L-DON (BioDeep_00000792442)

 

Secondary id: BioDeep_00000174920

Antitumor activity


代谢物信息卡片


6-Diazo-5-oxo-L-norleucine

化学式: C6H9N3O3 (171.0644)
中文名称: 6-重氮-5-氧代-L-正亮氨酸
谱图信息: 最多检出来源 Homo sapiens(blood) 52.94%

分子结构信息

SMILES: C(CC(=O)C=[N+]=[N-])C(C(=O)O)N
InChI: InChI=1S/C6H9N3O3/c7-5(6(11)12)2-1-4(10)3-9-8/h3,5H,1-2,7H2,(H,11,12)/t5-/m0/s1

描述信息

A non-proteinogenic L-alpha-amino acid that is L-norleucine which is substituted at position 5 by an oxo group and at position 6 by a diazo group. It is as inhibitor of various glutamine-utilising enzymes.
C274 - Antineoplastic Agent > C186664 - Cytotoxic Chemotherapeutic Agent > C272 - Antimetabolite
C471 - Enzyme Inhibitor > C2133 - Cytidine Triphosphate Synthetase Inhibitor
D009676 - Noxae > D000963 - Antimetabolites
D000970 - Antineoplastic Agents
6-Diazo-5-oxo-L-nor-Leucine (L-6-Diazo-5-oxonorleucine; DON) is a glutamine antagonist that irreversibly inhibits the catabolic effect of glutamine. 6-Diazo-5-oxo-L-nor-Leucine shows good anticancer activity (especially in pancreatic cancer) and reduces the self-renewal potential and metastatic capacity of tumour cells. 6-Diazo-5-oxo-L-nor-Leucine also possesses antibacterial and antiviral activity[1][2][3].

同义名列表

5 个代谢物同义名

6-Diazo-5-oxo-L-norleucine; L-DON; L-6-Diazo-5-oxonorleucine; DON; 6-Diazo-5-oxo-L-nor-Leucine



数据库引用编号

9 个数据库交叉引用编号

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)

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。

亚细胞结构定位 关联基因列表


文献列表

  • Shams Tabrez, Torki A Zughaibi, Mehboob Hoque, Mohd Suhail, Mohammad Imran Khan, Azhar U Khan. Targeting Glutaminase by Natural Compounds: Structure-Based Virtual Screening and Molecular Dynamics Simulation Approach to Suppress Cancer Progression. Molecules (Basel, Switzerland). 2022 08; 27(15):. doi: 10.3390/molecules27155042. [PMID: 35956989]
  • Wei Yu, XiangYu Yang, Qian Zhang, Li Sun, ShengTao Yuan, YongJie Xin. Targeting GLS1 to cancer therapy through glutamine metabolism. Clinical & translational oncology : official publication of the Federation of Spanish Oncology Societies and of the National Cancer Institute of Mexico. 2021 Nov; 23(11):2253-2268. doi: 10.1007/s12094-021-02645-2. [PMID: 34023970]
  • Hyeon Young Park, Mi-Jin Kim, Seunghyeong Lee, Jonghwa Jin, Sungwoo Lee, Jung-Guk Kim, Yeon-Kyung Choi, Keun-Gyu Park. Inhibitory Effect of a Glutamine Antagonist on Proliferation and Migration of VSMCs via Simultaneous Attenuation of Glycolysis and Oxidative Phosphorylation. International journal of molecular sciences. 2021 May; 22(11):. doi: 10.3390/ijms22115602. [PMID: 34070527]
  • Khoa Pham, Micah J Maxwell, Heather Sweeney, Jesse Alt, Rana Rais, Charles G Eberhart, Barbara S Slusher, Eric H Raabe. Novel Glutamine Antagonist JHU395 Suppresses MYC-Driven Medulloblastoma Growth and Induces Apoptosis. Journal of neuropathology and experimental neurology. 2021 03; 80(4):336-344. doi: 10.1093/jnen/nlab018. [PMID: 33712838]
  • Lukáš Tenora, Jesse Alt, Ranjeet P Dash, Alexandra J Gadiano, Kateřina Novotná, Vijayabhaskar Veeravalli, Jenny Lam, Quinn R Kirkpatrick, Kathryn M Lemberg, Pavel Majer, Rana Rais, Barbara S Slusher. Tumor-Targeted Delivery of 6-Diazo-5-oxo-l-norleucine (DON) Using Substituted Acetylated Lysine Prodrugs. Journal of medicinal chemistry. 2019 04; 62(7):3524-3538. doi: 10.1021/acs.jmedchem.8b02009. [PMID: 30892035]
  • Michael T Nedelcovych, Lukáš Tenora, Boe-Hyun Kim, Jennifer Kelschenbach, Wei Chao, Eran Hadas, Andrej Jančařík, Eva Prchalová, Sarah C Zimmermann, Ranjeet P Dash, Alexandra J Gadiano, Caroline Garrett, Georg Furtmüller, Byoungchol Oh, Gerald Brandacher, Jesse Alt, Pavel Majer, David J Volsky, Rana Rais, Barbara S Slusher. N-(Pivaloyloxy)alkoxy-carbonyl Prodrugs of the Glutamine Antagonist 6-Diazo-5-oxo-l-norleucine (DON) as a Potential Treatment for HIV Associated Neurocognitive Disorders. Journal of medicinal chemistry. 2017 08; 60(16):7186-7198. doi: 10.1021/acs.jmedchem.7b00966. [PMID: 28759224]
  • Rana Rais, Andrej Jančařík, Lukáš Tenora, Michael Nedelcovych, Jesse Alt, Judson Englert, Camilo Rojas, Anne Le, Amira Elgogary, Jessica Tan, Lenka Monincová, Kelly Pate, Robert Adams, Dana Ferraris, Jonathan Powell, Pavel Majer, Barbara S Slusher. Discovery of 6-Diazo-5-oxo-l-norleucine (DON) Prodrugs with Enhanced CSF Delivery in Monkeys: A Potential Treatment for Glioblastoma. Journal of medicinal chemistry. 2016 Sep; 59(18):8621-33. doi: 10.1021/acs.jmedchem.6b01069. [PMID: 27560860]
  • Jesse Alt, Michelle C Potter, Camilo Rojas, Barbara S Slusher. Bioanalysis of 6-diazo-5-oxo-l-norleucine in plasma and brain by ultra-performance liquid chromatography mass spectrometry. Analytical biochemistry. 2015 Apr; 474(?):28-34. doi: 10.1016/j.ab.2015.01.001. [PMID: 25584882]
  • K Thangavelu, Qing Yun Chong, Boon Chuan Low, J Sivaraman. Structural basis for the active site inhibition mechanism of human kidney-type glutaminase (KGA). Scientific reports. 2014 Jan; 4(?):3827. doi: 10.1038/srep03827. [PMID: 24451979]
  • Kitiporn Plaimas, Yulin Wang, Solomon O Rotimi, Grace Olasehinde, Segun Fatumo, Michael Lanzer, Ezekiel Adebiyi, Rainer König. Computational and experimental analysis identified 6-diazo-5-oxonorleucine as a potential agent for treating infection by Plasmodium falciparum. Infection, genetics and evolution : journal of molecular epidemiology and evolutionary genetics in infectious diseases. 2013 Dec; 20(?):389-95. doi: 10.1016/j.meegid.2013.09.019. [PMID: 24121016]
  • Brent A Penque, April M Hoggatt, B Paul Herring, Jeffrey S Elmendorf. Hexosamine biosynthesis impairs insulin action via a cholesterolgenic response. Molecular endocrinology (Baltimore, Md.). 2013 Mar; 27(3):536-47. doi: 10.1210/me.2012-1213. [PMID: 23315940]
  • Bei-Bei Cao, Xin-Hua Han, Yan Huang, Yi-Hua Qiu, Yu-Ping Peng. The hypothalamus mediates the effect of cerebellar fastigial nuclear glutamatergic neurons on humoral immunity. Neuro endocrinology letters. 2012; 33(4):393-400. doi: NULL. [PMID: 22936265]
  • Olatz Pampliega, María Domercq, Federico N Soria, Pablo Villoslada, Alfredo Rodríguez-Antigüedad, Carlos Matute. Increased expression of cystine/glutamate antiporter in multiple sclerosis. Journal of neuroinflammation. 2011 Jun; 8(?):63. doi: 10.1186/1742-2094-8-63. [PMID: 21639880]
  • Whitney Sealls, Brent A Penque, Jeffrey S Elmendorf. Evidence that chromium modulates cellular cholesterol homeostasis and ABCA1 functionality impaired by hyperinsulinemia--brief report. Arteriosclerosis, thrombosis, and vascular biology. 2011 May; 31(5):1139-40. doi: 10.1161/atvbaha.110.222158. [PMID: 21311039]
  • Anett Karl, Antje Wurm, Thomas Pannicke, Katja Krügel, Marta Obara-Michlewska, Peter Wiedemann, Andreas Reichenbach, Jan Albrecht, Andreas Bringmann. Synergistic action of hypoosmolarity and glutamine in inducing acute swelling of retinal glial (Müller) cells. Glia. 2011 Feb; 59(2):256-66. doi: 10.1002/glia.21095. [PMID: 21154559]
  • Laura M Shelton, Leanne C Huysentruyt, Thomas N Seyfried. Glutamine targeting inhibits systemic metastasis in the VM-M3 murine tumor model. International journal of cancer. 2010 Nov; 127(10):2478-85. doi: 10.1002/ijc.25431. [PMID: 20473919]
  • Andrew T Sage, Lisa A Walter, Yuanyuan Shi, Mohammad I Khan, Hideaki Kaneto, Alfredo Capretta, Geoff H Werstuck. Hexosamine biosynthesis pathway flux promotes endoplasmic reticulum stress, lipid accumulation, and inflammatory gene expression in hepatic cells. American journal of physiology. Endocrinology and metabolism. 2010 Mar; 298(3):E499-511. doi: 10.1152/ajpendo.00507.2009. [PMID: 19952345]
  • Roland Wakiec, Iwona Gabriel, Rajendra Prasad, Jeffrey M Becker, John W Payne, Slawomir Milewski. Enhanced susceptibility to antifungal oligopeptides in yeast strains overexpressing ABC multidrug efflux pumps. Antimicrobial agents and chemotherapy. 2008 Nov; 52(11):4057-63. doi: 10.1128/aac.01648-07. [PMID: 18794383]
  • Aleksander Talgøy Holten, Vidar Gundersen. Glutamine as a precursor for transmitter glutamate, aspartate and GABA in the cerebellum: a role for phosphate-activated glutaminase. Journal of neurochemistry. 2008 Feb; 104(4):1032-42. doi: 10.1111/j.1471-4159.2007.05065.x. [PMID: 17986214]
  • Kittiporn Phanvijhitsiri, Mark W Musch, Mark J Ropeleski, Eugene B Chang. Heat induction of heat shock protein 25 requires cellular glutamine in intestinal epithelial cells. American journal of physiology. Cell physiology. 2006 Aug; 291(2):C290-9. doi: 10.1152/ajpcell.00225.2005. [PMID: 16554407]
  • Daniel Teta, Andrée Tedjani, Michel Burnier, Alan Bevington, Jeremy Brown, Kevin Harris. Glucose-containing peritoneal dialysis fluids regulate leptin secretion from 3T3-L1 adipocytes. Nephrology, dialysis, transplantation : official publication of the European Dialysis and Transplant Association - European Renal Association. 2005 Jul; 20(7):1329-35. doi: 10.1093/ndt/gfh812. [PMID: 15814535]
  • S Ghosh, S Roy, M Banerjee, P Maity. Modulation of tumor induced angiogenesis in Ehrlich ascites tumor. Journal of experimental & clinical cancer research : CR. 2004 Dec; 23(4):681-90. doi: NULL. [PMID: 15743040]
  • Tusty-Jiuan Hsieh, Pierre Fustier, Shao-Ling Zhang, Janos G Filep, Shiow-Shih Tang, Julie R Ingelfinger, I George Fantus, Pavel Hamet, John S D Chan. High glucose stimulates angiotensinogen gene expression and cell hypertrophy via activation of the hexosamine biosynthesis pathway in rat kidney proximal tubular cells. Endocrinology. 2003 Oct; 144(10):4338-49. doi: 10.1210/en.2003-0220. [PMID: 12960040]
  • Robert H H van den Heuvel, Dmitri I Svergun, Maxim V Petoukhov, Alessandro Coda, Bruno Curti, Sergio Ravasio, Maria A Vanoni, Andrea Mattevi. The active conformation of glutamate synthase and its binding to ferredoxin. Journal of molecular biology. 2003 Jun; 330(1):113-28. doi: 10.1016/s0022-2836(03)00522-9. [PMID: 12818206]
  • Tania C Pithon-Curi, Robert Ivan Schumacher, Jofre J S Freitas, Claudia Lagranha, Philip Newsholme, Adrianne C Palanch, Sonia Q Doi, Rui Curi. Glutamine delays spontaneous apoptosis in neutrophils. American journal of physiology. Cell physiology. 2003 Jun; 284(6):C1355-61. doi: 10.1152/ajpcell.00224.2002. [PMID: 12529242]
  • Michael Wiessner, Erica L Fletcher, Frauke Fischer, Thomas Rauen. Localization and possible function of the glutamate transporter, EAAC1, in the rat retina. Cell and tissue research. 2002 Oct; 310(1):31-40. doi: 10.1007/s00441-002-0612-1. [PMID: 12242481]
  • Jun Hiratake, Makoto Inoue, Kanzo Sakata. gamma-Glutamyltranspeptidase and gamma-glutamyl peptide ligases: fluorophosphonate and phosphonodifluoromethyl ketone analogs as probes of tetrahedral transition state and gamma-glutamyl-phosphate intermediate. Methods in enzymology. 2002; 354(?):272-95. doi: 10.1016/s0076-6879(02)54023-4. [PMID: 12418234]
  • J A Engler, J M Gottesman, J C Harkins, A K Urazaev, E M Lieberman, R M Grossfeld. Properties of glutaminase of crayfish CNS: implications for axon-glia signaling. Neuroscience. 2002; 114(3):699-705. doi: 10.1016/s0306-4522(02)00357-3. [PMID: 12220571]
  • R V Considine, R C Cooksey, L B Williams, R L Fawcett, P Zhang, W T Ambrosius, R M Whitfield, R Jones, M Inman, J Huse, D A McClain. Hexosamines regulate leptin production in human subcutaneous adipocytes. The Journal of clinical endocrinology and metabolism. 2000 Oct; 85(10):3551-6. doi: 10.1210/jcem.85.10.6916. [PMID: 11061500]
  • G Wu, T E Haynes, H Li, C J Meininger. Glutamine metabolism in endothelial cells: ornithine synthesis from glutamine via pyrroline-5-carboxylate synthase. Comparative biochemistry and physiology. Part A, Molecular & integrative physiology. 2000 May; 126(1):115-23. doi: 10.1016/s1095-6433(00)00196-3. [PMID: 10908859]
  • F Wu, H Orlefors, M Bergström, G Antoni, H Omura, B Eriksson, Y Watanabe, B Långström. Uptake of 14C- and 11C-labeled glutamate, glutamine and aspartate in vitro and in vivo. Anticancer research. 2000 Jan; 20(1A):251-6. doi: NULL. [PMID: 10769663]
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  • M P Sullivan, J A Nelson, S Feldman, B Van Nguyen. Pharmacokinetic and phase I study of intravenous DON (6-diazo-5-oxo-L-norleucine) in children. Cancer chemotherapy and pharmacology. 1988; 21(1):78-84. doi: 10.1007/bf00262746. [PMID: 3342470]
  • J R Spencer, M Maizels. Inhibition of protein glycosylation causes renal dysplasia in the chick embryo. The Journal of urology. 1987 Oct; 138(4 Pt 2):984-90. doi: 10.1016/s0022-5347(17)43478-1. [PMID: 3309377]
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  • G Goldstein, L E Guskey. Poliovirus and vesicular stomatitis virus replication in the presence of 6-diazo-5-oxo-L-norleucine or 2-deoxy-D-glucose. Journal of medical virology. 1984; 14(2):159-67. doi: 10.1002/jmv.1890140210. [PMID: 6208320]
  • K Itoh, M Inoue, Y Morino. Rose bengal-sensitized photooxidation of rat kidney gamma-glutamyltransferase. Enzyme. 1984; 31(3):143-53. doi: 10.1159/000469517. [PMID: 6145586]
  • R R Markwald, F M Funderburg. Use of 6-diazo-5-oxo-L-norleucine to study interaction between myocardial glycoconjugate secretion and endothelial activation in the early embryonic chick heart. Developmental biology. 1983 Oct; 99(2):395-407. doi: 10.1016/0012-1606(83)90289-0. [PMID: 6618009]
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  • R H Earhart, J M Koeller, H L Davis. Phase I trial of 6-diazo-5-oxo-L-norleucine (DON) administered by 5-day courses. Cancer treatment reports. 1982 May; 66(5):1215-7. doi: NULL. [PMID: 7083223]
  • V M Clark, R A Shapiro, N P Curthoys. Comparison of the hydrolysis and the covalent binding of 6-diazo-5-oxo-L-[6-14C]norleucine by rat renal phosphate-dependent glutaminase. Archives of biochemistry and biophysics. 1982 Jan; 213(1):232-9. doi: 10.1016/0003-9861(82)90457-x. [PMID: 6120680]
  • J S Kovach, R T Eagan, G Powis, J Rubin, E T Creagan, C G Moertel. Phase I and pharmacokinetic studies of DON. Cancer treatment reports. 1981 Nov; 65(11-12):1031-6. doi: NULL. [PMID: 7296548]
  • K Okajima, M Inoue, Y Morino. Topology and some properties of the renal brush border membrane-bound peptidase(s) participating in the metabolism of S-carbamidomethyl glutathione. Biochimica et biophysica acta. 1981 Jul; 675(3-4):379-85. doi: 10.1016/0304-4165(81)90029-5. [PMID: 6115679]
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  • M Inoue, Y Morino. Inactivation of renal gamma-glutamyl transferase by 6-diazo-5-oxo-L-norleucylglycine, an inactive precursor of affinity-labeling reagent. Proceedings of the National Academy of Sciences of the United States of America. 1981 Jan; 78(1):46-9. doi: 10.1073/pnas.78.1.46. [PMID: 6113588]
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