxicology due to their presence in fossil fuel and coal sources and their mutagenic activity (5). In this study we report a different and heretofore unreported acid-catalyzed dehydration-rearrangement of two a-thienyl bicyclic cyclobutanols in which regiospecific a-ring opening is involved.…”

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confidence: 97%

Acid-catalyzed rearrangement of cyclobutanols. A novel rearrangement

Lee‐Ruff¹,

Ablenas²

1987

Can. J. Chem.

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E. LEE-RUFF and FRED J. ABLENAS. Can. J. Chern. 65, 1663 (1987). The acid-catalysed dehydration-rearrangement reaction of a-thienyl cyclobutanols 3 and 4 resulted in the formation of tetrahydronaphtho[2,3-blthiophenes 5a and 6 a . The rearrangement to the linearly fused PAH system instead of the expected angularly fused system reflects a-scission of the cyclobutyl ring. A mechanism based on deuterium labelling studies is proposed to account for the product formation. Bicyclic cyclobutanones with an a-aryl substituent undergo selective p-scission under acid catalysis to give tricyclic ketones by way of intramolecular orthoannelation of an intermediate carbocation (1)(2)(3). This observation has been used as a general approach towards the synthesis of polynuclear aromatic hydrocarbons (PAH) in which non-benzenoid and heterocyclic rings are incorporated in the PAH ring system as terminal units. These studies were also extended to bicyclic cyclobutanols bearing at least one a-aryl substituent. Acid reaction of typical bicyclic cyclobutanols effects dehydration and rearrangement to give angularly fused hydroarenes that are readily dehydrogenated to PAH's (4) (Scheme 1). The intermediate carbocations are the result of selective p-scission of the cyclobutanol ring and are stabilized by positive charge delocalizing groups such as a vinyl or heteroatom group. The cyclobutanols are readily obtained from the corresponding cyclobutanones, which in turn are prepared from aryl ketene cycloadditions to cycloolefins. As an extension to these studies we were interested in the possibility of cyclobutanols with a-heteroaromatic substituents undergoing similar transformations to give heteroaromatic PAH 's. Both aand P-thienylketene precursors are commercially available and such transformations would constitute a general synthetic route to PAH's incorporating a terminal thiophene nucleus. A number of these compounds are of interest in environmental chemistry and toxicology due to their presence in fossil fuel and coal sources and their mutagenic activity (5). In this study we report a different and heretofore unreported acid-catalyzed dehydration-rearrangement of two a-thienyl bicyclic cyclobutanols in which regiospecific a-ring opening is involved. Results and discussionThe preparation of cyclobutanones 1 and 2 was accomplished by generating 2-or 3-thienylketene in situ by dehydrochlorination of the acid chloride with triethylamine in the presence of 1,3-cyclohexadiene. In each case a stereoisomeric mixture was obtained in which the endo-substituted product predominates and column chromatography on silica gel causes the equilibration to the thermodynamic exo-substituted product (6). The endo-substituted derivative is predicted to be the kinetic product based on orbital symmetry considerations of the 2 n a + 2 n s transition state (7).Reduction of ketones 1 and 2 with excess lithium aluminum hydride gave alcohols 3 and 4 (X = H, Y = H) respectively as a mixture of diastereomers in 78-80% yields. The relative distribution of the dias...

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Microbial mutagenicity of 3- and 4-ring polycyclic aromatic sulfur heterocycles

Cited by 89 publications

References 5 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

Mass Spectra and Retention Indexes for Polycyclic Aromatic Sulfur Heterocycles and Some Alkylated Analogs

Acid-catalyzed rearrangement of cyclobutanols. A novel rearrangement

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