Synthesis of dibenzo[def,p]chrysene, its active metabolites, and their 13C-labeled analogues.
Dibenzo[def,p]chrysene (DBC) is a highly carcinogenic polycyclic aromatic hydrocarbon suspected to be involved in initiation of lung cancer in smokers. Efficient new syntheses of DBC, its active metabolites [DBC diol (1), DBC dione (2), DBC diol epoxide (3)], and their previously unknown 13C2-labeled analogues are reported. The 13C2-labeled analogues are required as standards for sensitive methods of analysis of their DNA adducts in human cells using stable isotope dilution liquid chromatography/tandem mass spectrometry.
Xu
Daiwang
D
Ben May Department for Cancer Research, University of Chicago, Chicago, IL 60637, USA.
Duan
Yazhen
Y
Blair
Ian A
IA
Penning
Trevor M
TM
Harvey
Ronald G
RG
D001580:Benzopyrenes / Q000138:chemical synthesis* / Q000737:chemistry; D002247:Carbon Isotopes / Q000737:chemistry; D002853:Chromatography, Liquid; D053719:Tandem Mass Spectrometry
D001580:Benzopyrenes; D002247:Carbon Isotopes; C041517:dibenzo(a,l)pyrene