Studies on the toxicology of hexachlorobenzene

Koss, G.; Seubert, S.; Seubert, Andreas; Koransky, W.; Ippen, H

doi:10.1007/bf00310334

Cited by 55 publications

(12 citation statements)

References 9 publications

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“…Fecal elimination in the last 72 h of dosing accounted for only 1 to 4% of the dose (data not shown). Higher fecal and negligible urinary elimination of the administered HCB was consistent with earlier reports [25,28,29].…”

Section: Fecal Elimination Of the Administered Hcbsupporting

confidence: 92%

Effect of organic carbon content, clay type, and aging on the oral bioavailability of hexachlorobenzene in rats

Saghir

Bartels

Budinsky

et al. 2007

Enviro Toxic and Chemistry

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Bioavailability of lipophilic chemicals is influenced by the physicochemical properties of soils/sediment such as particle size, pH, clay, and organic carbon content. The present study investigated the effects of sediment composition and aging on the oral bioavailability of hexachlorobenzene (HCB) in rats. Formulated sediments were prepared using various ratios of kaolinite and montmorillonite clay, sand, peat moss, and black carbon, spiked with (14)C-HCB, and orally administered to rats prior to and after one year of aging in dark at 10 degrees C. In the nonaged sediments there was a 21 to 45% reduction in the oral bioavailability of HCB when compared to the corn oil standard without any clear pattern of the impact of the sediment clay and/or organic carbon content. One year of aging resulted in statistically significant (p = 0.049) reduction in the oral bioavailability of HCB from the sediments compared to the corn oil standard and nonaged sediment indicating stronger interactions between HCB and sediment contents with aging. The mean reduction in oral bioavailability after one year of aging ranged from approximately 5 to 14% greater than that observed for nonaged sediments. The fecal elimination of the HCB-derived radioactivity from the one-year-aged sediments was much higher than the nonaged sediments, consistent with the lower absorption from the gastrointestinal tract due to lower desorption of HCB from the aged sediments. Increase in the fecal elimination and decrease in oral bioavailability of (14)C-HCB was related to the increase in clay and black carbon.

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Section: Fecal Elimination Of the Administered Hcbsupporting

confidence: 92%

Effect of organic carbon content, clay type, and aging on the oral bioavailability of hexachlorobenzene in rats

Saghir

Bartels

Budinsky

et al. 2007

Enviro Toxic and Chemistry

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“…This suggests that a minor part of the mercapturate may undergo in vivo cleavage of the C-S bond to yield free PCBT. This Environmental Health Perspectives * Volume 105, Number 1, January 1997 pathway has been clearly documented in rodents (12,15), but the possibility of some degree of bacterial mediated hydrolysis during urine collection or spontaneous hydrolysis during acidification cannot be ruled out.…”

Section: Discussionmentioning

confidence: 99%

“…Another major metabolic pathway observed in rodents is the conjugation of HCB with glutathione (12). The glutathione conjugate is further metabolized by cleavage of the glycine and glutamate residues to become pentachlorophenyl-Nacetyl-L-cysteine.…”

mentioning

confidence: 99%

Metabolism of Hexachlorobenzene in Humans: Association between Serum Levels and Urinary Metabolites in a Highly Exposed Population

To‐Figueras¹,

Sala²,

Rial-Otero³

et al. 1997

Environmental Health Perspectives

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JSTOR is a not-for-profit service that helps scholars, researchers, and students discover, use, and build upon a wide range of content in a trusted digital archive. We use information technology and tools to increase productivity and facilitate new forms of scholarship. For more information about JSTOR, please contact support@jstor.org.. The National Institute of Environmental Health Sciences (NIEHS) and Brogan & Partners are collaborating with JSTOR to digitize, preserve and extend access to Environmental Health Perspectives. Serum and urine from 100 subjects of a general population highly exposed to airborne hexachlorobenzene (HCB) were analyzed to obtain new insights into the metabolism of this ubiquitous compound. HCB was detected in all serum samples with concentraions ranging between 1.1 and 953 ng/ml. The major known metabolites of HCB were investigated in urine collected over 24 hr. Pnntachlorophenol (PCP) was detected in all urines ith values ranging between 0.58 and 13.9 pg excreted in 24 hr [mean ? standard deviation (SD), 2.52 ? 2.05; geometric mean, 2.05]. A sulfur derivative that, after hydrolysis, yielded pentachlorobenzenethiol (PCBT) could also be identified and quantified in all the urines with values raging between 0.18 and 84.0 pg of PCBT excreted in 24 hr (mean ? SD, 3.47 ? 10.8; geometric mean, 1.39). The sulfur derivative assessed as PCBT appeared to be the main metabolite, with urinary concentrations surpassing those of PCP in the subjects with higher HCB accumulation (HCB in serum >32 ng/ml). PCBT concentration in urine collected over 24 hr showed a very strong associaion with HCB concentration in serum; the association was stronger in males than in females. An increase of 1 ng/ml of HCB in serum led to an increase of 2.12 pg of PCBT excreted in urine collected over 24 hr in males (95% CI, 1.82-2.44) and to an increase of 0.67 pg of PCBT in females (CI, 0.33-1.09). A weaker association was found between PCP in urine and HCB in serum, which was only statistically significant in males (an increase of 1 ng/ml of HCB in serum led to an increase of 0.63 pg of PCP excreted in urine collected over 24 hr, (CI, 0.34-0.95). These results show that the formation of the cysteine conjugate is a quantitatively more important metabolic pathway in humans than the formation of PCP. Moreover, the association found suggests that PCBT is a good urinary marker of HCB internal dose and glltathione-mediated metabolism.

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“…Sulfhydryl HCB metabolites have been found in the urine and faeces of humans exposed to HCB and are believed to be derived from initial glutathione conjugation followed by further metabolism of the glutathione conjugate . Sulfur containing HCB metabolites have also been found in rodents exposed to HCB …”

Section: Resultsmentioning

confidence: 99%

Separation and fragmentation study of isocoproporphyrin derivatives by UHPLC-ESI-exact mass MS/MS and identification of a new isocoproporphyrin sulfonic acid metabolite

et al. 2014

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Isocoproporphyrin and its derivatives are commonly used as biomarkers of porphyria cutanea tarda, heavy metal toxicity and hexachlorobenzene (HCB) intoxication in humans and animals. However, most are isobaric with other porphyrins and reference materials are unavailable commercially. The structural characterisation of these porphyrins is important but very little data is available. We report here the separation and characterisation of isocoproporphyrin, deethylisocoproporphyrin, hydroxyisocoproporphyrin and ketoisocoproporphyrin, isolated in the faeces of rats fed with a diet containing HCB, by ultra high performance liquid chromatography-exact mass tandem mass spectrometry (UHPLC-MS/MS). Furthermore, we report the identification and characterisation of a previously unreported porphyrin metabolite, isocoproporphyrin sulfonic acid isolated in the rat faeces. The measured mass-to-charge ratio (m/z) of the precursor ion was m/z 735.2338, corresponding to a molecular formula of C36H39N4O11S with an error of 0.3 ppm from the calculated m/z 735.2336. The MS/MS data was consistent with an isocoproporphyrin sulfonic acid structure, derived from dehydroisocoproporphyrinogen by sulfonation of the vinyl group. The metabolite was present in a greater abundance than other isocoproporphyrin derivatives and may be a more useful biomarker for HCB intoxication.

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Studies on the toxicology of hexachlorobenzene

Cited by 55 publications

References 9 publications

Effect of organic carbon content, clay type, and aging on the oral bioavailability of hexachlorobenzene in rats

Effect of organic carbon content, clay type, and aging on the oral bioavailability of hexachlorobenzene in rats

Metabolism of Hexachlorobenzene in Humans: Association between Serum Levels and Urinary Metabolites in a Highly Exposed Population

Separation and fragmentation study of isocoproporphyrin derivatives by UHPLC-ESI-exact mass MS/MS and identification of a new isocoproporphyrin sulfonic acid metabolite

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