Identification of Benzo(a)pyrene Metabolites by Gas Chromatograph-Mass Spectrometer

作者: Kimio Yasuhira , Gonya Takahashi , Kazuyuki Kinoshita , Kenji Hashimoto

DOI:

关键词: Gas chromatography–mass spectrometryPyreneSpectrometerMass spectrumChromatographic separationPhenolsSilylationBenzo(a)pyreneChromatographyChemistry

摘要: A gas chromatograph-mass spectrometer was used in an attempt to achieve rapid separation and accurate identification of benzo(a)pyrene its synthesized derivatives. All derivatives, after being trimethylsilylated, were developed on Dexsil-300 OV-1 columns. The seven diols four stereoisomeric 7,8,9,10-tetraols studied separated successfully. the 12 phenols unsatisfactory; 8- 11-isomers appeared separately but other 10 isomers made 3 peaks column. Among five derivatives reported be present animal tissues, 6-, 7-, 9-phenols separated, 1- 3-phenols fused Quinones converted related dihydroxyl under silylation. chromatographic six successful column, 6,12- 7,10-isomers remained a single peak. two diol-epoxides unstable silylation therefore detected by their breakdown products, 7,8,9-trihydroxy-7,8-dihydrobenzo( )pyrene tetraols. Data are listed mass spectra retention times all benzo( studied.

参考文章(11)
P. Sims, P.L. Grover, Epoxides in polycyclic aromatic hydrocarbon metabolism and carcinogenesis. Advances in Cancer Research. ,vol. 20, pp. 165- 274 ,(1974) , 10.1016/S0065-230X(08)60111-6
Charles Heidelberger, Chemical Oncogenesis In Culture Advances in Cancer Research. ,vol. 18, pp. 317- 366 ,(1973) , 10.1016/S0065-230X(08)60756-3
Patrick M. Dansette, He Duck Mah, Wayne Levin, Alexander W. Wood, Richard L. Chang, Donald M. Jerina, Haruhiko Yagi, Oscar Hernandez, Allan H. Conney, Peter G. Wislocki, High Carcinogenicity of 2-Hydroxybenzo(a)pyrene on Mouse Skin Cancer Research. ,vol. 37, pp. 2608- 2611 ,(1977)
J. K. Selkirk, R. G. Croy, H. V. Gelboin, Benzo(a)pyrene metabolites: efficient and rapid separation by high-pressure liquid chromatography. Science. ,vol. 184, pp. 169- 171 ,(1974) , 10.1126/SCIENCE.184.4133.169
James K. Selkirk, Robert G Croy, Harry V. Gelboin, Isolation by high pressure liquid chromatography and characterization of benzo(a)pyrene-4,5-epoxide as a metabolite of benzo(a)pyrene Archives of Biochemistry and Biophysics. ,vol. 168, pp. 322- 326 ,(1975) , 10.1016/0003-9861(75)90256-8
S. K. Yang, D. W. McCourt, P. P. Roller, H. V. Gelboin, Enzymatic conversion of benzo(a)pyrene leading predominantly to the diol-epoxide r-7,t-8-dihydroxy-t-9,10-oxy-7,8,9,10-tetrahydrobenzo(a)pyrene through a single enantiomer of r-7, t-8-dihydroxy-7,8-dihydrobenzo(a)pyrene Proceedings of the National Academy of Sciences of the United States of America. ,vol. 73, pp. 2594- 2598 ,(1976) , 10.1073/PNAS.73.8.2594
JAIME KAPITULNIK, WAYNE LEVIN, ALLAN H. CONNEY, HARUHIKO YAGI, DONALD M. JERINA, Benzo[ a ]pyrene 7,8-dihydrodiol is more carcinogenic than benzo[ a ]pyrene in newborn mice Nature. ,vol. 266, pp. 378- 380 ,(1977) , 10.1038/266378A0
G. Holder, H. Yagi, P. Dansette, D. M. Jerina, W. Levin, A. Y. H. Lu, A. H. Conney, Effects of Inducers and Epoxide Hydrase on the Metabolism of Benzo[a]pyrene by Liver Microsomes and a Reconstituted System: Analysis by High Pressure Liquid Chromatography Proceedings of the National Academy of Sciences of the United States of America. ,vol. 71, pp. 4356- 4360 ,(1974) , 10.1073/PNAS.71.11.4356