Dimethyloxalylglycine (BioDeep_00000624958)

   


代谢物信息卡片


Dimethyloxalylglycine

化学式: C6H9NO5 (175.0480704)
中文名称: 二甲基乙二酰氨基乙酸
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: COC(=O)CNC(=O)C(=O)OC
InChI: InChI=1S/C6H9NO5/c1-11-4(8)3-7-5(9)6(10)12-2/h3H2,1-2H3,(H,7,9)

描述信息

DMOG (Dimethyloxallyl Glycine) is a cell permeable and competitive inhibitor of HIF-PH, which results in HIF-1α stabilisation and accmulation?in vitro and in vivo[1]. DMOG is an α-ketoglutarate analogue and inhibits α-KG-dependent hydroxylases. DMOG?acts as a pro-angiogenic agent and plays a protective role in experimental model of colitis and diarrhoea via HIF-1 related signal[2][4]. DMOG induces cell autophagy[5].

同义名列表

3 个代谢物同义名

Dimethyloxalylglycine; DMOG; Dimethyloxallyl Glycine



数据库引用编号

6 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

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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)

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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

  • Kang Qin, Yuan Gui, Yanchun Li, Xinyi Li, Fei Meng, Dianpeng Han, Lianqun Du, Shuang Li, Yu Wang, Huanying Zhou, Hongyuan Yan, Yuan Peng, Zhixian Gao. Biodegradable Microneedle Array-Mediated Transdermal Delivery of Dimethyloxalylglycine-Functionalized Zeolitic Imidazolate Framework-8 Nanoparticles for Bacteria-Infected Wound Treatment. ACS applied materials & interfaces. 2023 Feb; 15(5):6338-6353. doi: 10.1021/acsami.2c17328. [PMID: 36701257]
  • Li Chen, Xiao Huang, Hong Chen, Dingsu Bao, Xudong Su, Li Wei, Ning Hu, Wei Huang, Zhou Xiang. Hypoxia-mimicking scaffolds with controlled release of DMOG and PTHrP to promote cartilage regeneration via the HIF-1α/YAP signaling pathway. International journal of biological macromolecules. 2023 Jan; 226(?):716-729. doi: 10.1016/j.ijbiomac.2022.12.094. [PMID: 36526060]
  • Xiuan Zeng, Meng Li, Qibing Yang, Qiyuan Wang, Yongxin Chen, Xiangli Luo, Jidong Li, Xu Lan. [Effect of dimethyloxalylglycine on angiogenesis in Choke Ⅱ zone of cross-zone perforator flap and its mechanism]. Zhongguo xiu fu chong jian wai ke za zhi = Zhongguo xiufu chongjian waike zazhi = Chinese journal of reparative and reconstructive surgery. 2022 Feb; 36(2):224-230. doi: 10.7507/1002-1892.202107103. [PMID: 35172410]
  • Xiuzhen Lei, Wenbin Teng, Ying Fan, Yeke Zhu, Liuxu Yao, Yuhong Li, Shengmei Zhu. The protective effects of HIF-1α activation on sepsis induced intestinal mucosal barrier injury in rats model of sepsis. PloS one. 2022; 17(5):e0268445. doi: 10.1371/journal.pone.0268445. [PMID: 35576220]
  • Mohammad Sanaei-Ardekani, Shyreen Kamal, Whitney Handy, Sidrah Alam, Aya Salaheldin, Anderson Moore, Shahrzad Movafagh. Suppression of collagen IV alpha-2 subunit by prolyl hydroxylase domain inhibition via hypoxia-inducible factor-1 in chronic kidney disease. Pharmacology research & perspectives. 2021 10; 9(5):e00872. doi: 10.1002/prp2.872. [PMID: 34617686]
  • Senthilnathan Palaniyandi, Reena Kumari, Sabarinath Venniyil Radhakrishnan, Ethan Strattan, Natalya Hakim, Reinhold Munker, Melissa V Kesler, Gerhard C Hildebrandt. The Prolyl Hydroxylase Inhibitor Dimethyl Oxalyl Glycine Decreases Early Gastrointestinal GVHD in Experimental Allogeneic Hematopoietic Cell Transplantation. Transplantation. 2020 12; 104(12):2507-2515. doi: 10.1097/tp.0000000000003383. [PMID: 32639407]
  • Tze-Hong Wong, Ting-Yu Chen, Kuo-Yun Tseng, Zih-Ying Chen, Chung-Hsing Chen, Feng-Huei Lin, Hung-Ming Wu, Shankung Lin. Decorin inhibits the insulin-like growth factor I signaling in bone marrow mesenchymal stem cells of aged humans. Aging. 2020 11; 13(1):578-597. doi: 10.18632/aging.202166. [PMID: 33257596]
  • Sota Kato, Teisuke Takahashi, Noriyuki Miyata, Richard J Roman. DMOG, a Prolyl Hydroxylase Inhibitor, Increases Hemoglobin Levels without Exacerbating Hypertension and Renal Injury in Salt-Sensitive Hypertensive Rats. The Journal of pharmacology and experimental therapeutics. 2020 02; 372(2):166-174. doi: 10.1124/jpet.119.262782. [PMID: 31801803]
  • Simon Müller, Sonja Djudjaj, Janina Lange, Mihail Iacovescu, Margarete Goppelt-Struebe, Peter Boor. HIF stabilization inhibits renal epithelial cell migration and is associated with cytoskeletal alterations. Scientific reports. 2018 06; 8(1):9497. doi: 10.1038/s41598-018-27918-9. [PMID: 29934555]
  • Sasan Jalili-Firoozinezhad, Rachelle Prantil-Baun, Amanda Jiang, Ratnakar Potla, Tadanori Mammoto, James C Weaver, Thomas C Ferrante, Hyun Jung Kim, Joaquim M S Cabral, Oren Levy, Donald E Ingber. Modeling radiation injury-induced cell death and countermeasure drug responses in a human Gut-on-a-Chip. Cell death & disease. 2018 02; 9(2):223. doi: 10.1038/s41419-018-0304-8. [PMID: 29445080]
  • Anna Sonja Müller, Klara Janjić, Gunpreet Oberoi, Manuela Pensch, Christoph Kurzmann, Andreas Moritz, Hermann Agis. Deferoxamine but Not Dimethyloxalylglycine, L-Mimosine, or Cobalt Dichloride Can Interfere with the MTT Assay. BioMed research international. 2018; 2018(?):5872865. doi: 10.1155/2018/5872865. [PMID: 30581861]
  • Wei Zhang, Xiangjun Zhou, Qisheng Yao, Yutao Liu, Hao Zhang, Zheng Dong. HIF-1-mediated production of exosomes during hypoxia is protective in renal tubular cells. American journal of physiology. Renal physiology. 2017 Oct; 313(4):F906-F913. doi: 10.1152/ajprenal.00178.2017. [PMID: 28679592]
  • Joanna L Thomas, Hai Pham, Ying Li, Elanore Hall, Guy A Perkins, Sameh S Ali, Hemal H Patel, Prabhleen Singh. Hypoxia-inducible factor-1α activation improves renal oxygenation and mitochondrial function in early chronic kidney disease. American journal of physiology. Renal physiology. 2017 Aug; 313(2):F282-F290. doi: 10.1152/ajprenal.00579.2016. [PMID: 28331062]
  • Kyuhwa Seo, Suho Seo, Sung Hwan Ki, Sang Mi Shin. Sestrin2 inhibits hypoxia-inducible factor-1α accumulation via AMPK-mediated prolyl hydroxylase regulation. Free radical biology & medicine. 2016 12; 101(?):511-523. doi: 10.1016/j.freeradbiomed.2016.11.014. [PMID: 27840318]
  • Felix Preisser, Klaudia Giehl, Margot Rehm, Margarete Goppelt-Struebe. Inhibitors of oxygen sensing prolyl hydroxylases regulate nuclear localization of the transcription factors Smad2 and YAP/TAZ involved in CTGF synthesis. Biochimica et biophysica acta. 2016 08; 1863(8):2027-36. doi: 10.1016/j.bbamcr.2016.05.001. [PMID: 27155083]
  • Khalid Al-Qahtani, Bushra Jabeen, Rok Sekirnik, Naheed Riaz, Timothy D W Claridge, Christopher J Schofield, James S O McCullagh. The broad spectrum 2-oxoglutarate oxygenase inhibitor N-oxalylglycine is present in rhubarb and spinach leaves. Phytochemistry. 2015 Sep; 117(?):456-461. doi: 10.1016/j.phytochem.2015.06.028. [PMID: 26196940]
  • Constance S Harrell, Sydney A Rowson, Gretchen N Neigh. Pharmacological stimulation of hypoxia inducible factor-1α facilitates the corticosterone response to a mild acute stressor. Neuroscience letters. 2015 Jul; 600(?):75-9. doi: 10.1016/j.neulet.2015.05.051. [PMID: 26037418]
  • Ana Martins Metelo, Haley R Noonan, Xiang Li, Youngnam Jin, Rania Baker, Lee Kamentsky, Yiyun Zhang, Ellen van Rooijen, Jordan Shin, Anne E Carpenter, Jing-Ruey Yeh, Randall T Peterson, Othon Iliopoulos. Pharmacological HIF2α inhibition improves VHL disease-associated phenotypes in zebrafish model. The Journal of clinical investigation. 2015 May; 125(5):1987-97. doi: 10.1172/jci73665. [PMID: 25866969]
  • P Sukumaran, Y Sun, M Vyas, B B Singh. TRPC1-mediated Ca²⁺ entry is essential for the regulation of hypoxia and nutrient depletion-dependent autophagy. Cell death & disease. 2015 Mar; 6(?):e1674. doi: 10.1038/cddis.2015.7. [PMID: 25741599]
  • Quan Yuan, Oliver Bleiziffer, Anja M Boos, Jiaming Sun, Andreas Brandl, Justus P Beier, Andreas Arkudas, Marweh Schmitz, Ulrich Kneser, Raymund E Horch. PHDs inhibitor DMOG promotes the vascularization process in the AV loop by HIF-1a up-regulation and the preliminary discussion on its kinetics in rat. BMC biotechnology. 2014 Dec; 14(?):112. doi: 10.1186/s12896-014-0112-x. [PMID: 25543909]
  • Hao Ding, You-Shui Gao, Yang Wang, Chen Hu, Yuan Sun, Changqing Zhang. Dimethyloxaloylglycine increases the bone healing capacity of adipose-derived stem cells by promoting osteogenic differentiation and angiogenic potential. Stem cells and development. 2014 May; 23(9):990-1000. doi: 10.1089/scd.2013.0486. [PMID: 24328551]
  • Xiaoyu Li, Huanxin Zhao, Ye Wu, Suli Zhang, Xiaoqin Zhao, Yan Zhang, Jin Wang, Jie Wang, Huirong Liu. Up-regulation of hypoxia-inducible factor-1α enhanced the cardioprotective effects of ischemic postconditioning in hyperlipidemic rats. Acta biochimica et biophysica Sinica. 2014 Feb; 46(2):112-8. doi: 10.1093/abbs/gmt132. [PMID: 24389644]
  • Wei Deng, Yile Ren, Xuebing Feng, Genhong Yao, Weiwei Chen, Yue Sun, Hengjin Wang, Xiang Gao, Lingyun Sun. Hypoxia inducible factor-1 alpha promotes mesangial cell proliferation in lupus nephritis. American journal of nephrology. 2014; 40(6):507-15. doi: 10.1159/000369564. [PMID: 25531641]
  • Jia Peng, Zuo Gui Lai, Zhang Lian Fang, Shen Xing, Kang Hui, Chen Hao, Qi Jin, Zhou Qi, Wang Jin Shen, Qian Nian Dong, Zhou Han Bing, Deng Lian Fu. Dimethyloxalylglycine prevents bone loss in ovariectomized C57BL/6J mice through enhanced angiogenesis and osteogenesis. PloS one. 2014; 9(11):e112744. doi: 10.1371/journal.pone.0112744. [PMID: 25394221]
  • Nicholas S Kalson, Tobias Starborg, Yinhui Lu, Aleksandr Mironov, Sally M Humphries, David F Holmes, Karl E Kadler. Nonmuscle myosin II powered transport of newly formed collagen fibrils at the plasma membrane. Proceedings of the National Academy of Sciences of the United States of America. 2013 Dec; 110(49):E4743-52. doi: 10.1073/pnas.1314348110. [PMID: 24248360]
  • Matthias Wolff, Wolfgang Jelkmann, Jürgen Dunst, Reinhard Depping. The Aryl Hydrocarbon Receptor Nuclear Translocator (ARNT/HIF-1β) is influenced by hypoxia and hypoxia-mimetics. Cellular physiology and biochemistry : international journal of experimental cellular physiology, biochemistry, and pharmacology. 2013; 32(4):849-58. doi: 10.1159/000354487. [PMID: 24081025]
  • Constantin R Popescu, Megan R Sutherland, Anik Cloutier, Geneviève Benoît, Mariane Bertagnolli, Catherine Yzydorczyk, Nathalie Germain, Véronique Phan, Martine Lelièvre-Pegorier, Hervé Sartelet, Anne Monique Nuyt. Hyperoxia exposure impairs nephrogenesis in the neonatal rat: role of HIF-1α. PloS one. 2013; 8(12):e82421. doi: 10.1371/journal.pone.0082421. [PMID: 24358181]
  • Gunnar Schley, Bernd Klanke, Johannes Schödel, Sven Kröning, Gazi Türkoglu, Andreas Beyer, Yohannes Hagos, Kerstin Amann, Birgitta C Burckhardt, Nicolai Burzlaff, Kai-Uwe Eckardt, Carsten Willam. Selective stabilization of HIF-1α in renal tubular cells by 2-oxoglutarate analogues. The American journal of pathology. 2012 Nov; 181(5):1595-606. doi: 10.1016/j.ajpath.2012.07.010. [PMID: 22944601]
  • Yohannes Hagos, Gunnar Schley, Johannes Schödel, Wolfgang Krick, Gerhard Burckhardt, Carsten Willam, Birgitta C Burckhardt. α-Ketoglutarate-related inhibitors of HIF prolyl hydroxylases are substrates of renal organic anion transporters 1 (OAT1) and 4 (OAT4). Pflugers Archiv : European journal of physiology. 2012 Oct; 464(4):367-74. doi: 10.1007/s00424-012-1140-9. [PMID: 22875277]
  • Yasumasa Nishiyama, Nobuhito Goda, Mai Kanai, Daisuke Niwa, Kota Osanai, Yu Yamamoto, Nanami Senoo-Matsuda, Randall S Johnson, Soichiro Miura, Yasuaki Kabe, Makoto Suematsu. HIF-1α induction suppresses excessive lipid accumulation in alcoholic fatty liver in mice. Journal of hepatology. 2012 Feb; 56(2):441-7. doi: 10.1016/j.jhep.2011.07.024. [PMID: 21896344]
  • Jeong-myung Ahn, Sun Jin You, Yun-Mi Lee, Se-Won Oh, Shin-young Ahn, Sejoong Kim, Ho Jun Chin, Dong-Wan Chae, Ki Young Na. Hypoxia-inducible factor activation protects the kidney from gentamicin-induced acute injury. PloS one. 2012; 7(11):e48952. doi: 10.1371/journal.pone.0048952. [PMID: 23145036]
  • Xiao-Li Zhang, Zhen-Wen Yan, Wei-Wen Sheng, Jing Xiao, Zhen-Xing Zhang, Zhi-Bin Ye. Activation of hypoxia-inducible factor-1 ameliorates postischemic renal injury via inducible nitric oxide synthase. Molecular and cellular biochemistry. 2011 Dec; 358(1-2):287-95. doi: 10.1007/s11010-011-0979-y. [PMID: 21755458]
  • M N Khan, T Bhattacharyya, P Andrikopoulos, M A Esteban, R Barod, T Connor, M Ashcroft, P H Maxwell, S Kiriakidis. Factor inhibiting HIF (FIH-1) promotes renal cancer cell survival by protecting cells from HIF-1α-mediated apoptosis. British journal of cancer. 2011 Mar; 104(7):1151-9. doi: 10.1038/bjc.2011.73. [PMID: 21386837]
  • John R Horton, Anup K Upadhyay, Hideharu Hashimoto, Xing Zhang, Xiaodong Cheng. Structural basis for human PHF2 Jumonji domain interaction with metal ions. Journal of molecular biology. 2011 Feb; 406(1):1-8. doi: 10.1016/j.jmb.2010.12.013. [PMID: 21167174]
  • Aihua Deng, Mary Ann K Arndt, Joseph Satriano, Prabhleen Singh, Timo Rieg, Scott Thomson, Tong Tang, Roland C Blantz. Renal protection in chronic kidney disease: hypoxia-inducible factor activation vs. angiotensin II blockade. American journal of physiology. Renal physiology. 2010 Dec; 299(6):F1365-73. doi: 10.1152/ajprenal.00153.2010. [PMID: 20881034]
  • Sven Kroening, Emily Neubauer, Bernd Wullich, Jan Aten, Margarete Goppelt-Struebe. Characterization of connective tissue growth factor expression in primary cultures of human tubular epithelial cells: modulation by hypoxia. American journal of physiology. Renal physiology. 2010 Mar; 298(3):F796-806. doi: 10.1152/ajprenal.00528.2009. [PMID: 20032117]
  • Young Rim Song, Sun Jin You, Yun-Mi Lee, Ho Joon Chin, Dong-Wan Chae, Yun Kyu Oh, Kwon Wook Joo, Jin Suk Han, Ki Young Na. Activation of hypoxia-inducible factor attenuates renal injury in rat remnant kidney. Nephrology, dialysis, transplantation : official publication of the European Dialysis and Transplant Association - European Renal Association. 2010 Jan; 25(1):77-85. doi: 10.1093/ndt/gfp454. [PMID: 19737871]
  • Huan-Xin Zhao, Xiao-Liang Wang, Ye-Hong Wang, Ye Wu, Xiao-Yu Li, Xiao-Ping Lv, Zhi-Qing Zhao, Rong-Rui Zhao, Hui-Rong Liu. Attenuation of myocardial injury by postconditioning: role of hypoxia inducible factor-1alpha. Basic research in cardiology. 2010 Jan; 105(1):109-18. doi: 10.1007/s00395-009-0044-0. [PMID: 19597757]
  • Sven Kroening, Emily Neubauer, Julia Wessel, Michael Wiesener, Margarete Goppelt-Struebe. Hypoxia interferes with connective tissue growth factor (CTGF) gene expression in human proximal tubular cell lines. Nephrology, dialysis, transplantation : official publication of the European Dialysis and Transplant Association - European Renal Association. 2009 Nov; 24(11):3319-25. doi: 10.1093/ndt/gfp305. [PMID: 19549692]
  • Xian-Bao Liu, Jian-An Wang, Molly E Ogle, Ling Wei. Prolyl hydroxylase inhibitor dimethyloxalylglycine enhances mesenchymal stem cell survival. Journal of cellular biochemistry. 2009 Apr; 106(5):903-11. doi: 10.1002/jcb.22064. [PMID: 19229863]
  • Jonathan E Sears, George Hoppe, Quteba Ebrahem, Bela Anand-Apte. Prolyl hydroxylase inhibition during hyperoxia prevents oxygen-induced retinopathy. Proceedings of the National Academy of Sciences of the United States of America. 2008 Dec; 105(50):19898-903. doi: 10.1073/pnas.0805817105. [PMID: 19057008]
  • Ileana Ruxandra Botusan, Vivekananda Gupta Sunkari, Octavian Savu, Anca Irinel Catrina, Jacob Grünler, Stina Lindberg, Teresa Pereira, Seppo Ylä-Herttuala, Lorenz Poellinger, Kerstin Brismar, Sergiu-Bogdan Catrina. Stabilization of HIF-1alpha is critical to improve wound healing in diabetic mice. Proceedings of the National Academy of Sciences of the United States of America. 2008 Dec; 105(49):19426-31. doi: 10.1073/pnas.0805230105. [PMID: 19057015]
  • H Kasiganesan, V Sridharan, G Wright. Prolyl hydroxylase inhibitor treatment confers whole-animal hypoxia tolerance. Acta physiologica (Oxford, England). 2007 Jun; 190(2):163-9. doi: 10.1111/j.1748-1716.2007.01676.x. [PMID: 17394573]
  • Ramesh Natarajan, Bernard J Fisher, Alpha A Fowler. Hypoxia inducible factor-1 modulates hemin-induced IL-8 secretion in microvascular endothelium. Microvascular research. 2007 May; 73(3):163-72. doi: 10.1016/j.mvr.2007.01.002. [PMID: 17336340]
  • Jie Zhou, Roman Köhl, Barbara Herr, Ronald Frank, Bernhard Brüne. Calpain mediates a von Hippel-Lindau protein-independent destruction of hypoxia-inducible factor-1alpha. Molecular biology of the cell. 2006 Apr; 17(4):1549-58. doi: 10.1091/mbc.e05-08-0770. [PMID: 16421254]
  • Baoying Chen, Karen S L Lam, Yu Wang, Donghai Wu, Michael C Lam, Jiangang Shen, Laiching Wong, Ruby L C Hoo, Jialiang Zhang, Aimin Xu. Hypoxia dysregulates the production of adiponectin and plasminogen activator inhibitor-1 independent of reactive oxygen species in adipocytes. Biochemical and biophysical research communications. 2006 Mar; 341(2):549-56. doi: 10.1016/j.bbrc.2006.01.004. [PMID: 16427606]
  • Ramzi Ockaili, Ramesh Natarajan, Fadi Salloum, Bernard J Fisher, Drew Jones, Alpha A Fowler, Rakesh C Kukreja. HIF-1 activation attenuates postischemic myocardial injury: role for heme oxygenase-1 in modulating microvascular chemokine generation. American journal of physiology. Heart and circulatory physiology. 2005 Aug; 289(2):H542-8. doi: 10.1152/ajpheart.00089.2005. [PMID: 15805230]