4-nonylphenol (BioDeep_00001871688)
代谢物信息卡片
4-nonylphenol
化学式: C15H24O (220.18270539999997)
中文名称: 对壬基酚
谱图信息:
最多检出来源 () 0%
分子结构信息
SMILES: CCCCCCCCCC1=CC=C(C=C1)O
InChI: InChI=1S/C15H24O/c1-2-3-4-5-6-7-8-9-14-10-12-15(16)13-11-14/h10-13,16H,2-9H2,1H3
数据库引用编号
6 个数据库交叉引用编号
- ChEBI: CHEBI:34440
- PubChem: 1752
- ChEMBL: CHEMBL153062
- CAS: 211947-56-7
- CAS: 68081-86-7
- CAS: 104-40-5
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
- Mahmoud Abd-Elkareem, Alaa El-Din H Sayed, Nasser S Abou Khalil, Mohamed H Kotob. Nigella sativa seeds mitigate the hepatic histo-architectural and ultrastructural changes induced by 4-nonylphenol in Clarias gariepinus.
Scientific reports.
2023 Mar; 13(1):4109. doi:
10.1038/s41598-023-30929-w. [PMID: 36914664] - Hongyu Zhang, Weiran Ke, Xi Chen, Yu Han, Yan Xiong, Feng Zhu, Yang Xiang, Rong Yan, Hongbo Cai, Shunmei Huang, Xiaoyu Ke. High-Fat Diet Promotes Adipogenesis in Offspring Female Rats Induced by Perinatal Exposure to 4-Nonylphenol.
BioMed research international.
2023; 2023(?):6540585. doi:
10.1155/2023/6540585. [PMID: 37398946] - Bin-Tong Xia, Yan He, Yang Guo, Jiao-Long Huang, Xiao-Juan Tang, Jian-Ru Wang, Yan Tan, Peng Duan. Multi- and transgenerational biochemical effects of low-dose exposure to bisphenol A and 4-nonylphenol on testicular interstitial (Leydig) cells.
Environmental toxicology.
2022 May; 37(5):1032-1046. doi:
10.1002/tox.23462. [PMID: 35005817] - Murat Boyacioglu, Ozay Gules, Hande Sultan Sahiner. Protective Effect of Sodium Selenite on 4-Nonylphenol-Induced Hepatotoxicity and Nephrotoxicity in Rats.
Biological trace element research.
2021 Aug; 199(8):3001-3012. doi:
10.1007/s12011-020-02418-y. [PMID: 33026593] - Dilek Battal, Ayca Aktas Sukuroglu, Kumsal Kocadal, Ismet Cok, Irfan Unlusayin. Establishment of rapid, sensitive, and quantitative liquid chromatography-electrospray ionization-tandem mass spectrometry method coupled with liquid-liquid extraction for measurement of urinary bisphenol A, 4-t-octylphenol, and 4-nonylphenol.
Rapid communications in mass spectrometry : RCM.
2021 Jun; 35(12):e9084. doi:
10.1002/rcm.9084. [PMID: 33733529] - Benoit Lalonde, Christine Garron. Nonylphenol, Octylphenol, and Nonylphenol Ethoxylates Dissemination in the Canadian Freshwater Environment.
Archives of environmental contamination and toxicology.
2021 Feb; 80(2):319-330. doi:
10.1007/s00244-020-00807-x. [PMID: 33432443] - Jacineumo Falcão de Oliveira, Ronaldo Fia, Fernando Neris Rodrigues, Fátima Resende Luiz Fia, Mateus Pimentel de Matos, Luciene Alves Batista Siniscalchi, Ananda Lima Sanson. Quantification, removal and potential ecological risk of emerging contaminants in different organic loads of swine wastewater treated by integrated biological reactors.
Chemosphere.
2020 Dec; 260(?):127516. doi:
10.1016/j.chemosphere.2020.127516. [PMID: 32682131] - Mahmoud Abd-Elkareem, Nasser S Abou Khalil, Alaa El-Din H Sayed. Cytoprotective effect of Nigella sativa seed on 4-nonylphenol-induced renal damage in the African catfish (Clarias gariepinus).
Chemosphere.
2020 Nov; 259(?):127379. doi:
10.1016/j.chemosphere.2020.127379. [PMID: 32590174] - Na Ding, Lu Wang, Yuan Kang, Kesong Luo, Diya Zeng, Yu Bon Man, Qiuyun Zhang, Lixuan Zeng, Jiwen Luo, Feng Jiang. The comparison of transcriptomic response of green microalga Chlorella sorokiniana exposure to environmentally relevant concentration of cadmium(II) and 4-n-nonylphenol.
Environmental geochemistry and health.
2020 Sep; 42(9):2881-2894. doi:
10.1007/s10653-020-00526-1. [PMID: 32026273] - Jiao Yang, Qingyi Huang, Huan Liu, Xiong Zhou, Zhuoquan Huang, Quansheng Peng, Chunhong Liu. 4-Nonylphenol and 4-tert-octylphenol induce anxiety-related behaviors through alternation of 5-HT receptors and transporters in the prefrontal cortex.
Comparative biochemistry and physiology. Toxicology & pharmacology : CBP.
2020 Apr; 230(?):108701. doi:
10.1016/j.cbpc.2020.108701. [PMID: 31911191] - Itzel Y López-Pacheco, Carmen Salinas-Salazar, Arisbe Silva-Núñez, Laura Isabel Rodas-Zuluaga, Javier Donoso-Quezada, Sergio Ayala-Mar, Damiá Barceló, Hafiz M N Iqbal, Roberto Parra-Saldívar. Removal and biotransformation of 4-nonylphenol by Arthrospira maxima and Chlorella vulgaris consortium.
Environmental research.
2019 12; 179(Pt B):108848. doi:
10.1016/j.envres.2019.108848. [PMID: 31678727] - Alaa El-Din H Sayed, Ahmed M Kotb, Shoji Oda, Shosaku Kashiwada, Hiroshi Mitani. Protective effect of p53 knockout on 4-nonylphenol-induced nephrotoxicity in medaka (Oryzias latipes).
Chemosphere.
2019 Dec; 236(?):124314. doi:
10.1016/j.chemosphere.2019.07.045. [PMID: 31310970] - Seung-Hyun Jeong, Ji-Hun Jang, Hea-Young Cho, Yong-Bok Lee. Gender differences in pharmacokinetics and tissue distribution of 4-n-nonylphenol in rats.
Archives of toxicology.
2019 11; 93(11):3121-3139. doi:
10.1007/s00204-019-02581-9. [PMID: 31552477] - Yin-Zhi Lv, Li Yao, Li Wang, Wang-Rong Liu, Jian-Liang Zhao, Liang-Ying He, Guang-Guo Ying. Bioaccumulation, metabolism, and risk assessment of phenolic endocrine disrupting chemicals in specific tissues of wild fish.
Chemosphere.
2019 Jul; 226(?):607-615. doi:
10.1016/j.chemosphere.2019.03.187. [PMID: 30954895] - Krishna Ghosh, Biji Chatterjee, Uma Maheswari, Mariyam Athifa, Santosh R Kanade. 4-Nonylphenol-enhanced EZH2 and RNF2 expression, H3K27me3 and H2AK119ub1 marks resulting in silencing of p21CDKN1A in vitro.
Epigenomics.
2019 06; 11(8):899-916. doi:
10.2217/epi-2018-0175. [PMID: 31144530] - Mahdi Malmir, Malek Soleimani Mehranjani, Samira Naderi Noreini, Tayebe Faraji. Protective antioxidant effects of N-acetylcysteine against impairment of spermatogenesis caused by paranonylphenol.
Andrologia.
2018 Dec; 50(10):e13114. doi:
10.1111/and.13114. [PMID: 30069898] - Jason P Breves, Tara A Duffy, Ingibjörg E Einarsdottir, Björn Thrandur Björnsson, Stephen D McCormick. In vivo effects of 17α-ethinylestradiol, 17β-estradiol and 4-nonylphenol on insulin-like growth-factor binding proteins (igfbps) in Atlantic salmon.
Aquatic toxicology (Amsterdam, Netherlands).
2018 Oct; 203(?):28-39. doi:
10.1016/j.aquatox.2018.07.018. [PMID: 30075440] - Muhammad Ashfaq, Yan Li, Yuwen Wang, Dan Qin, Muhammad Saif Ur Rehman, Azhar Rashid, Chang-Ping Yu, Qian Sun. Monitoring and mass balance analysis of endocrine disrupting compounds and their transformation products in an anaerobic-anoxic-oxic wastewater treatment system in Xiamen, China.
Chemosphere.
2018 Aug; 204(?):170-177. doi:
10.1016/j.chemosphere.2018.04.028. [PMID: 29655110] - Madoka Nakagomi, Emako Suzuki, Yoshiaki Saito, Tetsuji Nagao. Endocrine disrupting chemicals, 4-nonylphenol, bisphenol A and butyl benzyl phthalate, impair metabolism of estradiol in male and female rats as assessed by levels of 15α-hydroxyestrogens and catechol estrogens in urine.
Journal of applied toxicology : JAT.
2018 05; 38(5):688-695. doi:
10.1002/jat.3574. [PMID: 29250801] - Ahmed M Kotb, Mahmoud Abd-Elkareem, Nasser S Abou Khalil, Alaa El-Din H Sayed. Protective effect of Nigella sativa on 4-nonylphenol-induced nephrotoxicity in Clarias gariepinus (Burchell, 1822).
The Science of the total environment.
2018 Apr; 619-620(?):692-699. doi:
10.1016/j.scitotenv.2017.11.131. [PMID: 29156287] - Alaa El-Din H Sayed, Hamdy A M Soliman. Modulatory effects of green tea extract against the hepatotoxic effects of 4-nonylphenol in catfish (Clarias gariepinus).
Ecotoxicology and environmental safety.
2018 Mar; 149(?):159-165. doi:
10.1016/j.ecoenv.2017.11.007. [PMID: 29156308] - Shuang-Hung Chung, Wang-Hsien Ding. Isotope-dilution gas chromatography-mass spectrometry coupled with injection-port butylation for the determination of 4-t-octylphenol, 4-nonylphenols and bisphenol A in human urine.
Journal of pharmaceutical and biomedical analysis.
2018 Feb; 149(?):572-576. doi:
10.1016/j.jpba.2017.11.063. [PMID: 29197299] - Ava Zare, Darren Henry, Gordon Chua, Paul Gordon, Hamid R Habibi. Differential Hepatic Gene Expression Profile of Male Fathead Minnows Exposed to Daily Varying Dose of Environmental Contaminants Individually and in Mixture.
Frontiers in endocrinology.
2018; 9(?):749. doi:
10.3389/fendo.2018.00749. [PMID: 30619083] - Hyejin Park, Kisok Kim. Urinary Levels of 4-Nonylphenol and 4-t-Octylphenol in a Representative Sample of the Korean Adult Population.
International journal of environmental research and public health.
2017 08; 14(8):. doi:
10.3390/ijerph14080932. [PMID: 28820486] - Shuqiang Zhu, Lijun Wang, Along Su, Haixia Zhang. Dispersive liquid-liquid microextraction of phenolic compounds from vegetable oils using a magnetic ionic liquid.
Journal of separation science.
2017 Aug; 40(15):3130-3137. doi:
10.1002/jssc.201700274. [PMID: 28581630] - Yu-Fang Huang, Pei-Wei Wang, Li-Wei Huang, Chun-Hao Lai, Winnie Yang, Kuen-Yuh Wu, Chensheng Alex Lu, Hsin-Chang Chen, Mei-Lien Chen. Prenatal Nonylphenol and Bisphenol A Exposures and Inflammation Are Determinants of Oxidative/Nitrative Stress: A Taiwanese Cohort Study.
Environmental science & technology.
2017 Jun; 51(11):6422-6429. doi:
10.1021/acs.est.7b00801. [PMID: 28490175] - Alaa El-Din H Sayed, Heba S Hamed. Induction of apoptosis and DNA damage by 4-nonylphenol in African catfish (Clarias gariepinus) and the antioxidant role of Cydonia oblonga.
Ecotoxicology and environmental safety.
2017 May; 139(?):97-101. doi:
10.1016/j.ecoenv.2017.01.024. [PMID: 28113117] - Madhu Sharma, Pooja Chadha. Widely used non-ionic surfactant 4-nonylphenol: showing genotoxic effects in various tissues of Channa punctatus.
Environmental science and pollution research international.
2017 Apr; 24(12):11331-11339. doi:
10.1007/s11356-017-8759-1. [PMID: 28303538] - Peng Duan, Chunhui Hu, Holly J Butler, Chao Quan, Wei Chen, Wenting Huang, Sha Tang, Wei Zhou, Meng Yuan, Yuqin Shi, Francis L Martin, Kedi Yang. 4-Nonylphenol induces disruption of spermatogenesis associated with oxidative stress-related apoptosis by targeting p53-Bcl-2/Bax-Fas/FasL signaling.
Environmental toxicology.
2017 Mar; 32(3):739-753. doi:
10.1002/tox.22274. [PMID: 27087316] - Sudhanshu Shekhar, Surbhi Sood, Sadiya Showkat, Christy Lite, Anjalakshi Chandrasekhar, Mariappanadar Vairamani, S Barathi, Winkins Santosh. Detection of phenolic endocrine disrupting chemicals (EDCs) from maternal blood plasma and amniotic fluid in Indian population.
General and comparative endocrinology.
2017 01; 241(?):100-107. doi:
10.1016/j.ygcen.2016.05.025. [PMID: 27235644] - Oju R Ibor, Aina O Adeogun, Olusegun A Fagbohun, Augustine Arukwe. Gonado-histopathological changes, intersex and endocrine disruptor responses in relation to contaminant burden in Tilapia species from Ogun River, Nigeria.
Chemosphere.
2016 Dec; 164(?):248-262. doi:
10.1016/j.chemosphere.2016.08.087. [PMID: 27591376] - Courtney E Hart, Michael J Lauth, Cassidy S Hunter, Brennan R Krasny, Kristin M Hardy. Effect of 4-nonylphenol on the immune response of the Pacific oyster Crassostrea gigas following bacterial infection with Vibrio campbellii.
Fish & shellfish immunology.
2016 Nov; 58(?):449-461. doi:
10.1016/j.fsi.2016.09.054. [PMID: 27693202] - Alaa El-Din H Sayed, Nadia H Mohamed, Mady A Ismail, Wael M Abdel-Mageed, Ahmed A M Shoreit. Antioxidant and antiapoptotic activities of Calotropis procera latex on Catfish (Clarias gariepinus) exposed to toxic 4-nonylphenol.
Ecotoxicology and environmental safety.
2016 Jun; 128(?):189-94. doi:
10.1016/j.ecoenv.2016.02.023. [PMID: 26946283] - David J Fairbairn, M Ekrem Karpuzcu, William A Arnold, Brian L Barber, Elizabeth F Kaufenberg, William C Koskinen, Paige J Novak, Pamela J Rice, Deborah L Swackhamer. Sources and transport of contaminants of emerging concern: A two-year study of occurrence and spatiotemporal variation in a mixed land use watershed.
The Science of the total environment.
2016 May; 551-552(?):605-13. doi:
10.1016/j.scitotenv.2016.02.056. [PMID: 26897403] - Karen L Ricciardi, Helen C Poynton, Brian J Duphily, Bonnie J Blalock, William E Robinson. Bioconcentration and depuration of (14)C-labeled 17α-ethinyl estradiol and 4-nonylphenol in individual organs of the marine bivalve Mytilus edulis L. .
Environmental toxicology and chemistry.
2016 Apr; 35(4):863-73. doi:
10.1002/etc.3137. [PMID: 26126666] - Pinggu Wu, Liqun Zhang, Dajin Yang, Jing Zhang, Zhengyan Hu, Liyuan Wang, Bingjie Ma. Isotope dilution gas chromatography with mass spectrometry for the analysis of 4-octyl phenol, 4-nonylphenol, and bisphenol A in vegetable oils.
Journal of separation science.
2016 Mar; 39(5):904-9. doi:
10.1002/jssc.201500887. [PMID: 26698324] - Madhu Sharma, Pooja Chadha. Study on DNA damaging effects of 4-nonylphenol using erythrocytes from peripheral circulation, gill and kidney of fish Channapunctatus.
Journal of environmental biology.
2016 Mar; 37(2):313-8. doi:
NULL. [PMID: 27097453] - Ana L Patrício-Silva, Mónica J B Amorim. Effect of freeze-thaw cycles and 4-nonylphenol on cellular energy allocation in the freeze-tolerant enchytraeid Enchytraeus albidus.
Environmental science and pollution research international.
2016 Feb; 23(4):3548-55. doi:
10.1007/s11356-015-5593-1. [PMID: 26490934] - Tirumuru V Reddy, Robert Flick, James M Lazorchak, Mark E Smith, Barry Wiechman, David L Lattier. Experimental paradigm for in-laboratory proxy aquatic studies under conditions of static, non-flow-through chemical exposures.
Environmental toxicology and chemistry.
2015 Dec; 34(12):2796-802. doi:
10.1002/etc.3121. [PMID: 26088724] - Mohammad Naderi, Davood Zargham, Asad Asadi, Tayebeh Bashti, Kianoosh Kamayi. Short-term responses of selected endocrine parameters in juvenile rainbow trout (Oncorhynchus mykiss) exposed to 4-nonylphenol.
Toxicology and industrial health.
2015 Dec; 31(12):1218-28. doi:
10.1177/0748233713491806. [PMID: 23771873] - Zhongxiu Jin, Xiangxue Wang, Yubing Sun, Yuejie Ai, Xiangke Wang. Adsorption of 4-n-Nonylphenol and Bisphenol-A on Magnetic Reduced Graphene Oxides: A Combined Experimental and Theoretical Studies.
Environmental science & technology.
2015 Aug; 49(15):9168-75. doi:
10.1021/acs.est.5b02022. [PMID: 26161689] - Harmanpreet S Sidhu, Patrick C Wilson, George A O'Connor. Endocrine-disrupting compounds in reclaimed water and residential ponds and exposure potential for dislodgeable residues in turf irrigated with reclaimed water.
Archives of environmental contamination and toxicology.
2015 Jul; 69(1):81-8. doi:
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Chemosphere.
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Environmental science & technology.
2015 Feb; 49(4):2044-51. doi:
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Toxicological sciences : an official journal of the Society of Toxicology.
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Environmental pollution (Barking, Essex : 1987).
2014 Oct; 193(?):29-36. doi:
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Archives of environmental contamination and toxicology.
2014 Oct; 67(3):335-47. doi:
10.1007/s00244-014-0023-9. [PMID: 24752748] - Martin Holmstrup, Hélène Bouvrais, Peter Westh, Chunhua Wang, Stine Slotsbo, Dorthe Waagner, Kirsten Enggrob, John H Ipsen. Lipophilic contaminants influence cold tolerance of invertebrates through changes in cell membrane fluidity.
Environmental science & technology.
2014 Aug; 48(16):9797-803. doi:
10.1021/es502221g. [PMID: 25050459] - Kaori Sadakane, Takamichi Ichinose, Hirohisa Takano, Rie Yanagisawa, Eiko Koike, Ken-ichiro Inoue. The alkylphenols 4-nonylphenol, 4-tert-octylphenol and 4-tert-butylphenol aggravate atopic dermatitis-like skin lesions in NC/Nga mice.
Journal of applied toxicology : JAT.
2014 Aug; 34(8):893-902. doi:
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Journal of hazardous materials.
2014 Jun; 275(?):107-15. doi:
10.1016/j.jhazmat.2014.04.055. [PMID: 24853140] - Laure Pasquini, Jean-François Munoz, Marie-Noëlle Pons, Jacques Yvon, Xavier Dauchy, Xavier France, Nang Dinh Le, Christian France-Lanord, Tatiana Görner. Occurrence of eight household micropollutants in urban wastewater and their fate in a wastewater treatment plant. Statistical evaluation.
The Science of the total environment.
2014 May; 481(?):459-68. doi:
10.1016/j.scitotenv.2014.02.075. [PMID: 24631609] - Mohammad Naderi, Seyed Mohammad Mousavi, Alireza Safahieh, Ebrahim Rajabzade Ghatrami, Davood Zargham. Effects of 4-nonylphenol on balance of steroid and thyroid hormones in sexually immature male yellowfin seabream (Acanthopagrus latus).
Environmental toxicology.
2014 Apr; 29(4):459-65. doi:
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Chemosphere.
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The Science of the total environment.
2013 Oct; 463-464(?):355-65. doi:
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Environmental science & technology.
2013 Aug; 47(16):9434-43. doi:
10.1021/es4012299. [PMID: 23855649] - Claire-Sophie Haudin, Yuhai Zhang, Valérie Dumény, Gwenaëlle Lashermes, Valérie Bergheaud, Enrique Barriuso, Sabine Houot. Fate of (14)C-organic pollutant residues in composted sludge after application to soil.
Chemosphere.
2013 Aug; 92(10):1280-5. doi:
10.1016/j.chemosphere.2013.02.041. [PMID: 23545187] - Samar Mortazavi, Alireza Riyahi Bakhtiari, Abbas Esmaili Sari, Nader Bahramifar, Fatemeh Rahbarizadeh. Occurrence of endocrine disruption chemicals (Bisphenol A, 4-nonylphenol, and Octylphenol) in muscle and liver of, Cyprinus Carpino Common, from Anzali wetland, Iran.
Bulletin of environmental contamination and toxicology.
2013 May; 90(5):578-84. doi:
10.1007/s00128-013-0964-0. [PMID: 23429963] - Minjian Chen, Rong Tang, Guangbo Fu, Bin Xu, Pengfei Zhu, Shanlei Qiao, Xiaojiao Chen, Bo Xu, Yufeng Qin, Chuncheng Lu, Bo Hang, Yankai Xia, Xinru Wang. Association of exposure to phenols and idiopathic male infertility.
Journal of hazardous materials.
2013 Apr; 250-251(?):115-21. doi:
10.1016/j.jhazmat.2013.01.061. [PMID: 23435201] - XiaoYun Xie, WenJuan Lü, XingGuo Chen. Binding of the endocrine disruptors 4-tert-octylphenol and 4-nonylphenol to human serum albumin.
Journal of hazardous materials.
2013 Mar; 248-249(?):347-54. doi:
10.1016/j.jhazmat.2013.01.036. [PMID: 23416871] - Xu Li, Guang-Guo Ying, Jian-Liang Zhao, Zhi-Feng Chen, Hua-Jie Lai, Hao-Chang Su. 4-Nonylphenol, bisphenol-A and triclosan levels in human urine of children and students in China, and the effects of drinking these bottled materials on the levels.
Environment international.
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Acta biochimica Polonica.
2013; 60(4):677-82. doi:
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Chemical research in toxicology.
2012 Nov; 25(11):2553-66. doi:
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Environment international.
2012 Nov; 48(?):78-83. doi:
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