Dichlororibofuranosylbenzimidazole (BioDeep_00000837882)

   


代谢物信息卡片


5,6-Dichlorobenzimidazole riboside

化学式: C12H12Cl2N2O4 (318.0174)
中文名称: 二氯苯并咪唑呋喃型核糖苷
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C1=C2C(=CC(=C1Cl)Cl)N(C=N2)C3C(C(C(O3)CO)O)O
InChI: InChI=1S/C12H12Cl2N2O4/c13-5-1-7-8(2-6(5)14)16(4-15-7)12-11(19)10(18)9(3-17)20-12/h1-2,4,9-12,17-19H,3H2/t9-,10-,11-,12-/m1/s1

描述信息

D004791 - Enzyme Inhibitors > D019384 - Nucleic Acid Synthesis Inhibitors
5,6-Dichlorobenzimidazole riboside (DRB) is a nucleoside analog that inhibits several carboxyl-terminal domain kinases, including casein kinase II and cell cycle-dependent kinases (CDK). 5, 6-dichlorobenzimidazole riboside has antitumor activity. 5, 6-dichlorobenzimidazole riboside can induce apoptosis[1][2][3][4][5][6][7].

同义名列表

3 个代谢物同义名

5,6-Dichlorobenzimidazole riboside; Dichlororibofuranosylbenzimidazole; DRB



数据库引用编号

8 个数据库交叉引用编号

分类词条

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0 个相关的代谢反应过程信息。

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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

  • Eleanor L Atkinson, Jessica Iegre, Paul D Brear, Elizabeth A Zhabina, Marko Hyvönen, David R Spring. Downfalls of Chemical Probes Acting at the Kinase ATP-Site: CK2 as a Case Study. Molecules (Basel, Switzerland). 2021 Mar; 26(7):. doi: 10.3390/molecules26071977. [PMID: 33807474]
  • Havva Keskin, Judit Garriga, Daphne Georlette, Xavier Graña. Complex effects of flavopiridol on the expression of primary response genes. Cell division. 2012 Mar; 7(?):11. doi: 10.1186/1747-1028-7-11. [PMID: 22458775]
  • L A McPartlin, P E Visconti, S J Bedford-Guaus. Guanine-nucleotide exchange factors (RAPGEF3/RAPGEF4) induce sperm membrane depolarization and acrosomal exocytosis in capacitated stallion sperm. Biology of reproduction. 2011 Jul; 85(1):179-88. doi: 10.1095/biolreprod.110.085555. [PMID: 21471298]
  • Elisabetta Chieli, Nadia Romiti, Idania Rodeiro, Gabino Garrido. In vitro modulation of ABCB1/P-glycoprotein expression by polyphenols from Mangifera indica. Chemico-biological interactions. 2010 Aug; 186(3):287-94. doi: 10.1016/j.cbi.2010.05.012. [PMID: 20513373]
  • Hee-Jin Park, Lei Ding, Mingqiu Dai, Rongcheng Lin, Haiyang Wang. Multisite phosphorylation of Arabidopsis HFR1 by casein kinase II and a plausible role in regulating its degradation rate. The Journal of biological chemistry. 2008 Aug; 283(34):23264-73. doi: 10.1074/jbc.m801720200. [PMID: 18556661]
  • Asuka Nakata, Hiroyuki Kamiguchi. Serine phosphorylation by casein kinase II controls endocytic L1 trafficking and axon growth. Journal of neuroscience research. 2007 Mar; 85(4):723-34. doi: 10.1002/jnr.21185. [PMID: 17253643]
  • Jang-Hee Oh, Aeyung Kim, Jong-Min Park, Shin-Hyoung Kim, An-Sik Chung. Ultraviolet B-induced matrix metalloproteinase-1 and -3 secretions are mediated via PTEN/Akt pathway in human dermal fibroblasts. Journal of cellular physiology. 2006 Dec; 209(3):775-85. doi: 10.1002/jcp.20754. [PMID: 16972255]
  • Soledad Negrotto, Natalia Pacienza, Lina Paola D'Atri, Roberto Gabriel Pozner, Elisa Malaver, Oscar Torres, Maria Angela Lazzari, Ricardo Martín Gómez, Mirta Schattner. Activation of cyclic AMP pathway prevents CD34(+) cell apoptosis. Experimental hematology. 2006 Oct; 34(10):1420-8. doi: 10.1016/j.exphem.2006.05.017. [PMID: 16982335]
  • Kuy-Sook Lee, Jin-Hee Park, Seahyoung Lee, Hyun-Joung Lim, Yangsoo Jang, Hyun-Young Park. Troglitazone inhibits endothelial cell proliferation through suppression of casein kinase 2 activity. Biochemical and biophysical research communications. 2006 Jul; 346(1):83-8. doi: 10.1016/j.bbrc.2006.05.069. [PMID: 16759638]
  • Karin Kohlstedt, Roland Kellner, Rudi Busse, Ingrid Fleming. Signaling via the angiotensin-converting enzyme results in the phosphorylation of the nonmuscle myosin heavy chain IIA. Molecular pharmacology. 2006 Jan; 69(1):19-26. doi: 10.1124/mol.105.016733. [PMID: 16186248]
  • Satoshi Uchiyama, Masayoshi Yamaguchi. beta-cryptoxanthin stimulates cell differentiation and mineralization in osteoblastic MC3T3-E1 cells. Journal of cellular biochemistry. 2005 Aug; 95(6):1224-34. doi: 10.1002/jcb.20496. [PMID: 15962303]
  • M Yamaguchi, M Fukagawa. Role of zinc in regulation of protein tyrosine phosphatase activity in osteoblastic MC3T3-E1 cells: zinc modulation of insulin-like growth factor-I's effect. Calcified tissue international. 2005 Jan; 76(1):32-8. doi: 10.1007/s00223-004-0052-x. [PMID: 15477998]
  • Eri Takeda, Miki Hieda, Jun Katahira, Yoshihiro Yoneda. Phosphorylation of RanGAP1 stabilizes its interaction with Ran and RanBP1. Cell structure and function. 2005; 30(2):69-80. doi: 10.1247/csf.30.69. [PMID: 16428860]
  • Renata Franchi-Gazzola, Francesca Gaccioli, Elena Bevilacqua, Rossana Visigalli, Valeria Dall'Asta, Roberto Sala, Hélène Varoqui, Jeffrey D Erickson, Gian C Gazzola, Ovidio Bussolati. The synthesis of SNAT2 transporters is required for the hypertonic stimulation of system A transport activity. Biochimica et biophysica acta. 2004 Dec; 1667(2):157-66. doi: 10.1016/j.bbamem.2004.09.012. [PMID: 15581851]
  • Koichi Ishida, Masayoshi Yamaguchi. Role of albumin in osteoblastic cells: enhancement of cell proliferation and suppression of alkaline phosphatase activity. International journal of molecular medicine. 2004 Dec; 14(6):1077-81. doi: . [PMID: 15547677]
  • Yuda Fang, Stephen Hearn, David L Spector. Tissue-specific expression and dynamic organization of SR splicing factors in Arabidopsis. Molecular biology of the cell. 2004 Jun; 15(6):2664-73. doi: 10.1091/mbc.e04-02-0100. [PMID: 15034145]
  • K F Rodriguez, C E Farin. Developmental capacity of bovine cumulus oocyte complexes after transcriptional inhibition of germinal vesicle breakdown. Theriogenology. 2004 May; 61(7-8):1499-511. doi: 10.1016/j.theriogenology.2003.08.016. [PMID: 15036980]
  • Stefania Sarno, Erika de Moliner, Maria Ruzzene, Mario A Pagano, Roberto Battistutta, Jenny Bain, Doriano Fabbro, Joseph Schoepfer, Matthew Elliott, Pascal Furet, Flavio Meggio, Giuseppe Zanotti, Lorenzo A Pinna. Biochemical and three-dimensional-structural study of the specific inhibition of protein kinase CK2 by [5-oxo-5,6-dihydroindolo-(1,2-a)quinazolin-7-yl]acetic acid (IQA). The Biochemical journal. 2003 Sep; 374(Pt 3):639-46. doi: 10.1042/bj20030674. [PMID: 12816539]
  • Konstantin I Ivanov, Pietri Puustinen, Rasa Gabrenaite, Helena Vihinen, Lars Rönnstrand, Leena Valmu, Nisse Kalkkinen, Kristiina Mäkinen. Phosphorylation of the potyvirus capsid protein by protein kinase CK2 and its relevance for virus infection. The Plant cell. 2003 Sep; 15(9):2124-39. doi: 10.1105/tpc.012567. [PMID: 12953115]
  • Ping Cui, Susana Moreno Díaz de la Espina. Sm and U2B' proteins redistribute to different nuclear domains in dormant and proliferating onion cells. Planta. 2003 May; 217(1):21-31. doi: 10.1007/s00425-002-0966-3. [PMID: 12721845]
  • Robert A Frost, Gerald J Nystrom, Charles H Lang. Lipopolysaccharide regulates proinflammatory cytokine expression in mouse myoblasts and skeletal muscle. American journal of physiology. Regulatory, integrative and comparative physiology. 2002 Sep; 283(3):R698-709. doi: 10.1152/ajpregu.00039.2002. [PMID: 12185005]
  • Shinobu Yamauchi, Yoshihito Tokita, Sachiko Aono, Fumiko Matsui, Takuya Shuo, Hidenori Ito, Kanefusa Kato, Kohji Kasahara, Atsuhiko Oohira. Phosphorylation of neuroglycan C, a brain-specific transmembrane chondroitin sulfate proteoglycan, and its localization in the lipid rafts. The Journal of biological chemistry. 2002 Jun; 277(23):20583-90. doi: 10.1074/jbc.m200909200. [PMID: 11929867]
  • H S Park, S M Lee, J H Lee, Y S Kim, Y S Bae, J W Park. Phosphorylation of the leucocyte NADPH oxidase subunit p47(phox) by casein kinase 2: conformation-dependent phosphorylation and modulation of oxidase activity. The Biochemical journal. 2001 Sep; 358(Pt 3):783-90. doi: 10.1042/0264-6021:3580783. [PMID: 11535139]
  • P Hidalgo, V Garretón, C G Berríos, H Ojeda, X Jordana, L Holuigue. A nuclear casein kinase 2 activity is involved in early events of transcriptional activation induced by salicylic acid in tobacco. Plant physiology. 2001 Jan; 125(1):396-405. doi: 10.1104/pp.125.1.396. [PMID: 11154347]
  • F Loreni, G Thomas, F Amaldi. Transcription inhibitors stimulate translation of 5' TOP mRNAs through activation of S6 kinase and the mTOR/FRAP signalling pathway. European journal of biochemistry. 2000 Nov; 267(22):6594-601. doi: 10.1046/j.1432-1327.2000.01753.x. [PMID: 11054111]
  • J Y Miao, S Araki, Y R Han, H Hayashi. Involvement of gene expressions in apoptosis of vascular endothelial cells induced by rattlesnake venom. Cell research. 1999 Sep; 9(3):237-42. doi: 10.1038/sj.cr.7290022. [PMID: 10520606]
  • I Raska, G Reimer. Human autoantibodies identify a protein in dense fibrillar and granular components of the nucleolus. Acta histochemica. 1999 Apr; 101(2):157-66. doi: 10.1016/s0065-1281(99)80015-4. [PMID: 10335359]
  • A W Jehle, H Hilfiker, M F Pfister, J Biber, E Lederer, R Krapf, H Murer. Type II Na-Pi cotransport is regulated transcriptionally by ambient bicarbonate/carbon dioxide tension in OK cells. The American journal of physiology. 1999 01; 276(1):F46-53. doi: 10.1152/ajprenal.1999.276.1.f46. [PMID: 9887079]
  • G Nickenig, J Röling, K Strehlow, P Schnabel, M Böhm. Insulin induces upregulation of vascular AT1 receptor gene expression by posttranscriptional mechanisms. Circulation. 1998 Dec; 98(22):2453-60. doi: 10.1161/01.cir.98.22.2453. [PMID: 9832492]
  • J A Maurer, S Wray. Luteinizing hormone-releasing hormone (LHRH) neurons maintained in hypothalamic slice explant cultures exhibit a rapid LHRH mRNA turnover rate. The Journal of neuroscience : the official journal of the Society for Neuroscience. 1997 Dec; 17(24):9481-91. doi: NULL. [PMID: 9391004]
  • V C Venkatesh, H D Katzberg. Glucocorticoid regulation of epithelial sodium channel genes in human fetal lung. The American journal of physiology. 1997 Jul; 273(1 Pt 1):L227-33. doi: 10.1152/ajplung.1997.273.1.l227. [PMID: 9252560]
  • S J Kim, C R Kahn. Insulin stimulates p70 S6 kinase in the nucleus of cells. Biochemical and biophysical research communications. 1997 May; 234(3):681-5. doi: 10.1006/bbrc.1997.6699. [PMID: 9175775]
  • Z X Xu, S A Rooney. Glucocorticoids increase fatty-acid synthase mRNA stability in fetal rat lung. The American journal of physiology. 1997 May; 272(5 Pt 1):L860-4. doi: 10.1152/ajplung.1997.272.5.l860. [PMID: 9176249]
  • R Yamamoto, T Yanagita, H Kobayashi, T Yuhi, H Yokoo, A Wada. Up-regulation of functional voltage-dependent sodium channels by insulin in cultured bovine adrenal chromaffin cells. Journal of neurochemistry. 1996 Oct; 67(4):1401-8. doi: 10.1046/j.1471-4159.1996.67041401.x. [PMID: 8858921]
  • A Belbrahem, D Godden-Kent, S Mittnacht. Regulation and activity of the retinoblastoma protein family in growth factor-deprived and TGF(beta)-treated keratinocytes. Experimental cell research. 1996 Jun; 225(2):286-93. doi: 10.1006/excr.1996.0178. [PMID: 8660916]
  • M Ljungman. Effect of differential gene expression on the chromatin structure of the DHFR gene domain in vivo. Biochimica et biophysica acta. 1996 Jun; 1307(2):171-7. doi: 10.1016/0167-4781(96)00037-1. [PMID: 8679702]
  • E I Goncharova, A Nádas, T G Rossman. Serum deprivation, but not inhibition of growth per se, induces a hypermutable state in Chinese hamster G12 cells. Cancer research. 1996 Feb; 56(4):752-6. doi: NULL. [PMID: 8631009]
  • H R Junéra, C Masson, G Géraud, D Hernandez-Verdun. The three-dimensional organization of ribosomal genes and the architecture of the nucleoli vary with G1, S and G2 phases. Journal of cell science. 1995 Nov; 108 ( Pt 11)(?):3427-41. doi: 10.1242/jcs.108.11.3427. [PMID: 8586655]
  • M Ljungman, P C Hanawalt. Presence of negative torsional tension in the promoter region of the transcriptionally poised dihydrofolate reductase gene in vivo. Nucleic acids research. 1995 May; 23(10):1782-9. doi: 10.1093/nar/23.10.1782. [PMID: 7784183]
  • J R Davie, L C Murphy. Inhibition of transcription selectively reduces the level of ubiquitinated histone H2B in chromatin. Biochemical and biophysical research communications. 1994 Aug; 203(1):344-50. doi: 10.1006/bbrc.1994.2188. [PMID: 8074677]
  • M B Goldring, K Fukuo, J R Birkhead, E Dudek, L J Sandell. Transcriptional suppression by interleukin-1 and interferon-gamma of type II collagen gene expression in human chondrocytes. Journal of cellular biochemistry. 1994 Jan; 54(1):85-99. doi: 10.1002/jcb.240540110. [PMID: 8126089]
  • O V Zatsepina, R Voit, I Grummt, H Spring, M V Semenov, M F Trendelenburg. The RNA polymerase I-specific transcription initiation factor UBF is associated with transcriptionally active and inactive ribosomal genes. Chromosoma. 1993 Nov; 102(9):599-611. doi: 10.1007/bf00352307. [PMID: 8306821]
  • J Yang, A H Tashjian. Regulation of endogenous thyrotropin-releasing hormone receptor messenger RNA in GH4C1 cells: roles of protein and RNA synthesis. Molecular endocrinology (Baltimore, Md.). 1993 Sep; 7(9):1144-50. doi: 10.1210/mend.7.9.8247016. [PMID: 8247016]
  • C Stefanelli, F Flamigni, F Ferrari, C Rossoni, C M Caldarera. Induction of ornithine decarboxylase by transcriptional inhibitors in quiescent thymocytes. Biochemistry international. 1992 May; 26(6):995-1001. doi: NULL. [PMID: 1632808]
  • U Schubert, T Schneider, P Henklein, K Hoffmann, E Berthold, H Hauser, G Pauli, T Porstmann. Human-immunodeficiency-virus-type-1-encoded Vpu protein is phosphorylated by casein kinase II. European journal of biochemistry. 1992 Mar; 204(2):875-83. doi: 10.1111/j.1432-1033.1992.tb16707.x. [PMID: 1541298]
  • E Kyeyune-Nyombi, K H Lau, D J Baylink, D D Strong. 1,25-Dihydroxyvitamin D3 stimulates both alkaline phosphatase gene transcription and mRNA stability in human bone cells. Archives of biochemistry and biophysics. 1991 Dec; 291(2):316-25. doi: 10.1016/0003-9861(91)90141-5. [PMID: 1952946]
  • J K Chesters, R Boyne. Nature of the Zn2+ requirement for DNA synthesis by 3T3 cells. Experimental cell research. 1991 Feb; 192(2):631-4. doi: 10.1016/0014-4827(91)90085-9. [PMID: 1988298]
  • C Genovese, C Milcarek. Increased half-life of mu immunoglobulin mRNA during mouse B cell development increases its abundancy. Molecular immunology. 1990 Aug; 27(8):733-43. doi: 10.1016/0161-5890(90)90082-b. [PMID: 2119479]
  • I Tamm, T Kikuchi. Insulin-like growth factor-1 (IGF-1), insulin, and epidermal growth factor (EGF) are survival factors for density-inhibited, quiescent Balb/c-3T3 murine fibroblasts. Journal of cellular physiology. 1990 Jun; 143(3):494-500. doi: 10.1002/jcp.1041430314. [PMID: 2193035]
  • E Green, B Todd, D Heath. Mechanism of glucocorticoid regulation of alkaline phosphatase gene expression in osteoblast-like cells. European journal of biochemistry. 1990 Feb; 188(1):147-53. doi: 10.1111/j.1432-1033.1990.tb15382.x. [PMID: 2318198]
  • A Widell, B G Hansson, E Nordenfelt, B Oberg. Enhancement of hepatitis A propagation in tissue culture with 5,6-dichloro-1-beta-D-ribofuranosylbenzimidazole. Journal of medical virology. 1988 Apr; 24(4):369-76. doi: 10.1002/jmv.1890240403. [PMID: 2835431]
  • S Sundström, D Lundblad, E Lundgren. Interferon inhibits preferentially the synthesis of proteins associated with growth stimulation of Swiss 3T3 mouse fibroblasts. Biochimica et biophysica acta. 1987 Apr; 908(3):275-84. doi: 10.1016/0167-4781(87)90108-4. [PMID: 3567200]
  • D R Edwards, C L Parfett, D T Denhardt. Transcriptional regulation of two serum-induced RNAs in mouse fibroblasts: equivalence of one species to B2 repetitive elements. Molecular and cellular biology. 1985 Nov; 5(11):3280-8. doi: 10.1128/mcb.5.11.3280-3288.1985. [PMID: 3837843]
  • D L Coppock, A B Pardee. Regulation of thymidine kinase activity in the cell cycle by a labile protein. Journal of cellular physiology. 1985 Aug; 124(2):269-74. doi: 10.1002/jcp.1041240215. [PMID: 2413051]
  • S Aké, C Péaud-Lenoël. 5,6-Dichlorobenzimidazole-1-beta-D-riboside, specific inhibitor of cytokinin activity in tobacco cell suspension cultures. Biochimie. 1985 Jan; 67(1):155-60. doi: 10.1016/s0300-9084(85)80243-1. [PMID: 3995092]
  • I Tamm. HeLa cell RNA and protein syntheses. Effects of long-term treatment with 5,6-dichloro-1-beta-D-ribofuranosylbenzimidazole (DRB). Biochemical pharmacology. 1984 Feb; 33(4):551-7. doi: 10.1016/0006-2952(84)90306-x. [PMID: 6200120]
  • G C Burmer, P S Rabinovitch, T H Norwood. Evidence for differences in the mechanism of cell cycle arrest between senescent and serum-deprived human fibroblasts: heterokaryon and metabolic inhibitor studies. Journal of cellular physiology. 1984 Jan; 118(1):97-103. doi: 10.1002/jcp.1041180116. [PMID: 6690456]
  • I Tamm. Recovery of HeLa cell population growth after treatment with 5,6-dichloro-1-beta-D-ribofuranosylbenzimidazole (DRB). Journal of cellular physiology. 1983 Jul; 116(1):26-34. doi: 10.1002/jcp.1041160106. [PMID: 6853610]
  • I Tamm, T Kikuchi. Inhibition of HeLa-S3 cell proliferation and biosynthesis by 5,6-dichloro-1-beta-D-ribofuranosylbenzimidazole (DRB). Proceedings of the Society for Experimental Biology and Medicine. Society for Experimental Biology and Medicine (New York, N.Y.). 1983 Jun; 173(2):238-43. doi: 10.3181/00379727-173-41638. [PMID: 6191332]
  • P E Montandon, N H Acheson. Synthesis of prematurely terminated late transcripts of polyoma virus DNA is resistant to inhibition by 5,6-dichloro-1-beta-D-ribofuranosylbenzimidazole. The Journal of general virology. 1982 Apr; 59(Pt 2):367-76. doi: 10.1099/0022-1317-59-2-367. [PMID: 6176679]
  • I Tamm, T Kikuchi, J S Murphy. Serum enhances the cycling and survival of HeLa cells treated with 5,6-dichloro-1-beta-D-ribofuranosylbenzimidazole. Proceedings of the National Academy of Sciences of the United States of America. 1982 Apr; 79(8):2569-73. doi: 10.1073/pnas.79.8.2569. [PMID: 6953414]