Abstract:
:Five selectively methylated analogs of the flame retardant tris(2,3-dibromopropyl)phosphate (Tris-BP) and of the nematocide 1,2-dibromo-3-chloropropane (DBCP) were synthesized and their relative mutagenicities determined in Salmonella typhimurium TA100 in the presence of rat liver microsomes. In all cases, methylation decreased mutagenicity relative to the parent compound, but the relative degree of reduced mutagenicity varied considerably depending on the position of the methyl substitution. The mutagenicity studies with the selectively methylated analogs and with suspected mutagenic metabolites (2-bromocrotonaldehyde and methyl 1-dibromovinyl ketone) supported earlier work with selectively deuterated analogs of Tris-BP and DBCP. They demonstrated that initial oxidation at C-3, followed by spontaneous dehydrohalogenation and dehydrophosphorylation, was the major route of formation of mutagenic metabolites from Tris-BP. In the case of DBCP, formation of mutagenic metabolites can result following initial oxidation at either C-1 or C-3.
journal_name
Mutagenesisjournal_title
Mutagenesisauthors
Omichinski JG,Søderlund EJ,Bausano JA,Dybing E,Nelson SDdoi
10.1093/mutage/2.4.287subject
Has Abstractpub_date
1987-07-01 00:00:00pages
287-92issue
4eissn
0267-8357issn
1464-3804journal_volume
2pub_type
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