Abstract:
:The 1,1,1-trichloro-2,2-bis(p-chlorophenyl)ethene (DDT) metabolic intermediate 1-chloro-2,2-bis(p-chlorophenyl)ethene (DDMU) is partially metabolized in vivo by mice to 2-hydroxy-2,2-bis(p-chlorophenyl)acetic acid (alpha OH-DDA) and other metabolites which are excreted in urine. The subsequent DDT metabolic intermediates 1-chloro-2,2-bis(p-chlorophenyl)ethane (DDMS) and 1,1-bis(p-chlorophenyl)ethene (DDNU) are metabolized to alpha OH-DDA to a much lesser extent. These results imply that DDMU may be metabolized via an alpha-chloroepoxide. The authentic DDMU-epoxide, which after oral administration is excreted as alpha OH-DDA, is mutagenic in the Ames assay, and thermally rearranges rapidly to the corresponding alpha-chloroaldehyde, 2,2-bis(p-chlorophenyl)-2-chloroacetaldehyde (alpha Cl-DDCHO). As expected alpha Cl-DDCHO yielded the same urinary metabolites as DDMU-epoxide. This suggested metabolic pathway for DDMU via a chloroepoxide intermediate may account for the tumorigenicity of DDT in mice.
journal_name
Chem Biol Interactjournal_title
Chemico-biological interactionsauthors
Gold B,Leuschen T,Brunk G,Gingell Rdoi
10.1016/0009-2797(81)90140-xsubject
Has Abstractpub_date
1981-05-01 00:00:00pages
159-76issue
2eissn
0009-2797issn
1872-7786pii
0009-2797(81)90140-Xjournal_volume
35pub_type
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