Genomes and Genes
Summary: A class of chemicals that contain an anthracene ring with a naphthalene ring attached to it.
- Yan S, Wu M, Patel D, Geacintov N, Broyde S. Simulating structural and thermodynamic properties of carcinogen-damaged DNA. Biophys J. 2003;84:2137-48 pubmed..The structural and thermodynamic features of these stereoisomeric adducts are also discussed in relation to their reported low susceptibilities to nucleotide excision repair. ..
- Park J, Troxel A, Harvey R, Penning T. Polycyclic aromatic hydrocarbon (PAH) o-quinones produced by the aldo-keto-reductases (AKRs) generate abasic sites, oxidized pyrimidines, and 8-oxo-dGuo via reactive oxygen species. Chem Res Toxicol. 2006;19:719-28 pubmed..However, in the presence of Fe(III)-mediated PAH o-quinone redox-cycling, the *OH radical scavengers and sodium azide consistently attenuated their formation, indicating that the ROS responsible was *OH. ..
- Dreij K, Seidel A, Jernström B. 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. 2005;18:655-64 pubmed
- Jia L, Geacintov N, Broyde S. The N-clasp of human DNA polymerase kappa promotes blockage or error-free bypass of adenine- or guanine-benzo[a]pyrenyl lesions. Nucleic Acids Res. 2008;36:6571-84 pubmed publisher..Absence of the N-clasp in Dpo4 explains the error-prone processing of the same lesion by this enzyme. Thus, our studies elucidate structure-function relationships in the fidelity of lesion bypass. ..
- Yoon J, Besaratinia A, Feng Z, Tang M, Amin S, Luch A, et al. DNA damage, repair, and mutation induction by (+)-Syn and (-)-anti-dibenzo[a,l]pyrene-11,12-diol-13,14-epoxides in mouse cells. Cancer Res. 2004;64:7321-8 pubmed..We discuss the implications of these findings for human cancer mutagenesis. ..
- Park J, Mangal D, Tacka K, Quinn A, Harvey R, Blair I, et al. Evidence for the aldo-keto reductase pathway of polycyclic aromatic trans-dihydrodiol activation in human lung A549 cells. Proc Natl Acad Sci U S A. 2008;105:6846-51 pubmed publisher..We conclude that activation of PAH-trans-dihydrodiols by AKRs in lung cells leads to ROS-mediated genotoxicity and contributes to lung carcinogenesis. ..
- Chakravarti D, Venugopal D, Mailander P, Meza J, Higginbotham S, Cavalieri E, et al. The role of polycyclic aromatic hydrocarbon-DNA adducts in inducing mutations in mouse skin. Mutat Res. 2008;649:161-78 pubmed..In conclusion, this study suggests that depurinating adducts play a major role in PAH mutagenesis. ..
- Shultz C, Quinn A, Park J, Harvey R, Bolton J, Maser E, et al. Specificity of human aldo-keto reductases, NAD(P)H:quinone oxidoreductase, and carbonyl reductases to redox-cycle polycyclic aromatic hydrocarbon diones and 4-hydroxyequilenin-o-quinone. Chem Res Toxicol. 2011;24:2153-66 pubmed publisher..ROS formation was unaffected by the addition of dicumarol, suggesting that NQO1 is not responsible for the two-electron reduction observed and does not offer protection against ROS formation from PAH o-quinones. ..
- Xu P, Oum L, Beese L, Geacintov N, Broyde S. Following an environmental carcinogen N2-dG adduct through replication: elucidating blockage and bypass in a high-fidelity DNA polymerase. Nucleic Acids Res. 2007;35:4275-88 pubmed..In vivo, a switch to a potentially error-prone bypass polymerase likely dominates translesion bypass. ..
- Seo K, Nagalingam A, Tiffany M, Loechler E. Mutagenesis studies with four stereoisomeric N2-dG benzo[a]pyrene adducts in the identical 5'-CGC sequence used in NMR studies: G->T mutations dominate in each case. Mutagenesis. 2005;20:441-8 pubmed..coli reveals that B[a]P-N2-dG adduct stereochemistry tends to have a lesser impact on mutagenic pattern (e.g. G-->T versus G-->A mutations) than does DNA sequence context, which is discussed. ..
- Tang Y, Liu Z, Ding S, Lin C, Cai Y, Rodríguez F, et al. Nuclear magnetic resonance solution structure of an N(2)-guanine DNA adduct derived from the potent tumorigen dibenzo[a,l]pyrene: intercalation from the minor groove with ruptured Watson-Crick base pairing. Biochemistry. 2012;51:9751-62 pubmed publisher
- Wang B, Sayer J, Yagi H, Frank H, Seidel A, Jerina D. Facile interstrand migration of the hydrocarbon moiety of a dibenzo[a,l]pyrene 11,12-diol 13,14-epoxide adduct at N2 of deoxyguanosine in a duplex oligonucleotide. J Am Chem Soc. 2006;128:10079-84 pubmed..This interstrand migration appears unique to DB[a,l]P adducts and has not been observed for their fjord-region benzo[c]phenanthrene or bay-region benzo[a]pyrene analogues. ..
- Lagerqvist A, Håkansson D, Prochazka G, Lundin C, Dreij K, Segerbäck D, et al. Both replication bypass fidelity and repair efficiency influence the yield of mutations per target dose in intact mammalian cells induced by benzo[a]pyrene-diol-epoxide and dibenzo[a,l]pyrene-diol-epoxide. DNA Repair (Amst). 2008;7:1202-12 pubmed publisher..This has been postulated earlier based on results using in vitro enzyme assays, but is now also being recognized in terms of forward mutations in intact mammalian cells. ..
- Balu N, Padgett W, Lambert G, Swank A, Richard A, Nesnow S. Identification and characterization of novel stable deoxyguanosine and deoxyadenosine adducts of benzo[a]pyrene-7,8-quinone from reactions at physiological pH. Chem Res Toxicol. 2004;17:827-38 pubmed
- van den Hurk P, Kubiczak G, Lehmler H, James M. Hydroxylated polychlorinated biphenyls as inhibitors of the sulfation and glucuronidation of 3-hydroxy-benzo[a]pyrene. Environ Health Perspect. 2002;110:343-8 pubmed..Inhibition of glucuronosyltransferase by low concentrations of OH-PCBs has not been reported before and may have important consequences for the bioavailability, bioaccumulation, and toxicity of other phenolic environmental contaminants. ..
- James M, Tong Z, Rowland Faux L, Venugopal C, Kleinow K. Intestinal bioavailability and biotransformation of 3-hydroxybenzo(a)pyrene in an isolated perfused preparation from channel catfish, Ictalurus punctatus. Drug Metab Dispos. 2001;29:721-8 pubmed..These studies demonstrate the rapid phase 2 conjugation of a phenolic benzo(a)pyrene metabolite in intestinal mucosa, and the transfer of the phase 2 sulfate and glucuronide conjugates to blood. ..
- Lin C, Huang X, Kolbanovskii A, Hingerty B, Amin S, Broyde S, et al. Molecular topology of polycyclic aromatic carcinogens determines DNA adduct conformation: a link to tumorigenic activity. J Mol Biol. 2001;306:1059-80 pubmed
- Huang M, Liu X, Basu S, Zhang L, Kushman M, Harvey R, et al. Metabolism and distribution of benzo[a]pyrene-7,8-dione (B[a]P-7,8-dione) in human lung cells by liquid chromatography tandem mass spectrometry: detection of an adenine B[a]P-7,8-dione adduct. Chem Res Toxicol. 2012;25:993-1003 pubmed publisher
- Mahadevan B, Dashwood W, Luch A, Pecaj A, Doehmer J, Seidel A, et al. Mutations induced by (-)-anti-11R,12S-dihydrodiol 13S,14R-epoxide of dibenzo[a,l]pyrene in the coding region of the hypoxanthine phosphoribosyltransferase (Hprt) gene in Chinese hamster V79 cells. Environ Mol Mutagen. 2003;41:131-9 pubmed..The results of this study demonstrate a correspondence between the concentration and types of DNA adducts and the frequency and types of mutations induced by (-)-anti-DB[a,l]PDE in V79 cells. ..
- Gu A, Ji G, Long Y, Zhou Y, Shi X, Song L, et al. Assessment of an association between an aryl hydrocarbon receptor gene (AHR) polymorphism and risk of male infertility. Toxicol Sci. 2011;122:415-21 pubmed publisher..These results suggested that the AHR polymorphism might be associated with individual risk of male infertility in the Chinese population study. ..
- Rodríguez F, Cai Y, Lin C, Tang Y, Kolbanovskiy A, Amin S, et al. Exocyclic amino groups of flanking guanines govern sequence-dependent adduct conformations and local structural distortions for minor groove-aligned benzo[a]pyrenyl-guanine lesions in a GG mutation hotspot context. Nucleic Acids Res. 2007;35:1555-68 pubmed..The minor groove width opens near the lesion in both cases, but more for 5'- ... CGG*C.... Differential sequence-dependent removal rates of this lesion result and may contribute to the mutation hotspot phenomenon. ..
- Yuan C, Lin H, Lee W, Lin Y, Wu T, Chen K. A new alternative fuel for reduction of polycyclic aromatic hydrocarbon and particulate matter emissions from diesel engines. J Air Waste Manag Assoc. 2007;57:465-71 pubmed..Moreover, paraffinic fuel will likely be a new alternative fuel in the future. Using BP9505 instead of PDF decreased PM (22.8%), THC (13.4%), CO (25.3%), total PAHs (88.9%), and total BaPeq (88.1%) emissions significantly. ..
- Rappolee D, Awonuga A, Puscheck E, Zhou S, Xie Y. Benzopyrene and experimental stressors cause compensatory differentiation in placental trophoblast stem cells. Syst Biol Reprod Med. 2010;56:168-83 pubmed publisher..In addition, we review the other effects caused by benzopyrene throughout placental development. ..
- Kim H, Han J, Kim H, Hagiwara A, Lee J. Identification of 28 cytochrome P450 genes from the transcriptome of the marine rotifer Brachionus plicatilis and analysis of their expression. Comp Biochem Physiol Part D Genomics Proteomics. 2017;23:1-7 pubmed publisher..This study sheds light on the molecular defense mechanisms of the rotifer B. plicatilis in response to exposure to various chemicals. ..
- Fan R, Dong Y, Zhang W, Wang Y, Yu Z, Sheng G, et al. Fast simultaneous determination of urinary 1-hydroxypyrene and 3-hydroxybenzo[a]pyrene by liquid chromatography-tandem mass spectrometry. J Chromatogr B Analyt Technol Biomed Life Sci. 2006;836:92-7 pubmed..8-8.9% for 1-OHP and 9.7-20.8% for 3-OHBaP, respectively. The developed method was successfully used to measure urinary PAH metabolites of student volunteers in a high school. ..
- Guo J, Pan S, Singh S. Exceptional activity of murine glutathione transferase A1-1 against (7R,8S)-dihydroxy-(9S,10R)-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene-induced DNA damage in stably transfected cells. Mol Carcinog. 2003;36:67-73 pubmed..The results of the present study indicated that mGSTA1-1 was exceptionally effective in affording protection against (+)-anti-BPDE-induced DNA damage in a cellular system. ..
- Yueh M, Huang Y, Hiller A, Chen S, Nguyen N, Tukey R. Involvement of the xenobiotic response element (XRE) in Ah receptor-mediated induction of human UDP-glucuronosyltransferase 1A1. J Biol Chem. 2003;278:15001-6 pubmed..These observations reveal that the Ah receptor is involved in human UGT1A1 induction. ..
- Csaba G, Kovacs P, Pallinger E. Endorphin content of white blood cells and peritoneal cells in neonatally benzpyrene treated adult rats. Acta Physiol Hung. 2003;90:207-15 pubmed
- Mahadevan B, Keshava C, Musafia Jeknic T, Pecaj A, Weston A, Baird W. Altered gene expression patterns in MCF-7 cells induced by the urban dust particulate complex mixture standard reference material 1649a. Cancer Res. 2005;65:1251-8 pubmed
- Wilson J, Cho Y, Tan S, Cuppoletti A, Kool E. Quenching of fluorescent nucleobases by neighboring DNA: the "insulator" concept. Chembiochem. 2008;9:279-85 pubmed..Adenine base reduced the quenching of pyrene 40-fold. The results underscore the importance of the nearest neighbors in DNA-quenching mechanisms, and establish simple strategies for enhancing fluorescence in labeled DNAs. ..
- Okona Mensah K, Battershill J, Boobis A, Fielder R. An approach to investigating the importance of high potency polycyclic aromatic hydrocarbons (PAHs) in the induction of lung cancer by air pollution. Food Chem Toxicol. 2005;43:1103-16 pubmed
- Brauze D, Mikstacka R, Pelkonen O. Monoclonal antibody characterization of NADH- and NADPH-dependent hydroxylation of benzo(a)pyrene in liver microsomes from 5,6-benzoflavone-induced C57Bl/6 mice. Acta Biochim Pol. 1990;37:219-25 pubmed..It is postulated that different cytochrome P-450 isoenzymes participate in benzo(a)pyrene hydroxylation, whereas the second one acts at high concentration of both NADH and NADPH. ..
- Lauer F, Walker M, Burchiel S. Dibenzo[def,p]chrysene (DBC) suppresses antibody formation in spleen cells following oral exposures of mice. J Toxicol Environ Health A. 2013;76:16-24 pubmed publisher..In conclusion, DBC appears to possess many of the same characteristics of DMBA in terms of its immunotoxicity. ..
- Sterling K, Cutroneo K. Constitutive and inducible expression of cytochromes P4501A (CYP1A1 and CYP1A2) in normal prostate and prostate cancer cells. J Cell Biochem. 2004;91:423-9 pubmed..These observations may be related to the potential smoking-linked higher risk of prostate cancer development and morbidity of prostate cancer patients who smoke. ..
- Masuda H, Saeki Y, Nomura M, Shida K, Matsumoto M, Ui M, et al. High levels of RAE-1 isoforms on mouse tumor cell lines assessed by anti-"pan" RAE-1 antibody confer tumor susceptibility to NK cells. Biochem Biophys Res Commun. 2002;290:140-5 pubmed..These and additional data using mouse cell lines with low MHC-I levels and various RAE-1 levels also demonstrated that RAE-1 level is critically associated with NK-susceptibility in tumor cells. ..
- Bogan B, Lahner L, Sullivan W, Paterek J. Degradation of straight-chain aliphatic and high-molecular-weight polycyclic aromatic hydrocarbons by a strain of Mycobacterium austroafricanum. J Appl Microbiol. 2003;94:230-9 pubmed..These findings indicate that this isolate of Myco. austroafricanum may be useful for bioremediation of soils contaminated with complex mixtures of aromatic and aliphatic hydrocarbons. ..
- Curfs D, Knaapen A, Pachen D, Gijbels M, Lutgens E, Smook M, et al. Polycyclic aromatic hydrocarbons induce an inflammatory atherosclerotic plaque phenotype irrespective of their DNA binding properties. FASEB J. 2005;19:1290-2 pubmed..Moreover, our data revealed a possible novel mechanism of PAH-mediated atherogenesis, which likely involves a TGFbeta-mediated local inflammatory reaction in the vessel wall. ..
- Nebert D, Considine N, Owens I. Genetic expression of aryl hydrocarbon hydroxylase induction. VI. Control of other aromatic hydrocarbon-inducible mono-oxygenase activities at or near the same genetic locus. Arch Biochem Biophys. 1973;157:148-59 pubmed
- Meehan T, Wolfe A, Negrete G, Song Q. Benzo[a]pyrene diol epoxide-DNA cis adduct formation through a trans chlorohydrin intermediate. Proc Natl Acad Sci U S A. 1997;94:1749-54 pubmed..This pathway may have biological significance because chlorohydrins could form in serum or in cells with relatively high intracellular concentrations of chloride...
- Smith W, Freeman J, Gupta R. 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. 2001;480-481:97-108 pubmed..Moreover, this model may also provide information regarding the effect of the test agents on carcinogen bioactivation and detoxification enzymes. ..
- Yamada K, Suzuki T, Kohara A, Hayashi M, Hakura A, Mizutani T, et al. Effect of 10-aza-substitution on benzo[a]pyrene mutagenicity in vivo and in vitro. Mutat Res. 2002;521:187-200 pubmed..These results indicate that 10-aza-substitution markedly modifies the nature of mutagenicity of benzo[a]pyrene in both in vivo and in vitro mutagenesis assays. ..
- Tekes K, Tothfalusi L, Hantos M, Csaba G. Effect of neonatal benzpyrene imprinting on the brain serotonin content and nocistatin level in adult male rats. Acta Physiol Hung. 2007;94:183-9 pubmed
- Platt K, Dienes H, Tommasone M, Luch A. Tumor formation in the neonatal mouse bioassay indicates that the potent carcinogen dibenzo[def,p]chrysene (dibenzo[a,l]pyrene) is activated in vivo via its trans-11,12-dihydrodiol. Chem Biol Interact. 2004;148:27-36 pubmed..This result provides strong evidence that the potent carcinogen DBP is activated in vivo in the mouse via its 11,12-dihydrodiol and not preferentially through alternative pathways. ..
- Zhang Q, Schlick T. Stereochemistry and position-dependent effects of carcinogens on TATA/TBP binding. Biophys J. 2006;90:1865-77 pubmed
- Pratt M, Reddy A, Hendricks J, Pereira C, Kensler T, Bailey G. The importance of carcinogen dose in chemoprevention studies: quantitative interrelationships between, dibenzo[a,l]pyrene dose, chlorophyllin dose, target organ DNA adduct biomarkers and final tumor outcome. Carcinogenesis. 2007;28:611-24 pubmed
- Li H, Luo Y, Song J, Wu L, Christie P. Degradation of benzo[a]pyrene in an experimentally contaminated paddy soil by vetiver grass (Vetiveria zizanioides). Environ Geochem Health. 2006;28:183-8 pubmed..Vetiver grass may promote the biodegradation of B[a]P under flooded conditions by plant roots by stimulating the microbial biomass. Microbial biomass was the main factor affecting dissipation of B[a]P under flooded conditions. ..
- McQuistan T, Simonich M, Pratt M, Pereira C, Hendricks J, Dashwood R, et al. Cancer chemoprevention by dietary chlorophylls: a 12,000-animal dose-dose matrix biomarker and tumor study. Food Chem Toxicol. 2012;50:341-52 pubmed publisher..This finding questions the human relevance of chemoprevention studies carried out at high carcinogen doses that are not proven to lie within a linear, or at least monotonic, endpoint dose-response range. ..
- Schwartz J, Baker V, Larios E, Desai D, Amin S. Inhibition of experimental tobacco carcinogen induced head and neck carcinogenesis. Oral Oncol. 2004;40:611-23 pubmed..5/7 DB[a,l]P) and 30 weeks (3/7 vs. 6/7 DB[a,l]P). Inhibition of oral carcinogenesis by VE(as) involved reversal of several cellular events that contribute towards oral cancer. ..
- Gielen J, Goujon F, Nebert D. Genetic regulation of aryl hydrocarbon hydroxylase induction. II. Simple Mendelian expression in mouse tissues in vivo. J Biol Chem. 1972;247:1125-37 pubmed
- Castro D, LOHR C, Fischer K, Pereira C, Williams D. Lymphoma and lung cancer in offspring born to pregnant mice dosed with dibenzo[a,l]pyrene: the importance of in utero vs. lactational exposure. Toxicol Appl Pharmacol. 2008;233:454-8 pubmed publisher..Our results demonstrate that short exposure to DBP during late gestation presents a greater risk to offspring than exposure to this very hydrophobic PAH following 3 weeks of nursing. ..