Synthesis and mutagenicity of selectively methylated analogs of tris(2,3-dibromopropyl)phosphate and 1,2-dibromo-3-chloropropane.

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

Mutagenesis

journal_title

Mutagenesis

authors

Omichinski JG,Søderlund EJ,Bausano JA,Dybing E,Nelson SD

doi

10.1093/mutage/2.4.287

subject

Has Abstract

pub_date

1987-07-01 00:00:00

pages

287-92

issue

4

eissn

0267-8357

issn

1464-3804

journal_volume

2

pub_type

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