63059-68-7Relevant academic research and scientific papers
Synthesis of 13C4-labelled oxidized metabolites of the carcinogenic polycyclic aromatic hydrocarbon benzo[a]pyrene
Wu, Anhui,Xu, Daiwang,Lu, Ding,Penning, Trevor M.,Blair, Ian A.,Harvey, Ronald G.
, p. 7217 - 7233 (2012/09/05)
Polycyclic aromatic hydrocarbons (PAHs), such as benzo[a]pyrene (BaP), are ubiquitous environmental contaminants that are implicated in causing lung cancer. BaP is a component of tobacco smoke that is transformed enzymatically to active forms that interact with DNA. We reported previously development of a sensitive stable isotope dilution LC/MS method for analysis of BaP metabolites. We now report efficient syntheses of 13C4-BaP and the complete set of its 13C4-labelled oxidized metabolites needed as internal standards They include the metabolites not involved in carcinogenesis (Group A) and the metabolites implicated in initiation of cancer (Group B). The synthetic approach is novel, entailing use of Pd-catalyzed Suzuki, Sonogashira, and Hartwig cross-coupling reactions combined with PtCl2-catalyzed cyclization of acetylenic compounds. This synthetic method requires fewer steps, employs milder conditions, and product isolation is simpler than conventional methods of PAH synthesis. The syntheses of 13C4-BaP and 13C4-BaP-8-ol each require only four steps, and the 13C-atoms are all introduced in a single step. 13C4-BaP-8-ol serves as the synthetic precursor of all the oxidized metabolites of 13C-BaP implicated in initiation of cancer. The isotopic purities of the synthetic 13C 4-BaP metabolites were estimated to be ≥99.9%.
Synthesis of phenol and quinone metabolites of benzo[a]pyrene, a carcinogenic component of tobacco smoke implicated in lung cancer
Xu, Daiwang,Penning, Trevor M.,Blair, Ian A.,Harvey, Ronald G.
experimental part, p. 597 - 604 (2009/06/20)
Polycyclic aromatic hydrocarbons (PAHs) are widespread environmental pollutants produced in the combustion of organic matter. PAHs are present in automobile exhaust and tobacco smoke, and they have recently been designated as human carcinogens. Current ev
A RAPID, CONVERGENT, AND REGIOSELECTIVE SYNTHESIS OF 3,7,8-TRIHYDROXY-TRANS-7,8-DIHYDROBENZOPYRENE
Kumar, Subodh,Singh, Sudhir K.
, p. 1213 - 1216 (2007/10/02)
A new, highly efficient, and regioselective synthesis of 3,7,8-trihydroxy-trans-7,8-dihydrobenzopyrene and its 3-methoxy analogue is described.
Chemical derivatization and Shpol'skii spectrofluorometric determination of benzo[a]pyrene metabolites in fish bile
Ariese, Freek,Kok, Steven J.,Verkaik, Marieke,Hoornweg, Gerard Ph.,Gooijer, Cees,Velthorst, Nel H.,Hofstraat, Johannes W.
, p. 1100 - 1106 (2007/10/02)
The practical applicability and analytical performance of laser-excited Shpol'skii spectroscopy (LESS) for the determination of benzo[a]pyrene (BaP) metabolites was studied. Quantitation of these compounds in fish bile can provide insight into the BaP uptake from a contaminated aquatic environment (biomonitoring). Chemical derivatization of hydroxylated BaP metabolites with methyl iodide (to improve the compatibility with the Shpol'skii matrix) was tested. The methylation of phenolic metabolites was rapid and quantitative, but with BaP-dihydro diol metabolites, mixtures of methylation and elimination products were formed. An analytical procedure was developed for the quantitative determination of 3-OH-BaP, the major BaP metabolite detected in bile from flounder (Platichthys flesus). With LESS, the detection limit was 0.005 ng/mL (200 amol); the repeatability was 16%. The method was applied to a mesocosm experiment in which flounders were exposed to different sediments. The average BaP uptake from Rotterdam harbor sediment was 40 times higher than the uptake from Wadden Sea sand. Direct contact with the sediments was a major route of exposure. The usefulness of the method for the biomonitoring of polycyclic aromatic hydrocarbon stress in the aquatic environment is discussed.
