Structural requirements for mutation formation from polycyclic aromatic hydrocarbon dihydrodiol epoxides in their interaction with food chemopreventive compounds

Arimoto, 1993, Binding of polycyclic planar mutagens to chlorophyllin resulting in inhibition of the mutagenic activity, Mutat. Res., 287, 293, 10.1016/0027-5107(93)90022-8 Bostrom, 2002, Cancer risk assessment, indicators, and guidelines for polycyclic aromatic hydrocarbons in the ambient air, Environ. Health Perspect., 110, 451, 10.1289/ehp.02110s3451 Carter, 2004, The dietary phytochemical chlorophyllin alters E-cadherin and beta-catenin expression in human colon cancer cells, J. Nutr., 134, S3441, 10.1093/jn/134.12.3441S Castro, 2009, Identifying efficacious approaches to chemoprevention with chlorophyllin, purified chlorophylls and freeze-dried spinach in a mouse model of transplacental carcinogenesis, Carcinogenesis, 30, 315, 10.1093/carcin/bgn280 Chan, 2003, Screening of chemopreventive tea polyphenols against PAH genotoxicity in breast cancer cells by a XRE-luciferase reporter construct, Nutr. Cancer, 46, 93, 10.1207/S15327914NC4601_12 Chaung, 1997, The p53 status of Chinese hamster V79 cells frequently used for studies on DNA damage and DNA repair, Nucleic Acids Res., 25, 992, 10.1093/nar/25.5.992 Collins JF, 1998, Potency equivalency factors for some polycyclic aromatic hydrocarbons and polycyclic aromatic hydrocarbon derivatives, Regul. Toxicol. Pharmacol., 28, 45, 10.1006/rtph.1998.1235 Davis, 2004, Frontiers in nutrigenomics, proteomics, metabolomics and cancer prevention, Mutat. Res., 551, 51, 10.1016/j.mrfmmm.2004.01.012 de Mejia, 1999, Antimutagenic effects of natural phenolic compounds in beans, Mutat. Res., 441, 1, 10.1016/S1383-5718(99)00040-6 Dogra, 1990, Stable expression of rat cytochrome P-450IA1 cDNA in V79 Chinese hamster cells and their use in mutagenicity testing, Mol. Pharmacol., 37, 608 Dou, 2009, Molecular mechanisms of green tea polyphenols, Nutr. Cancer, 61, 827, 10.1080/01635580903285049 Dreij, 2004, DNA adducts of benzo[a]pyrene- and dibenzo[a, l]pyrene-diol epoxides in human lung epithelial cells: Kinetics of adduct-removal, effects on cell cycle check points and gene expression, Polycycl. Arom. Compd., 24, 549, 10.1080/10406630490471645 Dreij, 2005, Differential removal of DNA adducts derived from anti-diol epoxides of dibenzo[a, l]pyrene and benzo[a]pyrene in human cells, Chem. Res. Toxicol., 18, 655, 10.1021/tx0497090 Egner, 2003, Chemoprevention with chlorophyllin in individuals exposed to dietary aflatoxin, Mutat. Res., 523–524, 209, 10.1016/S0027-5107(02)00337-8 Egner, 2001, Chlorophyllin intervention reduces aflatoxin-DNA adducts in individuals at high risk for liver cancer, Proc. Natl Acad. Sci. USA, 98, 14601, 10.1073/pnas.251536898 Fahey, 2005, Chlorophyll, chlorophyllin and related tetrapyrroles are significant inducers of mammalian phase 2 cytoprotective genes, Carcinogenesis, 26, 1247, 10.1093/carcin/bgi068 Ferruzzi, 2002, Sodium copper chlorophyllin: in vitro digestive stability and accumulation by Caco-2 human intestinal cells, J. Agric. Food. Chem., 50, 2173, 10.1021/jf010869g Geacintov, 2002, Thermodynamic and structural factors in the removal of bulky DNA adducts by the nucleotide excision repair machinery, Biopolymers, 65, 202, 10.1002/bip.10239 Geacintov, 1997, NMR solution structures of stereoisometric covalent polycyclic aromatic carcinogen-DNA adduct: principles, patterns, and diversity, Chem. Res. Toxicol., 10, 111, 10.1021/tx9601418 Glatt, 1991, Fjord- and bay-region diol-epoxides investigated for stability, SOS induction in Escherichia coli, and mutagenicity in Salmonella typhimurium and mammalian cells, Cancer Res., 51, 1659 Han, 2006, Antioxidant and apoptosis-inducing activities of ellagic acid, Anticancer Res., 26, 3601 Hannum, 2004, Potential impact of strawberries on human health: a review of the science, Crit. Rev. Food Sci. Nutr., 44, 1, 10.1080/10408690490263756 Helleday, 2001, The DRAG test: an assay for detection of genotoxic damage, Altern. Lab. Anim., 29, 233, 10.1177/026119290102900309 Hou, 2004, Effects of tea polyphenols on signal transduction pathways related to cancer chemoprevention, Mutat. Res., 555, 3, 10.1016/j.mrfmmm.2004.06.040 Huetz, 2005, Reaction between ellagic acid and an ultimate carcinogen, J. Chem. Inf. Model., 45, 1564, 10.1021/ci050163c Hwang, 1998, P48 Activates a UV-damaged-DNA binding factor and is defective in xeroderma pigmentosum group E cells that lack binding activity, Mol. Cell. Biol., 18, 4391, 10.1128/MCB.18.7.4391 Jankowiak, 1998, Structure, conformations, and repair of DNA adducts from dibenzo[a, l]pyrene: 32P-postlabeling and fluorescence studies, Chem. Res. Toxicol., 11, 674, 10.1021/tx970232k Jankun, 1997, Why drinking green tea could prevent cancer?, Nature, 387, 561, 10.1038/42381 Jenssen, D. 1984. A quantitative test for mutagenicity in V79 Chinese hamster cells. In: Kilbey, B.J., Legator, M., Nichols, W., and Ramel, C. (Eds.). Elsevier, Amsterdam, pp. 269–290. Jernstrom, 1994, Covalent binding of benzo[a]pyrene 7, 8-dihydrodiol 9, 10-epoxides to DNA: molecular structures, induced mutations and biological consequences, Biophys. Chem., 49, 185, 10.1016/0301-4622(93)E0087-L Johansson, 2004, Screening for genotoxicity using the DRAG assay: investigation of halogenated environmental contaminants, Mutat. Res., 563, 35, 10.1016/j.mrgentox.2004.05.017 Johansson, 2004, A method to monitor replication fork progression in mammalian cells: nucleotide excision repair enhances and homologous recombination delays elongation along damaged DNA, Nucleic Acids Res., 32, e157, 10.1093/nar/gnh154 Karle, J., Mah, H., Jerina, D, Yagi, H., 1977. Synthesis of dihydrodiols of chrysene and dibenz[a,h]anthracene. Tetrahedron Lett 4021–4027. Keshava, 2009, Chlorophyllin significantly reduces benzo[a]pyrene-DNA adduct formation and alters cytochrome P450 1A1 and 1B1 expression and EROD activity in normal human mammary epithelial cells, Environ. Mol. Mutagen., 50, 134, 10.1002/em.20449 Keum, 2004, Chemoprevention by isothiocyanates and their underlying molecular signaling mechanisms, Mutat. Res., 555, 191, 10.1016/j.mrfmmm.2004.05.024 Kuroda, 1996, Bio-antimutagenic activity of green tea catechins in cultured Chinese hamster V79 cells, Mutat. Res., 361, 179, 10.1016/S0165-1161(96)00039-8 Lagerqvist, A., Hakansson, D., Prochazka, G., Lundin, C., Dreij, K., Segerback, D., Jernstrom, B., Tornqvist, M., Seidel, A., Erixon, K., Jenssen, D. 2008. Both replication bypass fidelity and repair efficiency influence the yield of mutations per target dose in mammalian cells induced by benzo(a)pyrene-diol-epoxide and dibenzo(a,l)pyrene-diol-epoxide. DNA Repair (Amst). Laky, 2002, Protective effects of Brussels sprouts towards B[a]P-induced DNA damage: a model study with the single-cell gel electrophoresis (SCGE)/Hep G2 assay, Food Chem. Toxicol., 40, 1077, 10.1016/S0278-6915(02)00031-5 Lee, 1980, Synthesis of biologically active metabolites of dibenz[a, h]anthracene, J. Org. Chem., 45, 588, 10.1021/jo01292a007 Lin, 2001, Molecular topology of polycyclic aromatic carcinogens determines DNA adduct conformation: a link to tumorigenic activity, J Mol Biol, 306, 1059, 10.1006/jmbi.2001.4425 Luch, 1994, Synthesis and mutagenicity of the diastereomeric fjord-region 11, 12-dihydrodiol 13, 14-epoxides of dibenzo[a, l]pyrene, Carcinogenesis, 15, 2507, 10.1093/carcin/15.11.2507 Mata, 2004, Effects of chlorophyllin on transport of dibenzo(a, l)pyrene, 2-amino-1-methyl-6-phenylimidazo-[4, 5-b]pyridine, and aflatoxin B(1) across Caco-2 cell monolayers, Toxicology, 196, 117, 10.1016/j.tox.2003.11.008 Moller, 2004, Interventions with antioxidants and nutrients in relation to oxidative DNA damage and repair, Mutat. Res., 551, 79, 10.1016/j.mrfmmm.2004.02.018 Nakamura, 2000, Redox regulation of glutathione S-transferase induction by benzyl isothiocyanate: correlation of enzyme induction with the formation of reactive oxygen intermediates, Cancer Res., 60, 219 Negraes, 2004, Anticlastogenicity of chlorophyllin in the different cell cycle phases in cultured mammalian cells, Mutat. Res., 557, 177, 10.1016/j.mrgentox.2003.10.012 Okazaki, 2003, Enhancement of urinary bladder carcinogenesis by combined treatment with benzyl isothiocyanate and N-butyl-N-(4-hydroxybutyl)nitrosamine in rats after initiation, Cancer Sci., 94, 948, 10.1111/j.1349-7006.2003.tb01383.x Phillips, 1999, Polycyclic aromatic hydrocarbons in the diet, Mutat. Res., 443, 139, 10.1016/S1383-5742(99)00016-2 Phillips, 1991, Relationship between mutagenicity and DNA adduct formation in mammalian cells for fjord- and bay-region diol-epoxides of polycyclic aromatic hydrocarbons, Chem. Biol. Interact., 80, 177, 10.1016/0009-2797(91)90023-Z Platt, 1982, Synthesis of non-K-region ortho-quinones of polycyclic aromatic hydrocarbons from cyclic ketones, Tetrahedron Lett., 23, 163, 10.1016/S0040-4039(00)86775-1 Platt, 1983, Efficient synthesis of non-K-region trans-dihydro diols of polycyclic aromatic hydrocarbons from o-quinones and catechols, J. Org. Chem., 48, 265, 10.1021/jo00150a027 Reddy, 1999, Inhibition of dibenzo[a, l]pyrene-induced multi-organ carcinogenesis by dietary chlorophyllin in rainbow trout, Carcinogenesis, 20, 1919, 10.1093/carcin/20.10.1919 Romert, 1992, Chlorophyllin is both a positive and negative modifier of mutagenicity, Mutagenesis, 7, 349, 10.1093/mutage/7.5.349 Romert, 1989, Effects of glutathione transferase activity on benzo[a]pyrene 7, 8-dihydrodiol metabolism and mutagenesis studied in a mammalian cell co-cultivation assay, Carcinogenesis, 10, 1701, 10.1093/carcin/10.9.1701 Romert, 1994, Screening for agents inhibiting the mutagenicity of extracts and constituents of tobacco products, Mutat. Res., 322, 97, 10.1016/0165-1218(94)00015-8 Sayer, 1982, Extremely facile reaction between the ultimate carcinogen benzo[a]pyrene-7, 8-diol 9, 10-epoxide and ellagic acid, J. Am. Chem. Soc., 104, 5562, 10.1021/ja00384a081 Seidel, 1998, Regio- and stereoselectivity in the metabolism of benzo[c]phenanthrene mediated by genetically engineered V79 Chinese hamster cells expressing rat and human cytochromes P450, Environ. Toxicol. Pharmacol., 5, 179, 10.1016/S1382-6689(97)10073-4 Smith, 2001, Effect of chemopreventive agents on DNA adduction induced by the potent mammary carcinogen dibenzo[a, l]pyrene in the human breast cells MCF-7, Mutat. Res., 480–481, 97, 10.1016/S0027-5107(01)00173-7 Soobrattee, 2006, Chemopreventive actions of polyphenolic compounds in cancer, Biofactors, 27, 19, 10.1002/biof.5520270103 Soobrattee, 2005, Phenolics as potential antioxidant therapeutic agents: mechanism and actions, Mutat. Res., 579, 200, 10.1016/j.mrfmmm.2005.03.023 Staal, 2006, Modulation of gene expression and DNA adduct formation in HepG2 cells by polycyclic aromatic hydrocarbons with different carcinogenic potencies, Carcinogenesis, 27, 646, 10.1093/carcin/bgi255 Sundberg, 1997, Glutathione conjugation of bay- and fjord-region diol epoxides of polycyclic aromatic hydrocarbons by glutathione transferases M1–1 and P1–1, Chem. Res. Toxicol., 10, 1221, 10.1021/tx970099w Surh, 2003, Cancer chemoprevention with dietary phytochemicals, Nat. Rev. Cancer, 3, 768, 10.1038/nrc1189 Teel, 1985, The effect of ellagic acid on the uptake, persistence, metabolism and DNA-binding of benzo[a]pyrene in cultured explants of strain A/J mouse lung, Carcinogenesis, 6, 391, 10.1093/carcin/6.3.391 Thiem, 2003, Cloudberry: an important source of ellagic acid, an anti-oxidant, Tidsskr. Nor. Laegeforen, 123, 1856 Whitley, 2003, Intestinal epithelial cell accumulation of the cancer preventive polyphenol ellagic acid–extensive binding to protein and DNA, Biochem. Pharmacol., 66, 907, 10.1016/S0006-2952(03)00413-1 Whitley, 2006, Site-specific accumulation of the cancer preventive dietary polyphenol ellagic acid in epithelial cells of the aerodigestive tract, J. Pharm. Pharmacol., 58, 1201, 10.1211/jpp.58.9.0006 Wood, 1982, Inhibition of the mutagenicity of bay-region diol epoxides of polycyclic aromatic hydrocarbons by naturally occurring plant phenols: exceptional activity of ellagic acid, Proc. Natl. Acad. Sci. USA., 79, 5513, 10.1073/pnas.79.18.5513 Xue, 2005, Metabolic activation of polycyclic and heterocyclic aromatic hydrocarbons and DNA damage: a review, Toxicol. Appl. Pharmacol., 206, 73, 10.1016/j.taap.2004.11.006