2-Nonenal, 4-oxo- (BioDeep_00000173400)
human metabolite blood metabolite
代谢物信息卡片
2-Nonenal, 4-oxo-
化学式: C9H14O2 (154.09937440000002)
中文名称:
谱图信息:
最多检出来源 Bos taurus(blood) 52.17%
分子结构信息
SMILES: CCCCCC(=O)C=CC=O
InChI: InChI=1S/C9H14O2/c1-2-3-4-6-9(11)7-5-8-10/h5,7-8H,2-4,6H2,1H3
数据库引用编号
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)
2 个相关的物种来源信息
- 9606 - Homo sapiens: -
- 9606 - Homo sapiens: 10.1038/NBT.2488
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
- Rafael Pineda-Alemán, Camila Cabarcas-Herrera, Antistio Alviz-Amador, Rodrigo Galindo-Murillo, Humberto Pérez-Gonzalez, Erika Rodríguez-Cavallo, Darío Méndez-Cuadro. Molecular dynamics of structural effects of reactive carbonyl species derivate of lipid peroxidation on bovine serum albumin.
Biochimica et biophysica acta. General subjects.
2024 Jun; 1868(6):130613. doi:
10.1016/j.bbagen.2024.130613. [PMID: 38593934] - Rafael Pineda-Alemán, Camila Cabarcas-Herrera, Antistio Alviz-Amador, Humberto Pérez-Gonzalez, Erika Rodríguez-Cavallo, Darío Méndez-Cuadro. Synthesizing Amino Acids Modified with Reactive Carbonyls in Silico to Assess Structural Effects Using Molecular Dynamics Simulations.
Journal of visualized experiments : JoVE.
2024 Apr; ?(206):. doi:
10.3791/66605. [PMID: 38738901] - Tie Wang, Weijin Liu, Qidi Zhang, Jie Jiao, Zihao Wang, Ge Gao, Hui Yang. 4-Oxo-2-Nonenal- and Agitation-Induced Aggregates of α-Synuclein and Phosphorylated α-Synuclein with Distinct Biophysical Properties and Biomedical Applications.
Cells.
2024 Apr; 13(9):. doi:
10.3390/cells13090739. [PMID: 38727274] - Camilla B Andersen, Astrid K Lausdahl, Janni Nielsen, Mathias P Clausen, Frans A A Mulder, Daniel E Otzen, Eva C Arnspang. 4-Oxo-2-nonenal-Induced α-Synuclein Oligomers Interact with Membranes in the Cell, Leading to Mitochondrial Fragmentation.
Biochemistry.
2023 08; 62(16):2417-2425. doi:
10.1021/acs.biochem.3c00114. [PMID: 37487228] - Loren Klein, Dennis Phillips, Fanbin Kong, Brian Bowker, Anand Mohan. 4-Oxo-2-nonenal (4-ONE)-Induced Degradation of Bovine Skeletal Muscle Proteins.
Journal of agricultural and food chemistry.
2022 Oct; 70(39):12641-12650. doi:
10.1021/acs.jafc.2c05550. [PMID: 36129340] - Jennifer S Strehse, Daniel Hoffmann, Nikolaos Protopapas, Hans-Jörg Martin, Edmund Maser. Carbonyl reduction of 4-oxonon-2-enal (4-ONE) by Sniffer from D. magna and D.pulex.
Chemico-biological interactions.
2022 Feb; 354(?):109833. doi:
10.1016/j.cbi.2022.109833. [PMID: 35085582] - Camilla Andersen, Anne Louise Grønnemose, Jannik N Pedersen, Jan S Nowak, Gunna Christiansen, Janni Nielsen, Frans A A Mulder, Daniel Erik Otzen, Thomas J D Jørgensen. Lipid Peroxidation Products HNE and ONE Promote and Stabilize Alpha-Synuclein Oligomers by Chemical Modifications.
Biochemistry.
2021 11; 60(47):3644-3658. doi:
10.1021/acs.biochem.1c00478. [PMID: 34730940] - Linda S May-Zhang, Valery Yermalitsky, John T Melchior, Jamie Morris, Keri A Tallman, Mark S Borja, Tiffany Pleasent, Venkataraman Amarnath, Wenliang Song, Patricia G Yancey, W Sean Davidson, MacRae F Linton, Sean S Davies. Modified sites and functional consequences of 4-oxo-2-nonenal adducts in HDL that are elevated in familial hypercholesterolemia.
The Journal of biological chemistry.
2019 12; 294(50):19022-19033. doi:
10.1074/jbc.ra119.009424. [PMID: 31666337] - Seon Hwa Lee, Shuhei Fujioka, Ryo Takahashi, Tomoyuki Oe. Angiotensin II-Induced Oxidative Stress in Human Endothelial Cells: Modification of Cellular Molecules through Lipid Peroxidation.
Chemical research in toxicology.
2019 07; 32(7):1412-1422. doi:
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Food chemistry.
2018 Feb; 240(?):822-830. doi:
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Molecular & cellular proteomics : MCP.
2017 10; 16(10):1789-1800. doi:
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Free radical biology & medicine.
2017 09; 110(?):421-431. doi:
10.1016/j.freeradbiomed.2017.07.004. [PMID: 28690195] - Eşref Demir, Ricard Marcos. Assessing the genotoxic effects of two lipid peroxidation products (4-oxo-2-nonenal and 4-hydroxy-hexenal) in haemocytes and midgut cells of Drosophila melanogaster larvae.
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2017 Jul; 105(?):1-7. doi:
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Chemical research in toxicology.
2017 03; 30(3):840-850. doi:
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2017 Jan; 8(5):8173-8188. doi:
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ACS chemical biology.
2017 01; 12(1):47-51. doi:
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Free radical biology & medicine.
2015 Dec; 89(?):1067-76. doi:
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Chemical research in toxicology.
2015 Oct; 28(10):1888-90. doi:
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Chemico-biological interactions.
2015 Jun; 234(?):261-73. doi:
10.1016/j.cbi.2014.12.028. [PMID: 25559856] - Christopher D Aluise, Jeannie M Camarillo, Yuki Shimozu, James J Galligan, Kristie L Rose, Keri A Tallman, Lawrence J Marnett. Site-specific, intramolecular cross-linking of Pin1 active site residues by the lipid electrophile 4-oxo-2-nonenal.
Chemical research in toxicology.
2015 Apr; 28(4):817-27. doi:
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FASEB journal : official publication of the Federation of American Societies for Experimental Biology.
2015 Jan; 29(1):263-73. doi:
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Journal of the American Chemical Society.
2014 Aug; 136(34):11864-6. doi:
10.1021/ja503604t. [PMID: 25099620] - James J Galligan, Kristofer S Fritz, Donald S Backos, Colin T Shearn, Rebecca L Smathers, Hua Jiang, Kenneth N MacLean, Philip R Reigan, Dennis R Petersen. Oxidative stress-mediated aldehyde adduction of GRP78 in a mouse model of alcoholic liver disease: functional independence of ATPase activity and chaperone function.
Free radical biology & medicine.
2014 Aug; 73(?):411-20. doi:
10.1016/j.freeradbiomed.2014.06.002. [PMID: 24924946] - Laura Bertoletti, Luca Regazzoni, Alessandra Altomare, Raffaella Colombo, Mara Colzani, Giulio Vistoli, Loredana Marchese, Marina Carini, Ersilia De Lorenzi, Giancarlo Aldini. Advanced glycation end products of beta2-microglobulin in uremic patients as determined by high resolution mass spectrometry.
Journal of pharmaceutical and biomedical analysis.
2014 Mar; 91(?):193-201. doi:
10.1016/j.jpba.2013.12.021. [PMID: 24469019] - Simona G Codreanu, Jody C Ullery, Jing Zhu, Keri A Tallman, William N Beavers, Ned A Porter, Lawrence J Marnett, Bing Zhang, Daniel C Liebler. Alkylation damage by lipid electrophiles targets functional protein systems.
Molecular & cellular proteomics : MCP.
2014 Mar; 13(3):849-59. doi:
10.1074/mcp.m113.032953. [PMID: 24429493] - Rosario Zamora, Esmeralda Alcón, Francisco J Hidalgo. Effect of amino acids on the formation of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) in creatinine/phenylalanine and creatinine/phenylalanine/4-oxo-2-nonenal reaction mixtures.
Food chemistry.
2013 Dec; 141(4):4240-5. doi:
10.1016/j.foodchem.2013.06.036. [PMID: 23993611] - Satoshi Endo, Toshiyuki Matsunaga, Atsuko Matsumoto, Yuki Arai, Satoshi Ohno, Ossama El-Kabbani, Kazuo Tajima, Yasuo Bunai, Shigeru Yamano, Akira Hara, Yukio Kitade. Rabbit 3-hydroxyhexobarbital dehydrogenase is a NADPH-preferring reductase with broad substrate specificity for ketosteroids, prostaglandin D₂, and other endogenous and xenobiotic carbonyl compounds.
Biochemical pharmacology.
2013 Nov; 86(9):1366-75. doi:
10.1016/j.bcp.2013.08.024. [PMID: 23994167] - Rosario Zamora, Esmeralda Alcón, Francisco J Hidalgo. Strecker-type degradation of phenylalanine initiated by 4-oxo-2-alkenals in comparison to that initiated by 2,4-alkadienals, 4,5-epoxy-2-alkenals, or 4-hydroxy-2-nonenal.
Journal of agricultural and food chemistry.
2013 Oct; 61(43):10231-7. doi:
10.1021/jf305007y. [PMID: 23360317] - Kazuaki Kawai, Yuya Kawasaki, Yumiko Kubota, Tomoyuki Kimura, Ryuichi Sawa, Tomonari Matsuda, Hiroshi Kasai. Identification of octenal-related dA and dC adducts formed by reactions with a hemin-ω-6-fat peroxidation model system.
Chemical research in toxicology.
2013 Oct; 26(10):1554-60. doi:
10.1021/tx400245a. [PMID: 24032558] - Rosario Zamora, Esmeralda Alcón, Francisco J Hidalgo. Comparative formation of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) in creatinine/phenylalanine and creatinine/phenylalanine/4-oxo-2-nonenal reaction mixtures.
Food chemistry.
2013 May; 138(1):180-5. doi:
10.1016/j.foodchem.2012.09.116. [PMID: 23265474] - 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] - Satoshi Endo, Airi Fujimoto, Sho Kumada, Toshiyuki Matsunaga, Satoshi Ohno, Jun'ichi Mano, Kazuo Tajima, Ossama El-Kabbani, Akira Hara. Modulation of activity and inhibitor sensitivity of rabbit aldose reductase-like protein (AKR1B19) by oxidized glutathione and SH-reagents.
Chemico-biological interactions.
2013 Feb; 202(1-3):146-52. doi:
10.1016/j.cbi.2012.11.026. [PMID: 23261715] - Seon Hwa Lee. [Oxidative stress-mediated chemical modifications to biomacromolecules: mechanism and implication of modifications to human skin keratins and angiotensin II].
Yakugaku zasshi : Journal of the Pharmaceutical Society of Japan.
2013; 133(10):1055-63. doi:
10.1248/yakushi.13-00176. [PMID: 24088349] - Miho Chikazawa, Natsuki Otaki, Takahiro Shibata, Takehiko Yasueda, Tsukasa Matsuda, Koji Uchida. An apoptosis-associated mammary protein deficiency leads to enhanced production of IgM antibodies against multiple damage-associated molecules.
PloS one.
2013; 8(7):e68468. doi:
10.1371/journal.pone.0068468. [PMID: 23874637] - Rosario Zamora, Esmeralda Alcón, Francisco J Hidalgo. Effect of lipid oxidation products on the formation of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP) in model systems.
Food chemistry.
2012 Dec; 135(4):2569-74. doi:
10.1016/j.foodchem.2012.06.062. [PMID: 22980844] - Jessica M Curtis, Wendy S Hahn, Matthew D Stone, Jacob J Inda, David J Droullard, Jovan P Kuzmicic, Margaret A Donoghue, Eric K Long, Anibal G Armien, Sergio Lavandero, Edgar Arriaga, Timothy J Griffin, David A Bernlohr. Protein carbonylation and adipocyte mitochondrial function.
The Journal of biological chemistry.
2012 Sep; 287(39):32967-80. doi:
10.1074/jbc.m112.400663. [PMID: 22822087] - Lilu Guo, Zhongyi Chen, Venkataraman Amarnath, Sean S Davies. Identification of novel bioactive aldehyde-modified phosphatidylethanolamines formed by lipid peroxidation.
Free radical biology & medicine.
2012 Sep; 53(6):1226-38. doi:
10.1016/j.freeradbiomed.2012.07.077. [PMID: 22898174] - Rosario Zamora, Rosa M Delgado, Francisco J Hidalgo. Chemical conversion of phenylethylamine into phenylacetaldehyde by carbonyl-amine reactions in model systems.
Journal of agricultural and food chemistry.
2012 May; 60(21):5491-6. doi:
10.1021/jf301258s. [PMID: 22578256] - James J Galligan, Rebecca L Smathers, Kristofer S Fritz, L E Epperson, Lawrence E Hunter, Dennis R Petersen. Protein carbonylation in a murine model for early alcoholic liver disease.
Chemical research in toxicology.
2012 May; 25(5):1012-21. doi:
10.1021/tx300002q. [PMID: 22502949] - Qingling Li, Kristyen Tomcik, Shenghui Zhang, Michelle A Puchowicz, Guo-Fang Zhang. Dietary regulation of catabolic disposal of 4-hydroxynonenal analogs in rat liver.
Free radical biology & medicine.
2012 Mar; 52(6):1043-53. doi:
10.1016/j.freeradbiomed.2011.12.022. [PMID: 22245097] - Xiaodong Gu, Robert G Salomon. Fragmentation of a linoleate-derived γ-hydroperoxy-α,β-unsaturated epoxide to γ-hydroxy- and γ-oxo-alkenals involves a unique pseudo-symmetrical diepoxycarbinyl radical.
Free radical biology & medicine.
2012 Feb; 52(3):601-606. doi:
10.1016/j.freeradbiomed.2011.11.013. [PMID: 22155057] - Sung Young Kim, Sang Chul Park. Physiological antioxidative network of the bilirubin system in aging and age-related diseases.
Frontiers in pharmacology.
2012; 3(?):45. doi:
10.3389/fphar.2012.00045. [PMID: 22457648] - Hitomi Okada, Yuji Naito, Tomohisa Takagi, Megumi Takaoka, Tomoko Oya-Ito, Kohei Fukumoto, Kazuhiko Uchiyama, Osamu Handa, Satoshi Kokura, Yumiko Nagano, Hirofumi Matsui, Yoji Kato, Toshihiko Osawa, Toshikazu Yoshikawa. Detection of N-(hexanoyl)lysine in the tropomyosin 1 protein in N-methyl-N'-nitro-N-nitrosoguanidine-induced rat gastric cancer cells.
Journal of clinical biochemistry and nutrition.
2012 Jan; 50(1):47-52. doi:
10.3164/jcbn.11-39. [PMID: 22247600] - Rebecca L Smathers, Kristofer S Fritz, James J Galligan, Colin T Shearn, Philip Reigan, Michael J Marks, Dennis R Petersen. Characterization of 4-HNE modified L-FABP reveals alterations in structural and functional dynamics.
PloS one.
2012; 7(6):e38459. doi:
10.1371/journal.pone.0038459. [PMID: 22701647] - 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] - N Speed, I A Blair. Cyclooxygenase- and lipoxygenase-mediated DNA damage.
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2011 Dec; 30(3-4):437-47. doi:
10.1007/s10555-011-9298-8. [PMID: 22009064] - Juan D Chavez, Jianyong Wu, William Bisson, Claudia S Maier. Site-specific proteomic analysis of lipoxidation adducts in cardiac mitochondria reveals chemical diversity of 2-alkenal adduction.
Journal of proteomics.
2011 Oct; 74(11):2417-29. doi:
10.1016/j.jprot.2011.03.031. [PMID: 21513823] - Satoshi Endo, Toshiyuki Matsunaga, Anna Fujita, Tsukasa Kuragano, Midori Soda, Krithika Sundaram, Urmi Dhagat, Kazuo Tajima, Ossama El-Kabbani, Akira Hara. Activation of aldo-keto reductase family member 1B14 (AKR1B14) by bile acids: Activation mechanism and bile acid-binding site.
Biochimie.
2011 Sep; 93(9):1476-86. doi:
10.1016/j.biochi.2011.04.022. [PMID: 21586312] - Hans-Jörg Martin, Marta Ziemba, Michael Kisiela, José A Botella, Stephan Schneuwly, Edmund Maser. The Drosophila carbonyl reductase sniffer is an efficient 4-oxonon-2-enal (4ONE) reductase.
Chemico-biological interactions.
2011 May; 191(1-3):48-54. doi:
10.1016/j.cbi.2010.12.006. [PMID: 21167142] - André Moreira Neto Silva, Ana Carolina Borralho, Sónia Andreia Pinho, M Rosário M Domingues, Pedro Domingues. Cross-oxidation of angiotensin II by glycerophosphatidylcholine oxidation products.
Rapid communications in mass spectrometry : RCM.
2011 May; 25(10):1413-21. doi:
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Chemical research in toxicology.
2011 Mar; 24(3):357-70. doi:
10.1021/tx100323m. [PMID: 21291287] - Tahira Farooqui, Akhlaq A Farooqui. Lipid-mediated oxidative stress and inflammation in the pathogenesis of Parkinson's disease.
Parkinson's disease.
2011 Feb; 2011(?):247467. doi:
10.4061/2011/247467. [PMID: 21403820] - Heather C Kuiper, Jan F Stevens. LC-MS/MS quantitation of mercapturic acid conjugates of lipid peroxidation products as markers of oxidative stress.
Current protocols in toxicology.
2011 Feb; Chapter 17(?):Unit17.14.2. doi:
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Free radical biology & medicine.
2011 Feb; 50(3):428-37. doi:
10.1016/j.freeradbiomed.2010.11.027. [PMID: 21130160] - Matthew J Picklo, Alexander Azenkeng, Mark R Hoffmann. Trans-4-oxo-2-nonenal potently alters mitochondrial function.
Free radical biology & medicine.
2011 Jan; 50(2):400-7. doi:
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Journal of nucleic acids.
2010 Dec; 2010(?):929047. doi:
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Molecular and cellular biochemistry.
2010 Dec; 345(1-2):91-104. doi:
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Toxicology and applied pharmacology.
2010 Dec; 249(2):127-31. doi:
10.1016/j.taap.2010.08.025. [PMID: 20816884] - Seon Hwa Lee, Ryo Takahashi, Takaaki Goto, Tomoyuki Oe. Mass spectrometric characterization of modifications to angiotensin II by lipid peroxidation products, 4-oxo-2(E)-nonenal and 4-hydroxy-2(E)-nonenal.
Chemical research in toxicology.
2010 Nov; 23(11):1771-85. doi:
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Journal of proteome research.
2010 Nov; 9(11):5887-95. doi:
10.1021/pr100643m. [PMID: 20857983] - 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] - Pei-Hsin Chou, Shinji Kageyama, Shun Matsuda, Keishi Kanemoto, Yoshiaki Sasada, Megumi Oka, Kazuya Shinmura, Hiroki Mori, Kazuaki Kawai, Hiroshi Kasai, Haruhiko Sugimura, Tomonari Matsuda. Detection of lipid peroxidation-induced DNA adducts caused by 4-oxo-2(E)-nonenal and 4-oxo-2(E)-hexenal in human autopsy tissues.
Chemical research in toxicology.
2010 Sep; 23(9):1442-8. doi:
10.1021/tx100047d. [PMID: 20849149] - Plamen P Christov, Katya V Petrova, Ganesh Shanmugam, Ivan D Kozekov, Albena Kozekova, F Peter Guengerich, Michael P Stone, Carmelo J Rizzo. Comparison of the in vitro replication of the 7-(2-oxoheptyl)-1,N2-etheno-2'-deoxyguanosine and 1,N2-etheno-2'-deoxyguanosine lesions by Sulfolobus solfataricus P2 DNA polymerase IV (Dpo4).
Chemical research in toxicology.
2010 Aug; 23(8):1330-41. doi:
10.1021/tx100082e. [PMID: 20578729] - Satoshi Endo, Toshiyuki Matsunaga, Anna Fujita, Kazuo Tajima, Ossama El-Kabbani, Akira Hara. Rat aldose reductase-like protein (AKR1B14) efficiently reduces the lipid peroxidation product 4-oxo-2-nonenal.
Biological & pharmaceutical bulletin.
2010; 33(11):1886-90. doi:
10.1248/bpb.33.1886. [PMID: 21048316] - Heather C Kuiper, Brandi L Langsdorf, Cristobal L Miranda, Jacqueline Joss, Carole Jubert, John E Mata, Jan F Stevens. Quantitation of mercapturic acid conjugates of 4-hydroxy-2-nonenal and 4-oxo-2-nonenal metabolites in a smoking cessation study.
Free radical biology & medicine.
2010 Jan; 48(1):65-72. doi:
10.1016/j.freeradbiomed.2009.10.025. [PMID: 19819328] - Fumie Saito, Satoshi Iwamoto, Ryo Yamauchi. Reaction products of gamma-tocopherol with (E)-4-oxo-2-nonenal in acidic acetonitrile.
Bioscience, biotechnology, and biochemistry.
2010; 74(1):168-74. doi:
10.1271/bbb.90681. [PMID: 20057122] - Peijuan Zhu, Wenying Jian, Ian A Blair. A 4-oxo-2(E)-nonenal-derived glutathione adduct from 15-lipoxygenase-1-mediated oxidation of cytosolic and esterified arachidonic acid.
Free radical biology & medicine.
2009 Oct; 47(7):953-61. doi:
10.1016/j.freeradbiomed.2009.06.035. [PMID: 19576981] - Beata Janowska, Marek Komisarski, Paulina Prorok, Beata Sokołowska, Jarosław Kuśmierek, Celina Janion, Barbara Tudek. Nucleotide excision repair and recombination are engaged in repair of trans-4-hydroxy-2-nonenal adducts to DNA bases in Escherichia coli.
International journal of biological sciences.
2009 Sep; 5(6):611-20. doi:
10.7150/ijbs.5.611. [PMID: 19834545] - Satoru Sakuma, Hiromi Sumi, Tetsuya Kohda, Yukio Arakawa, Yohko Fujimoto. Effects of Lipid Peroxidation-Derived Products on the Growth of Human Colorectal Cancer Cell Line HT-29.
Journal of clinical biochemistry and nutrition.
2009 Sep; 45(2):171-7. doi:
10.3164/jcbn.09-09. [PMID: 19794925] - Benjamin J Stewart, James R Roede, Jonathan A Doorn, Dennis R Petersen. Lipid aldehyde-mediated cross-linking of apolipoprotein B-100 inhibits secretion from HepG2 cells.
Biochimica et biophysica acta.
2009 Aug; 1791(8):772-80. doi:
10.1016/j.bbalip.2009.04.004. [PMID: 19393338] - Xiaochun Zhu, Xiaoxia Tang, Vernon E Anderson, Lawrence M Sayre. Mass spectrometric characterization of protein modification by the products of nonenzymatic oxidation of linoleic acid.
Chemical research in toxicology.
2009 Aug; 22(8):1386-97. doi:
10.1021/tx9000072. [PMID: 19537826] - Wenying Jian, Seon Hwa Lee, Michelle V Williams, Ian A Blair. 5-Lipoxygenase-mediated endogenous DNA damage.
The Journal of biological chemistry.
2009 Jun; 284(25):16799-16807. doi:
10.1074/jbc.m109.011841. [PMID: 19390118] - Xiaochun Zhu, Molly M Gallogly, John J Mieyal, Vernon E Anderson, Lawrence M Sayre. Covalent cross-linking of glutathione and carnosine to proteins by 4-oxo-2-nonenal.
Chemical research in toxicology.
2009 Jun; 22(6):1050-9. doi:
10.1021/tx9000144. [PMID: 19480392] - Yuuki Shimozu, Takahiro Shibata, Makoto Ojika, Koji Uchida. Identification of advanced reaction products originating from the initial 4-oxo-2-nonenal-cysteine Michael adducts.
Chemical research in toxicology.
2009 May; 22(5):957-64. doi:
10.1021/tx900059k. [PMID: 19368367] - Simona G Codreanu, Bing Zhang, Scott M Sobecki, Dean D Billheimer, Daniel C Liebler. Global analysis of protein damage by the lipid electrophile 4-hydroxy-2-nonenal.
Molecular & cellular proteomics : MCP.
2009 Apr; 8(4):670-80. doi:
10.1074/mcp.m800070-mcp200. [PMID: 19054759] - Hans-Jörg Martin, Edmund Maser. Role of human aldo-keto-reductase AKR1B10 in the protection against toxic aldehydes.
Chemico-biological interactions.
2009 Mar; 178(1-3):145-50. doi:
10.1016/j.cbi.2008.10.021. [PMID: 19013440] - Rajaraman Kanagasabai, Kothandaraman Narasimhan, Hong-Sang Low, Wee Tiong Ang, Aaron Z Fernandis, Markus R Wenk, Mahesh A Choolani, Christopher J O Baker. Mining to find the lipid interaction networks involved in Ovarian Cancers.
Summit on translational bioinformatics.
2009 Mar; 2009(?):61-5. doi:
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Journal of neurochemistry.
2009 Mar; 108(6):1434-41. doi:
10.1111/j.1471-4159.2009.05883.x. [PMID: 19183271] - Charles G Knutson, Emily H Rubinson, Dapo Akingbade, Carolyn S Anderson, Donald F Stec, Katya V Petrova, Ivan D Kozekov, F Peter Guengerich, Carmelo J Rizzo, Lawrence J Marnett. Oxidation and glycolytic cleavage of etheno and propano DNA base adducts.
Biochemistry.
2009 Feb; 48(4):800-9. doi:
10.1021/bi801654j. [PMID: 19132922] - Tomas Näsström, Therese Wahlberg, Mikael Karlsson, Fredrik Nikolajeff, Lars Lannfelt, Martin Ingelsson, Joakim Bergström. The lipid peroxidation metabolite 4-oxo-2-nonenal cross-links alpha-synuclein causing rapid formation of stable oligomers.
Biochemical and biophysical research communications.
2009 Jan; 378(4):872-6. doi:
10.1016/j.bbrc.2008.12.005. [PMID: 19070597] - Seon Hwa Lee, Takaaki Goto, Tomoyuki Oe. A novel 4-oxo-2(E)-nonenal-derived modification to angiotensin II: oxidative decarboxylation of N-terminal aspartic acid.
Chemical research in toxicology.
2008 Dec; 21(12):2237-44. doi:
10.1021/tx800316v. [PMID: 19548347] - Matthew E Szapacs, Hye-Young H Kim, Ned A Porter, Daniel C Liebler. Identification of proteins adducted by lipid peroxidation products in plasma and modifications of apolipoprotein A1 with a novel biotinylated phospholipid probe.
Journal of proteome research.
2008 Oct; 7(10):4237-46. doi:
10.1021/pr8001222. [PMID: 18778096] - Encarnación Goicoechea, Klaas Van Twillert, Menno Duits, Esther D F A Brandon, Peter R Kootstra, Marco H Blokland, María D Guillén. Use of an in vitro digestion model to study the bioaccessibility of 4-hydroxy-2-nonenal and related aldehydes present in oxidized oils rich in omega-6 acyl groups.
Journal of agricultural and food chemistry.
2008 Sep; 56(18):8475-83. doi:
10.1021/jf801212k. [PMID: 18729379] - Ganesh Shanmugam, Ivan D Kozekov, F Peter Guengerich, Carmelo J Rizzo, Michael P Stone. Structure of the 1,N2-ethenodeoxyguanosine adduct opposite cytosine in duplex DNA: Hoogsteen base pairing at pH 5.2.
Chemical research in toxicology.
2008 Sep; 21(9):1795-805. doi:
10.1021/tx8001466. [PMID: 18693701] - Colin T Shearn, Kristofer S Fritz, Brent W Meier, Oleg V Kirichenko, John A Thompson. Carbonyl reductase inactivation may contribute to mouse lung tumor promotion by electrophilic metabolites of butylated hydroxytoluene: protein alkylation in vivo and in vitro.
Chemical research in toxicology.
2008 Aug; 21(8):1631-41. doi:
10.1021/tx800162p. [PMID: 18597497] - T E Taylor-Clark, M A McAlexander, C Nassenstein, S A Sheardown, S Wilson, J Thornton, M J Carr, B J Undem. Relative contributions of TRPA1 and TRPV1 channels in the activation of vagal bronchopulmonary C-fibres by the endogenous autacoid 4-oxononenal.
The Journal of physiology.
2008 Jul; 586(14):3447-59. doi:
10.1113/jphysiol.2008.153585. [PMID: 18499726] - Heather C Kuiper, Cristobal L Miranda, John D Sowell, Jan F Stevens. Mercapturic acid conjugates of 4-hydroxy-2-nonenal and 4-oxo-2-nonenal metabolites are in vivo markers of oxidative stress.
The Journal of biological chemistry.
2008 Jun; 283(25):17131-8. doi:
10.1074/jbc.m802797200. [PMID: 18442969] - David A Andersson, Clive Gentry, Sian Moss, Stuart Bevan. Transient receptor potential A1 is a sensory receptor for multiple products of oxidative stress.
The Journal of neuroscience : the official journal of the Society for Neuroscience.
2008 Mar; 28(10):2485-94. doi:
10.1523/jneurosci.5369-07.2008. [PMID: 18322093] - Peijuan Zhu, Tomoyuki Oe, Ian A Blair. Determination of cellular redox status by stable isotope dilution liquid chromatography/mass spectrometry analysis of glutathione and glutathione disulfide.
Rapid communications in mass spectrometry : RCM.
2008; 22(4):432-40. doi:
10.1002/rcm.3380. [PMID: 18215009] - Kazuyo Toyoda, Ritsuko Nagae, Mitsugu Akagawa, Kosuke Ishino, Takahiro Shibata, Sohei Ito, Noriyuki Shibata, Tomoko Yamamoto, Makio Kobayashi, Yoshinari Takasaki, Tsukasa Matsuda, Koji Uchida. Protein-bound 4-hydroxy-2-nonenal: an endogenous triggering antigen of antI-DNA response.
The Journal of biological chemistry.
2007 Aug; 282(35):25769-78. doi:
10.1074/jbc.m703039200. [PMID: 17588942] - Liang Lu, Penny Erhard, Robert G Salomon, Miriam F Weiss. Serum vitamin E and oxidative protein modification in hemodialysis: a randomized clinical trial.
American journal of kidney diseases : the official journal of the National Kidney Foundation.
2007 Aug; 50(2):305-13. doi:
10.1053/j.ajkd.2007.05.001. [PMID: 17660032] - Benjamin J Stewart, Jonathan A Doorn, Dennis R Petersen. Residue-specific adduction of tubulin by 4-hydroxynonenal and 4-oxononenal causes cross-linking and inhibits polymerization.
Chemical research in toxicology.
2007 Aug; 20(8):1111-9. doi:
10.1021/tx700106v. [PMID: 17630713] - Wenying Jian, Seon Hwa Lee, Clementina Mesaros, Tomoyuki Oe, Maria V Silva Elipe, Ian A Blair. A novel 4-oxo-2(E)-nonenal-derived endogenous thiadiazabicyclo glutathione adduct formed during cellular oxidative stress.
Chemical research in toxicology.
2007 Jul; 20(7):1008-18. doi:
10.1021/tx700001t. [PMID: 17550273] - Michelle V Williams, John S Wishnok, Steven R Tannenbaum. Covalent adducts arising from the decomposition products of lipid hydroperoxides in the presence of cytochrome c.
Chemical research in toxicology.
2007 May; 20(5):767-75. doi:
10.1021/tx600289r. [PMID: 17407328] - Jeffrey D Coleman, K Sandeep Prabhu, Jerry T Thompson, P Sreenivasula Reddy, Jeffrey M Peters, Blake R Peterson, C Channa Reddy, John P Vanden Heuvel. The oxidative stress mediator 4-hydroxynonenal is an intracellular agonist of the nuclear receptor peroxisome proliferator-activated receptor-beta/delta (PPARbeta/delta).
Free radical biology & medicine.
2007 Apr; 42(8):1155-64. doi:
10.1016/j.freeradbiomed.2007.01.003. [PMID: 17382197] - Angela O Choi, Sung Ju Cho, Julie Desbarats, Jasmina Lovrić, Dusica Maysinger. Quantum dot-induced cell death involves Fas upregulation and lipid peroxidation in human neuroblastoma cells.
Journal of nanobiotechnology.
2007 Feb; 5(?):1. doi:
10.1186/1477-3155-5-1. [PMID: 17295922] - Quan Yuan, Xiaochun Zhu, Lawrence M Sayre. Chemical nature of stochastic generation of protein-based carbonyls: metal-catalyzed oxidation versus modification by products of lipid oxidation.
Chemical research in toxicology.
2007 Jan; 20(1):129-39. doi:
10.1021/tx600270f. [PMID: 17226935] - Ian A Blair. Endogenous glutathione adducts.
Current drug metabolism.
2006 Dec; 7(8):853-72. doi:
10.2174/138920006779010601. [PMID: 17168687] - Reshma F Kurangi, Santosh G Tilve, Ian A Blair. Convenient and efficient syntheses of 4-hydroxy-2(E)-nonenal and 4-oxo-2(E)-nonenal.
Lipids.
2006 Sep; 41(9):877-80. doi:
10.1007/s11745-006-5043-4. [PMID: 17152925]