Zebularine (BioDeep_00000624916)

   


代谢物信息卡片


Zebularine

化学式: C9H12N2O5 (228.07461819999997)
中文名称: 泽布拉林
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C1=CN(C(=O)N=C1)C2C(C(C(O2)CO)O)O
InChI: InChI=1S/C9H12N2O5/c12-4-5-6(13)7(14)8(16-5)11-3-1-2-10-9(11)15/h1-3,5-8,12-14H,4H2/t5-,6-,7-,8-/m1/s1

描述信息

C471 - Enzyme Inhibitor > C2083 - DNA Methyltransferase Inhibitor
C274 - Antineoplastic Agent > C132686 - Demethylating Agent
Zebularine (NSC309132; 4-Deoxyuridine) is a DNA methyltransferase inhibitor. Zebularine also inhibits cytidine deaminase with a Ki of 0.95 μM.

同义名列表

3 个代谢物同义名

Zebularine; NSC309132; 4-Deoxyuridine



数据库引用编号

7 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(5)

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

  • Rajat Pant, Shaheen Wasil Kabeer, Shivam Sharma, Vinod Kumar, Debarun Patra, Durba Pal, Kulbhushan Tikoo. Pharmacological inhibition of DNMT1 restores macrophage autophagy and M2 polarization in western diet-induced Nonalcoholic fatty liver disease. The Journal of biological chemistry. 2023 May; ?(?):104779. doi: 10.1016/j.jbc.2023.104779. [PMID: 37142224]
  • Junhua Kong, Virginie Garcia, Enric Zehraoui, Linda Stammitti, Ghislaine Hilbert, Christel Renaud, Stéphane Maury, Alain Delaunay, Stéphanie Cluzet, Fatma Lecourieux, David Lecourieux, Emeline Teyssier, Philippe Gallusci. Zebularine, a DNA Methylation Inhibitor, Activates Anthocyanin Accumulation in Grapevine Cells. Genes. 2022 07; 13(7):. doi: 10.3390/genes13071256. [PMID: 35886036]
  • Klara Prochazkova, Andreas Finke, Eva Dvořák Tomaštíková, Jaroslav Filo, Heinrich Bente, Petr Dvořák, Miroslav Ovečka, Jozef Šamaj, Ales Pecinka. Zebularine induces enzymatic DNA-protein crosslinks in 45S rDNA heterochromatin of Arabidopsis nuclei. Nucleic acids research. 2022 01; 50(1):244-258. doi: 10.1093/nar/gkab1218. [PMID: 34904670]
  • David Roquis, Marta Robertson, Liang Yu, Michael Thieme, Magdalena Julkowska, Etienne Bucher. Genomic impact of stress-induced transposable element mobility in Arabidopsis. Nucleic acids research. 2021 10; 49(18):10431-10447. doi: 10.1093/nar/gkab828. [PMID: 34551439]
  • Mingtan Tang, Lina Lozano Hernandez, Joy N Reginald-Opara, Darren Svirskis, Euphemia Leung, Hongbo Wang, Zimei Wu. Zebularine suppressed gemcitabine-induced senescence and improved the cellular and plasma pharmacokinetics of gemcitabine, augmented by liposomal co-delivery. International journal of pharmaceutics. 2021 Jun; 602(?):120659. doi: 10.1016/j.ijpharm.2021.120659. [PMID: 33933647]
  • Klára Konečná, Pavla Polanská Sováková, Karin Anteková, Jiří Fajkus, Miloslava Fojtová. Distinct Responses of Arabidopsis Telomeres and Transposable Elements to Zebularine Exposure. International journal of molecular sciences. 2021 Jan; 22(1):. doi: 10.3390/ijms22010468. [PMID: 33466545]
  • Patwira Boonjing, Yukari Masuta, Kosuke Nozawa, Atsushi Kato, Hidetaka Ito. The effect of zebularine on the heat-activated retrotransposon ONSEN in Arabidopsis thaliana and Vigna angularis. Genes & genetic systems. 2020 Oct; 95(4):165-172. doi: 10.1266/ggs.19-00046. [PMID: 32741853]
  • Anna Nowicka, Barbara Tokarz, Jana Zwyrtková, Eva Dvořák Tomaštíková, Klára Procházková, Ugur Ercan, Andreas Finke, Wilfried Rozhon, Brigitte Poppenberger, Miroslav Otmar, Igor Niezgodzki, Marcela Krečmerová, Ingo Schubert, Ales Pecinka. Comparative analysis of epigenetic inhibitors reveals different degrees of interference with transcriptional gene silencing and induction of DNA damage. The Plant journal : for cell and molecular biology. 2020 04; 102(1):68-84. doi: 10.1111/tpj.14612. [PMID: 31733119]
  • Michael L Hayes, Paola I Santibanez. A plant pentatricopeptide repeat protein with a DYW-deaminase domain is sufficient for catalyzing C-to-U RNA editing in vitro. The Journal of biological chemistry. 2020 03; 295(11):3497-3505. doi: 10.1074/jbc.ra119.011790. [PMID: 31996373]
  • Pavla Polanská Sováková, Alžbeta Magdolenová, Klára Konečná, Veronika Rájecká, Jiří Fajkus, Miloslava Fojtová. Telomere elongation upon transfer to callus culture reflects the reprogramming of telomere stability control in Arabidopsis. Plant molecular biology. 2018 Sep; 98(1-2):81-99. doi: 10.1007/s11103-018-0765-2. [PMID: 30128721]
  • E Jean Finnegan, Brett Ford, Xiaomei Wallace, Filomena Pettolino, Patrick T Griffin, Robert J Schmitz, Peng Zhang, Jose M Barrero, Matthew J Hayden, Scott A Boden, Colin A Cavanagh, Steve M Swain, Ben Trevaskis. Zebularine treatment is associated with deletion of FT-B1 leading to an increase in spikelet number in bread wheat. Plant, cell & environment. 2018 06; 41(6):1346-1360. doi: 10.1111/pce.13164. [PMID: 29430678]
  • C M Fulkerson, D Dhawan, D R Jones, V E Marquez, P A Jones, Z Wang, Q Wu, J E Klaunig, L M Fourez, P L Bonney, D W Knapp. Pharmacokinetics and toxicity of the novel oral demethylating agent zebularine in laboratory and tumor bearing dogs. Veterinary and comparative oncology. 2017 Mar; 15(1):226-236. doi: 10.1111/vco.12159. [PMID: 26178438]
  • Patrick T Griffin, Chad E Niederhuth, Robert J Schmitz. A Comparative Analysis of 5-Azacytidine- and Zebularine-Induced DNA Demethylation. G3 (Bethesda, Md.). 2016 09; 6(9):2773-80. doi: 10.1534/g3.116.030262. [PMID: 27402357]
  • Xuhui Ma, Qing Wang, Yanzhi Wang, Jieyun Ma, Nan Wu, Shuang Ni, Tengxiao Luo, Lifang Zhuang, Chenggen Chu, Seong-Woo Cho, Hisashi Tsujimoto, Zengjun Qi. Chromosome aberrations induced by zebularine in triticale. Genome. 2016 Jul; 59(7):485-92. doi: 10.1139/gen-2016-0047. [PMID: 27334255]
  • Ramin Khanabdali, Anbarieh Saadat, Maizatul Fazilah, Khairul Fidaa' Khairul Bazli, Rida-e-Maria Qazi, Ramla Sana Khalid, Durriyyah Sharifah Hasan Adli, Soheil Zorofchian Moghadamtousi, Nadia Naeem, Irfan Khan, Asmat Salim, ShamsulAzlin Ahmad Shamsuddin, Gokula Mohan. Promoting effect of small molecules in cardiomyogenic and neurogenic differentiation of rat bone marrow-derived mesenchymal stem cells. Drug design, development and therapy. 2016; 10(?):81-91. doi: 10.2147/dddt.s89658. [PMID: 26766903]
  • Xiaoyan Jia, Bidisha Chanda, Mingzhe Zhao, Amy M Brunner, Eric P Beers. Instability of the Arabidopsis mutant csn5a-2 caused by epigenetic modification of intronic T-DNA. Plant science : an international journal of experimental plant biology. 2015 Sep; 238(?):53-63. doi: 10.1016/j.plantsci.2015.05.015. [PMID: 26259174]
  • Chun-Hsin Liu, Andreas Finke, Mariana Díaz, Wilfried Rozhon, Brigitte Poppenberger, Tuncay Baubec, Ales Pecinka. Repair of DNA Damage Induced by the Cytidine Analog Zebularine Requires ATR and ATM in Arabidopsis. The Plant cell. 2015 Jun; 27(6):1788-800. doi: 10.1105/tpc.114.135467. [PMID: 26023162]
  • Sukhwinder S Aulakh, Richard E Veilleux, Guozhu Tang, Barry S Flinn. Characterization of a potato activation-tagged mutant, nikku, and its partial revertant. Planta. 2015 Jun; 241(6):1481-95. doi: 10.1007/s00425-015-2272-x. [PMID: 25772042]
  • Imad Alkamal, Odiljon Ikromov, Angelika Tölle, Tom Florian Fuller, Ahmed Magheli, Kurt Miller, Hans Krause, Carsten Kempkensteffen. An epigenetic screen unmasks metallothioneins as putative contributors to renal cell carcinogenesis. Urologia internationalis. 2015; 94(1):99-110. doi: 10.1159/000357282. [PMID: 24662736]
  • C Arimany-Nardi, E Errasti-Murugarren, G Minuesa, J Martinez-Picado, V Gorboulev, H Koepsell, M Pastor-Anglada. Nucleoside transporters and human organic cation transporter 1 determine the cellular handling of DNA-methyltransferase inhibitors. British journal of pharmacology. 2014 Aug; 171(16):3868-80. doi: 10.1111/bph.12748. [PMID: 24780098]
  • Mahmoud W Yaish, Mingsheng Peng, Steven J Rothstein. Global DNA methylation analysis using methyl-sensitive amplification polymorphism (MSAP). Methods in molecular biology (Clifton, N.J.). 2014; 1062(?):285-98. doi: 10.1007/978-1-62703-580-4_16. [PMID: 24057373]
  • Henrietta Nittby, Peter Ericsson, Karolina Förnvik, Susanne Strömblad, Linda Jansson, Zhongtian Xue, Gunnar Skagerberg, Bengt Widegren, Hans-Olov Sjögren, Leif G Salford. Zebularine induces long-term survival of pancreatic islet allotransplants in streptozotocin treated diabetic rats. PloS one. 2013; 8(8):e71981. doi: 10.1371/journal.pone.0071981. [PMID: 23991016]
  • Sachiko Arase, Megumi Kasai, Akira Kanazawa. In planta assays involving epigenetically silenced genes reveal inhibition of cytosine methylation by genistein. Plant methods. 2012 Mar; 8(?):10. doi: 10.1186/1746-4811-8-10. [PMID: 22424588]
  • Ben J Tolley, Helen Woodfield, Samart Wanchana, Richard Bruskiewich, Julian M Hibberd. Light-regulated and cell-specific methylation of the maize PEPC promoter. Journal of experimental botany. 2012 Feb; 63(3):1381-90. doi: 10.1093/jxb/err367. [PMID: 22143916]
  • Sunipa Majumdar, Eric Buckles, John Estrada, Shahriar Koochekpour. Aberrant DNA methylation and prostate cancer. Current genomics. 2011 Nov; 12(7):486-505. doi: 10.2174/138920211797904061. [PMID: 22547956]
  • Eva Majerová, Miloslava Fojtová, Iva Mozgová, Miroslava Bittová, Jiří Fajkus. Hypomethylating drugs efficiently decrease cytosine methylation in telomeric DNA and activate telomerase without affecting telomere lengths in tobacco cells. Plant molecular biology. 2011 Nov; 77(4-5):371-80. doi: 10.1007/s11103-011-9816-7. [PMID: 21866390]
  • Andrea M Foerster, Huy Q Dinh, Laura Sedman, Bonnie Wohlrab, Ortrun Mittelsten Scheid. Genetic rearrangements can modify chromatin features at epialleles. PLoS genetics. 2011 Oct; 7(10):e1002331. doi: 10.1371/journal.pgen.1002331. [PMID: 22028669]
  • Elena Synesiou, Lynnette D Fairbanks, H Anne Simmonds, Ewa M Slominska, Ryszard T Smolenski, Elizabeth A Carrey. 4-Pyridone-3-carboxamide-1-β-D-ribonucleoside triphosphate (4PyTP), a novel NAD metabolite accumulating in erythrocytes of uremic children: a biomarker for a toxic NAD analogue in other tissues?. Toxins. 2011 06; 3(6):520-37. doi: 10.3390/toxins3060520. [PMID: 22069723]
  • Marcel Lafos, Phillip Kroll, Mareike L Hohenstatt, Frazer L Thorpe, Oliver Clarenz, Daniel Schubert. Dynamic regulation of H3K27 trimethylation during Arabidopsis differentiation. PLoS genetics. 2011 Apr; 7(4):e1002040. doi: 10.1371/journal.pgen.1002040. [PMID: 21490956]
  • Steven K Huang, Aaron S Fisher, Anne M Scruggs, Eric S White, Cory M Hogaboam, Bruce C Richardson, Marc Peters-Golden. Hypermethylation of PTGER2 confers prostaglandin E2 resistance in fibrotic fibroblasts from humans and mice. The American journal of pathology. 2010 Nov; 177(5):2245-55. doi: 10.2353/ajpath.2010.100446. [PMID: 20889571]
  • Thomas H Dawson. Scaling laws for plasma concentrations and tolerable doses of anticancer drugs. Cancer research. 2010 Jun; 70(12):4801-8. doi: 10.1158/0008-5472.can-09-3261. [PMID: 20530681]
  • Esther M E van Straten, Vincent W Bloks, Nicolette C A Huijkman, Julius F W Baller, Hester van Meer, Dieter Lütjohann, Folkert Kuipers, Torsten Plösch. The liver X-receptor gene promoter is hypermethylated in a mouse model of prenatal protein restriction. American journal of physiology. Regulatory, integrative and comparative physiology. 2010 Feb; 298(2):R275-82. doi: 10.1152/ajpregu.00413.2009. [PMID: 19889862]
  • Tuncay Baubec, Huy Q Dinh, Ales Pecinka, Branislava Rakic, Wilfried Rozhon, Bonnie Wohlrab, Arndt von Haeseler, Ortrun Mittelsten Scheid. Cooperation of multiple chromatin modifications can generate unanticipated stability of epigenetic States in Arabidopsis. The Plant cell. 2010 Jan; 22(1):34-47. doi: 10.1105/tpc.109.072819. [PMID: 20097869]
  • Krishna Vanaja Donkena, Charles Y F Young, Donald J Tindall. Oxidative stress and DNA methylation in prostate cancer. Obstetrics and gynecology international. 2010; 2010(?):302051. doi: 10.1155/2010/302051. [PMID: 20671914]
  • Laurence Colin, Carine Van Lint. Molecular control of HIV-1 postintegration latency: implications for the development of new therapeutic strategies. Retrovirology. 2009 Dec; 6(?):111. doi: 10.1186/1742-4690-6-111. [PMID: 19961595]
  • Jana Blazkova, Katerina Trejbalova, Françoise Gondois-Rey, Philippe Halfon, Patrick Philibert, Allan Guiguen, Eric Verdin, Daniel Olive, Carine Van Lint, Jiri Hejnar, Ivan Hirsch. CpG methylation controls reactivation of HIV from latency. PLoS pathogens. 2009 Aug; 5(8):e1000554. doi: 10.1371/journal.ppat.1000554. [PMID: 19696893]
  • Tuncay Baubec, Ales Pecinka, Wilfried Rozhon, Ortrun Mittelsten Scheid. Effective, homogeneous and transient interference with cytosine methylation in plant genomic DNA by zebularine. The Plant journal : for cell and molecular biology. 2009 Feb; 57(3):542-54. doi: 10.1111/j.1365-313x.2008.03699.x. [PMID: 18826433]
  • Maryse Lemaire, Louise F Momparler, Noël J-M Raynal, Mark L Bernstein, Richard L Momparler. Inhibition of cytidine deaminase by zebularine enhances the antineoplastic action of 5-aza-2'-deoxycytidine. Cancer chemotherapy and pharmacology. 2009 Feb; 63(3):411-6. doi: 10.1007/s00280-008-0750-6. [PMID: 18398609]
  • Ales Pecinka, Marisa Rosa, Adam Schikora, Marc Berlinger, Heribert Hirt, Christian Luschnig, Ortrun Mittelsten Scheid. Transgenerational stress memory is not a general response in Arabidopsis. PloS one. 2009; 4(4):e5202. doi: 10.1371/journal.pone.0005202. [PMID: 19381297]
  • Maryse Lemaire, Guy G Chabot, Noël Jm Raynal, Louise F Momparler, Annie Hurtubise, Mark L Bernstein, Richard L Momparler. Importance of dose-schedule of 5-aza-2'-deoxycytidine for epigenetic therapy of cancer. BMC cancer. 2008 May; 8(?):128. doi: 10.1186/1471-2407-8-128. [PMID: 18454857]
  • F Christoph, C Kempkensteffen, S Weikert, J Köllermann, H Krause, K Miller, M Schostak, M Schrader. Methylation of tumour suppressor genes APAF-1 and DAPK-1 and in vitro effects of demethylating agents in bladder and kidney cancer. British journal of cancer. 2006 Dec; 95(12):1701-7. doi: 10.1038/sj.bjc.6603482. [PMID: 17133271]
  • Jan H Beumer, Erin Joseph, Merrill J Egorin, Robert S Parker, David Z D'argenio, Joseph M Covey, Julie L Eiseman. A mass balance and disposition study of the DNA methyltransferase inhibitor zebularine (NSC 309132) and three of its metabolites in mice. Clinical cancer research : an official journal of the American Association for Cancer Research. 2006 Oct; 12(19):5826-33. doi: 10.1158/1078-0432.ccr-06-1234. [PMID: 17020990]
  • Elaine M Hurt, Suneetha B Thomas, Benjamin Peng, William L Farrar. Reversal of p53 epigenetic silencing in multiple myeloma permits apoptosis by a p53 activator. Cancer biology & therapy. 2006 Sep; 5(9):1154-60. doi: 10.4161/cbt.5.9.3001. [PMID: 16855375]
  • Julie Couillard, Mélanie Demers, Geneviève Lavoie, Yves St-Pierre. The role of DNA hypomethylation in the control of stromelysin gene expression. Biochemical and biophysical research communications. 2006 Apr; 342(4):1233-9. doi: 10.1016/j.bbrc.2006.02.068. [PMID: 16516860]
  • Jan H Beumer, Erin Joseph, Merrill J Egorin, Joseph M Covey, Julie L Eiseman. Quantitative determination of zebularine (NSC 309132), a DNA methyltransferase inhibitor, and three metabolites in murine plasma by high-performance liquid chromatography coupled with on-line radioactivity detection. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences. 2006 Feb; 831(1-2):147-55. doi: 10.1016/j.jchromb.2005.11.048. [PMID: 16364698]
  • Alfonso Dueñas-González, Marcela Lizano, Myrna Candelaria, Lucely Cetina, Claudia Arce, Eduardo Cervera. Epigenetics of cervical cancer. An overview and therapeutic perspectives. Molecular cancer. 2005 Oct; 4(?):38. doi: 10.1186/1476-4598-4-38. [PMID: 16248899]
  • Julianne L Holleran, Robert A Parise, Erin Joseph, Julie L Eiseman, Joseph M Covey, Elizabeth R Glaze, Alexander V Lyubimov, Ya-Fei Chen, David Z D'Argenio, Merrill J Egorin. Plasma pharmacokinetics, oral bioavailability, and interspecies scaling of the DNA methyltransferase inhibitor, zebularine. Clinical cancer research : an official journal of the American Association for Cancer Research. 2005 May; 11(10):3862-8. doi: 10.1158/1078-0432.ccr-04-2406. [PMID: 15897587]
  • David R Hodge, Benjamin Peng, Celine Pompeia, Suneetha Thomas, Edward Cho, Peter A Clausen, Victor E Marquez, William L Farrar. Epigenetic silencing of manganese superoxide dismutase (SOD-2) in KAS 6/1 human multiple myeloma cells increases cell proliferation. Cancer biology & therapy. 2005 May; 4(5):585-92. doi: 10.4161/cbt.4.5.1704. [PMID: 15908783]
  • Stephen A Baldwin, Sylvia Y M Yao, Ralph J Hyde, Amy M L Ng, Sophie Foppolo, Kay Barnes, Mabel W L Ritzel, Carol E Cass, James D Young. Functional characterization of novel human and mouse equilibrative nucleoside transporters (hENT3 and mENT3) located in intracellular membranes. The Journal of biological chemistry. 2005 Apr; 280(16):15880-7. doi: 10.1074/jbc.m414337200. [PMID: 15701636]
  • Wade G Alleman, Ray L Tabios, Gadisetti V R Chandramouli, Olga N Aprelikova, Carlos Torres-Cabala, Arnulfo Mendoza, Craig Rogers, Craig Rodgers, Nikolai A Sopko, W Marston Linehan, James R Vasselli. The in vitro and in vivo effects of re-expressing methylated von Hippel-Lindau tumor suppressor gene in clear cell renal carcinoma with 5-aza-2'-deoxycytidine. Clinical cancer research : an official journal of the American Association for Cancer Research. 2004 Oct; 10(20):7011-21. doi: 10.1158/1078-0432.ccr-04-0516. [PMID: 15501981]
  • C H Kim, V E Marquez, D T Mao, D R Haines, J J McCormack. Synthesis of pyrimidin-2-one nucleosides as acid-stable inhibitors of cytidine deaminase. Journal of medicinal chemistry. 1986 Aug; 29(8):1374-80. doi: 10.1021/jm00158a009. [PMID: 3735306]