Benzo(a)pyrene-7,8-dihydrodiol (BioDeep_00001875413)

Main id: BioDeep_00000010187

 


代谢物信息卡片


Benzo(a)pyrene-7,8-dihydrodiol

化学式: C20H14O2 (286.0994)
中文名称:
谱图信息: 最多检出来源 Viridiplantae(plant) 46.15%

分子结构信息

SMILES: C1=CC2=C3C(=C1)C=CC4=C3C(=CC5=C4C=CC(C5O)O)C=C2
InChI: InChI=1S/C20H14O2/c21-17-9-8-14-15-7-6-12-3-1-2-11-4-5-13(19(15)18(11)12)10-16(14)20(17)22/h1-10,17,20-22H



数据库引用编号

8 个数据库交叉引用编号

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。

亚细胞结构定位 关联基因列表
Cytoplasm 12 AHRR, ALB, ANXA5, BCL2, CAT, CYP1A1, CYP2S1, GSTP1, HPGDS, HPRT1, PTK2B, RAD51
Peripheral membrane protein 4 ANXA5, CYP1A1, CYP1B1, CYP2S1
Endoplasmic reticulum membrane 8 BCL2, CYP1A1, CYP1A2, CYP1B1, CYP2S1, NRAS, UGT1A1, UGT1A7
Nucleus 7 AHRR, ALB, BCL2, GSTP1, MPO, PTK2B, RAD51
cytosol 11 AHRR, ALB, ANXA5, BCL2, CAT, GSTP1, HPGDS, HPRT1, NRAS, PTK2B, RAD51
dendrite 1 PTK2B
centrosome 2 ALB, RAD51
nucleoplasm 4 AHRR, HPGDS, MPO, RAD51
Cell membrane 1 NRAS
Lipid-anchor 1 NRAS
Cytoplasmic side 1 NRAS
lamellipodium 1 PTK2B
Multi-pass membrane protein 1 SLC45A2
Golgi apparatus membrane 1 NRAS
cell cortex 1 PTK2B
glutamatergic synapse 1 PTK2B
Golgi apparatus 2 ALB, NRAS
Golgi membrane 1 NRAS
growth cone 1 PTK2B
mitochondrial inner membrane 1 CYP1A1
neuronal cell body 1 PTK2B
sarcolemma 1 ANXA5
Lysosome 1 MPO
Presynapse 1 PTK2B
plasma membrane 3 NRAS, PTK2B, UGT1A1
Membrane 9 ANXA5, BCL2, CAT, CYP1B1, CYP2S1, NRAS, SLC45A2, UGT1A1, UGT1A7
extracellular exosome 7 ALB, ANXA5, CAT, GSTP1, HPRT1, MPO, NRAS
endoplasmic reticulum 5 ALB, BCL2, CYP2S1, UGT1A1, UGT1A7
extracellular space 4 ALB, GSTP1, IGFBP4, MPO
perinuclear region of cytoplasm 3 PTK2B, RAD51, UGT1A1
Schaffer collateral - CA1 synapse 1 PTK2B
mitochondrion 6 BCL2, CAT, CYP1A1, CYP1B1, GSTP1, RAD51
protein-containing complex 4 ALB, BCL2, CAT, RAD51
intracellular membrane-bounded organelle 7 CAT, CYP1A1, CYP1A2, CYP1B1, CYP2S1, HPGDS, MPO
Microsome membrane 4 CYP1A1, CYP1A2, CYP1B1, CYP2S1
postsynaptic density 1 PTK2B
Secreted 1 ALB
extracellular region 6 ALB, ANXA5, CAT, GSTP1, IGFBP4, MPO
Mitochondrion outer membrane 1 BCL2
Single-pass membrane protein 3 BCL2, UGT1A1, UGT1A7
mitochondrial outer membrane 1 BCL2
Mitochondrion matrix 1 RAD51
mitochondrial matrix 2 CAT, RAD51
anchoring junction 1 ALB
Cytoplasm, cytoskeleton, microtubule organizing center, centrosome 1 RAD51
Nucleus membrane 1 BCL2
Bcl-2 family protein complex 1 BCL2
nuclear membrane 1 BCL2
external side of plasma membrane 1 ANXA5
dendritic spine 1 PTK2B
nucleolus 1 RAD51
Melanosome membrane 1 SLC45A2
vesicle 1 GSTP1
Cytoplasm, perinuclear region 1 UGT1A1
Mitochondrion inner membrane 1 CYP1A1
pore complex 1 BCL2
focal adhesion 3 ANXA5, CAT, PTK2B
Peroxisome 1 CAT
Peroxisome matrix 1 CAT
peroxisomal matrix 1 CAT
peroxisomal membrane 1 CAT
PML body 1 RAD51
collagen-containing extracellular matrix 1 ANXA5
secretory granule 1 MPO
Zymogen granule membrane 1 ANXA5
ciliary basal body 1 ALB
chromatin 2 AHRR, RAD51
Chromosome 1 RAD51
cytoskeleton 1 PTK2B
centriole 1 ALB
spindle pole 1 ALB
chromosome, telomeric region 1 RAD51
nuclear chromosome 1 RAD51
blood microparticle 1 ALB
postsynaptic density, intracellular component 1 PTK2B
site of double-strand break 1 RAD51
lateral element 1 RAD51
aryl hydrocarbon receptor complex 1 AHRR
tertiary granule membrane 1 NRAS
cell body 1 PTK2B
myelin sheath 1 BCL2
azurophil granule 1 MPO
ficolin-1-rich granule lumen 2 CAT, GSTP1
secretory granule lumen 2 CAT, GSTP1
endoplasmic reticulum lumen 2 ALB, IGFBP4
male germ cell nucleus 1 RAD51
platelet alpha granule lumen 1 ALB
azurophil granule lumen 1 MPO
condensed nuclear chromosome 1 RAD51
vesicle membrane 1 ANXA5
phagocytic vesicle lumen 1 MPO
NMDA selective glutamate receptor complex 1 PTK2B
apical dendrite 1 PTK2B
condensed chromosome 1 RAD51
catalase complex 1 CAT
presynaptic intermediate filament cytoskeleton 1 RAD51
endoplasmic reticulum chaperone complex 1 UGT1A1
endothelial microparticle 1 ANXA5
TRAF2-GSTP1 complex 1 GSTP1
BAD-BCL-2 complex 1 BCL2
cytochrome complex 1 UGT1A1
nuclear ubiquitin ligase complex 1 RAD51
ciliary transition fiber 1 ALB


文献列表

  • 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]
  • 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]
  • Ryan T Bushey, Gang Chen, Andrea S Blevins-Primeau, Jacek Krzeminski, Shantu Amin, Philip Lazarus. Characterization of UDP-glucuronosyltransferase 2A1 (UGT2A1) variants and their potential role in tobacco carcinogenesis. Pharmacogenetics and genomics. 2011 Feb; 21(2):55-65. doi: 10.1097/fpc.0b013e328341db05. [PMID: 21164388]
  • 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]
  • Peter H Bui, Erin L Hsu, Oliver Hankinson. Fatty acid hydroperoxides support cytochrome P450 2S1-mediated bioactivation of benzo[a]pyrene-7,8-dihydrodiol. Molecular pharmacology. 2009 Nov; 76(5):1044-52. doi: 10.1124/mol.109.057760. [PMID: 19713357]
  • 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]
  • 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]
  • 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]
  • 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]
  • Dieter Schwarz, Pyotr Kisselev, Ivar Roots. St. John's wort extracts and some of their constituents potently inhibit ultimate carcinogen formation from benzo[a]pyrene-7,8-dihydrodiol by human CYP1A1. Cancer research. 2003 Nov; 63(22):8062-8. doi: . [PMID: 14633740]
  • 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]
  • R Edenharder, H Krieg, V Köttgen, K L Platt. Inhibition of clastogenicity of benzo[a]pyrene and of its trans-7,8-dihydrodiol in mice in vivo by fruits, vegetables, and flavonoids. Mutation research. 2003 Jun; 537(2):169-81. doi: 10.1016/s1383-5718(03)00078-0. [PMID: 12787821]
  • 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]
  • 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]
  • A J Likhachev, D Sh Beniashvili, V J Bykov, P P Dikun, M L Tyndyk, I V Savochkina, V B Yermilov, M A Zabezhinski. Biomarkers for individual susceptibility to carcinogenic agents: excretion and carcinogenic risk of benzo[a]pyrene metabolites. Environmental health perspectives. 1992 Nov; 98(?):211-4. doi: 10.1289/ehp.9298211. [PMID: 1336725]
  • J Z Byczkowski, A P Kulkarni. Vanadium redox cycling, lipid peroxidation and co-oxygenation of benzo(a)pyrene-7,8-dihydrodiol. Biochimica et biophysica acta. 1992 Apr; 1125(2):134-41. doi: 10.1016/0005-2760(92)90037-v. [PMID: 1315157]
  • 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]
  • M A Zabezhinskiĭ, P P Dikun, I V Savochkina, M L Tyndyk, V N Filatov, A Ia Likhachev. [A comparative study of the individual characteristics of the excretion of metabolites of benzo(a)pyrene and its carcinogenic effect in rats]. Voprosy onkologii. 1992; 38(8):950-6. doi: NULL. [PMID: 1300805]
  • 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]
  • L J Marnett. Peroxyl free radicals: biological reactive intermediates produced during lipid oxidation. Advances in experimental medicine and biology. 1991; 283(?):65-70. doi: 10.1007/978-1-4684-5877-0_6. [PMID: 2069034]
  • W R Brian, M A Sari, M Iwasaki, T Shimada, L S Kaminsky, F P Guengerich. Catalytic activities of human liver cytochrome P-450 IIIA4 expressed in Saccharomyces cerevisiae. Biochemistry. 1990 Dec; 29(51):11280-92. doi: 10.1021/bi00503a018. [PMID: 2271712]
  • G Y Kwei, L F Bjeldanes. Stimulation of binding of benzo[a]pyrene metabolites to DNA by diet-induced peroxidative stress. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 1990 Jul; 28(7):491-5. doi: 10.1016/0278-6915(90)90119-8. [PMID: 2210521]
  • I V Savochkina, P P Dikun, M A Zabezhinskiĭ, V A Iamshanov, A Ia Likhachev. [The individual characteristics of the excretion of benzo(a)pyrene metabolites in rats]. Voprosy onkologii. 1990; 36(10):1221-6. doi: NULL. [PMID: 2251818]
  • J Z Byczkowski, A P Kulkarni. Lipid peroxidation-coupled co-oxygenation of benzo(a)pyrene and benzo(a)pyrene-7,8-dihydrodiol in human term placental microsomes. Placenta. 1990 Jan; 11(1):17-26. doi: 10.1016/s0143-4004(05)80439-4. [PMID: 2326234]
  • M F Hughes, W Chamulitrat, R P Mason, T E Eling. Epoxidation of 7,8-dihydroxy-7,8-dihydrobenzo[a]pyrene via a hydroperoxide-dependent mechanism catalyzed by lipoxygenases. Carcinogenesis. 1989 Nov; 10(11):2075-80. doi: 10.1093/carcin/10.11.2075. [PMID: 2553290]
  • A Sevanian, H Peterson. Induction of cytotoxicity and mutagenesis is facilitated by fatty acid hydroperoxidase activity in Chinese hamster lung fibroblasts (V79 cells). Mutation research. 1989 Oct; 224(2):185-96. doi: 10.1016/0165-1218(89)90155-9. [PMID: 2552309]
  • S S Ball, M S Neshat, M R Mickey, R L Walford. DNA damage and repair in female C57BL/10 mice of different ages injected with the carcinogen benzo[a]pyrene-trans-7,8-diol. Mutation research. 1989 Jul; 219(4):241-6. doi: 10.1016/0921-8734(89)90006-4. [PMID: 2770771]
  • R Labeque, L J Marnett. Reaction of hematin with allylic fatty acid hydroperoxides: identification of products and implications for pathways of hydroperoxide-dependent epoxidation of 7,8-dihydroxy-7,8-dihydrobenzo[a]pyrene. Biochemistry. 1988 Sep; 27(18):7060-70. doi: 10.1021/bi00418a059. [PMID: 3196701]
  • M Uziel, R Haglund. Persistence of benzo[a]pyrene and 7,8-dihydro-7,8-dihydroxybenzo[a] pyrene in Fischer 344 rats: time distribution of total metabolites in blood, urine and feces. Carcinogenesis. 1988 Feb; 9(2):233-8. doi: 10.1093/carcin/9.2.233. [PMID: 3338106]
  • J D Gower, E D Wills. The oxidation of benzo[a]pyrene-7,8-dihydrodiol mediated by lipid peroxidation in the rat intestine and the effect of dietary lipids. Chemico-biological interactions. 1987; 63(1):63-74. doi: 10.1016/0009-2797(87)90105-0. [PMID: 3652285]
  • T Eling, J Curtis, J Battista, L J Marnett. Oxidation of (+)-7,8-dihydroxy-7,8-dihydrobenzo[a]pyrene by mouse keratinocytes: evidence for peroxyl radical- and monoxygenase-dependent metabolism. Carcinogenesis. 1986 Dec; 7(12):1957-63. doi: 10.1093/carcin/7.12.1957. [PMID: 2430728]
  • G M Shah, R K Bhattacharya. Modulation by plant flavonoids and related phenolics of microsome catalyzed adduct formation between benzo[a]pyrene and DNA. Chemico-biological interactions. 1986 Jul; 59(1):1-15. doi: 10.1016/s0009-2797(86)80051-5. [PMID: 3757143]
  • T E Smithgall, T M Penning. Inhibition of trans-dihydrodiol oxidation by the non-steroidal anti-inflammatory drugs. Carcinogenesis. 1986 Apr; 7(4):583-8. doi: 10.1093/carcin/7.4.583. [PMID: 3457649]
  • R W Teel, M S Babcock, R Dixit, G D Stoner. Ellagic acid toxicity and interaction with benzo[a]pyrene and benzo[a]pyrene 7,8-dihydrodiol in human bronchial epithelial cells. Cell biology and toxicology. 1986 Mar; 2(1):53-62. doi: 10.1007/bf00117707. [PMID: 3267445]
  • E Hietanen, C Malaveille, A M Camus, J C Béréziat, G Brun, M Castegnaro, J Michelon, J R Idle, H Bartsch. Interstrain comparison of hepatic and renal microsomal carcinogen metabolism and liver S9-mediated mutagenicity in DA and Lewis rats phenotyped as poor and extensive metabolizers of debrisoquine. Drug metabolism and disposition: the biological fate of chemicals. 1986 Jan; 14(1):118-26. doi: . [PMID: 2868854]
  • R Dixit, R W Teel, F B Daniel, G D Stoner. Inhibition of benzo(a)pyrene and benzo(a)pyrene-trans-7,8-diol metabolism and DNA binding in mouse lung explants by ellagic acid. Cancer research. 1985 Jul; 45(7):2951-6. doi: ". [PMID: 4039974]
  • T A Dix, R Fontana, A Panthani, L J Marnett. Hematin-catalyzed epoxidation of 7,8-dihydroxy-7,8-dihydrobenzo[a]pyrene by polyunsaturated fatty acid hydroperoxides. The Journal of biological chemistry. 1985 May; 260(9):5358-65. doi: . [PMID: 4039321]
  • T A Dix, L J Marnett. Detection of the metabolism of polycyclic aromatic hydrocarbon derivatives to ultimate carcinogens during lipid peroxidation. Methods in enzymology. 1984; 105(?):347-52. doi: 10.1016/s0076-6879(84)05046-1. [PMID: 6539415]
  • M B Roberfroid, C Malaveille, A Hautefeuille, G Brun, T K Vo, H Bartsch. Interrelationships in mice of antipyrine half-life, hepatic monooxygenase activities and liver S9-mediated mutagenicity of aflatoxin B1, benzo[alpha]pyrene 7,8-dihydrodiol, 2-acetylaminofluorene and N-nitrosomorpholine. Chemico-biological interactions. 1983 Nov; 47(2):175-94. doi: 10.1016/0009-2797(83)90156-4. [PMID: 6418395]
  • T A Dix, L J Marnett. Metabolism of polycyclic aromatic hydrocarbon derivatives to ultimate carcinogens during lipid peroxidation. Science (New York, N.Y.). 1983 Jul; 221(4605):77-9. doi: 10.1126/science.6304879. [PMID: 6304879]
  • B Lambert, I Berndtsson, J Lindsten, M Nordenskjöld, S Söderhäll, B Holmstedt, L Palmèr, B Jernström, L Marsk. Smoking and sister chromatid exchange. Progress in clinical and biological research. 1982; 109(?):401-14. doi: NULL. [PMID: 6891965]
  • H P Shu, A V Nichols. Uptake of lipophilic carcinogens by plasma lipoproteins. Structure-activity studies. Biochimica et biophysica acta. 1981 Sep; 665(3):376-84. doi: 10.1016/0005-2760(81)90249-6. [PMID: 6271227]
  • K Sivarajah, J M Lasker, T E Eling. Prostaglandin synthetase-dependent cooxidation of (+/-)-benzo(a)pyrene-7,8-dihydrodiol by human lung and other mammalian tissues. Cancer research. 1981 May; 41(5):1834-9. doi: NULL. [PMID: 6783301]
  • L J Marnett, M J Bienkowski. Hydroperoxide-dependent oxygenation of trans-7,8-dihydroxy-7,8-dihydro benzo[a]pyrene by ram seminal vesicle microsomes. Source of the oxygen. Biochemical and biophysical research communications. 1980 Sep; 96(2):639-47. doi: 10.1016/0006-291x(80)91403-5. [PMID: 7191704]