Benzo(a)pyrene diol epoxide (BioDeep_00001874461)
Main id: BioDeep_00000010188
代谢物信息卡片
7,8,8A,9A-TETRAHYDROBENZO[1,12]TETRAPHENO[10,11-B]OXIRENE-7,8-DIOL
化学式: C20H14O3 (302.0943)
中文名称: 7,8-二羟基-9,10-环氧-7,8,9,10-四氢苯并[A]芘
谱图信息:
最多检出来源 Mus musculus(plant) 13.28%
分子结构信息
SMILES: C1=CC2=C3C(=C1)C=CC4=C3C(=CC5=C4C6C(O6)C(C5O)O)C=C2
InChI: InChI=1S/C20H14O3/c21-17-13-8-11-5-4-9-2-1-3-10-6-7-12(15(11)14(9)10)16(13)19-20(23-19)18(17)22/h1-8,17-22H
描述信息
D009676 - Noxae > D002273 - Carcinogens
D009676 - Noxae > D009153 - Mutagens
同义名列表
数据库引用编号
9 个数据库交叉引用编号
- ChEBI: CHEBI:30614
- KEGG: C14853
- PubChem: 41322
- ChEMBL: CHEMBL1743211
- MeSH: 7,8-Dihydro-7,8-dihydroxybenzo(a)pyrene 9,10-oxide
- CAS: 55097-80-8
- PubChem: 17395851
- NIKKAJI: J282.916I
- KNApSAcK: 30614
分类词条
相关代谢途径
Reactome(0)
BioCyc(0)
PlantCyc(0)
代谢反应
0 个相关的代谢反应过程信息。
Reactome(0)
BioCyc(0)
WikiPathways(0)
Plant Reactome(0)
INOH(0)
PlantCyc(0)
COVID-19 Disease Map(0)
PathBank(0)
PharmGKB(0)
0 个相关的物种来源信息
在这里通过桑基图来展示出与当前的这个代谢物在我们的BioDeep知识库中具有相关联信息的其他代谢物。在这里进行关联的信息来源主要有：
- PubMed: 来源于PubMed文献库中的文献信息，我们通过自然语言数据挖掘得到的在同一篇文献中被同时提及的相关代谢物列表，这个列表按照代谢物同时出现的文献数量降序排序，取前10个代谢物作为相关研究中关联性很高的代谢物集合展示在桑基图中。
- NCBI Taxonomy: 通过文献数据挖掘，得到的代谢物物种来源信息关联。这个关联信息同样按照出现的次数降序排序，取前10个代谢物作为高关联度的代谢物集合展示在桑吉图上。
- Chemical Taxonomy: 在物质分类上处于同一个分类集合中的其他代谢物
- Chemical Reaction: 在化学反应过程中，存在为当前代谢物相关联的生化反应过程中的反应底物或者反应产物的关联代谢物信息。
点击图上的相关代谢物的名称，可以跳转到相关代谢物的信息页面。
文献列表
- Ying Zhang, Yang Yang, Weina Chen, Chenyang Mi, Xiaole Xu, Yanqiu Shen, Zhaodian Zheng, Zhongyan Xu, Jingsong Zhao, Shukun Wan, Xiaoqing Wang, Huidong Zhang. BaP/BPDE suppressed endothelial cell angiogenesis to induce miscarriage by promoting MARCHF1/GPX4-mediated ferroptosis.
Environment international.
2023 10; 180(?):108237. doi:
10.1016/j.envint.2023.108237. [PMID: 37802009] - Yi Lyu, Xue-Ke Ren, Can-Can Guo, Zhao-Fei Li, Jin-Ping Zheng. Benzo(a)pyrene-7,8-dihydrodiol-9,10-epoxide induces ferroptosis in neuroblastoma cells through redox imbalance.
The Journal of toxicological sciences.
2022; 47(12):519-529. doi:
10.2131/jts.47.519. [PMID: 36450496] - Hongxuan Kuang, Yanyan Dai, Xiang Ding, Yonghong Li, Caihui Cha, Wenhui Jiang, Haibin Zhang, Wenji Zhou, Yingwei Zeng, Qihua Pang, Ruifang Fan. Association among blood BPDE-DNA adduct, serum interleukin-8 (IL-8) and DNA strand breaks for children with pulmonary diseases.
International journal of environmental health research.
2021 Nov; 31(7):823-834. doi:
10.1080/09603123.2019.1690638. [PMID: 31722538] - Hua Meng, Guyanan Li, Wei Wei, Yansen Bai, Yue Feng, Ming Fu, Xin Guan, Mengying Li, Hang Li, Chenming Wang, Jiali Jie, Xiulong Wu, Meian He, Xiaomin Zhang, Sheng Wei, Yangkai Li, Huan Guo. Epigenome-wide DNA methylation signature of benzo[a]pyrene exposure and their mediation roles in benzo[a]pyrene-associated lung cancer development.
Journal of hazardous materials.
2021 08; 416(?):125839. doi:
10.1016/j.jhazmat.2021.125839. [PMID: 33887567] - Fabian C Fischer, Cedric Abele, Luise Henneberger, Nils Klüver, Maria König, Marie Mühlenbrink, Rita Schlichting, Beate I Escher. Cellular Metabolism in High-Throughput In Vitro Reporter Gene Assays and Implications for the Quantitative In Vitro-In Vivo Extrapolation.
Chemical research in toxicology.
2020 07; 33(7):1770-1779. doi:
10.1021/acs.chemrestox.0c00037. [PMID: 32227843] - Jie Li, Ting Wang, Yanhua Wang, Mengmeng Xu, Liping Zhang, Xinwei Li, Zhong Liu, Sheng Gao, Qiang Jia, Yaochun Fan, Zhenjie Wang, Nan Wu, Xiao Zhang, Yufei Dai, Fanling Kong, Wenrui Wang, Huawei Duan. Particulate matter air pollution and the expression of microRNAs and pro-inflammatory genes: Association and mediation among children in Jinan, China.
Journal of hazardous materials.
2020 05; 389(?):121843. doi:
10.1016/j.jhazmat.2019.121843. [PMID: 31843406] - Niels Hadrup, Danuta Mielżyńska-Švach, Agnieszka Kozłowska, Manuela Campisi, Sofia Pavanello, Ulla Vogel. Association between a urinary biomarker for exposure to PAH and blood level of the acute phase protein serum amyloid A in coke oven workers.
Environmental health : a global access science source.
2019 09; 18(1):81. doi:
10.1186/s12940-019-0523-1. [PMID: 31477116] - Aisha Mohamed Samir, Dalia Abdel-Hamid Shaker, Mona Mohamed Fathy, Salwa Farouk Hafez, Mona Mohsen Abdullatif, Laila Ahmed Rashed, Hany Ahmed Fouad Alghobary. Urinary and Genetic Biomonitoring of Polycyclic Aromatic Hydrocarbons in Egyptian Coke Oven Workers: Associations between Exposure, Effect, and Carcinogenic Risk Assessment.
The international journal of occupational and environmental medicine.
2019 07; 10(3):124-136. doi:
10.15171/ijoem.2019.1541. [PMID: 31325295] - Peter W Villalta, J Bradley Hochalter, Stephen S Hecht. Ultrasensitive High-Resolution Mass Spectrometric Analysis of a DNA Adduct of the Carcinogen Benzo[a]pyrene in Human Lung.
Analytical chemistry.
2017 12; 89(23):12735-12742. doi:
10.1021/acs.analchem.7b02856. [PMID: 29111668] - Pavel Borský, Ctirad Andrýs, Jan Krejsek, Květoslava Hamáková, Jan Kremláček, Andrea Málková, Lenka Bartošová, Zdeněk Fiala, Vladimír Palička, Lenka Borská. Serum Level of Antibodies (IgG, IgM) Against Benzo[a]pyrene-7,8-diol-9,10-epoxide-DNA Adducts in Children Dermatologically Exposed to Coal Tar.
Acta medica (Hradec Kralove).
2017 ; 60(1):27-31. doi:
10.14712/18059694.2017.46. [PMID: 28467299] - Hitesh V Motwani, Emelie Westberg, Margareta Törnqvist. Interaction of benzo[a]pyrene diol epoxide isomers with human serum albumin: Site specific characterisation of adducts and associated kinetics.
Scientific reports.
2016 11; 6(?):36243. doi:
10.1038/srep36243. [PMID: 27805056] - Qi Lin, Liu Xiao-Chen, Yang Bo, Liu Na, Shi Min, Chen Gang, Liu Hui, Zhou Jie, Li Fa-Sheng. Quantitative analysis of 3-OHB[a]P and (+)-anti-BPDE as biomarkers of B[a]P exposure in rats.
Biomedical chromatography : BMC.
2016 Mar; 30(3):474-83. doi:
10.1002/bmc.3574. [PMID: 26230188] - Bridget R Simon-Friedt, Mark J Wilson, Diane A Blake, Haini Yu, Yasmin Eriksson, Jeffrey K Wickliffe. The RPTEC/TERT1 Cell Line as an Improved Tool for In Vitro Nephrotoxicity Assessments.
Biological trace element research.
2015 Jul; 166(1):66-71. doi:
10.1007/s12011-015-0339-y. [PMID: 25893367] - Rukshan T Perera, Aaron M Fleming, Robert P Johnson, Cynthia J Burrows, Henry S White. Detection of benzo[a]pyrene-guanine adducts in single-stranded DNA using the α-hemolysin nanopore.
Nanotechnology.
2015 Feb; 26(7):074002. doi:
10.1088/0957-4484/26/7/074002. [PMID: 25629967] - W Zhang, N Liu, X Wang, X Jin, H Du, G Peng, J Xue. Benzo(a)pyrene-7,8-diol-9,10-epoxide induced p53-independent necrosis via the mitochondria-associated pathway involving Bax and Bak activation.
Human & experimental toxicology.
2015 Feb; 34(2):179-90. doi:
10.1177/0960327114533358. [PMID: 24837741] - Emelie A C Westberg, Rajinder Singh, Ulla Hedebrant, Georgios Koukouves, Vassilis L Souliotis, Peter B Farmer, Dan Segerbäck, Soterios Kyrtopoulos, Margareta Å Törnqvist. Adduct levels from benzo[a]pyrenediol epoxide: Relative formation to histidine in serum albumin and to deoxyguanosine in DNA in vitro and in vivo in mice measured by LC/MS-MS methods.
Toxicology letters.
2015 Jan; 232(1):28-36. doi:
10.1016/j.toxlet.2014.09.019. [PMID: 25261590] - Lenka Borska, Ctirad Andrys, Jan Krejsek, Vladimir Palicka, Marcela Chmelarova, Kvetoslava Hamakova, Jan Kremlacek, Pavel Borsky, Zdenek Fiala. Serum level of antibody against benzo[a]pyrene-7,8-diol-9,10-epoxide-DNA adducts in people dermally exposed to PAHs.
Journal of immunology research.
2014; 2014(?):834389. doi:
10.1155/2014/834389. [PMID: 24822226] - Dan Kuang, Wangzhen Zhang, Qifei Deng, Xiao Zhang, Kun Huang, Lei Guan, Die Hu, Tangchun Wu, Huan Guo. Dose-response relationships of polycyclic aromatic hydrocarbons exposure and oxidative damage to DNA and lipid in coke oven workers.
Environmental science & technology.
2013 Jul; 47(13):7446-56. doi:
10.1021/es401639x. [PMID: 23745771] - Stefanie Hessel, Andrea John, Albrecht Seidel, Alfonso Lampen. Multidrug resistance-associated proteins are involved in the transport of the glutathione conjugates of the ultimate carcinogen of benzo[a]pyrene in human Caco-2 cells.
Archives of toxicology.
2013 Feb; 87(2):269-80. doi:
10.1007/s00204-012-0917-0. [PMID: 22899102] - Guoxiang Huang, Huan Guo, Tangchun Wu. Genetic variations of CYP2B6 gene were associated with plasma BPDE-Alb adducts and DNA damage levels in coke oven workers.
Toxicology letters.
2012 Jun; 211(3):232-8. doi:
10.1016/j.toxlet.2012.04.004. [PMID: 22521834] - Piya Temviriyanukul, Matty Meijers, Sandrine van Hees-Stuivenberg, Jan J W A Boei, Frédéric Delbos, Haruo Ohmori, Niels de Wind, Jacob G Jansen. Different sets of translesion synthesis DNA polymerases protect from genome instability induced by distinct food-derived genotoxins.
Toxicological sciences : an official journal of the Society of Toxicology.
2012 May; 127(1):130-8. doi:
10.1093/toxsci/kfs074. [PMID: 22331492] - Caroline Marie-Desvergne, Anne Maître, Michèle Bouchard, Jean-Luc Ravanat, Claude Viau. Evaluation of DNA adducts, DNA and RNA oxidative lesions, and 3-hydroxybenzo(a)pyrene as biomarkers of DNA damage in lung following intravenous injection of the parent compound in rats.
Chemical research in toxicology.
2010 Jul; 23(7):1207-14. doi:
10.1021/tx100081p. [PMID: 20593881] - Haitian Lu, Robert B Crawford, Colin M North, Barbara L F Kaplan, Norbert E Kaminski. Establishment of an immunoglobulin m antibody-forming cell response model for characterizing immunotoxicity in primary human B cells.
Toxicological sciences : an official journal of the Society of Toxicology.
2009 Dec; 112(2):363-73. doi:
10.1093/toxsci/kfp224. [PMID: 19767444] - J Topinka, A Milcova, H Libalova, Z Novakova, P Rossner, I Balascak, R J Sram. Biomarkers of exposure to tobacco smoke and environmental pollutants in mothers and their transplacental transfer to the foetus. Part I: bulky DNA adducts.
Mutation research.
2009 Oct; 669(1-2):13-9. doi:
10.1016/j.mrfmmm.2009.04.011. [PMID: 19433098] - Manju Mehta, Lung-Chi Chen, Terry Gordon, William Rom, Moon-Shong Tang. Particulate matter inhibits DNA repair and enhances mutagenesis.
Mutation research.
2008 Dec; 657(2):116-21. doi:
10.1016/j.mrgentox.2008.08.015. [PMID: 18804180] - Yaqin Pang, Wenxue Li, Rulin Ma, Weidong Ji, Qing Wang, Daochuan Li, Yongmei Xiao, Qing Wei, Yandong Lai, Ping Yang, Liping Chen, Shifu Tang, Yuchun Lin, Zhixiong Zhuang, Yuxin Zheng, Wen Chen. Development of human cell models for assessing the carcinogenic potential of chemicals.
Toxicology and applied pharmacology.
2008 Nov; 232(3):478-86. doi:
10.1016/j.taap.2008.08.009. [PMID: 18778725] - Yimin Zhu, Yohei Horikawa, Hushan Yang, Christopher G Wood, Tomonori Habuchi, Xifeng Wu. BPDE induced lymphocytic chromosome 3p deletions may predict renal cell carcinoma risk.
The Journal of urology.
2008 Jun; 179(6):2416-21. doi:
10.1016/j.juro.2008.01.092. [PMID: 18433782] - Jingxia Li, Dongyun Zhang, Gary D Stoner, Chuanshu Huang. Differential effects of black raspberry and strawberry extracts on BaPDE-induced activation of transcription factors and their target genes.
Molecular carcinogenesis.
2008 Apr; 47(4):286-94. doi:
10.1002/mc.20377. [PMID: 18085529] - Haruhiko Yagi, Donald M Jerina. Fluorinated alcohol mediated displacement of the C10 acetoxy group of benzo[a]pyrene-7,8,9,10-tetrahydrotetraol tetraacetates: a new route to diol epoxide-deoxyguanosine adducts.
The Journal of organic chemistry.
2007 Dec; 72(26):9983-90. doi:
10.1021/jo701705c. [PMID: 18047370] - Hong Wang, Weihong Chen, Hongyan Zheng, Liang Guo, Huashan Liang, Xiaobo Yang, Yun Bai, Jianya Sun, Yougong Su, Yongwen Chen, Jing Yuan, Yongyi Bi, Qingyi Wei, Tangchun Wu. Association between plasma BPDE-Alb adduct concentrations and DNA damage of peripheral blood lymphocytes among coke oven workers.
Occupational and environmental medicine.
2007 Nov; 64(11):753-8. doi:
10.1136/oem.2006.030445. [PMID: 17449561] - Lonneke C Wilms, Agnes W Boots, Vincent C J de Boer, Lou M Maas, Daniëlle M F A Pachen, Ralph W H Gottschalk, Hans B Ketelslegers, Roger W L Godschalk, Guido R M M Haenen, Frederik J van Schooten, Jos C S Kleinjans. Impact of multiple genetic polymorphisms on effects of a 4-week blueberry juice intervention on ex vivo induced lymphocytic DNA damage in human volunteers.
Carcinogenesis.
2007 Aug; 28(8):1800-6. doi:
10.1093/carcin/bgm145. [PMID: 17602170] - Hong Wang, Xiao-Bo Yang, Ai-Lin Liu, Hong-Yan Zhen, Liang Guo, Hua-Shan Liang, Yong-Yi Bi, Yun Bai, Yong-Wen Chen, Tang-Chun Wu. Significant positive correlation of plasma BPDE-albumin adducts to urinary 1-hydroxypyrene in coke oven workers.
Biomedical and environmental sciences : BES.
2007 Jun; 20(3):179-83. doi:
. [PMID: 17672206] - Bettina Ebert, Albrecht Seidel, Alfonso Lampen. Phytochemicals induce breast cancer resistance protein in Caco-2 cells and enhance the transport of benzo[a]pyrene-3-sulfate.
Toxicological sciences : an official journal of the Society of Toxicology.
2007 Apr; 96(2):227-36. doi:
10.1093/toxsci/kfl147. [PMID: 17077187] - Chuanshu Huang, Dongyun Zhang, Jingxia Li, Qiangsong Tong, Gary D Stoner. Differential inhibition of UV-induced activation of NF kappa B and AP-1 by extracts from black raspberries, strawberries, and blueberries.
Nutrition and cancer.
2007; 58(2):205-12. doi:
10.1080/01635580701328453. [PMID: 17640167] - Zhaohui Feng, Wenwei Hu, Lawrence J Marnett, Moon-shong Tang. Malondialdehyde, a major endogenous lipid peroxidation product, sensitizes human cells to UV- and BPDE-induced killing and mutagenesis through inhibition of nucleotide excision repair.
Mutation research.
2006 Oct; 601(1-2):125-36. doi:
10.1016/j.mrfmmm.2006.06.003. [PMID: 16872641] - Stephen S Hecht, Chuanshu Huang, Gary D Stoner, Jingxia Li, Patrick M J Kenney, Shana J Sturla, Steven G Carmella. Identification of cyanidin glycosides as constituents of freeze-dried black raspberries which inhibit anti-benzo[a]pyrene-7,8-diol-9,10-epoxide induced NFkappaB and AP-1 activity.
Carcinogenesis.
2006 Aug; 27(8):1617-26. doi:
10.1093/carcin/bgi366. [PMID: 16522666] - Chuanshu Huang, Jingxia Li, Lun Song, Dongyun Zhang, Qiangsong Tong, Min Ding, Linda Bowman, Robeena Aziz, Gary D Stoner. Black raspberry extracts inhibit benzo(a)pyrene diol-epoxide-induced activator protein 1 activation and VEGF transcription by targeting the phosphotidylinositol 3-kinase/Akt pathway.
Cancer research.
2006 Jan; 66(1):581-7. doi:
10.1158/0008-5472.can-05-1951. [PMID: 16397275] - Hans Steinkellner, Christine Hoelzl, Maria Uhl, Christophe Cavin, Gerald Haidinger, Andrea Gsur, Rainer Schmid, Michael Kundi, Julia Bichler, Siegfried Knasmüller. Coffee consumption induces GSTP in plasma and protects lymphocytes against (+/-)-anti-benzo[a]pyrene-7,8-dihydrodiol-9,10-epoxide induced DNA-damage: results of controlled human intervention trials.
Mutation research.
2005 Dec; 591(1-2):264-75. doi:
10.1016/j.mrfmmm.2005.04.016. [PMID: 16099480] - S Pavanello, A Pulliero, A Lai, A Gaiardo, G Mastrangelo, E Clonfero. [Anti-B[a]PDE-DNA formation in lymphomonocytes of humans environmentally exposed to polycyclic aromatic hydrocarbons].
Giornale italiano di medicina del lavoro ed ergonomia.
2005 Jul; 27(3):312-4. doi:
NULL. [PMID: 16240582] - Lonneke C Wilms, Peter C H Hollman, Agnes W Boots, Jos C S Kleinjans. Protection by quercetin and quercetin-rich fruit juice against induction of oxidative DNA damage and formation of BPDE-DNA adducts in human lymphocytes.
Mutation research.
2005 Apr; 582(1-2):155-62. doi:
10.1016/j.mrgentox.2005.01.006. [PMID: 15781220] - Michael J Kelley, Elizabeth M Glaser, James E Herndon, Frank Becker, Rajesh Bhagat, Yu-Jing Zhang, Regina M Santella, Steven G Carmella, Stephen S Hecht, Lilia Gallot, Lawrence Schilder, James A Crowell, Marjorie Perloff, Rodney J Folz, Raymond C Bergan. Safety and efficacy of weekly oral oltipraz in chronic smokers.
Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology.
2005 Apr; 14(4):892-9. doi:
10.1158/1055-9965.epi-04-0585. [PMID: 15824161] - Wei Yang. Portraits of a Y-family DNA polymerase.
FEBS letters.
2005 Feb; 579(4):868-72. doi:
10.1016/j.febslet.2004.11.047. [PMID: 15680965] - Huan Dong, Radha Rani Bonala, Naomi Suzuki, Francis Johnson, Arthur P Grollman, Shinya Shibutani. Mutagenic potential of benzo[a]pyrene-derived DNA adducts positioned in codon 273 of the human P53 gene.
Biochemistry.
2004 Dec; 43(50):15922-8. doi:
10.1021/bi0482194. [PMID: 15595848] - E A Carlson, Y Li, J T Zelikoff. Suppressive effects of benzo[a]pyrene upon fish immune function: evolutionarily conserved cellular mechanisms of immunotoxicity.
Marine environmental research.
2004 Aug; 58(2-5):731-4. doi:
10.1016/j.marenvres.2004.03.023. [PMID: 15178106] - Zhaohui Feng, Wenwei Hu, Moon-Shong Tang. Trans-4-hydroxy-2-nonenal inhibits nucleotide excision repair in human cells: a possible mechanism for lipid peroxidation-induced carcinogenesis.
Proceedings of the National Academy of Sciences of the United States of America.
2004 Jun; 101(23):8598-602. doi:
10.1073/pnas.0402794101. [PMID: 15187227] - Adela Tzekova, Ross Thuot, Claude Viau. Correlation between biomarkers of polycyclic aromatic hydrocarbon exposure and electrophilic tissue burden in a rat model.
Archives of toxicology.
2004 Jun; 78(6):351-61. doi:
10.1007/s00204-003-0539-7. [PMID: 14749914] - Hong Ling, Jane M Sayer, Brian S Plosky, Haruhiko Yagi, François Boudsocq, Roger Woodgate, Donald M Jerina, Wei Yang. Crystal structure of a benzo[a]pyrene diol epoxide adduct in a ternary complex with a DNA polymerase.
Proceedings of the National Academy of Sciences of the United States of America.
2004 Feb; 101(8):2265-9. doi:
10.1073/pnas.0308332100. [PMID: 14982998] - Stephen S Hecht, Menglan Chen, Haruhiko Yagi, Donald M Jerina, Steven G Carmella. r-1,t-2,3,c-4-Tetrahydroxy-1,2,3,4-tetrahydrophenanthrene in human urine: a potential biomarker for assessing polycyclic aromatic hydrocarbon metabolic activation.
Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology.
2003 Dec; 12(12):1501-8. doi:
. [PMID: 14693744] - Roger Godschalk, Daniëlle Curfs, Helmut Bartsch, Frederik-Jan Van Schooten, Jagadeesan Nair. Benzo[a]pyrene enhances lipid peroxidation induced DNA damage in aorta of apolipoprotein E knockout mice.
Free radical research.
2003 Dec; 37(12):1299-305. doi:
10.1080/10715760310001621333. [PMID: 14753754] - S Pavanello, E Clonfero. [CYP1A2, NAT2, and GSTM1 phenotype/genotype modulate human exposure and various environmental mutagens: our experience].
Giornale italiano di medicina del lavoro ed ergonomia.
2003 Jul; 25(3):344-5. doi:
. [PMID: 14582254] - Chuanshu Huang, Yi Huang, Jingxia Li, Wenwei Hu, Robeena Aziz, Moon-shong Tang, Nanjun Sun, John Cassady, Gary D Stoner. Inhibition of benzo(a)pyrene diol-epoxide-induced transactivation of activated protein 1 and nuclear factor kappaB by black raspberry extracts.
Cancer research.
2002 Dec; 62(23):6857-63. doi:
. [PMID: 12460899] - Hilde E van Gijssel, Rao L Divi, Ofelia A Olivero, Mark J Roth, Guo-Qing Wang, Sanford M Dawsey, Paul S Albert, You-Lin Qiao, Philip R Taylor, Zhi-Wei Dong, Jeffrey A Schrager, David E Kleiner, Miriam C Poirier. Semiquantitation of polycyclic aromatic hydrocarbon-DNA adducts in human esophagus by immunohistochemistry and the automated cellular imaging system.
Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology.
2002 Dec; 11(12):1622-9. doi:
NULL. [PMID: 12496053] - Sucheta Sharma, H M Dani. In vitro formation of organ specific proximate carcinogen of benzo(a)pyrene by rat homogenates.
Indian journal of experimental biology.
2002 Sep; 40(9):1067-70. doi:
NULL. [PMID: 12587739] - Sanjay K Srivastava, Simon C Watkins, Erin Schuetz, Shivendra V Singh. Role of glutathione conjugate efflux in cellular protection against benzo[a]pyrene-7,8-diol-9,10-epoxide-induced DNA damage.
Molecular carcinogenesis.
2002 Mar; 33(3):156-62. doi:
. [PMID: 11870881] - Grazyna Motykiewicz, Beatrice Faraglia, Lian Wen Wang, Mary Beth Terry, Ruby T Senie, Regina M Santella. Removal of benzo(a)pyrene diol epoxide (BPDE)-DNA adducts as a measure of DNA repair capacity in lymphoblastoid cell lines from sisters discordant for breast cancer.
Environmental and molecular mutagenesis.
2002; 40(2):93-100. doi:
10.1002/em.10095. [PMID: 12203401] - Huifeng Zhang, Margaret R Spitz, Gail E Tomlinson, Matthew B Schabath, John D Minna, Xifeng Wu. Modification of lung cancer susceptibility by green tea extract as measured by the comet assay.
Cancer detection and prevention.
2002; 26(6):411-8. doi:
10.1016/s0361-090x(02)00127-7. [PMID: 12507225] - R Galati, A Zijno, R Crebelli, G Falasca, F Tomei, F Iecher, P Carta, A Verdina. Detection of antibodies to the benzo(a)pyrene diol epoxide-DNA adducts in sera from individuals exposed to low doses of polycyclic aromatic hydrocarbons.
Journal of experimental & clinical cancer research : CR.
2001 Sep; 20(3):359-64. doi:
NULL. [PMID: 11718215] - P Pradhan, S Tirumala, X Liu, J M Sayer, D M Jerina, H J Yeh. Solution structure of a trans-opened (10S)-dA adduct of (+)-(7S,8R,9S,10R)-7,8-dihydroxy-9,10-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene in a fully complementary DNA duplex: evidence for a major syn conformation.
Biochemistry.
2001 May; 40(20):5870-81. doi:
10.1021/bi002896q. [PMID: 11352722] - A R Ramesha, H Kroth, D M Jerina. Solvent-free synthesis of benzo[a]pyrene 7,8-diol 9,10-epoxide adducts at the N(2)-position of deoxyguanosine.
Organic letters.
2001 Feb; 3(4):531-3. doi:
10.1021/ol0003580. [PMID: 11178817] - H Kroth, H Yagi, A Seidel, D M Jerina. New and highly efficient synthesis of cis- and trans-opened Benzo[a]pyrene 7,8-diol 9,10-epoxide adducts at the exocyclic N(2)-amino group of deoxyguanosine.
The Journal of organic chemistry.
2000 Sep; 65(18):5558-64. doi:
10.1021/jo000522x. [PMID: 10970294] - C C Ozbal, P L Skipper, M C Yu, S J London, R R Dasari, S R Tannenbaum. Quantification of (7S,8R)-dihydroxy-(9R,10S)-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene adducts in human serum albumin by laser-induced fluorescence: implications for the in vivo metabolism of benzo[a]pyrene.
Cancer epidemiology, biomarkers & prevention : a publication of the American Association for Cancer Research, cosponsored by the American Society of Preventive Oncology.
2000 Jul; 9(7):733-9. doi:
. [PMID: 10919745] - J Padrós, E Pelletier. In vivo formation of (+)-anti-benzo[a]pyrene diol-epoxide-plasma albumin adducts in fish.
Marine environmental research.
2000 Jul; 50(1-5):347-51. doi:
10.1016/s0141-1136(00)00064-7. [PMID: 11460716] - X Wu, H Yu, C I Amos, W K Hong, M R Spitz. Joint effect of insulin-like growth factors and mutagen sensitivity in lung cancer risk.
Journal of the National Cancer Institute.
2000 May; 92(9):737-43. doi:
10.1093/jnci/92.9.737. [PMID: 10793110] - C D Simpson, M T Wu, D C Christiani, R M Santella, S G Carmella, S S Hecht. Determination of r-7,t-8,9,c-10-tetrahydroxy-7,8,9, 10-tetrahydrobenzo[a]pyrene in human urine by gas chromatography/negative ion chemical ionization/mass spectrometry.
Chemical research in toxicology.
2000 Apr; 13(4):271-80. doi:
10.1021/tx990202c. [PMID: 10775327] - M Rojas, I Cascorbi, K Alexandrov, E Kriek, G Auburtin, L Mayer, A Kopp-Schneider, I Roots, H Bartsch. Modulation of benzo[a]pyrene diolepoxide-DNA adduct levels in human white blood cells by CYP1A1, GSTM1 and GSTT1 polymorphism.
Carcinogenesis.
2000 Jan; 21(1):35-41. doi:
10.1093/carcin/21.1.35. [PMID: 10607731] - H Helleberg, M Törnqvist. A new approach for measuring protein adducts from benzo[a]pyrene diolepoxide by high performance liquid chromatography/tandem mass spectrometry.
Rapid communications in mass spectrometry : RCM.
2000; 14(18):1644-53. doi:
10.1002/1097-0231(20000930)14:18<1644::aid-rcm74>3.0.co;2-#. [PMID: 10962485] - S K Srivastava, X Hu, H Xia, S Awasthi, S Amin, S V Singh. Metabolic fate of glutathione conjugate of benzo[a]pyrene-(7R,8S)-diol (9S,10R)-epoxide in human liver.
Archives of biochemistry and biophysics.
1999 Nov; 371(2):340-4. doi:
10.1006/abbi.1999.1475. [PMID: 10545223] - M T Zenzes, R Bielecki, T E Reed. Detection of benzo(a)pyrene diol epoxide-DNA adducts in sperm of men exposed to cigarette smoke.
Fertility and sterility.
1999 Aug; 72(2):330-5. doi:
10.1016/s0015-0282(99)00230-7. [PMID: 10439006] - S Pavanello, G Gabbani, G Mastrangelo, F Brugnone, G Maccacaro, E Clonfero. Influence of GSTM1 genotypes on anti-BPDE-DNA adduct levels in mononuclear white blood cells of humans exposed to PAH.
International archives of occupational and environmental health.
1999 Jul; 72(4):238-46. doi:
10.1007/s004200050367. [PMID: 10491778] - S Pavanello, D Favretto, F Brugnone, G Mastrangelo, G Dal Pra, E Clonfero. HPLC/fluorescence determination of anti-BPDE-DNA adducts in mononuclear white blood cells from PAH-exposed humans.
Carcinogenesis.
1999 Mar; 20(3):431-5. doi:
10.1093/carcin/20.3.431. [PMID: 10190558] - H Jyonouchi, S Sun, K Iijima, M Wang, S S Hecht. Effects of anti-7,8-dihydroxy-9,10-epoxy-7,8,9,10-tetrahydrobenzo[a]pyrene on human small airway epithelial cells and the protective effects of myo-inositol.
Carcinogenesis.
1999 Jan; 20(1):139-45. doi:
10.1093/carcin/20.1.139. [PMID: 9934861] - J P Arnould, A Hermant, P Levi-Valensi, J Belegaud. Detection of benzo[a]pyrene-DNA adducts from leukocytes from heavy smokers.
Pathologie-biologie.
1998 Dec; 46(10):787-90. doi:
NULL. [PMID: 9922995] - A Fernandes, T Liu, S Amin, N E Geacintov, A P Grollman, M Moriya. Mutagenic potential of stereoisomeric bay region (+)- and (-)-cis-anti-benzo[a]pyrene diol epoxide-N2-2'-deoxyguanosine adducts in Escherichia coli and simian kidney cells.
Biochemistry.
1998 Jul; 37(28):10164-72. doi:
10.1021/bi980401f. [PMID: 9665722] - S K Srivastava, X Hu, H Xia, R J Bleicher, H A Zaren, J L Orchard, S Awasthi, S V Singh. ATP-dependent transport of glutathione conjugate of 7beta, 8alpha-dihydroxy-9alpha,10alpha-oxy-7,8,9,10-tetrahydrobenzo[a]pyrene in murine hepatic canalicular plasma membrane vesicles.
The Biochemical journal.
1998 Jun; 332 ( Pt 3)(?):799-805. doi:
10.1042/bj3320799. [PMID: 9620885] - H Xia, S S Pan, X Hu, S K Srivastava, A Pal, S V Singh. Cloning, expression, and biochemical characterization of a functionally novel alpha class glutathione S-transferase with exceptional activity in the glutathione conjugation of (+)-anti-7,8-dihydroxy-9,10-oxy-7,8,9,10-tetrahydrobenzo(a)pyrene.
Archives of biochemistry and biophysics.
1998 May; 353(2):337-48. doi:
10.1006/abbi.1998.0668. [PMID: 9606968] - R A Baan, M J Steenwinkel, S van Asten, R Roggeband, J H van Delft. The use of benzo[a]pyrene diolepoxide-modified DNA standards for adduct quantification in 32P-postlabelling to assess exposure to polycyclic aromatic hydrocarbons: application in a biomonitoring study.
Mutation research.
1997 Aug; 378(1-2):41-50. doi:
10.1016/s0027-5107(97)00096-1. [PMID: 9288884] - T Meehan, A R Wolfe, G R Negrete, Q Song. Benzo[a]pyrene diol epoxide-DNA cis adduct formation through a trans chlorohydrin intermediate.
Proceedings of the National Academy of Sciences of the United States of America.
1997 Mar; 94(5):1749-54. doi:
10.1073/pnas.94.5.1749. [PMID: 9050850] - N Pulerà, S Petruzzelli, A Celi, R Puntoni, E Fornai, U Säwe, P Paoletti, C Giuntini. Presence and persistence of serum anti-benzo[a]pyrene diolepoxide-DNA adduct antibodies in smokers: effects of smoking reduction and cessation.
International journal of cancer.
1997 Jan; 70(2):145-9. doi:
10.1002/(sici)1097-0215(19970117)70:2<145::aid-ijc1>3.0.co;2-x. [PMID: 9009151] - M Moriya, S Spiegel, A Fernandes, S Amin, T Liu, N Geacintov, A P Grollman. Fidelity of translesional synthesis past benzo[a]pyrene diol epoxide-2'-deoxyguanosine DNA adducts: marked effects of host cell, sequence context, and chirality.
Biochemistry.
1996 Dec; 35(51):16646-51. doi:
10.1021/bi9608875. [PMID: 8988000] - S Swedmark, B Jernström, D Jenssen. Comparison of the mRNA sequences for Pi class glutathione transferases in different hamster species and the corresponding enzyme activities with anti-benzo[a]pyrene-7,8-dihydrodiol 9,10-epoxide.
The Biochemical journal.
1996 Sep; 318 ( Pt 2)(?):533-8. doi:
10.1042/bj3180533. [PMID: 8809043] - J L Mumford, K Williams, T C Wilcosky, R B Everson, T L Young, R M Santella. A sensitive color ELISA for detecting polycyclic aromatic hydrocarbon-DNA adducts in human tissues.
Mutation research.
1996 Apr; 359(3):171-7. doi:
10.1016/s0165-1161(96)90264-2. [PMID: 8618549] - J D Adams, H Yagi, W Levin, D M Jerina. Stereo-selectivity and regio-selectivity in the metabolism of 7,8-dihydrobenzo[a]pyrene by cytochrome P450, epoxide hydrolase and hepatic microsomes from 3-methylcholanthrene-treated rats.
Chemico-biological interactions.
1995 Mar; 95(1-2):57-77. doi:
10.1016/0009-2797(94)03354-4. [PMID: 7697754] - M Bouchard, C Viau. Benzo(a)pyrenediolepoxide-hemoglobin adducts and 3-hydroxy-benzo(a)pyrene urinary excretion profiles in rats subchronically exposed to benzo(a)pyrene.
Archives of toxicology.
1995; 69(8):540-6. doi:
10.1007/s002040050209. [PMID: 8534197] - B W Day, P L Skipper, J Zaia, K Singh, S R Tannenbaum. Enantiospecificity of covalent adduct formation by benzo[a]pyrene anti-diol epoxide with human serum albumin.
Chemical research in toxicology.
1994 Nov; 7(6):829-35. doi:
10.1021/tx00042a017. [PMID: 7696539] - S Tas, J P Buchet, R Lauwerys. Determinants of benzo[a]pyrene diol epoxide adducts to albumin in workers exposed to polycyclic aromatic hydrocarbons.
International archives of occupational and environmental health.
1994; 66(5):343-8. doi:
10.1007/bf00378368. [PMID: 7896420] - J D Kelly, M Dutchuk, N Takahashi, A Reddy, J D Hendricks, D E Williams. Covalent binding of (+) 7S-trans-7,8-dihydrobenzo [a]pyrene-7,8-diol to trout DNA: P-450- and peroxidation-dependent pathways.
Cancer letters.
1993 Oct; 74(1-2):111-7. doi:
10.1016/0304-3835(93)90052-b. [PMID: 8287364] - T Iizasa, S Momiki, B Bauer, J Caamano, R Metcalf, J Lechner, C C Harris, A J Klein-Szanto. Invasive tumors derived from xenotransplanted, immortalized human cells after in vivo exposure to chemical carcinogens.
Carcinogenesis.
1993 Sep; 14(9):1789-94. doi:
10.1093/carcin/14.9.1789. [PMID: 8403201] - P G Shields, E D Bowman, A M Harrington, V T Doan, A Weston. Polycyclic aromatic hydrocarbon-DNA adducts in human lung and cancer susceptibility genes.
Cancer research.
1993 Aug; 53(15):3486-92. doi:
. [PMID: 8339251] - A Weston, E D Bowman, P G Shields, G E Trivers, M C Poirier, R M Santella, D K Manchester. Detection of polycyclic aromatic hydrocarbon-DNA adducts in human lung.
Environmental health perspectives.
1993 Mar; 99(?):257-9. doi:
10.1289/ehp.9399257. [PMID: 8319638] - C Viau, M Mercier, O Blondin. Measurement of hemoglobin and albumin adducts of benzo(a)pyrenediolepoxide and their rate of elimination in the female Sprague-Dawley rat.
Archives of toxicology.
1993; 67(7):468-72. doi:
10.1007/bf01969917. [PMID: 8239995] - W Baer-Dubowska, A Kulińska, M Jarmuz, D Brauze, J Gnojkowski. DNA adducts detected by synchronous fluorescence spectrophotometry in rat liver, kidney, lung and spleen after intraperitoneal administration of benzo[a]pyrene.
Acta biochimica Polonica.
1993; 40(1):63-5. doi:
10.18388/abp.1993_4847. [PMID: 8372569] - K Vähäkangas, L Pyy, E Yrjänheikki. Assessment of PAH-exposure among coke oven workers.
Pharmacogenetics.
1992 Dec; 2(6):304-8. doi:
10.1097/00008571-199212000-00009. [PMID: 1306131] - D Yang, C Louden, D S Reinhold, S K Kohler, V M Maher, J J McCormick. Malignant transformation of human fibroblast cell strain MSU-1.1 by (+-)-7 beta,8 alpha-dihydroxy-9 alpha,10 alpha-epoxy-7,8,9,10-tetrahydrobenzo [a]pyrene.
Proceedings of the National Academy of Sciences of the United States of America.
1992 Mar; 89(6):2237-41. doi:
10.1073/pnas.89.6.2237. [PMID: 1549589] - G Y Kwei, J Zaleski, S E Irwin, R G Thurman, F C Kauffman. Conjugation of benzo(a)pyrene 7,8-dihydrodiol-9,10-epoxide in infant Swiss-Webster mice.
Cancer research.
1992 Mar; 52(6):1639-42. doi:
NULL. [PMID: 1540972] - B Y Wong, B H Lau, R W Teel. Chinese medicinal herbs modulate mutagenesis, DNA binding and metabolism of benzo[a]pyrene 7,8-dihydrodiol and benzo[a]pyrene 7,8-dihydrodiol-9,10-epoxide.
Cancer letters.
1992 Feb; 62(2):123-31. doi:
10.1016/0304-3835(92)90182-u. [PMID: 1540939] - B W Day, M M Doxtader, R H Rich, P L Skipper, K Singh, R R Dasari, S R Tannenbaum. Human serum albumin-benzo[a]pyrene anti-diol epoxide adduct structure elucidation by fluorescence line narrowing spectroscopy.
Chemical research in toxicology.
1992 Jan; 5(1):71-6. doi:
10.1021/tx00025a012. [PMID: 1581540] - A N Tischler, G A Levine, J C Bartley. Metabolism of benzo[a]pyrene and benzo[a]pyrene-7,8-dihydrodiol in human mammary epithelial cells: feedback inhibition by 7-hydroxybenzo[a]pyrene.
Carcinogenesis.
1991 Sep; 12(9):1539-43. doi:
10.1093/carcin/12.9.1539. [PMID: 1909936] - D Brauze, R Mikstacka, W Baer-Dubowska. Formation and persistence of benzo[a]pyrene--DNA adducts in different tissues of C57BL/10 and DBA/2 mice.
Carcinogenesis.
1991 Sep; 12(9):1607-11. doi:
10.1093/carcin/12.9.1607. [PMID: 1909937] - B Yuan, J L Wong. Inactivity of acrylonitrile epoxide to modify a Ha-ras DNA in a non-focus transfection-transformation assay.
Carcinogenesis.
1991 May; 12(5):787-91. doi:
10.1093/carcin/12.5.787. [PMID: 1903090]
