Methylsulfonyl metabolites of PCBs and DDE in human tissues.

Abstract

Methylsulfonyl metabolites of chlorinated biphenyls (MeSO2-CBs) and p,p'-DDE (MeSO2-DDEs) were determined in human adipose and liver tissues obtained at autopsy of seven Swedish individuals 47-80 years of age. Twenty MeSO2-CBs and two MeSO2-DDEs were found in the analyzed samples. In adipose tissue, most of the 4-MeSO2-CBs were found at higher concentrations than the corresponding 3-MeSO2-CBs and, in all samples of adipose tissue, 4-MeSO2-2,2',3',4',5-pentaCB (4-87) and 4-MeSO2-2,2',3,4',5',6-hexaCB (4-149) occurred at higher concentrations than other MeSO2-CBs. In the liver, 3-MeSO2-2,2',3',4',5,6-hexaCB (3-132) was by far the most abundant MeSO2-CB, contributing to 61-82% of the sum of MeSO2-CBs. In this tissue, most of the other 3-MeSO2-CBs were also found at higher concentrations than the corresponding 4-MeSO2-CBs. The ratios of the sum of MeSO2-CBs to the sum of determined chlorinated biphenyls (CBs) were 1/250 and 1/28 in adipose tissue and the liver, respectively, calculated from the median values. The concentration of 2-MeSO2-DDE was lower than that of 3-MeSO2-DDE in both adipose tissue and liver, except in the liver from one of the individuals. The concentration ratios of 2-MeSO2-DDE to 3-MeSO2-DDE were about 10 times higher in liver than in adipose tissue. The ratios of the sum of MeSO2-DDEs to p,p'-DDE were 1/455 and 1/61 in adipose tissue and liver, respectively, calculated from the median values. MeSO2-CBs and MeSO2-DDEs were also determined in lung tissue from one of the individuals. In this sample, the profiles of MeSO2-CBs and MeSO2-DDEs were similar to the profiles of these compounds in adipose tissue.ImagesFigure 1.Figure 2.Figure 3.

Hydroxylation and Methylthiolation of Mono-Ortho-Substituted Polychlorinated Biphenyls in Rats: Identification of Metabolites with Tissue Affinity

“…The metabolic behavior of some of PCBs with 3,4-substitution is similar to the metabolism of PCBs with 2,5-substitution (44). To date, a number of MeSO 2 metabolites have been identified in marine mammals (45)(46)(47) as well as in human milk (48) and tissues (49). Most of them are those arising from pentaCB and hexaCB with a 2,5-dichloro or a 2,3,6-trichloro substitution.…”

Metabolism and metabolites of polychlorinated biphenyls

“…They accumulate with high selectivity in certain tissues, such as liver and lung (Letcher et al, 2000, Bergman et al, 1979, Larsson and Bergman, 1998). The MeSO 2 -PCB concentrations are notably high in the liver of mammals (Larsson and Bergman, 1998, Bergman et al, 1994b) and likewise, human livers have been shown to accumulate MeSO 2 -PCBs (Weistrand and Noren, 1997, Ellerichmann et al, 1998). The majority of these metabolites have the MeSO 2 substituent in the meta -position of their respective biphenyl ring.…”

“…= not detected; LOQ = limit of quantification; a) Sampling year; b) Number of MeSO 2 -PCB congeners in the ΣMeSO 2 -PCB; c) include concentration of the MeSO 2 -hexaCB (unknown); d) The publication year; e) pooled sample/number of subjects in the pool; f) Data has been recalculated for a lipid content of 4%; g) Mean values. References: R1 : (Weistrand et al, 1997); R12 : (Noren et al, 1996); R13 : (Newsome and Davies, 1996); R14 : (Weistrand and Noren, 1997); R15 : (Weistrand and Noren, 1997); R16 : (Guvenius et al, 2002); R17 : (Chu et al, 2003b); R18 : (Chu et al, 2003b). …”

Disruption of glucocorticoid action by environmental chemicals: Potential mechanisms and relevance

“…The environmental chemical 3-methylsulfonyl-DDE, a metabolite of the lipophilic insecticide DDT, was found to be present in mother's milk, blood and adipose tissue [47,48] and was shown to accumulate in the adrenal cortex. Using human H295R and mouse Y1 adrenocortical cells it was shown that several persistent aryl methylsulfone metabolites of PCBs and DDT, including 3-methylsulfonyl-DDE, competitively inhibit mitochondrial 11␤-hydroxylase, which catalyzes the last step of glucocorticoid synthesis by converting 11-deoxycortisol to cortisol.…”