Topanel (BioDeep_00000618920)

Main id: BioDeep_00000004212

 


代谢物信息卡片


Crotonaldehyde, stabilized [UN1143] [Poison]

化学式: C4H6O (70.0418626)
中文名称: 2-丁烯醛, 巴豆醛
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C/C=C\C=O
InChI: InChI=1S/C4H6O/c1-2-3-4-5/h2-4H,1H3/b3-2+

描述信息

同义名列表

76 个代谢物同义名

Crotonaldehyde, stabilized [UN1143] [Poison]; Crotonaldehyde, mixture OF cis and trans; InChI=1\C4H6O\c1-2-3-4-5\h2-4H,1H3\b3-2; 2-Butenal, mixture OF cis and trans; Crotonaldehyde, predominantly trans; 2-BUTENAL (TRANS) CROTONALDEHYDE; InChI=1\C4H6O\c1-2-3-4-5\h2-4H,1H; Aldehyde crotonique [French]; 3-Methylacrolein, inhibited; (e)-Crotonaldehyde (iupac); Crotonaldehyde, inhibited; Krotonaldehyd [Czech]; Crotonaldehyde, cis-; beta-Methyl acrolein; CROTONALDEHYDE, (E)-; trans-Crotonaldehyde; (cis)-crotonaldehyde; 2-Butenal, inhibited; RCRA waste no. U053; beta-Methylacrolein; (Z)-Crotonaldehyde; (e)-Crotonaldehyde; AI3-18303 (USDA); 2-Butenal, (2E)-; EINECS 224-030-0; EINECS 204-647-1; 2-Butenal, (E)-; 1-Formylpropene; 2-Butenaldehyde; trans-2-Butenal; (2E)-BUT-2-enal; 2-Butenal, (Z)-; NCGC00090830-01; trans- Crotonal; 275212_ALDRICH; 262668_ALDRICH; (e)-But-2-enal; Crotonaldehyde; Methylpropenal; ZINC01686876; e-2-Butenal; 27990_FLUKA; 27980_FLUKA; CCRIS 4501; 15798-64-8; NCI-C56279; Topanel ca; but-2-enal; NSC 56354; HSDB 2871; AI3-18303; CCRIS 909; 123-73-9; HSDB 252; UN 1143; Topanel; UN1143; CRD; Crotonaldehyde, stabilized [UN1143] [Poison]; 2-BUTENAL (trans) crotonaldehyde; Aldehyde crotonique; cis-Crotonaldehyde; Crotonic aldehyde; (2Z)-but-2-enal; Nchem.215-comp8; But-(e)-2-enal; (2E)-2-Butenal; Crotenaldehyde; Crotylaldehyde; (2Z)-2-Butenal; (e)-2-Butenal; (Z)-2-Butenal; Krotonaldehyd; t-2-Butenal; 2-Butenal; Crotonal



数据库引用编号

13 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(1)

PlantCyc(1)

代谢反应

121 个相关的代谢反应过程信息。

Reactome(0)

BioCyc(2)

WikiPathways(0)

Plant Reactome(0)

INOH(0)

PlantCyc(119)

COVID-19 Disease Map(0)

PathBank(0)

PharmGKB(0)

6 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

  • Eva Tejedor-Calvo, Sergi Garcia-Barreda, José Sebastián Dambolena, David Pelissero, Sergio Sánchez, Pedro Marco, Eduardo Nouhra. Aromatic profile of black truffle grown in Argentina: Characterization of commercial categories and alterations associated to maturation, harvesting date and orchard management practices. Food research international (Ottawa, Ont.). 2023 11; 173(Pt 1):113300. doi: 10.1016/j.foodres.2023.113300. [PMID: 37803611]
  • Guang Cheng, Jiehong Guo, Renwei Wang, Jian-Min Yuan, Silvia Balbo, Stephen S Hecht. Quantitation by Liquid Chromatography-Nanoelectrospray Ionization-High-Resolution Tandem Mass Spectrometry of Multiple DNA Adducts Related to Cigarette Smoking in Oral Cells in the Shanghai Cohort Study. Chemical research in toxicology. 2023 Feb; 36(2):305-312. doi: 10.1021/acs.chemrestox.2c00393. [PMID: 36719849]
  • Jordan Lynch, Lexiao Jin, Andre Richardson, Ganapathy Jagatheesan, Pawel Lorkiewicz, Zhengzhi Xie, Whitney S Theis, Gregg Shirk, Marina V Malovichko, Aruni Bhatnagar, Sanjay Srivastava, Daniel J Conklin. Acute and chronic vascular effects of inhaled crotonaldehyde in mice: Role of TRPA1. Toxicology and applied pharmacology. 2020 09; 402(?):115120. doi: 10.1016/j.taap.2020.115120. [PMID: 32634517]
  • Menglan Chen, Steven G Carmella, Yupeng Li, Yingchun Zhao, Stephen S Hecht. Resolution and Quantitation of Mercapturic Acids Derived from Crotonaldehyde, Methacrolein, and Methyl Vinyl Ketone in the Urine of Smokers and Nonsmokers. Chemical research in toxicology. 2020 02; 33(2):669-677. doi: 10.1021/acs.chemrestox.9b00491. [PMID: 31957442]
  • Rosario Zamora, Cristina M Lavado-Tena, Francisco J Hidalgo. Oligomerization of reactive carbonyls in the presence of ammonia-producing compounds: A route for the production of pyridines in foods. Food chemistry. 2020 Jan; 304(?):125284. doi: 10.1016/j.foodchem.2019.125284. [PMID: 31476546]
  • Biao Zhang, Ping Wei, Jinlong Men, Shuman Zhang, Hua Shao, Zhihu Zhang. Crotonaldehyde-induced alterations in testicular enzyme function and hormone levels, and apoptosis in the testes of male Wistar rats are associated with oxidative damage. Toxicology mechanisms and methods. 2020 Jan; 30(1):19-32. doi: 10.1080/15376516.2019.1646369. [PMID: 31345100]
  • Hasmik Grigoryan, Courtney Schiffman, Marc J Gunter, Alessio Naccarati, Silvia Polidoro, Sonia Dagnino, Sandrine Dudoit, Paolo Vineis, Stephen M Rappaport. Cys34 Adductomics Links Colorectal Cancer with the Gut Microbiota and Redox Biology. Cancer research. 2019 12; 79(23):6024-6031. doi: 10.1158/0008-5472.can-19-1529. [PMID: 31641032]
  • S S Li, B Zhang, S M Zhang, Z H Zhang, Y N Wei. [Study on lung injury induced by subchronic exposure to crotonaldehyde in male rats]. Zhonghua lao dong wei sheng zhi ye bing za zhi = Zhonghua laodong weisheng zhiyebing zazhi = Chinese journal of industrial hygiene and occupational diseases. 2019 Oct; 37(10):728-731. doi: 10.3760/cma.j.issn.1001-9391.2019.10.003. [PMID: 31726501]
  • Yanbin Su, Chengyu Sun, Yan Chen, Shichang Liu, Ning Jing, Shuxin Li. Toxic trans-crotonaldehyde in mitochondria intercepted by oxyresveratrol contributing to anticancer. IUBMB life. 2019 07; 71(7):1014-1020. doi: 10.1002/iub.2051. [PMID: 31012998]
  • Biao Zhang, Shuangshuang Li, Jinlong Men, Cheng Peng, Hua Shao, Zhihu Zhang. Long-term exposure to crotonaldehyde causes heart and kidney dysfunction through induction of inflammatory and oxidative damage in male Wistar rats. Toxicology mechanisms and methods. 2019 May; 29(4):263-275. doi: 10.1080/15376516.2018.1542474. [PMID: 30426860]
  • S S Li, B Zhang, Z H Zhang. [Study on oxidative stress damage of reproductive organs in male rats induced by long-term exposure to crotonaldehyde]. Zhonghua lao dong wei sheng zhi ye bing za zhi = Zhonghua laodong weisheng zhiyebing zazhi = Chinese journal of industrial hygiene and occupational diseases. 2019 Apr; 37(4):241-246. doi: 10.3760/cma.j.issn.1001-9391.2019.04.001. [PMID: 31177687]
  • Asja A Kroeger, Amir Karton. A computational foray into the mechanism and catalysis of the adduct formation reaction of guanine with crotonaldehyde. Journal of computational chemistry. 2019 02; 40(4):630-637. doi: 10.1002/jcc.25595. [PMID: 30368841]
  • B Zhang, S S Li, J L Men, Z H Zhang. [Effect of long-term crotonaldehyde exposure on heart damage in male rats]. Zhonghua lao dong wei sheng zhi ye bing za zhi = Zhonghua laodong weisheng zhiyebing zazhi = Chinese journal of industrial hygiene and occupational diseases. 2018 Sep; 36(9):647-652. doi: 10.3760/cma.j.issn.1001-9391.2018.09.002. [PMID: 30419665]
  • B Zhang, S S Li, L Li, R Han, Z H Zhang. [Effect of crotonaldehyde long-term exposure induced kidney inflammatory and oxidative injury in male rats]. Zhonghua lao dong wei sheng zhi ye bing za zhi = Zhonghua laodong weisheng zhiyebing zazhi = Chinese journal of industrial hygiene and occupational diseases. 2018 Aug; 36(8):580-584. doi: 10.3760/cma.j.issn.1001-9391.2018.08.004. [PMID: 30317805]
  • Pritha Bagchi, Nathan Geldner, B Rey deCastro, Víctor R De Jesús, Sang Ki Park, Benjamin C Blount. Crotonaldehyde exposure in U.S. tobacco smokers and nonsmokers: NHANES 2005-2006 and 2011-2012. Environmental research. 2018 05; 163(?):1-9. doi: 10.1016/j.envres.2018.01.033. [PMID: 29407484]
  • Petr Grúz, Masatomi Shimizu, Masami Yamada, Kei-Ichi Sugiyama, Masamitsu Honma. Opposing roles of Y-family DNA polymerases in lipid peroxide mutagenesis at the hisG46 target in the Ames test. Mutation research. Genetic toxicology and environmental mutagenesis. 2018 May; 829-830(?):43-49. doi: 10.1016/j.mrgentox.2018.04.003. [PMID: 29704992]
  • Bebiana C Sousa, Andrew R Pitt, Corinne M Spickett. Chemistry and analysis of HNE and other prominent carbonyl-containing lipid oxidation compounds. Free radical biology & medicine. 2017 10; 111(?):294-308. doi: 10.1016/j.freeradbiomed.2017.02.003. [PMID: 28192230]
  • Yanbin Su, Xiaowei Ma, Yanwen Su, Tongxing Mu, Yanhe Li, Ning Jiang, Yuyun Su, Qi Zhang. Influences of ethanol on the structure of toxic trans-crotonaldehyde in mitochondria coming from rat myocardium. Scientific reports. 2017 08; 7(1):10081. doi: 10.1038/s41598-017-09656-6. [PMID: 28855539]
  • Joon Hyuk Suh, Yue S Niu, Wei-Lun Hung, Chi-Tang Ho, Yu Wang. Lipidomic analysis for carbonyl species derived from fish oil using liquid chromatography-tandem mass spectrometry. Talanta. 2017 Jun; 168(?):31-42. doi: 10.1016/j.talanta.2017.03.023. [PMID: 28391860]
  • Wojciech Łuczaj, Anna Moniuszko, Iwona Jarocka-Karpowicz, Sławomir Pancewicz, Luka Andrisic, Neven Zarkovic, Elżbieta Skrzydlewska. Tick-borne encephalitis--lipid peroxidation and its consequences. Scandinavian journal of clinical and laboratory investigation. 2016; 76(1):1-9. doi: 10.3109/00365513.2015.1084040. [PMID: 26414861]
  • Yu Wang, Ping Cui. Reactive Carbonyl Species Derived from Omega-3 and Omega-6 Fatty Acids. Journal of agricultural and food chemistry. 2015 Jul; 63(28):6293-6. doi: 10.1021/acs.jafc.5b02376. [PMID: 26151719]
  • Jun-Feng Huang, Du-Ming Zhu, Jie-Fei Ma, Ming Zhong. Acute respiratory distress syndrome due to exposure to high-concentration mixture of ethenone and crotonaldehyde. Toxicology and industrial health. 2015 Jul; 31(7):585-7. doi: 10.1177/0748233713480205. [PMID: 23448861]
  • Yasuo Yamauchi, Mikiko Kunishima, Masaharu Mizutani, Yukihiro Sugimoto. Reactive short-chain leaf volatiles act as powerful inducers of abiotic stress-related gene expression. Scientific reports. 2015 Jan; 5(?):8030. doi: 10.1038/srep08030. [PMID: 25619826]
  • Stephen S Hecht, Woon-Puay Koh, Renwei Wang, Menglan Chen, Steven G Carmella, Sharon E Murphy, Jian-Min Yuan. Elevated levels of mercapturic acids of acrolein and crotonaldehyde in the urine of Chinese women in Singapore who regularly cook at home. PloS one. 2015; 10(3):e0120023. doi: 10.1371/journal.pone.0120023. [PMID: 25807518]
  • Sungshim L Park, Steven G Carmella, Menglan Chen, Yesha Patel, Daniel O Stram, Christopher A Haiman, Loic Le Marchand, Stephen S Hecht. Mercapturic Acids Derived from the Toxicants Acrolein and Crotonaldehyde in the Urine of Cigarette Smokers from Five Ethnic Groups with Differing Risks for Lung Cancer. PloS one. 2015; 10(6):e0124841. doi: 10.1371/journal.pone.0124841. [PMID: 26053186]
  • Marwa Fathy Bakr Ali, Naoya Kishikawa, Kaname Ohyama, Horria Abdel-Mageed Mohamed, Hanaa Mohamed Abdel-Wadood, Ashraf Mohamed Mahmoud, Takahiro Imazato, Yukitaka Ueki, Mitsuhiro Wada, Naotaka Kuroda. Chromatographic determination of low-molecular mass unsaturated aliphatic aldehydes with peroxyoxalate chemiluminescence detection after fluorescence labeling with 4-(N,N-dimethylaminosulfonyl)-7-hydrazino-2,1,3-benzoxadiazole. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2014 Mar; 953-954(?):147-52. doi: 10.1016/j.jchromb.2014.02.009. [PMID: 24614624]
  • Michael Granvogl. Development of three stable isotope dilution assays for the quantitation of (E)-2-butenal (crotonaldehyde) in heat-processed edible fats and oils as well as in food. Journal of agricultural and food chemistry. 2014 Feb; 62(6):1272-82. doi: 10.1021/jf404902m. [PMID: 24428123]
  • Dong Sun Ryu, Hana Yang, Seung Eun Lee, Cheung-Seog Park, Young-Ho Jin, Yong Seek Park. Crotonaldehyde induces heat shock protein 72 expression that mediates anti-apoptotic effects in human endothelial cells. Toxicology letters. 2013 Nov; 223(2):116-23. doi: 10.1016/j.toxlet.2013.09.010. [PMID: 24070736]
  • Camila C M Garcia, Florêncio P Freitas, Angélica B Sanchez, Paolo Di Mascio, Marisa H G Medeiros. Elevated α-methyl-γ-hydroxy-1,N2-propano-2'-deoxyguanosine levels in urinary samples from individuals exposed to urban air pollution. Chemical research in toxicology. 2013 Nov; 26(11):1602-4. doi: 10.1021/tx400273q. [PMID: 24168144]
  • Steven G Carmella, Menglan Chen, Adam Zarth, Stephen S Hecht. High throughput liquid chromatography-tandem mass spectrometry assay for mercapturic acids of acrolein and crotonaldehyde in cigarette smokers' urine. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2013 Sep; 935(?):36-40. doi: 10.1016/j.jchromb.2013.07.004. [PMID: 23934173]
  • Eşref Demir, Fatma Turna, Bülent Kaya, Amadeu Creus, Ricard Marcos. Mutagenic/recombinogenic effects of four lipid peroxidation products in Drosophila. Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association. 2013 Mar; 53(?):221-7. doi: 10.1016/j.fct.2012.11.053. [PMID: 23238235]
  • Dan Li, Michele Ferrari, Elizabeth M Ellis. Human aldo-keto reductase AKR7A2 protects against the cytotoxicity and mutagenicity of reactive aldehydes and lowers intracellular reactive oxygen species in hamster V79-4 cells. Chemico-biological interactions. 2012 Jan; 195(1):25-34. doi: 10.1016/j.cbi.2011.09.007. [PMID: 22001351]
  • Seung Eun Lee, Hana Yang, Seong Il Jeong, Young-Ho Jin, Cheung-Seog Park, Yong Seek Park. Induction of heme oxygenase-1 inhibits cell death in crotonaldehyde-stimulated HepG2 cells via the PKC-δ-p38-Nrf2 pathway. PloS one. 2012; 7(7):e41676. doi: 10.1371/journal.pone.0041676. [PMID: 22848562]
  • Thomas W Kensler, Derek Ng, Steven G Carmella, Menglan Chen, Lisa P Jacobson, Alvaro Muñoz, Patricia A Egner, Jian Guo Chen, Geng Sun Qian, Tao Yang Chen, Jed W Fahey, Paul Talalay, John D Groopman, Jian-Min Yuan, Stephen S Hecht. Modulation of the metabolism of airborne pollutants by glucoraphanin-rich and sulforaphane-rich broccoli sprout beverages in Qidong, China. Carcinogenesis. 2012 Jan; 33(1):101-7. doi: 10.1093/carcin/bgr229. [PMID: 22045030]
  • Eşref Demir, Bülent Kaya, Carolina Soriano, Amadeu Creus, Ricard Marcos. Genotoxic analysis of four lipid-peroxidation products in the mouse lymphoma assay. Mutation research. 2011 Dec; 726(2):98-103. doi: 10.1016/j.mrgentox.2011.07.001. [PMID: 21763450]
  • Seung Eun Lee, Seong Il Jeong, Gun-Dong Kim, Hana Yang, Cheung-Seog Park, Young-Ho Jin, Yong Seek Park. Upregulation of heme oxygenase-1 as an adaptive mechanism for protection against crotonaldehyde in human umbilical vein endothelial cells. Toxicology letters. 2011 Mar; 201(3):240-8. doi: 10.1016/j.toxlet.2011.01.006. [PMID: 21238556]
  • Natsuki Otaki, Miho Chikazawa, Ritsuko Nagae, Yuki Shimozu, Takahiro Shibata, Sohei Ito, Yoshinari Takasaki, Junichi Fujii, Koji Uchida. Identification of a lipid peroxidation product as the source of oxidation-specific epitopes recognized by anti-DNA autoantibodies. The Journal of biological chemistry. 2010 Oct; 285(44):33834-42. doi: 10.1074/jbc.m110.165175. [PMID: 20736172]
  • Xing-Yu Liu, Zhi-Hua Yang, Xiu-Jie Pan, Mao-Xiang Zhu, Jian-Ping Xie. Gene expression profile and cytotoxicity of human bronchial epithelial cells exposed to crotonaldehyde. Toxicology letters. 2010 Aug; 197(2):113-22. doi: 10.1016/j.toxlet.2010.05.005. [PMID: 20471460]
  • Xing-yu Liu, Zhi-hua Yang, Xiu-jie Pan, Mao-xiang Zhu, Jian-ping Xie. Crotonaldehyde induces oxidative stress and caspase-dependent apoptosis in human bronchial epithelial cells. Toxicology letters. 2010 May; 195(1):90-8. doi: 10.1016/j.toxlet.2010.02.004. [PMID: 20153411]
  • Yasuo Yamauchi, Yukihiro Sugimoto. Effect of protein modification by malondialdehyde on the interaction between the oxygen-evolving complex 33 kDa protein and photosystem II core proteins. Planta. 2010 Apr; 231(5):1077-88. doi: 10.1007/s00425-010-1112-2. [PMID: 20157726]
  • Graziano Colombo, Giancarlo Aldini, Marica Orioli, Daniela Giustarini, Rosalba Gornati, Ranieri Rossi, Roberto Colombo, Marina Carini, Aldo Milzani, Isabella Dalle-Donne. Water-Soluble alpha,beta-unsaturated aldehydes of cigarette smoke induce carbonylation of human serum albumin. Antioxidants & redox signaling. 2010 Mar; 12(3):349-64. doi: 10.1089/ars.2009.2806. [PMID: 19686037]
  • Hauh-Jyun Candy Chen, Wen-Peng Lin. Simultaneous quantification of 1,N2-propano-2'-deoxyguanosine adducts derived from acrolein and crotonaldehyde in human placenta and leukocytes by isotope dilution nanoflow LC nanospray ionization tandem mass spectrometry. Analytical chemistry. 2009 Dec; 81(23):9812-8. doi: 10.1021/ac9019472. [PMID: 19899782]
  • Jun'ichi Mano, Fumitaka Miyatake, Eiji Hiraoka, Masahiro Tamoi. Evaluation of the toxicity of stress-related aldehydes to photosynthesis in chloroplasts. Planta. 2009 Sep; 230(4):639-48. doi: 10.1007/s00425-009-0964-9. [PMID: 19578873]
  • Irina G Minko, Ivan D Kozekov, Thomas M Harris, Carmelo J Rizzo, R Stephen Lloyd, Michael P Stone. Chemistry and biology of DNA containing 1,N(2)-deoxyguanosine adducts of the alpha,beta-unsaturated aldehydes acrolein, crotonaldehyde, and 4-hydroxynonenal. Chemical research in toxicology. 2009 May; 22(5):759-78. doi: 10.1021/tx9000489. [PMID: 19397281]
  • John R Ridpath, Ayumi Nakamura, Keizo Tano, April M Luke, Eiichiro Sonoda, Hiroshi Arakawa, Jean-Marie Buerstedde, David A F Gillespie, Julian E Sale, Mitsuyoshi Yamazoe, Douglas K Bishop, Minoru Takata, Shunichi Takeda, Masami Watanabe, James A Swenberg, Jun Nakamura. Cells deficient in the FANC/BRCA pathway are hypersensitive to plasma levels of formaldehyde. Cancer research. 2007 Dec; 67(23):11117-22. doi: 10.1158/0008-5472.can-07-3028. [PMID: 18056434]
  • Noriyuki Shibata, Motoko Kawaguchi, Koji Uchida, Akiyoshi Kakita, Hitoshi Takahashi, Ryoichi Nakano, Harutoshi Fujimura, Saburo Sakoda, Yuetsu Ihara, Keigo Nobukuni, Yasushi Takehisa, Shigetoshi Kuroda, Yasumasa Kokubo, Shigeki Kuzuhara, Taku Honma, Yoko Mochizuki, Tomohiko Mizutani, Satoshi Yamada, Sono Toi, Shoichi Sasaki, Makoto Iwata, Asao Hirano, Tomoko Yamamoto, Yoichiro Kato, Tatsuo Sawada, Makio Kobayashi. Protein-bound crotonaldehyde accumulates in the spinal cord of superoxide dismutase-1 mutation-associated familial amyotrophic lateral sclerosis and its transgenic mouse model. Neuropathology : official journal of the Japanese Society of Neuropathology. 2007 Feb; 27(1):49-61. doi: 10.1111/j.1440-1789.2006.00746.x. [PMID: 17319283]
  • G Scherer, M Urban, H W Hagedorn, S Feng, R D Kinser, M Sarkar, Q Liang, H J Roethig. Determination of two mercapturic acids related to crotonaldehyde in human urine: influence of smoking. Human & experimental toxicology. 2007 Jan; 26(1):37-47. doi: 10.1177/0960327107073829. [PMID: 17334178]
  • Gerhard Scherer, Michael Urban, Johannes Engl, Heinz-Werner Hagedorn, Kirsten Riedel. Influence of smoking charcoal filter tipped cigarettes on various biomarkers of exposure. Inhalation toxicology. 2006 Sep; 18(10):821-9. doi: 10.1080/08958370600747945. [PMID: 16774872]
  • Motoko Kawaguchi-Niida, Noriyuki Shibata, Shunichi Morikawa, Koji Uchida, Tomoko Yamamoto, Tatsuo Sawada, Makio Kobayashi. Crotonaldehyde accumulates in glial cells of Alzheimer's disease brain. Acta neuropathologica. 2006 May; 111(5):422-9. doi: 10.1007/s00401-006-0044-1. [PMID: 16538519]
  • Lisa M Kaminskas, Simon M Pyke, Philip C Burcham. Reactivity of hydrazinophthalazine drugs with the lipid peroxidation products acrolein and crotonaldehyde. Organic & biomolecular chemistry. 2004 Sep; 2(18):2578-84. doi: 10.1039/b408796h. [PMID: 15351821]
  • Masayuki Fujita, Mohammad Z Hossain. Modulation of pumpkin glutathione S-transferases by aldehydes and related compounds. Plant & cell physiology. 2003 May; 44(5):481-90. doi: 10.1093/pcp/pcg060. [PMID: 12773634]
  • Hossein Niknahad, Arno G Siraki, Adam Shuhendler, Sumsullah Khan, Shirley Teng, Giuseppe Galati, Elaine Easson, Raymond Poon, Peter J O'Brien. Modulating carbonyl cytotoxicity in intact rat hepatocytes by inhibiting carbonyl-metabolizing enzymes. I. Aliphatic alkenals. Chemico-biological interactions. 2003 Feb; 143-144(?):107-17. doi: 10.1016/s0009-2797(02)00185-0. [PMID: 12604195]
  • Wojciech Łuczaj, Elzbieta Skrzydlewska. DNA damage caused by lipid peroxidation products. Cellular & molecular biology letters. 2003; 8(2):391-413. doi: ". [PMID: 12813574]
  • Linda S Von Tungeln, Ping Yi, Thomas J Bucci, Victor M Samokyszyn, Ming W Chou, Fred F Kadlubar, Peter P Fu. Tumorigenicity of chloral hydrate, trichloroacetic acid, trichloroethanol, malondialdehyde, 4-hydroxy-2-nonenal, crotonaldehyde, and acrolein in the B6C3F(1) neonatal mouse. Cancer letters. 2002 Nov; 185(1):13-9. doi: 10.1016/s0304-3835(02)00231-8. [PMID: 12142074]
  • Frank R Fontaine, Rachael A Dunlop, Dennis R Petersen, Philip C Burcham. Oxidative bioactivation of crotyl alcohol to the toxic endogenous aldehyde crotonaldehyde: association of protein carbonylation with toxicity in mouse hepatocytes. Chemical research in toxicology. 2002 Aug; 15(8):1051-8. doi: 10.1021/tx0255119. [PMID: 12184789]
  • Jishen Pan, Fung-Lung Chung. Formation of cyclic deoxyguanosine adducts from omega-3 and omega-6 polyunsaturated fatty acids under oxidative conditions. Chemical research in toxicology. 2002 Mar; 15(3):367-72. doi: 10.1021/tx010136q. [PMID: 11896684]
  • R A Dick, M K Kwak, T R Sutter, T W Kensler. Antioxidative function and substrate specificity of NAD(P)H-dependent alkenal/one oxidoreductase. A new role for leukotriene B4 12-hydroxydehydrogenase/15-oxoprostaglandin 13-reductase. The Journal of biological chemistry. 2001 Nov; 276(44):40803-10. doi: 10.1074/jbc.m105487200. [PMID: 11524419]
  • K Satoh, M Hayakari, K Ookawa, M Satou, S Aizawa, M Tanaka, I Hatayama, S Tsuchida, K Uchida. Lipid peroxidation end products-responded induction of a preneoplastic marker enzyme glutathione S-transferase P-form (GST-P) in rat liver on admistration via the portal vein. Mutation research. 2001 Nov; 483(1-2):65-72. doi: 10.1016/s0027-5107(01)00225-1. [PMID: 11600134]
  • K Ichihashi, T Osawa, S Toyokuni, K Uchida. Endogenous formation of protein adducts with carcinogenic aldehydes: implications for oxidative stress. The Journal of biological chemistry. 2001 Jun; 276(26):23903-13. doi: 10.1074/jbc.m101947200. [PMID: 11283024]
  • I Miwa, N Ichimura, M Sugiura, Y Hamada, S Taniguchi. Inhibition of glucose-induced insulin secretion by 4-hydroxy-2-nonenal and other lipid peroxidation products. Endocrinology. 2000 Aug; 141(8):2767-72. doi: 10.1210/endo.141.8.7614. [PMID: 10919261]
  • S Srivastava, S J Watowich, J M Petrash, S K Srivastava, A Bhatnagar. Structural and kinetic determinants of aldehyde reduction by aldose reductase. Biochemistry. 1999 Jan; 38(1):42-54. doi: 10.1021/bi981794l. [PMID: 9890881]
  • F L Chung, L Zhang, J E Ocando, R G Nath. Role of 1,N2-propanodeoxyguanosine adducts as endogenous DNA lesions in rodents and humans. IARC scientific publications. 1999; ?(150):45-54. doi: . [PMID: 10626207]
  • K Yang, J L Fang, D Li, F L Chung, K Hemminki. 32P-postlabelling with high-performance liquid chromatography for analysis of abundant DNA adducts in human tissues. IARC scientific publications. 1999; ?(150):205-17. doi: . [PMID: 10626222]
  • D R Doerge, P Yi, M I Churchwell, S W Preece, J Langridge, P P Fu. Mass spectrometric analysis of 2-deoxyribonucleoside and 2'-deoxyribonucleotide adducts with aldehydes derived from lipid peroxidation. Rapid communications in mass spectrometry : RCM. 1998; 12(22):1665-72. doi: 10.1002/(sici)1097-0231(19981130)12:22<1665::aid-rcm384>3.0.co;2-8. [PMID: 9853382]
  • E Eder, Budiawan, D Schuler, M Otteneder. Assessment of the tumor-initiating potential of alpha, beta-unsaturated carbonyl compounds by 32P postlabeling quantification of DNA adducts in vivo. Recent results in cancer research. Fortschritte der Krebsforschung. Progres dans les recherches sur le cancer. 1997; 143(?):65-75. doi: 10.1007/978-3-642-60393-8_5. [PMID: 8912412]
  • R G Nath, J E Ocando, F L Chung. Detection of 1, N2-propanodeoxyguanosine adducts as potential endogenous DNA lesions in rodent and human tissues. Cancer research. 1996 Feb; 56(3):452-6. doi: NULL. [PMID: 8564951]
  • A van der Vliet, C E Cross, B Halliwell, C A O'Neill. Plasma protein sulfhydryl oxidation: effect of low molecular weight thiols. Methods in enzymology. 1995; 251(?):448-55. doi: 10.1016/0076-6879(95)51148-2. [PMID: 7651226]
  • H J Chen, F L Chung. Formation of etheno adducts in reactions of enals via autoxidation. Chemical research in toxicology. 1994 Nov; 7(6):857-60. doi: 10.1021/tx00042a021. [PMID: 7696543]
  • R G Nath, F L Chung. Detection of exocyclic 1,N2-propanodeoxyguanosine adducts as common DNA lesions in rodents and humans. Proceedings of the National Academy of Sciences of the United States of America. 1994 Aug; 91(16):7491-5. doi: 10.1073/pnas.91.16.7491. [PMID: 8052609]
  • M Benamira, L J Marnett. The lipid peroxidation product 4-hydroxynonenal is a potent inducer of the SOS response. Mutation research. 1992 Nov; 293(1):1-10. doi: 10.1016/0921-8777(92)90002-k. [PMID: 1383804]
  • K O Cooper, G Witz, C M Witmer. Mutagenicity and toxicity studies of several alpha,beta-unsaturated aldehydes in the Salmonella typhimurium mutagenicity assay. Environmental mutagenesis. 1987; 9(3):289-95. doi: 10.1002/em.2860090308. [PMID: 3552648]
  • G Witz, N J Lawrie, M A Amoruso, B D Goldstein. Inhibition by reactive aldehydes of superoxide anion radical production in stimulated human neutrophils. Chemico-biological interactions. 1985 Feb; 53(1-2):13-23. doi: 10.1016/s0009-2797(85)80080-6. [PMID: 2986857]
  • M Warholm, B Holmberg, J Högberg, T Kronevi, A Götharson. The acute effects of single and repeated injections of acrolein and other aldehydes. International journal of tissue reactions. 1984; 6(1):61-70. doi: . [PMID: 6715120]
  • A Baĭnova, N Madzhunov. [Quantitative determination of the irritating effect on human skin of butanol, octanol, acetaldehyde and crotonaldehyde]. Problemi na khigienata. 1984; 9(?):66-72. doi: ". [PMID: 6237358]