Metabolism and cytotoxicity of benzo(a)pyrene in the human lung tumour cell line NCI-H322

References

• Baird W. M., O'Brian T. G., Diamond L. Comparison of the metabolism of benzo(a)pyrene and its activation to biologically active metabolites by low-passage hamster and rat embryo cells. Carcinogeneses 1981; 2: 81–88
   PubMed Web of Science ®Google Scholar
• Bock K. W., Lilienblum W., Pfeil H. Conversion of benzo‘a’pyrene-3,6-quinone to quinol glucuronides with rat liver microsomes or purified NADPH-cytochrome c reductase and UDP-glucuronosyltransferase. FEBS Letters 1980; 121: 269–272
   PubMed Web of Science ®Google Scholar
• Borenfreund E., Puerner J. A. A simple quantitative procedure using monolayer cultures for cytotoxicity assay (HTD/NR90). Journal of Tissue Culture Methods 1984; 9: 7–8
   Google Scholar
• Chasseaud L. F. The role of glutathione and glutathione S-transferase in the metabolism of chemical carcinogens and other electrophilic agents. Advances in Cancer Research 1979; 29: 175–274
   PubMedGoogle Scholar
• Cumpelik O., Krupski G., Stich S. Conjugation of benzo(a)pyrene with glutathione (GSH) in epithelial and fibroblastoid cell lines. Naunyn-Schmiedeberg's Archives of Pharmacology 1985; 329: R18
   PubMedGoogle Scholar
• Fahl W. E., Shen A. L., Jefcoate C. R. UDP-glucuronosyltransferase and the conjugation of benzo(a)pyrene metabolites to DNA. Biochemical and Biophysical Research Communications 1978; 85: 891–899
   PubMed Web of Science ®Google Scholar
• Falzon M., McMahon J. B., Schuller H. M. Xenobioticmetaholizing enzyme activity in human non-small-cell derived lung cancer cell lines. Biochemical Pharmacology 1986a; 35: 563–568
   PubMed Web of Science ®Google Scholar
• Falzon M., McMahon J. B., Gazdar A. F., Schuller H. M. Preferential metabolism of N-nitrosodiethylamine by two cell lines derived from human pulmonary adenocarcinomas. Carcinogenesis 1986b; 7: 17–22
   PubMed Web of Science ®Google Scholar
• Falzon M., McMahon J. B., Schuller H. M., Boyd M. R. Metabolic activation and cytotoxicity of 4-ipomeanol in human non-small cell lung cancer lines. Cancer Research 1986c; 46: 3484–3489
   PubMed Web of Science ®Google Scholar
• Gehly E. B., Landolph J., Heidelberger C., Nagasawa H., Little J. Induction of cytotoxicity, mutation, cytogenetic changes, and neoplastic transformation by benzo‘a’pyrene and derivates in C3H/10T1/2 clone 8 mouse fibroblasts. Cancer Research 1982; 42: 1866–1875
   PubMed Web of Science ®Google Scholar
• Gelboin H. V., Huberman E., Sachs L. Enzymatic hydroxylation of benzo(a)pyrene and its relationship to cytotoxicity. Proceedings of the National Academy of Sciences, USA 1969; 64: 1118–1194
   Web of Science ®Google Scholar
• Glatt H. R., Oesch F. Inactivation of electrophilic metabolites by glutathione S-transferases and limitation of the system due to subcellular localization. Archives of Toxicology 1977; 39: 87–96
   PubMed Web of Science ®Google Scholar
• Hesse S., Jernström B., Martinez M., Moldeus P., Christodoulides L., Ketterer B. Inactivation of DNA-binding metabolites of benzo(a)pyrene and benzo(a)pyrene-7,8-dihydrodiol by glutathione and glutathione S-transferases. Carcinogenesis 1982; 3: 757–760
   PubMed Web of Science ®Google Scholar
• Huberman E., Yang S. K., McCourt D. W., Gelboin H. V. Mutagenicity to mammalian cells in culture by (+) and (-) trans-7,8-dihydroxy-7,8-dihydrobenzo(a)pyrenes and the hydrolysis and reduction products of two stereoisomeric benzo(a)pyrene 7,8-diol-9,10-epoxides. Cancer Letters 1977; 4: 35–43
   Web of Science ®Google Scholar
• Jernström B., Babson J. R., Moldeus P., Holmgren A., Reed D. J. Glutathione conjugation and DNA-binding of ()-trans-7,8-dihydroxy-7,8-dihydrobenzo(a)pyrene and ()7β,8α-dihydroxy-9α,10α-epoxy-7,8,9,10-tetrahydrobenzo‘a’pyrene in isolated rat hepatocytes. Carcinogenesis 1982; 3: 861–866
   PubMed Web of Science ®Google Scholar
• Kapitulnik J., Wislocki P. G., Levin W., Yagi H., Jerina D. M., Conney A. H. Tumorigenicity studies with diolepoxides of benzo(a)pyrene which indicate that ()trans-7β,8α-dihydroxy-9α,10α-epoxy-7,8,9,10-tetrahydrobenzo(a)pyrene is an ultimate carcinogen in newborn mice. Cancer Research 1978; 38: 354–358
   PubMed Web of Science ®Google Scholar
• Kuroki T., Hosomi J., Munakata K., Onizuka T., Terauchi M., Nemoto N. Metabolism of benzo(a)pyrene in epidermal keratinocytes and dermal fibroblasts of humans and mice with reference to variation among species, individuals, and cell types. Cancer Research 1982; 42: 1859–1865
   PubMed Web of Science ®Google Scholar
• Landolph J. R., Becker J. F., Gamper H., Bartholomew J. C., Calvin M. Biochemical basis for the acquisition of resistance to benzo(a)pyrene in clones of mouse liver cells in culture. Chemical-Biological Interactions 1978; 23: 331–344
   PubMed Web of Science ®Google Scholar
• Lau S. S., McMahon J. B., McMenamin M. G., Hubbard W. C., Schuller H. M., Boyd M. R. Metabolism of arachidonic acid in human lung cancer cell lines. Cancer Research 1987; 47: 3757–3762
   PubMedGoogle Scholar
• Lesko S. A., Trpis L., Zheng R. Somatic mutation, DNA damage and cytotoxicity induced by benzo(a)pyrenedione/benzo(a)pyrenediol redox couples in cultured mammalian cells. Mutation Research 1986; 161: 173–180
   PubMed Web of Science ®Google Scholar
• Lilienblum W., Bock-Hennlg B. S., Bock K. W. Protection against toxic redox cycles between benzo(a)pyrene-3,6-quinone and its quinol by 3-methylcholanthrene-inducible formation of the quinol mono- and diglucuronide. Molecular Pharmacology 1985; 27: 451–458
   PubMed Web of Science ®Google Scholar
• Lind C. Formation of benzo(a)pyrene-3,6-quinol mono- and diglucuronides in rat liver microsomes. Archives of Biochemistry and Biophysics 1985; 240: 226–235
   PubMed Web of Science ®Google Scholar
• Lorentzen R. J., Ts'o P. O. P. Benzo‘a’pyrenedione/benzo‘a’pyrenediol oxidation-reduction couples and the generation of reactive reduced molecular oxygen. Biochemistry 1977; 15: 1467–1473
   Google Scholar
• Lubet R. A., Brown D. Q., Kouri R. E. The role of 3-OH benzo(a)pyrene in mediating benzo(a)pyrene induced toxicity and transformation in cell culture. Research Communications in chemical Pathology and Pharmacology 1973; 6: 929–942
   PubMedGoogle Scholar
• Morgenstern R., Guthenberg C., Mannervik B., DePierre J. W., Ernster L. benzo(a)pyrene metabolism by rat liver microsomes: Effects of adding purified glutathione S-transferases A, B, and C. Cancer Research 1982; 42: 4215–4221
   PubMed Web of Science ®Google Scholar
• Nemoto N., Gelboin H. V. Enzymatic conjugation of benzo(a)pyrene oxides, phenols and dihydrodiols with UDP-glucuronic acid. Biochemical Pharmacology 1976; 25: 1221–1226
   PubMed Web of Science ®Google Scholar
• Nemoto N., Takayama S., Gelboin H. V. Sulphate conjugation of benzo‘a’pyrene metabolites and derivatives. Chemical-Biological Interactions 1978; 23: 19–30
   PubMed Web of Science ®Google Scholar
• Owens I. S., Legraverend C., Pelkonen O. Deoxyribo nucleic acid binding of 3-hydroxy-and 9-hydroxybenzo(a)pyrene following further metabolism hy mouse liver-micro-somal cyto-chrome P1-450. Biochemical Pharmacology 1979; 28: 1623–1629
   PubMed Web of Science ®Google Scholar
• Recio L., Hsie A. W. Glucuronide conjugation reduces the cytotoxicity but not the mutagenicity of benzo(a)pyrene in the CHO/HGPRT assay. Teratogenesis, Carcinogenesis, and Mutagenesis 1984; 4: 391–402
   PubMedGoogle Scholar
• Ribeiro O., Kirkby C. A., Hirom P. C., Millburn P. Secondary metabolites of benzo(a)pyrene: 3-hydroxy-trans-7,8-dihydro-7,8-dihydroxybenzo(a)pyrene, a biliary metabolite of 3-hydroxybenzo(a)pyrene in the rat. Carcinogenesis 1985; 6: 1507–1511
   PubMed Web of Science ®Google Scholar
• Schuller H. M., Del Campo A. A., McMahon J. B., Oie H. B., Boyd M. R., Gazdar A. F. Ultrastructural classification of human lung cancer cell lines as a basis to study the response of different types of lung tumors to chemicals and drugs in vitro. Proceedings of the American Association for Cancer Research 1985; 26: 27
   Google Scholar
• Shopsis C., Eng B. Rapid cytotoxicity testing using a semi-automated protein determination on cultured cells. Toxicology Letters 1985; 26: 1–8
   PubMed Web of Science ®Google Scholar
• Smith A. C., McMahon J. B., Schuller H. M., Boyd M. R. Phospholipid synthesis in small cell (SCCL) and non-small cell (NSCCL) carcinoma cell lines from human lung tumors. Proceedings of the American Association for Cancer Research 1985; 26: 9
   Google Scholar
• Stampffr M. R., Bartholomew J. C., Smith H. S., Hartley J. C. Metabolism of benzo(a)pyrene by human mammary epithelial cells: Toxicity and DNA adduct formation. Proceedings of the National Academy of Sciences, USA 1981; 78: 6251–6255
   PubMed Web of Science ®Google Scholar
• Thfall G., Eisinger M., Grunberger D. Metabolism of benzo(a)pyrtne and DNA adduct formation in cultured human epidermal keratinocytes. Carcinogenesis 1981; 2: 581–587
   PubMed Web of Science ®Google Scholar
• Van Cantfort J., De Graeve J., Gielen J. E. Radioactive assay for aryl hydrocarbon hydroxylase. Improved method and biological importance. Biochemical and Biophysical Research Communication 1977; 79: 505–512
   PubMed Web of Science ®Google Scholar
• Weinstein I. B., Jeffrey A. M., Leffler S., Pulkrabek P., Yamamsaki H., Grunberger D. Interactions between polycyclic aromatic hydrocarbons and cellular macromolecules. Polycyclic Hydrocarbons and Cancer, H. V. Gelboin, P. O. P. Ts'o. Academic Press. 1978; 4–36
   Google Scholar
• Wiebel F. J. Metabolism of monohydroxybenzo(a)pyrenes by rat liver microsomes and mammalian cells in culture. Archives of Biochemistry and Biophysics 1975; 69: 609–621
   Google Scholar
• Wiebel F. J., Kiefer F., Krupski G., Schuller H. M. Expression of glutathione S-transferase and phenol sulphotransferase, but not of UDP-glucuronosyltransferase, in the human lung tumor cell lines NCI-H322 and NCI-H358. Biochemical Pharmacology 1986; 35: 1337–1343
   PubMed Web of Science ®Google Scholar
• Wislocki P. G., Wood A. W., Chang R. L., Levin W., Yagi H., Hernandez O., Dansette P. M., Jerina D. M., Conney A. H. Mutagenicity and cytotoxicity of benzo(a)pyrene arene oxides, phenols, quinones, and dihydrodiols in bacterial and mammalian cells. Cancer Research 1976; 36: 3350–3357
   PubMed Web of Science ®Google Scholar
• Yang S., McCourt D. W., Roller P. P., Gelboin H. V. 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, USA 1976; 73: 2594–2598
   PubMed Web of Science ®Google Scholar