3-bromopyruvic acid (BioDeep_00000390413)

   


代谢物信息卡片


3-bromopyruvic acid

化学式: C3H3BrO3 (165.9265548)
中文名称: 3-溴丙酮酸
谱图信息: 最多检出来源 Anoectochilus roxburghii(viridiplantae) 94.44%

分子结构信息

SMILES: C(C(=O)C(=O)O)Br
InChI: InChI=1S/C3H3BrO3/c4-1-2(5)3(6)7/h1H2,(H,6,7)

描述信息

D019995 - Laboratory Chemicals > D007202 - Indicators and Reagents > D000345 - Affinity Labels
D004791 - Enzyme Inhibitors

同义名列表

1 个代谢物同义名

3-bromopyruvic acid



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)

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。



文献列表

  • Hui Liu, Qi Zhang, Hesong Huang, Mingliang Qiu, Lvjiang Hu, Xiaojuan Zhao, Chuanxi Xu, Zhiqiang Wang, Chenlei Zhang, Yang Zhan, Yongbing Sun. Quantification of 3-bromopyruvate in rat plasma by HPLC-MS/MS employing precolumn derivatization and the application to a pharmacokinetics study. Biomedical chromatography : BMC. 2022 Dec; 36(12):e5477. doi: 10.1002/bmc.5477. [PMID: 35916081]
  • Grzegorz Bartosz, Natalia Pieńkowska, Izabela Sadowska-Bartosz. Dosing metric in cellular experiments: The mol/cell metric has its limitations. Toxicology in vitro : an international journal published in association with BIBRA. 2022 Feb; 78(?):105272. doi: 10.1016/j.tiv.2021.105272. [PMID: 34740775]
  • Ting Wang, Kaiju Xu, Liyun Zhao, Rongsheng Tong, Liang Xiong, Jianyou Shi. Recent research and development of NDM-1 inhibitors. European journal of medicinal chemistry. 2021 Nov; 223(?):113667. doi: 10.1016/j.ejmech.2021.113667. [PMID: 34225181]
  • Honglin Yu, Jingbo Zhu, Lingyu Chang, Chaozhao Liang, Xiaohu Li, Wei Wang. 3-Bromopyruvate decreased kidney fibrosis and fibroblast activation by suppressing aerobic glycolysis in unilateral ureteral obstruction mice model. Life sciences. 2021 May; 272(?):119206. doi: 10.1016/j.lfs.2021.119206. [PMID: 33577854]
  • Jitendra Kumar Arya, Raushan Kumar, Shambhoo Sharan Tripathi, Syed Ibrahim Rizvi. 3-Bromopyruvate elevates ROS and induces hormesis to exert a caloric restriction mimetic effect in young and old rats. Archives of physiology and biochemistry. 2020 Oct; ?(?):1-8. doi: 10.1080/13813455.2020.1828485. [PMID: 33026905]
  • Fangyan Hou, Hairong Wang, Yawen Zhang, Na Zhu, Hao Liu, Jianchun Li. Construction and Evaluation of Folic Acid-Modified 3-Bromopyruvate Cubosomes. Medical science monitor : international medical journal of experimental and clinical research. 2020 Sep; 26(?):e924620. doi: 10.12659/msm.924620. [PMID: 32956335]
  • Somayeh Yousefi, Parisa Darvishi, Zeynab Yousefi, Ali Akbar Pourfathollah. Effect of methyl jasmonate and 3-bromopyruvate combination therapy on mice bearing the 4 T1 breast cancer cell line. Journal of bioenergetics and biomembranes. 2020 04; 52(2):103-111. doi: 10.1007/s10863-019-09811-w. [PMID: 31960257]
  • Anna Michno, Katarzyna Grużewska, Hanna Bielarczyk, Marlena Zyśk, Andrzej Szutowicz. Inhibition of pyruvate dehydrogenase complex activity by 3-bromopyruvate affects blood platelets responses in type 2 diabetes. Pharmacological reports : PR. 2020 Feb; 72(1):225-237. doi: 10.1007/s43440-019-00005-0. [PMID: 32016856]
  • Chengchuang Zhan, Guangzhong Liu, Jianqiang Li, Guangnan Li, Tiankai Li, Hongyan Zhao, Luyifei Li, Wen Yang, Nan Bai, Min Zheng, Junfen Yang, Weimin Li. Rotenone and 3-bromopyruvate toxicity impacts electrical and structural cardiac remodeling in rats. Toxicology letters. 2020 Jan; 318(?):57-64. doi: 10.1016/j.toxlet.2019.09.024. [PMID: 31585160]
  • Qi Xin, Miaomiao Yuan, Huanping Li, Xiaoxia Song, Jun Lu, Tao Jing. In vitro and in vivo effects of 3-bromopyruvate against Echinococcus metacestodes. Veterinary research. 2019 Nov; 50(1):96. doi: 10.1186/s13567-019-0710-7. [PMID: 31744550]
  • Agnieszka Korga, Marta Ostrowska, Magdalena Iwan, Mariola Herbet, Jaroslaw Dudka. Inhibition of glycolysis disrupts cellular antioxidant defense and sensitizes HepG2 cells to doxorubicin treatment. FEBS open bio. 2019 05; 9(5):959-972. doi: 10.1002/2211-5463.12628. [PMID: 30973680]
  • Katarzyna Niedźwiecka, David Ribas, Margarida Casal, Stanisław Ułaszewski. The Cryptococcus neoformans monocarboxylate transporter Jen4 is responsible for increased 3-bromopyruvate sensitivity. FEMS yeast research. 2019 05; 19(3):. doi: 10.1093/femsyr/foz029. [PMID: 30993332]
  • Saveg Yadav, Shrish Kumar Pandey, Yugal Goel, Praveen Kumar Kujur, Babu Nandan Maurya, Ashish Verma, Ajay Kumar, Rana Pratap Singh, Sukh Mahendra Singh. Protective and recuperative effects of 3-bromopyruvate on immunological, hepatic and renal homeostasis in a murine host bearing ascitic lymphoma: Implication of niche dependent differential roles of macrophages. Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie. 2018 Mar; 99(?):970-985. doi: 10.1016/j.biopha.2018.01.149. [PMID: 29689702]
  • Salah Mohamed El Sayed. Enhancing anticancer effects, decreasing risks and solving practical problems facing 3-bromopyruvate in clinical oncology: 10 years of research experience. International journal of nanomedicine. 2018; 13(?):4699-4709. doi: 10.2147/ijn.s170564. [PMID: 30154655]
  • Salah Mohamed El Sayed, Hussam Baghdadi, Mohammed Zolaly, Hamdi H Almaramhy, Mongi Ayat, Jagadish G Donki. The promising anticancer drug 3-bromopyruvate is metabolized through glutathione conjugation which affects chemoresistance and clinical practice: An evidence-based view. Medical hypotheses. 2017 Mar; 100(?):67-77. doi: 10.1016/j.mehy.2017.01.014. [PMID: 28236852]
  • Jorg Baltzer. [Not Available]. Kinderkrankenschwester : Organ der Sektion Kinderkrankenpflege. 2017 01; 36(1):10-13. doi: ". [PMID: 30388334]
  • Qiong Pan, Yiming Sun, Qili Jin, Qixiang Li, Qing Wang, Hao Liu, Surong Zhao. Hepatotoxicity and nephrotoxicity of 3-bromopyruvate in mice. Acta cirurgica brasileira. 2016 Nov; 31(11):724-729. doi: 10.1590/s0102-865020160110000004. [PMID: 27982259]
  • Suellen Ferro, João Azevedo-Silva, Margarida Casal, Manuela Côrte-Real, Fatima Baltazar, Ana Preto. Characterization of acetate transport in colorectal cancer cells and potential therapeutic implications. Oncotarget. 2016 Oct; 7(43):70639-70653. doi: 10.18632/oncotarget.12156. [PMID: 28874966]
  • Izabela Sadowska-Bartosz, Jacek Grębowski, Ewa Kępka, Maciej Studzian, Grzegorz Bartosz, Łukasz Pułaski. ABCB1-overexpressing MDCK-II cells are hypersensitive to 3-bromopyruvic acid. Life sciences. 2016 Oct; 162(?):138-44. doi: 10.1016/j.lfs.2016.08.012. [PMID: 27534909]
  • Douglas Jardim-Messeder, Fabiana Moreira-Pacheco. 3-Bromopyruvic Acid Inhibits Tricarboxylic Acid Cycle and Glutaminolysis in HepG2 Cells. Anticancer research. 2016 May; 36(5):2233-41. doi: NULL. [PMID: 27127128]
  • João Azevedo-Silva, Odília Queirós, Ana Ribeiro, Fátima Baltazar, Ko H Young, Peter L Pedersen, Ana Preto, Margarida Casal. The cytotoxicity of 3-bromopyruvate in breast cancer cells depends on extracellular pH. The Biochemical journal. 2015 Apr; 467(2):247-58. doi: 10.1042/bj20140921. [PMID: 25641640]
  • H Nilsson, D Lindgren, A Mandahl Forsberg, H Mulder, H Axelson, M E Johansson. Primary clear cell renal carcinoma cells display minimal mitochondrial respiratory capacity resulting in pronounced sensitivity to glycolytic inhibition by 3-Bromopyruvate. Cell death & disease. 2015 Jan; 6(?):e1585. doi: 10.1038/cddis.2014.545. [PMID: 25569102]
  • Salah Mohamed El Sayed, Walaa Gamal Mohamed, Minnat-Allah Hassan Seddik, Al-Shimaa Ahmed Ahmed, Asmaa Gamal Mahmoud, Wael Hassan Amer, Manal Mohamed Helmy Nabo, Ahmed Roshdi Hamed, Nagwa Sayed Ahmed, Ali Abdel-Rahman Abd-Allah. Safety and outcome of treatment of metastatic melanoma using 3-bromopyruvate: a concise literature review and case study. Chinese journal of cancer. 2014 Jul; 33(7):356-64. doi: 10.5732/cjc.013.10111. [PMID: 24636230]
  • Adam D Lietzan, Martin St Maurice. Insights into the carboxyltransferase reaction of pyruvate carboxylase from the structures of bound product and intermediate analogs. Biochemical and biophysical research communications. 2013 Nov; 441(2):377-82. doi: 10.1016/j.bbrc.2013.10.066. [PMID: 24157795]
  • Rani Kunjithapatham, Jean-Francois H Geschwind, Pramod P Rao, Tatiana N Boronina, Robert N Cole, Shanmugasundaram Ganapathy-Kanniappan. Systemic administration of 3-bromopyruvate reveals its interaction with serum proteins in a rat model. BMC research notes. 2013 Jul; 6(?):277. doi: 10.1186/1756-0500-6-277. [PMID: 23866825]
  • Harrie A Verhoeven, Leo J L D van Griensven. Flow cytometric evaluation of the effects of 3-bromopyruvate (3BP) and dichloracetate (DCA) on THP-1 cells: a multiparameter analysis. Journal of bioenergetics and biomembranes. 2012 Feb; 44(1):91-9. doi: 10.1007/s10863-012-9414-7. [PMID: 22318358]
  • Odília Queirós, Ana Preto, António Pacheco, Céline Pinheiro, João Azevedo-Silva, Roxana Moreira, Madalena Pedro, Young H Ko, Peter L Pedersen, Fátima Baltazar, Margarida Casal. Butyrate activates the monocarboxylate transporter MCT4 expression in breast cancer cells and enhances the antitumor activity of 3-bromopyruvate. Journal of bioenergetics and biomembranes. 2012 Feb; 44(1):141-53. doi: 10.1007/s10863-012-9418-3. [PMID: 22350013]
  • Magdalena Davidescu, Miriam Sciaccaluga, Lara Macchioni, Roberto Angelini, Patrizia Lopalco, Maria Grazia Rambotti, Rita Roberti, Angela Corcelli, Emilia Castigli, Lanfranco Corazzi. Bromopyruvate mediates autophagy and cardiolipin degradation to monolyso-cardiolipin in GL15 glioblastoma cells. Journal of bioenergetics and biomembranes. 2012 Feb; 44(1):51-60. doi: 10.1007/s10863-012-9411-x. [PMID: 22318357]
  • E Babu, S Ramachandran, V CoothanKandaswamy, S Elangovan, P D Prasad, V Ganapathy, M Thangaraju. Role of SLC5A8, a plasma membrane transporter and a tumor suppressor, in the antitumor activity of dichloroacetate. Oncogene. 2011 Sep; 30(38):4026-37. doi: 10.1038/onc.2011.113. [PMID: 21499304]
  • Alberto Macone, Mario Fontana, Marco Barba, Bruno Botta, Mirella Nardini, Francesca Ghirga, Andrea Calcaterra, Laura Pecci, Rosa Marina Matarese. Antioxidant properties of aminoethylcysteine ketimine decarboxylated dimer: a review. International journal of molecular sciences. 2011; 12(5):3072-84. doi: 10.3390/ijms12053072. [PMID: 21686170]
  • R Abbas, R S Kombu, R A Ibarra, K K Goyal, H Brunengraber, J R Sanabria. The dynamics of glutathione species and ophthalmate concentrations in plasma from the VX2 rabbit model of secondary liver tumors. HPB surgery : a world journal of hepatic, pancreatic and biliary surgery. 2011; 2011(?):709052. doi: 10.1155/2011/709052. [PMID: 21350723]
  • Xianhua Cao, Guang Jia, Tao Zhang, Ming Yang, Bing Wang, Peter A Wassenaar, Hao Cheng, Michael V Knopp, Duxin Sun. Non-invasive MRI tumor imaging and synergistic anticancer effect of HSP90 inhibitor and glycolysis inhibitor in RIP1-Tag2 transgenic pancreatic tumor model. Cancer chemotherapy and pharmacology. 2008 Nov; 62(6):985-94. doi: 10.1007/s00280-008-0688-8. [PMID: 18253734]
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  • Hong Zhao, Toshiki Tanaka, H Dorota Halicka, Frank Traganos, Miroslaw Zarebski, Jurek Dobrucki, Zbigniew Darzynkiewicz. Cytometric assessment of DNA damage by exogenous and endogenous oxidants reports aging-related processes. Cytometry. Part A : the journal of the International Society for Analytical Cytology. 2007 Nov; 71(11):905-14. doi: 10.1002/cyto.a.20469. [PMID: 17879239]
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