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Tamoxifen metabolite R-isomer forms more DNA adducts in liver cells.
2004 AUG 5 - (NewsRx.com & NewsRx.net) -- A tamoxifen metabolite R-isomer forms more DNA adducts in liver cells.
"The antiestrogenic drug tamoxifen forms DNA adducts in rat liver through two genotoxic metabolites, a-hydroxytamoxifen and alpha-hydroxy-N-desmethyltamoxifen. These have now each been resolved into R- and S-enantiomers.
"The work with a-hydroxytamoxifen was published earlier [Osborne, et al, (2001) Chem. Res. Toxicol. 14, 888-893]. Here, we publish results with a-hydroxy-N-desmethyltamoxifen," wrote scientists in the journal Chemical Research in Toxicology.
"We prepared the derivative N-ethoxycarbonyl-N-desmethyltamoxifen-alpha-S-camphanate, separated it into two diastereoisomers and hydrolyzed them to give (+)- and (-)-alpha-hydroxy-N-desmethyltamoxifen. The configuration of the (-)-isomer was shown to be S- by degradation of the above ester to a derivative of (-)-2-hydroxy-1-phenyl-1-propanone, which has already been shown to have S-configuration," M.R. Osborne and coworkers reported.
"The two enantiomers have the same chemical properties and were equally reactive toward DNA in vitro at pH 6. However," scientists said, "on treatment of rat hepatocytes in ...
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Source: HighBeam Research, Tamoxifen metabolite R-isomer forms more DNA adducts in liver cells.