3,3',4,4'-Tetrachlorobiphenyl (BioDeep_00000008468)

 

Secondary id: BioDeep_00001873780

human metabolite blood metabolite Industrial Pollutants


代谢物信息卡片


3,4,3,4-Tetra coplanar polychlorinated biphenyl

化学式: C12H6Cl4 (289.9224)
中文名称: 3,3,4,4-四氯联苯
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C1=CC(=C(C=C1C2=CC(=C(C=C2)Cl)Cl)Cl)Cl
InChI: InChI=1S/C12H6Cl4/c13-9-3-1-7(5-11(9)15)8-2-4-10(14)12(16)6-8/h1-6H



数据库引用编号

12 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)

1 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 11 AHR, AHRR, ALB, ARNT, CAT, CYP1A1, CYP2B6, CYP2E1, HPGDS, NPPA, NQO1
Peripheral membrane protein 4 CYP1A1, CYP1B1, CYP2B6, CYP2E1
Endoplasmic reticulum membrane 7 CD4, CYP1A1, CYP1A2, CYP1B1, CYP2B6, CYP2E1, HSP90B1
Nucleus 6 AHR, AHRR, ALB, ARNT, HSP90B1, NQO1
cytosol 9 AHR, AHRR, ALB, CAT, GSR, HPGDS, HSP90B1, NQO1, UROD
dendrite 1 NQO1
nuclear body 1 ARNT
centrosome 1 ALB
nucleoplasm 5 AHR, AHRR, ARNT, HPGDS, UROD
RNA polymerase II transcription regulator complex 1 ARNT
Cell membrane 2 CD4, CD8A
Multi-pass membrane protein 1 SLC45A2
Synapse 1 NQO1
Golgi apparatus 1 ALB
mitochondrial inner membrane 2 CYP1A1, CYP2E1
neuronal cell body 1 NQO1
smooth endoplasmic reticulum 1 HSP90B1
Cytoplasm, cytosol 1 NQO1
plasma membrane 2 CD4, CD8A
Membrane 5 CAT, CYP1B1, HSP90B1, NQO1, SLC45A2
extracellular exosome 5 ALB, CAT, GSR, HSP90B1, TTR
endoplasmic reticulum 2 ALB, HSP90B1
extracellular space 3 ALB, NPPA, TTR
perinuclear region of cytoplasm 1 HSP90B1
mitochondrion 4 CAT, CYP1A1, CYP1B1, GSR
protein-containing complex 5 AHR, ALB, CAT, HSP90B1, NPPA
intracellular membrane-bounded organelle 7 CAT, CYP1A1, CYP1A2, CYP1B1, CYP2B6, CYP2E1, HPGDS
Microsome membrane 5 CYP1A1, CYP1A2, CYP1B1, CYP2B6, CYP2E1
Single-pass type I membrane protein 2 CD4, CD8A
Secreted 3 ALB, NPPA, TTR
extracellular region 6 ALB, CAT, CD8A, HSP90B1, NPPA, TTR
[Isoform 2]: Secreted 1 CD8A
mitochondrial matrix 2 CAT, GSR
anchoring junction 1 ALB
transcription regulator complex 2 AHR, ARNT
external side of plasma membrane 3 CD4, CD8A, GSR
perikaryon 1 NPPA
Melanosome membrane 1 SLC45A2
midbody 1 HSP90B1
Early endosome 1 CD4
Mitochondrion inner membrane 2 CYP1A1, CYP2E1
Membrane raft 1 CD4
focal adhesion 2 CAT, HSP90B1
Peroxisome 1 CAT
Peroxisome matrix 1 CAT
peroxisomal matrix 1 CAT
peroxisomal membrane 1 CAT
collagen-containing extracellular matrix 2 HSP90B1, NPPA
receptor complex 1 CD8A
ciliary basal body 1 ALB
chromatin 3 AHR, AHRR, ARNT
cell projection 1 NPPA
centriole 1 ALB
spindle pole 1 ALB
blood microparticle 1 ALB
aryl hydrocarbon receptor complex 3 AHR, AHRR, ARNT
Melanosome 1 HSP90B1
sperm plasma membrane 1 HSP90B1
plasma membrane raft 1 CD8A
ficolin-1-rich granule lumen 1 CAT
secretory granule lumen 1 CAT
endoplasmic reticulum lumen 3 ALB, CD4, HSP90B1
platelet alpha granule lumen 1 ALB
azurophil granule lumen 1 TTR
clathrin-coated endocytic vesicle membrane 1 CD4
Sarcoplasmic reticulum lumen 1 HSP90B1
[Isoform 1]: Cell membrane 1 CD8A
endocytic vesicle lumen 1 HSP90B1
[Long-acting natriuretic peptide]: Secreted 1 NPPA
[Vessel dilator]: Secreted 1 NPPA
[Kaliuretic peptide]: Secreted 1 NPPA
[Urodilatin]: Secreted 1 NPPA
[Atrial natriuretic peptide]: Secreted 1 NPPA
[Atriopeptin-3]: Secreted 1 NPPA
T cell receptor complex 2 CD4, CD8A
catalase complex 1 CAT
endoplasmic reticulum chaperone complex 1 HSP90B1
nuclear aryl hydrocarbon receptor complex 2 AHR, ARNT
cytosolic aryl hydrocarbon receptor complex 1 AHR
ciliary transition fiber 1 ALB


文献列表

  • Qing Huang, Cao Fang. Degradation of 3,3',4,4'-tetrachlorobiphenyl (PCB77) by dielectric barrier discharge (DBD) non-thermal plasma: Degradation mechanism and toxicity evaluation. The Science of the total environment. 2020 Oct; 739(?):139926. doi: 10.1016/j.scitotenv.2020.139926. [PMID: 32540661]
  • Md Saydur Rahman, Richard J Kline, Omar A Vázquez, Izhar A Khan, Peter Thomas. Molecular characterization and expression of arginine vasotocin V1a2 receptor in Atlantic croaker brain: Potential mechanisms of its downregulation by PCB77. Journal of biochemical and molecular toxicology. 2020 Jul; 34(7):e22500. doi: 10.1002/jbt.22500. [PMID: 32220049]
  • Meriem Koual, German Cano-Sancho, Anne-Sophie Bats, Céline Tomkiewicz, Yael Kaddouch-Amar, Nathalie Douay-Hauser, Charlotte Ngo, Hélène Bonsang, Myriam Deloménie, Fabrice Lecuru, Bruno Le Bizec, Philippe Marchand, Jeremie Botton, Robert Barouki, Jean-Philippe Antignac, Xavier Coumoul. Associations between persistent organic pollutants and risk of breast cancer metastasis. Environment international. 2019 11; 132(?):105028. doi: 10.1016/j.envint.2019.105028. [PMID: 31382183]
  • Yulang Chi, Hongou Wang, Yi Lin, Yanyang Lu, Qiansheng Huang, Guozhu Ye, Sijun Dong. Gut microbiota characterization and lipid metabolism disorder found in PCB77-treated female mice. Toxicology. 2019 05; 420(?):11-20. doi: 10.1016/j.tox.2019.03.011. [PMID: 30935970]
  • Chen Tu, Luyao Ma, Pengpeng Guo, Fang Song, Ying Teng, Haibo Zhang, Yongming Luo. Rhizoremediation of a dioxin-like PCB polluted soil by alfalfa: Dynamic characterization at temporal and spatial scale. Chemosphere. 2017 Dec; 189(?):517-524. doi: 10.1016/j.chemosphere.2017.09.091. [PMID: 28961537]
  • N Ramanujam, M Sivaselvakumar, S Ramalingam. Fast and parallel determination of PCB 77 and PCB 180 in plasma using ultra performance liquid chromatography with diode array detection: A pharmacokinetic study in Swiss albino mouse. Biomedical chromatography : BMC. 2017 Nov; 31(11):. doi: 10.1002/bmc.4000. [PMID: 28485018]
  • Ke Su, Xifeng Lv, Hui Song, Xuesong Luo, Cheng Chen. PCB77 Inducing Renal Tubular Cell Apoptosis. Ultrastructural pathology. 2015 May; 39(3):192-7. doi: 10.3109/01913123.2014.973130. [PMID: 25347139]
  • Hongtao Shang, Yingming Li, Thanh Wang, Pu Wang, Haidong Zhang, Qinghua Zhang, Guibin Jiang. The presence of polychlorinated biphenyls in yellow pigment products in China with emphasis on 3,3'-dichlorobiphenyl (PCB 11). Chemosphere. 2014 Mar; 98(?):44-50. doi: 10.1016/j.chemosphere.2013.09.075. [PMID: 24231041]
  • Yoshihisa Kato, Koichi Haraguchi, Mao Onishi, Shinichi Ikushiro, Tetsuya Endo, Chiho Ohta, Nobuyuki Koga, Shizuo Yamada, Masakuni Degawa. 3,3',4,4'-Tetrachlorobiphenyl-mediated decrease of serum thyroxine level in C57BL/6 and DBA/2 mice occurs mainly through enhanced accumulation of thyroxine in the liver. Biological & pharmaceutical bulletin. 2014; 37(3):504-9. doi: 10.1248/bpb.b13-00775. [PMID: 24351552]
  • Lei Wang, Shuping Zhang, Ronghai Lin, Long Li, Daoqiang Zhang, Xinghong Li, Sijin Liu. PCB-77 disturbs iron homeostasis through regulating hepcidin gene expression. Gene. 2013 Dec; 532(1):146-51. doi: 10.1016/j.gene.2013.09.023. [PMID: 24055725]
  • Nicki A Baker, Victoria English, Manjula Sunkara, Andrew J Morris, Kevin J Pearson, Lisa A Cassis. Resveratrol protects against polychlorinated biphenyl-mediated impairment of glucose homeostasis in adipocytes. The Journal of nutritional biochemistry. 2013 Dec; 24(12):2168-74. doi: 10.1016/j.jnutbio.2013.08.009. [PMID: 24231106]
  • Nicki A Baker, Michael Karounos, Victoria English, Jun Fang, Yinan Wei, Arnold Stromberg, Manjula Sunkara, Andrew J Morris, Hollie I Swanson, Lisa A Cassis. Coplanar polychlorinated biphenyls impair glucose homeostasis in lean C57BL/6 mice and mitigate beneficial effects of weight loss on glucose homeostasis in obese mice. Environmental health perspectives. 2013 Jan; 121(1):105-10. doi: 10.1289/ehp.1205421. [PMID: 23099484]
  • Fadheela Al-Salman, Nick Plant. Non-coplanar polychlorinated biphenyls (PCBs) are direct agonists for the human pregnane-X receptor and constitutive androstane receptor, and activate target gene expression in a tissue-specific manner. Toxicology and applied pharmacology. 2012 Aug; 263(1):7-13. doi: 10.1016/j.taap.2012.05.016. [PMID: 22664347]
  • Rance Nault, Samar Al-Hameedi, Thomas W Moon. Effects of polychlorinated biphenyls on whole animal energy mobilization and hepatic cellular respiration in rainbow trout, Oncorhynchus mykiss. Chemosphere. 2012 May; 87(9):1057-62. doi: 10.1016/j.chemosphere.2012.02.012. [PMID: 22410624]
  • Périne Doyen, François Rodius, Lionel L'hoste, Lucien Hoffmann, Henry-Michel Cauchie. Identification and mRNA expression of pi-class glutathione S-transferase and selenium-dependent glutathione peroxidase in the gudgeon Gobio gobio exposed to PCB 77. Comparative biochemistry and physiology. Toxicology & pharmacology : CBP. 2012 Mar; 155(2):300-6. doi: 10.1016/j.cbpc.2011.09.009. [PMID: 21983335]
  • Guangshu Zhai, Hans-Joachim Lehmler, Jerald L Schnoor. New hydroxylated metabolites of 4-monochlorobiphenyl in whole poplar plants. Chemistry Central journal. 2011 Dec; 5(?):87. doi: 10.1186/1752-153x-5-87. [PMID: 22185578]
  • Violeta Arsenescu, Razvan Arsenescu, Madhura Parulkar, Michael Karounos, Xuan Zhang, Nicki Baker, Lisa A Cassis. Polychlorinated biphenyl 77 augments angiotensin II-induced atherosclerosis and abdominal aortic aneurysms in male apolipoprotein E deficient mice. Toxicology and applied pharmacology. 2011 Nov; 257(1):148-54. doi: 10.1016/j.taap.2011.08.028. [PMID: 21925196]
  • Michel Aubé, Christian Larochelle, Pierre Ayotte. Differential effects of a complex organochlorine mixture on the proliferation of breast cancer cell lines. Environmental research. 2011 Apr; 111(3):337-47. doi: 10.1016/j.envres.2011.01.010. [PMID: 21295777]
  • Somiranjan Ghosh, Supriyo De, Yongqing Chen, Darryl C Sutton, Folahan O Ayorinde, Sisir K Dutta. Polychlorinated biphenyls (PCB-153) and (PCB-77) absorption in human liver (HepG2) and kidney (HK2) cells in vitro: PCB levels and cell death. Environment international. 2010 Nov; 36(8):893-900. doi: 10.1016/j.envint.2010.06.010. [PMID: 20723988]
  • R J Jandacek, T Rider, E R Keller, P Tso. The effect of olestra on the absorption, excretion and storage of 2,2',5,5' tetrachlorobiphenyl; 3,3',4,4' tetrachlorobiphenyl; and perfluorooctanoic acid. Environment international. 2010 Nov; 36(8):880-3. doi: 10.1016/j.envint.2009.06.010. [PMID: 19616301]
  • Hye-Youn Park, Irva Hertz-Picciotto, Eva Sovcikova, Anton Kocan, Beata Drobna, Tomas Trnovec. Neurodevelopmental toxicity of prenatal polychlorinated biphenyls (PCBs) by chemical structure and activity: a birth cohort study. Environmental health : a global access science source. 2010 Aug; 9(?):51. doi: 10.1186/1476-069x-9-51. [PMID: 20731829]
  • Jiyan Liu, Dingfei Hu, Guibin Jiang, Jerald L Schnoor. In vivo biotransformation of 3,3',4,4'-tetrachlorobiphenyl by whole plants-poplars and switchgrass. Environmental science & technology. 2009 Oct; 43(19):7503-9. doi: 10.1021/es901244h. [PMID: 19848168]
  • Xabier Arzuaga, Na Ren, Arnold Stromberg, Esther P Black, Violeta Arsenescu, Lisa A Cassis, Zuzana Majkova, Michal Toborek, Bernhard Hennig. Induction of gene pattern changes associated with dysfunctional lipid metabolism induced by dietary fat and exposure to a persistent organic pollutant. Toxicology letters. 2009 Sep; 189(2):96-101. doi: 10.1016/j.toxlet.2009.05.008. [PMID: 19467301]
  • Zuzana Majkova, Eric Smart, Michal Toborek, Bernhard Hennig. Up-regulation of endothelial monocyte chemoattractant protein-1 by coplanar PCB77 is caveolin-1-dependent. Toxicology and applied pharmacology. 2009 May; 237(1):1-7. doi: 10.1016/j.taap.2009.02.016. [PMID: 19265715]
  • Valeria Tigini, Valeria Prigione, Sara Di Toro, Fabio Fava, Giovanna C Varese. Isolation and characterisation of polychlorinated biphenyl (PCB) degrading fungi from a historically contaminated soil. Microbial cell factories. 2009 Jan; 8(?):5. doi: 10.1186/1475-2859-8-5. [PMID: 19138404]
  • Eun Jin Lim, Zuzana Májková, Shifen Xu, Leonidas Bachas, Xabier Arzuaga, Eric Smart, Michael T Tseng, Michal Toborek, Bernhard Hennig. Coplanar polychlorinated biphenyl-induced CYP1A1 is regulated through caveolae signaling in vascular endothelial cells. Chemico-biological interactions. 2008 Nov; 176(2-3):71-8. doi: 10.1016/j.cbi.2008.08.007. [PMID: 18786521]
  • Richard M Green, Nikolas J Hodges, J Kevin Chipman, Michael R O'Donovan, Mark Graham. Reactive oxygen species from the uncoupling of human cytochrome P450 1B1 may contribute to the carcinogenicity of dioxin-like polychlorinated biphenyls. Mutagenesis. 2008 Nov; 23(6):457-63. doi: 10.1093/mutage/gen035. [PMID: 18583386]
  • Violeta Arsenescu, Razvan I Arsenescu, Victoria King, Hollie Swanson, Lisa A Cassis. Polychlorinated biphenyl-77 induces adipocyte differentiation and proinflammatory adipokines and promotes obesity and atherosclerosis. Environmental health perspectives. 2008 Jun; 116(6):761-8. doi: 10.1289/ehp.10554. [PMID: 18560532]
  • Mercedes Fernández Santiago, Pilar López-Aparicio, María N Recio, Miguel A Pérez-Albarsanz. Effect of aroclor 1248 and two pure PCB congeners on phospholipase D activity in rat renal tubular cell cultures. Journal of biochemical and molecular toxicology. 2007; 21(2):68-75. doi: 10.1002/jbt.20160. [PMID: 17427178]
  • Veerle Beck, Simon A Roelens, Veerle M Darras. Exposure to PCB 77 induces tissue-dependent changes in iodothyronine deiodinase activity patterns in the embryonic chicken. General and comparative endocrinology. 2006 Sep; 148(3):327-35. doi: 10.1016/j.ygcen.2006.04.003. [PMID: 16765350]
  • Y Q Chen, S De, S Ghosh, S K Dutta. Congener-specific polychlorinated biphenyl-induced cell death in human kidney cells in vitro: potential role of caspase. International journal of toxicology. 2006 Sep; 25(5):341-7. doi: 10.1080/10915810600840859. [PMID: 16940006]
  • Mercedes Fernández Santiago, Pedro L Pérez-Reyes, Pilar López-Aparicio, María N Recio, Miguel A Pérez-Albarsanz. Differential effects of PCBs on the induction of apoptosis machinery and PKCalpha translocation in rat renal tubular cell cultures. Toxicology letters. 2006 May; 163(2):91-100. doi: 10.1016/j.toxlet.2005.09.032. [PMID: 16263226]
  • Matti T Leppänen, Jussi V K Kukkonen. Evaluating the role of desorption in bioavailability of sediment-associated contaminants using oligochaetes, semipermeable membrane devices and Tenax extraction. Environmental pollution (Barking, Essex : 1987). 2006 Mar; 140(1):150-63. doi: 10.1016/j.envpol.2005.06.010. [PMID: 16144733]
  • Simon A Roelens, Veerle Beck, Johan Maervoet, Goele Aerts, Geert E Reyns, Paul Schepens, Veerle M Darras. The dioxin-like PCB 77 but not the ortho-substituted PCB 153 interferes with chicken embryo thyroid hormone homeostasis and delays hatching. General and comparative endocrinology. 2005 Aug; 143(1):1-9. doi: 10.1016/j.ygcen.2005.02.015. [PMID: 15993099]
  • Jussi V K Kukkonen, Siddhartha Mitra, Peter F Landrum, Duane C Gossiaux, Jonas Gunnarsson, Donald Weston. The contrasting roles of sedimentary plant-derived carbon and black carbon on sediment-spiked hydrophobic organic contaminant bioavailability to Diporeia species and Lumbriculus variegatus. Environmental toxicology and chemistry. 2005 Apr; 24(4):877-85. doi: 10.1897/04-171r.1. [PMID: 15839562]
  • Johan Maervoet, Veerle Beck, Simon A Roelens, Adrian Covaci, Stefan Voorspoels, Jan M C Geuns, Veerle M Darras, Paul Schepens. Uptake and tissue-specific distribution of selected polychlorinated biphenyls in developing chicken embryos. Environmental toxicology and chemistry. 2005 Mar; 24(3):597-602. doi: 10.1897/04-266r.1. [PMID: 15779759]
  • Douglas A Donahue, Edward J Dougherty, Lee A Meserve. Influence of a combination of two tetrachlorobiphenyl congeners (PCB 47; PCB 77) on thyroid status, choline acetyltransferase (ChAT) activity, and short- and long-term memory in 30-day-old Sprague-Dawley rats. Toxicology. 2004 Oct; 203(1-3):99-107. doi: 10.1016/j.tox.2004.06.011. [PMID: 15363586]
  • Yuansheng Tan, Chang-Hwei Chen, David Lawrence, David O Carpenter. Ortho-substituted PCBs kill cells by altering membrane structure. Toxicological sciences : an official journal of the Society of Toxicology. 2004 Jul; 80(1):54-9. doi: 10.1093/toxsci/kfh119. [PMID: 15056809]
  • Ping-Chi Hsu, Yueliang Leon Guo, Mei-Hui Li. Effects of acute postnatal exposure to 3,3',4,4'-tetrachlorobiphenyl on sperm function and hormone levels in adult rats. Chemosphere. 2004 Feb; 54(5):611-8. doi: 10.1016/j.chemosphere.2003.09.006. [PMID: 14599506]
  • S Aït-Aïssa, O Ausseil, O Palluel, E Vindimian, J Garnier-Laplace, J M Porcher. Biomarker responses in juvenile rainbow trout (Oncorhynchus mykiss) after single and combined exposure to low doses of cadmium, zinc, PCB77 and 17beta-oestradiol. Biomarkers : biochemical indicators of exposure, response, and susceptibility to chemicals. 2003 Nov; 8(6):491-508. doi: 10.1080/13547500310001640037. [PMID: 15195680]
  • J V K Kukkonen, P F Landrum, S Mitra, D C Gossiaux, J Gunnarsson, D Weston. Sediment characteristics affecting desorption kinetics of select PAH and PCB congeners for seven laboratory spiked sediments. Environmental science & technology. 2003 Oct; 37(20):4656-63. doi: 10.1021/es0342594. [PMID: 14594375]
  • Zijing Lu, Job C Tharappel, Eun Y Lee, Larry W Robertson, Brett T Spear, Howard P Glauert. Effect of a single dose of polychlorinated biphenyls on hepatic cell proliferation and the DNA binding activity of NF-kappaB and AP-1 in rats. Molecular carcinogenesis. 2003 Aug; 37(4):171-80. doi: 10.1002/mc.10135. [PMID: 12891626]
  • Nilufer Tampal, Steven Myers, Larry W Robertson. Binding of polychlorinated biphenyls/metabolites to hemoglobin. Toxicology letters. 2003 Apr; 142(1-2):53-60. doi: 10.1016/s0378-4274(02)00484-8. [PMID: 12765239]
  • Tsutomu Shimada, Atsushi Sugie, Masaki Shindo, Takae Nakajima, Emiko Azuma, Masafumi Hashimoto, Kiyoshi Inoue. Tissue-specific induction of cytochromes P450 1A1 and 1B1 by polycyclic aromatic hydrocarbons and polychlorinated biphenyls in engineered C57BL/6J mice of arylhydrocarbon receptor gene. Toxicology and applied pharmacology. 2003 Feb; 187(1):1-10. doi: 10.1016/s0041-008x(02)00035-2. [PMID: 12628579]
  • A Mörck, G Larsen, E Klasson Wehler. Covalent binding of PCB metabolites to lipids: route of formation and characterization. Xenobiotica; the fate of foreign compounds in biological systems. 2002 Jul; 32(7):625-40. doi: 10.1080/00498250210130573. [PMID: 12162858]
  • Zaineb Fadhel, Zijing Lu, Larry W Robertson, Howard P Glauert. Effect of 3,3',4,4'-tetrachlorobiphenyl and 2,2',4,4',5,5'-hexachlorobiphenyl on the induction of hepatic lipid peroxidation and cytochrome P-450 associated enzyme activities in rats. Toxicology. 2002 Jun; 175(1-3):15-25. doi: 10.1016/s0300-483x(02)00086-0. [PMID: 12049832]
  • Hiroshi Fujise, Takeshi Annoura, Shigemi Sasawatari, Teruo Ikeda, Kazumitsu Ueda. Transepithelial transport and cellular accumulation of steroid hormones and polychlorobiphenyl in porcine kidney cells expressed with human P-glycoprotein. Chemosphere. 2002 Mar; 46(9-10):1505-11. doi: 10.1016/s0045-6535(01)00273-9. [PMID: 12002483]
  • G L Qiao, J E Riviere. Enhanced systemic tissue distribution after dermal versus intravenous 3,3',4,4'-tetrachlorobiphenyl exposure: limited utility of radiolabel blood area under the curve and excretion data in dermal absorption calculations and tissue exposure assessment. Toxicology and applied pharmacology. 2001 Nov; 177(1):26-37. doi: 10.1006/taap.2001.9284. [PMID: 11708897]
  • V P Palace, S M Allen-Gil, S B Brown, R E Evans, D A Metner, D H Landers, L R Curtis, J F Klaverkamp, C L Baron, W L Lockhart. Vitamin and thyroid status in arctic grayling (Thymallus arcticus) exposed to doses of 3,3',4,4'-tetrachlorobiphenyl that induce the phase I enzyme system. Chemosphere. 2001 Oct; 45(2):185-93. doi: 10.1016/s0045-6535(00)00577-4. [PMID: 11572610]
  • D Pereg, N Tampal, P Espandiari, L W Robertson. Distribution and macromolecular binding of benzo[a]pyrene and two polychlorinated biphenyl congeners in female mice. Chemico-biological interactions. 2001 Sep; 137(3):243-58. doi: 10.1016/s0009-2797(01)00256-3. [PMID: 11566292]
  • C Y Chen, J T Hamm, J R Hass, L S Birnbaum. Disposition of polychlorinated dibenzo-p-dioxins, dibenzofurans, and non-ortho polychlorinated biphenyls in pregnant long evans rats and the transfer to offspring. Toxicology and applied pharmacology. 2001 Jun; 173(2):65-88. doi: 10.1006/taap.2001.9143. [PMID: 11384209]
  • C Zaccaro, S Sweitzer, S Pipino, N Gorman, P R Sinclair, J F Sinclair, D W Nebert, F De Matteis. Role of cytochrome P450 1A2 in bilirubin degradation Studies in Cyp1a2 (-/-) mutant mice. Biochemical pharmacology. 2001 Apr; 61(7):843-9. doi: 10.1016/s0006-2952(01)00568-8. [PMID: 11274970]
  • T P Twaroski, M L O'Brien, N Larmonier, H P Glauert, L W Robertson. Polychlorinated biphenyl-induced effects on metabolic enzymes, AP-1 binding, vitamin E, and oxidative stress in the rat liver. Toxicology and applied pharmacology. 2001 Mar; 171(2):85-93. doi: 10.1006/taap.2000.9114. [PMID: 11222084]
  • M F Santiago, P López-Aparicio, M N Recio, M A Pérez-Albarsanz. Redistribution of cPLA(2) in rat renal tubular cell cultures in response to PCBs. Cellular signalling. 2001 Feb; 13(2):111-8. doi: 10.1016/s0898-6568(00)00148-0. [PMID: 11257455]
  • S E Rier, W E Turner, D C Martin, R Morris, G W Lucier, G C Clark. Serum levels of TCDD and dioxin-like chemicals in Rhesus monkeys chronically exposed to dioxin: correlation of increased serum PCB levels with endometriosis. Toxicological sciences : an official journal of the Society of Toxicology. 2001 Jan; 59(1):147-59. doi: 10.1093/toxsci/59.1.147. [PMID: 11134554]
  • B A Adams, D G Cyr, J G Eales. Thyroid hormone deiodination in tissues of American plaice, Hippoglossoides platessoides: characterization and short-term responses to polychlorinated biphenyls (PCBs) 77 and 126. Comparative biochemistry and physiology. Toxicology & pharmacology : CBP. 2000 Dec; 127(3):367-78. doi: 10.1016/s0742-8413(00)00164-x. [PMID: 11246509]
  • J J Schlezinger, J J Stegeman. Dose and inducer-dependent induction of cytochrome P450 1A in endothelia of the eel, including in the swimbladder rete mirabile, a model microvascular structure. Drug metabolism and disposition: the biological fate of chemicals. 2000 Jun; 28(6):701-8. doi: NULL. [PMID: 10820144]
  • E Sánchez, M Fernández Santiago, P López-Aparicio, M N Recio, M A Pérez-Albarsanz. Selective fatty acid release from intracellular phospholipids caused by PCBs in rat renal tubular cell cultures. Chemico-biological interactions. 2000 Mar; 125(2):117-31. doi: 10.1016/s0009-2797(00)00142-3. [PMID: 10699572]
  • E V Hestermann, J J Stegeman, M E Hahn. Serum alters the uptake and relative potencies of halogenated aromatic hydrocarbons in cell culture bioassays. Toxicological sciences : an official journal of the Society of Toxicology. 2000 Feb; 53(2):316-25. doi: 10.1093/toxsci/53.2.316. [PMID: 10696780]
  • D M Otto, C K Sen, W L Casley, T W Moon. Regulation of cytochrome P4501A metabolism by glutathione. Pharmacology & toxicology. 1999 May; 84(5):201-10. doi: 10.1111/j.1600-0773.1999.tb01484.x. [PMID: 10361976]
  • A S Faqi, P R Dalsenter, H J Merker, I Chahoud. Effects on developmental landmarks and reproductive capability of 3,3',4,4'-tetrachlorobiphenyl and 3,3',4,4',5-pentachlorobiphenyl in offspring of rats exposed during pregnancy. Human & experimental toxicology. 1998 Jul; 17(7):365-72. doi: 10.1177/096032719801700702. [PMID: 9726532]
  • A S Faqi, P R Dalsenter, W Mathar, B Heinrich-Hirsch, I Chahoud. Reproductive toxicity and tissue concentrations of 3,3',4,4'-tetrachlorobiphenyl (PCB 77) in male adult rats. Human & experimental toxicology. 1998 Mar; 17(3):151-6. doi: 10.1177/096032719801700305. [PMID: 9587783]
  • A J Warren, A E Maccubbin, J W Hamilton. Detection of mitomycin C-DNA adducts in vivo by 32P-postlabeling: time course for formation and removal of adducts and biochemical modulation. Cancer research. 1998 Feb; 58(3):453-61. doi: . [PMID: 9458089]
  • D Desaulniers, R Poon, W Phan, K Leingartner, W G Foster, I Chu. Reproductive and thyroid hormone levels in rats following 90-day dietary exposure to PCB 28 (2,4,4'-trichlorobiphenyl) or PCB 77 (3,3'4,4'-tetrachlorobiphenyl). Toxicology and industrial health. 1997 Sep; 13(5):627-38. doi: 10.1177/074823379701300504. [PMID: 9284533]
  • K Haraguchi, Y Kato, Y Masuda, R Kimura. Metabolism of 3,3',4,4'-tetrachlorobiphenyl via sulphur-containing pathway in rat: liver-specific retention of methylsulphonyl metabolite. Xenobiotica; the fate of foreign compounds in biological systems. 1997 Aug; 27(8):831-42. doi: 10.1080/004982597240190. [PMID: 9293619]
  • P R Sinclair, N Gorman, H S Walton, J F Sinclair, C A Lee, A B Rifkind. Identification of CYP1A5 as the CYP1A enzyme mainly responsible for uroporphyrinogen oxidation induced by AH receptor ligands in chicken liver and kidney. Drug metabolism and disposition: the biological fate of chemicals. 1997 Jul; 25(7):779-83. doi: . [PMID: 9224771]
  • E Monosson, R G Hogson, W J Fleming, C V Sullivan. Blood plasma levels of sex steroid hormones and vitellogenin in striped bass (Morone saxatilis) exposed to 3,3',4,4'-tetrachlorobiphenyl (TCB). Bulletin of environmental contamination and toxicology. 1996 May; 56(5):782-7. doi: 10.1007/s001289900114. [PMID: 8661862]
  • P O Darnerud, D Morse, E Klasson-Wehler, A Brouwer. Binding of a 3,3', 4,4'-tetrachlorobiphenyl (CB-77) metabolite to fetal transthyretin and effects on fetal thyroid hormone levels in mice. Toxicology. 1996 Jan; 106(1-3):105-14. doi: 10.1016/0300-483x(95)03169-g. [PMID: 8571380]
  • M Dubois, I De Waziers, J P Thome, P Kremers. P450 induction by Aroclor 1254 and 3,3',4,4'-tetrachlorobiphenyl in cultured hepatocytes from rat, quail and man: interspecies comparison. Comparative biochemistry and physiology. Part C, Pharmacology, toxicology & endocrinology. 1996 Jan; 113(1):51-9. doi: 10.1016/0742-8413(95)02037-3. [PMID: 8665401]
  • D M Otto, T W Moon. 3,3',4,4'-tetrachlorobiphenyl effects on antioxidant enzymes and glutathione status in different tissues of rainbow trout. Pharmacology & toxicology. 1995 Oct; 77(4):281-7. doi: 10.1111/j.1600-0773.1995.tb01028.x. [PMID: 8577641]
  • B W Seo, M H Li, L G Hansen, R W Moore, R E Peterson, S L Schantz. Effects of gestational and lactational exposure to coplanar polychlorinated biphenyl (PCB) congeners or 2,3,7,8-tetrachlorodibenzo-p-dioxin (TCDD) on thyroid hormone concentrations in weanling rats. Toxicology letters. 1995 Aug; 78(3):253-62. doi: 10.1016/0378-4274(95)03329-j. [PMID: 7624895]
  • I Chu, D C Villeneuve, A Yagminas, P Lecavalier, H Håkansson, U G Ahlborg, V E Valli, S W Kennedy, A Bergman, R F Seegal. Toxicity of PCB 77 (3,3',4,4'-tetrachlorobiphenyl) and PCB 118 (2,3',4,4'5-pentachlorobiphenyl) in the rat following subchronic dietary exposure. Fundamental and applied toxicology : official journal of the Society of Toxicology. 1995 Jul; 26(2):282-92. doi: 10.1006/faat.1995.1099. [PMID: 7589917]
  • D C Morse, E K Wehler, M van de Pas, A T de Bie, P J van Bladeren, A Brouwer. Metabolism and biochemical effects of 3,3',4,4'-tetrachlorobiphenyl in pregnant and fetal rats. Chemico-biological interactions. 1995 Mar; 95(1-2):41-56. doi: 10.1016/0009-2797(94)03347-1. [PMID: 7697753]
  • K MacLellan, A Singh, I Chu, D C Villeneuve. Subchronic toxicity of 3,3',4,4'-tetrachlorobiphenyl in the rat liver: an electron microscope study. Histology and histopathology. 1994 Jul; 9(3):453-9. doi: . [PMID: 7981493]
  • M K McKinley, L B Kedderis, L S Birnbaum. The effect of pretreatment on the biliary excretion of 2,3,7,8-tetrachlorodibenzo-p-dioxin, 2,3,7,8-tetrachlorodibenzofuran, and 3,3',4,4'-tetrachlorobiphenyl in the rat. Fundamental and applied toxicology : official journal of the Society of Toxicology. 1993 Nov; 21(4):425-32. doi: 10.1006/faat.1993.1118. [PMID: 8253296]
  • D C Morse, D Groen, M Veerman, C J van Amerongen, H B Koëter, A E Smits van Prooije, T J Visser, J H Koeman, A Brouwer. Interference of polychlorinated biphenyls in hepatic and brain thyroid hormone metabolism in fetal and neonatal rats. Toxicology and applied pharmacology. 1993 Sep; 122(1):27-33. doi: 10.1006/taap.1993.1168. [PMID: 8378931]
  • D Wölfle, E Becker, C Schmutte. Growth stimulation of primary rat hepatocytes by 2,3,7,8-tetrachlorodibenzo-p-dioxin. Cell biology and toxicology. 1993 Jan; 9(1):15-31. doi: 10.1007/bf00755137. [PMID: 8100183]
  • M F Hughes, S P Shrivastava, M R Sumler, B C Edwards, J H Goodwin, P V Shah, H L Fisher, L L Hall. Dermal absorption of chemicals: effect of application of chemicals as a solid, aqueous paste, suspension, or in volatile vehicle. Journal of toxicology and environmental health. 1992 Sep; 37(1):57-71. doi: 10.1080/15287399209531657. [PMID: 1522614]
  • F De Matteis, S J Dawson, A R Boobis, A Comoglio. Inducible bilirubin-degrading system of rat liver microsomes: role of cytochrome P450IA1. Molecular pharmacology. 1991 Nov; 40(5):686-91. doi: NULL. [PMID: 1944239]
  • J J Stegeman, R M Smolowitz, M E Hahn. Immunohistochemical localization of environmentally induced cytochrome P450IA1 in multiple organs of the marine teleost Stenotomus chrysops (Scup). Toxicology and applied pharmacology. 1991 Sep; 110(3):486-504. doi: 10.1016/0041-008x(91)90049-k. [PMID: 1949016]
  • R M Smolowitz, M E Hahn, J J Stegeman. Immunohistochemical localization of cytochrome P-450IA1 induced by 3,3',4,4'-tetrachlorobiphenyl and by 2,3,7,8-tetrachlorodibenzoafuran in liver and extrahepatic tissues of the teleost Stenotomus chrysops (scup). Drug metabolism and disposition: the biological fate of chemicals. 1991 Jan; 19(1):113-23. doi: . [PMID: 1708328]
  • M Mercier, G Pascal, V Azais-Braesco. Retinyl ester hydrolase and vitamin A status in rats treated with 3,3',4, 4'-tetrachlorobiphenyl. Biochimica et biophysica acta. 1990 Oct; 1047(1):70-6. doi: 10.1016/0005-2760(90)90262-v. [PMID: 2123403]
  • S K Durham, A Brouwer. 3,4,3',4'-Tetrachlorobiphenyl distribution and induced effects in the rat adrenal gland. Localization in the zona fasciculata. Laboratory investigation; a journal of technical methods and pathology. 1990 Feb; 62(2):232-9. doi: . [PMID: 2106055]
  • A B Kobusch, K W Bock. Zinc increases EGF-stimulated DNA synthesis in primary mouse hepatocytes. Studies in tumor promoter-treated cell cultures. Biochemical pharmacology. 1990 Feb; 39(3):555-8. doi: 10.1016/0006-2952(90)90063-q. [PMID: 2106323]
  • N Koga, M Beppu, C Ishida, H Yoshimura. Further studies on metabolism in vivo of 3,4,3',4'-tetrachlorobiphenyl in rats: identification of minor metabolites in rat faeces. Xenobiotica; the fate of foreign compounds in biological systems. 1989 Nov; 19(11):1307-18. doi: 10.3109/00498258909043182. [PMID: 2515663]
  • M A Clevenger, S M Roberts, D L Lattin, R D Harbison, R C James. The pharmacokinetics of 2,2',5,5'-tetrachlorobiphenyl and 3,3',4,4'-tetrachlorobiphenyl and its relationship to toxicity. Toxicology and applied pharmacology. 1989 Sep; 100(2):315-27. doi: 10.1016/0041-008x(89)90317-7. [PMID: 2506674]
  • E K Wehler, A Bergman, I Brandt, P O Darnerud, C A Wachtmeister. 3,3',4,4'-Tetrachlorobiphenyl. Excretion and tissue retention of hydroxylated metabolites in the mouse. Drug metabolism and disposition: the biological fate of chemicals. 1989 Jul; 17(4):441-8. doi: NULL. [PMID: 2571487]
  • A B Kobusch, G Fischer, K W Bock. Tumor-promoting activity and cytotoxicity of 3,4,3',4'-tetrachlorobiphenyl on N-nitrosomorpholine-induced murine liver foci. Journal of cancer research and clinical oncology. 1989; 115(3):247-52. doi: 10.1007/bf00391697. [PMID: 2546956]
  • S K Durham, A Brouwer. 3,4,3',4'-tetrachlorobiphenyl-induced effects in the rat liver. II. Electron microscopic autoradiographic localization of 3H-TCB. Toxicologic pathology. 1989; 17(4 Pt 2):782-8. doi: 10.1177/0192623389017004206. [PMID: 2516643]
  • S K Durham, A Brouwer. 3,4,3',4'-tetrachlorobiphenyl-induced effects in the rat liver. I. Serum and hepatic retinoid reduction and morphologic changes. Toxicologic pathology. 1989; 17(3):536-44. doi: 10.1177/019262338901700308. [PMID: 2510240]
  • A Brouwer, A Kukler, K J Van den Berg. Alterations in retinoid concentrations in several extrahepatic organs of rats by 3,4,3',4'-tetrachlorobiphenyl. Toxicology. 1988 Aug; 50(3):317-30. doi: 10.1016/0300-483x(88)90047-9. [PMID: 3134751]
  • D Wölfle, P Münzel, G Fischer, K W Bock. Altered growth control of rat hepatocytes after treatment with 3,4,3',4'-tetrachlorobiphenyl in vivo and in vitro. Carcinogenesis. 1988 Jun; 9(6):919-24. doi: 10.1093/carcin/9.6.919. [PMID: 3131034]
  • K J van den Berg, C Zurcher, A Brouwer. Effects of 3,4,3',4'-tetrachlorobiphenyl on thyroid function and histology in marmoset monkeys. Toxicology letters. 1988 Apr; 41(1):77-86. doi: 10.1016/0378-4274(88)90010-0. [PMID: 3128898]
  • A Brouwer, W S Blaner, A Kukler, K J Van den Berg. Study on the mechanism of interference of 3,4,3',4'-tetrachlorobiphenyl with the plasma retinol-binding proteins in rodents. Chemico-biological interactions. 1988; 68(3-4):203-17. doi: 10.1016/0009-2797(88)90017-8. [PMID: 3145817]
  • R H Powers, L C Gilbert, S D Aust. The effect of 3,4,3',4'-tetrachlorobiphenyl on plasma retinol and hepatic retinyl palmitate hydrolase activity in female Sprague-Dawley rats. Toxicology and applied pharmacology. 1987 Jul; 89(3):370-7. doi: 10.1016/0041-008x(87)90156-6. [PMID: 3111014]
  • R d'Argy, L Dencker, E Klasson-Wehler, A Bergman, P O Darnerud, I Brandt. 3,3'4,4'-Tetrachlorobiphenyl in pregnant mice: embryotoxicity, teratogenicity, and toxic effects on the cultured embryonic thymus. Pharmacology & toxicology. 1987 Jul; 61(1):53-7. doi: 10.1111/j.1600-0773.1987.tb01772.x. [PMID: 3114731]
  • J B Silkworth, L A Antrim, G Sack. Ah receptor mediated suppression of the antibody response in mice is primarily dependent on the Ah phenotype of lymphoid tissue. Toxicology and applied pharmacology. 1986 Dec; 86(3):380-90. doi: 10.1016/0041-008x(86)90365-0. [PMID: 3024358]
  • A Brouwer, K J van den Berg. Binding of a metabolite of 3,4,3',4'-tetrachlorobiphenyl to transthyretin reduces serum vitamin A transport by inhibiting the formation of the protein complex carrying both retinol and thyroxin. Toxicology and applied pharmacology. 1986 Sep; 85(3):301-12. doi: 10.1016/0041-008x(86)90337-6. [PMID: 3094194]
  • P A Spear, T W Moon. Thyroid-vitamin A interactions in chicks exposed to 3,4,3',4'-tetrachlorobiphenyl: influence of low dietary vitamin A and iodine. Environmental research. 1986 Jun; 40(1):188-98. doi: 10.1016/s0013-9351(86)80095-0. [PMID: 3086082]