Analysis of benzo[a]pyrene metabolites formed by rat hepatic microsomes using high pressure liquid chromatography: Optimization of the method

Interdisciplinary Toxicology

Volumn 2, Issue 4, 2009, Pages 239-244

  Moserovä, Michaela ^a   Kotrbovä, Vira ^a   Aimovä, Dagmar ^a   Šulc, Miroslav ^a   Frei, Eva ^b   Stiborovä, Marie ^a  

^a CHARLES UNIVERSITY   (Czech Republic)

^b GERMAN CANCER RESEARCH CENTER DKFZ   (Germany)

Author keywords

benzo a pyrene; HPLC; metabolism

Indexed keywords

EID: 80053653487     PISSN: 13376853     EISSN: 13379569     Source Type: Journal    
DOI: 10.2478/v10102-009-0024-0     Document Type: Article

References (32)

1. Angerer J, Mannschreck C, Gündel J. (1997). Biological monitoring and biochemical effect monitoring of exposure to polycyclic aromatic hydrocarbons. Int Arch Occup Environ Health 70: 365-377.
2. Arlt VM, Stiborová M, Henderson CJ, Thiemann M, Frei E, Aimová D, Singhs R, da Costa GG, Schmitz OJ, Farmer PB, Wolf CR, Phillips DH. (2008). Metabolic activation of benzo[a]pyrene in vitro by hepatic cytochrome P450 contrasts with detoxification in vivo: experim ents with hepatic cytochrome P450 reductase null mice. Carcinogenesis 29: 656-665.
3. Baird WM, Hooven LA, Mahadevan B. (2005). Carcinogenic polycyclic aromatic hydrocarbon-DNA adducts and mechanism of action. Environ Mol Mutagen 45: 106-114.
4. Ellard S, Mohammed Y, Dogra S, Wolfel C, Doehmer J, Parry JM. (1991). Use of genetically engineered V79 Chinese hamster cultures expressing rat liver CYP1A1, 1A2 and 2B1 cDNAs in micronucleus assays. Mutagenesis 6: 461-470
5. Gündel J, Angerer J. (2000). High-performance liquid chromatographic method with fl uorescence detection for the determination of 3-hydroxybenzo[a]pyrene and 3-hydroxybenz[a]anthracene in the urine of polycyclic aromatic hydrocarbon-exposed workers. J Chromatogr B Biomed Sci Appl 738: 47-55.
6. Hecht SS. (2001). Carcinogen biomarkers for lung or oral cancer chemoprevention trials. IARC Sci Publ 154: 245-255.
7. IARC Monogr Eval Carcinog Risk Chem Hum. (1983). Polynuclear Aromatic Compounds 32, 211.
8. James MO, Altman AH, Li CL, Schell JD Jr. (1995). Biotransformation, hepatopancreas DNA binding and pharmacokinetics of benzo[a]pyrene after oral and parenteral administration to the American lobster, Homarus americanus. Chem Biol Interact 95: 141-160.
9. James MO, Altman AH, Morris K, Kleinow KM, Tong Z. (1997). Dietary modulation of phase 1 and phase 2 activities with benzo pyrene and related compounds in the intestine but not the liver of the channel catfish, Ictalurus punctatus. Drug Metab Dispos 25: 346-354.
10. Jiang H, Gelhaus SL, Mangal D, Harvey RG, Blair IA, Penning TM. (2007). Metabolism of benzo[a]pyrene in human bronchoalveolar H358 cells using liquid chromatography-mass spectrometry. Chem Res Toxicol 20: 1331-1341.
11. Kim JH, Stansbury KH, Walker NJ, Trush MA, Strickland PT, Sutter TR. (1998). Metabolism of benzo[a]pyrene and benzo[a]pyrene-7,8-diol by human cytochrome P450 1B1. Carcinogenesis 19: 1847-1853.
12. Krahn MM, Myers MS, Burrows DG, Malins DC. (1984). Determination of metabolites of xenobiotics in the bile of fish from polluted waterways. Xenobiotica 14: 633-646.
13. Lubet RA, Connolly G, Kouri RE, Nebert DW, Bigelow SW. (1983). Biological effects of Sudan I dyes. Role of the cytosolic Ah receptor. Biochem Pharmacol 32: 3053-3058.
14. Luch A, Baird WM. (2005). Metabolic activation and detoxification of polycyclic aromatic hydrocarbons. The Carcinogenic Effects of Polycyclic Aromatic Hydrocarbons. Imperial College Press, London, 19-96.
15. Martínek V, Stiborová M. (2002). Metabolism of carcinogenic azo dye Sudan I by rat, rabbit, minipig and human hepatic microsomes. Collect Czech Chem Commun 67: 1883-1898.
16. Nebert DW. (1989). The Ah locus: genetic differences in toxicity, cancer, mutation and birth defects. Crit Rev Toxicol 20: 153-174.
17. Omura T, Sato R. (1964). The carbon monoxide-binding pigment of liver microsomes. II. Solubilization, purification, and properties. J Biol Chem 239: 2379-85 Phillips DH. (1999). Polycyclic aromatic hydrocarbons in the diet. Mutat Res 443: 139-47.
18. Phillips DH. (2002). Smoking-related DNA and protein adducts in human tissues Carcinogenesis 23: 1979-2004
19. Phillips DH. (2005). Macromolecular adducts as biomarkers of human exposure to polycyclic aromatic hydrocarbons. The Carcinogenic Effects of Polycyclic Aromatic Hydrocarbons. Imperial College Press, London, 137-169.
20. Sagredo C, Øvrebø S, Haugen A, Fujii-Kuriyama Y, Baera R, Botnen IV, Mollerup S. (2006). Quantitative analysis of benzo[a]pyrene biotransformation and adduct formation in Ahr knockout mice. Toxicol Lett 167: 173-182.
21. Sasaki H, Yonekubo J, Kanai M, Toriba A, Kizu R, Hayakawa K. (2002). Simultaneous detection of monohydroxybenzo[a]pyrene positional isomers by reversed-phase liquid chromatography coupled to electrospray ionization mass spectrometry. Biomed Chromatogr 16: 432-436.
22. Selkirk JK, Croy RG, Gelboin HV. (1974). Benzo[a]pyrene metabolites: efficient and rapid separation by high-pressure liquid chromatography. Science 184: 169-171. Selkirk JK. (1977). Benzo[a]pyrene carcinogenesis: a biochemical selection mechanism. J Toxicol Environ Health 2: 1245-1258.
23. Stiborová M, Martínek V, Rýdlová H, Hodek P, Frei E. (2002). Sudan I is a potential carcinogen for humans: Evidence for its metabolic activation and detoxication by human recombinant cytochrome P450 1A1 and liver microsomes. Cancer Res 62: 5678-5684.
24. Stiborová M, Stiborová-Rupertová M, Borek-Dohalská L, Wiessler M, Frei E. (2003). Rat microsomes activating the anticancer drug ellipticine to species covalently binding to deoxyguanosine in DNA are a suitable model mimicking ellipticine bioactivation in humans. Chem Res Toxicol 16: 38-47.
25. Toriba A, Nakamura H, Chetiyanukornkul T, Kizu R, Makino T, Nakazawa H, Yokoi T, Hayakawa K. (2003). Method for determining monohydroxybenzo[a]pyrene isomers using column-switching high-performance liquid chromatography. Anal Biochem 312: 14-22.
26. Uno S, Dalton TP, Derkenne S, Curran CP, Miller ML, Shertzer HG, Nebert DW. (2004). Oral exposure to benzo [a] pyrene in the mouse: detoxication by inducible cytochrome P450 is more important than metabolic activation. Mol Pharmacol 65: 1225-37.
27. Uno S, Dalton TP, Dragin N, Curran CP, Derkenne S, Miller ML, Shertzer HG, Gonzalez FJ, Nebert DW. (2006). Oral benzo[a]pyrene in Cyp1 knockout mouse lines: CYP1A1 important in detoxication, CYP1B1 metabolism required for immune damage independent of total-body burden and clearance rate. Mol Pharmacol 69: 1103-14.
28. van Schanke A, Holtz F, van der Meer JP, Boon JP, Ariese F, Stroomberg G, van den Berg M, Everaarts JM. (2001). Dose-and time-dependent formation of biliary benzo[a]pyrene metabolites in the marine fl atfish dab (Limanda limanda). Environ Toxicol Chem 20: 1641-1647.
29. Wang JJ, Frazer DG, Law B, Lewis DM. (2003). Identification and quantification of urinary benzo[a]pyrene and its metabolites from asphalt fume exposed mice by microfl ow LC coupled to hybrid quadrupole time-of-fl ight mass spectrometry. Analyst 128: 864-870.
30. Wiechelman KJ, Braun RD, Fitzpatrick JD. (1988). Investigation of the bicinchoninic acid protein assay: identification of the groups responsible for color formation. Anal Biochem 175: 231-237.
31. Zhu S, Li L, Thornton C, Carvalho P, Avery BA, Willett KL. (2008). Simultaneous determination of benzo[a]pyrene and eight of its metabolites in Fundulus heteroclitus bile using ultra-performance liquid chromatography with mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci 863: 141-149.
32. spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci 863: 141-149.