ccpa (BioDeep_00000406270)

   

Antitumor activity


代谢物信息卡片


2-Chloro-N6-cyclopentyladenosine

化学式: C15H20ClN5O4 (369.120375)
中文名称: 2-氯-N 6 -环戊基腺苷
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: C1CCC(C1)NC2=C3C(=NC(=N2)Cl)N(C=N3)C4C(C(C(O4)CO)O)O
InChI: InChI=1S/C15H20ClN5O4/c16-15-19-12(18-7-3-1-2-4-7)9-13(20-15)21(6-17-9)14-11(24)10(23)8(5-22)25-14/h6-8,10-11,14,22-24H,1-5H2,(H,18,19,20)/t8-,10-,11-,14-/m1/s1

描述信息

CCPA (2-Chloro-N6-cyclopentyladenosine) is a purine nucleoside analog. Purine nucleoside analogs have broad antitumor activity targeting indolent lymphoid malignancies. Anticancer mechanisms in this process rely on inhibition of DNA synthesis, induction of apoptosis, etc[1].

同义名列表

2 个代谢物同义名

2-Chloro-N6-cyclopentyladenosine; ccpa



数据库引用编号

5 个数据库交叉引用编号

分类词条

相关代谢途径

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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

  • Hitesh Soni, Dieniffer Peixoto-Neves, Randal K Buddington, Adebowale Adebiyi. Adenosine A1 receptor-operated calcium entry in renal afferent arterioles is dependent on postnatal maturation of TRPC3 channels. American journal of physiology. Renal physiology. 2017 Dec; 313(6):F1216-F1222. doi: 10.1152/ajprenal.00335.2017. [PMID: 28855189]
  • Jinha Yu, Seyeon Ahn, Hee Jin Kim, Moonyoung Lee, Sungjin Ahn, Jungmin Kim, Sun Hee Jin, Eunyoung Lee, Gyudong Kim, Jae Hoon Cheong, Kenneth A Jacobson, Lak Shin Jeong, Minsoo Noh. Polypharmacology of N6-(3-Iodobenzyl)adenosine-5'-N-methyluronamide (IB-MECA) and Related A3 Adenosine Receptor Ligands: Peroxisome Proliferator Activated Receptor (PPAR) γ Partial Agonist and PPARδ Antagonist Activity Suggests Their Antidiabetic Potential. Journal of medicinal chemistry. 2017 09; 60(17):7459-7475. doi: 10.1021/acs.jmedchem.7b00805. [PMID: 28799755]
  • Andreas K Dacho, Andreas Dietz, Kristin Mueller. Histological effect on the adipocutaneous flap in rats after preconditioning with 2-chloro-N(6) -cyclopentyladenosine. Head & neck. 2014 Aug; 36(8):1189-99. doi: 10.1002/hed.23433. [PMID: 23893540]
  • Joo Yun Kim, Mihwa Kim, Ahrom Ham, Kevin M Brown, Robert W Greene, Vivette D D'Agati, H Thomas Lee. IL-11 is required for A1 adenosine receptor-mediated protection against ischemic AKI. Journal of the American Society of Nephrology : JASN. 2013 Oct; 24(10):1558-70. doi: 10.1681/asn.2013010114. [PMID: 23813214]
  • Silvia Paoletta, Dilip K Tosh, Amanda Finley, Elizabeth T Gizewski, Steven M Moss, Zhan-Guo Gao, John A Auchampach, Daniela Salvemini, Kenneth A Jacobson. Rational design of sulfonated A3 adenosine receptor-selective nucleosides as pharmacological tools to study chronic neuropathic pain. Journal of medicinal chemistry. 2013 Jul; 56(14):5949-63. doi: 10.1021/jm4007966. [PMID: 23789857]
  • Edwin K Jackson, Dongmei Cheng, Zaichuan Mi, Jonathan D Verrier, Keri Janesko-Feldman, Patrick M Kochanek. Role of A1 receptors in renal sympathetic neurotransmission in the mouse kidney. American journal of physiology. Renal physiology. 2012 Oct; 303(7):F1000-5. doi: 10.1152/ajprenal.00363.2012. [PMID: 22874760]
  • Sang W Park, Mihwa Kim, Joo Y Kim, Kevin M Brown, Volker H Haase, Vivette D D'Agati, H Thomas Lee. Proximal tubule sphingosine kinase-1 has a critical role in A1 adenosine receptor-mediated renal protection from ischemia. Kidney international. 2012 Oct; 82(8):878-91. doi: 10.1038/ki.2012.224. [PMID: 22695326]
  • Dilip K Tosh, Silvia Paoletta, Francesca Deflorian, Khai Phan, Steven M Moss, Zhan-Guo Gao, Xiaohui Jiang, Kenneth A Jacobson. Structural sweet spot for A1 adenosine receptor activation by truncated (N)-methanocarba nucleosides: receptor docking and potent anticonvulsant activity. Journal of medicinal chemistry. 2012 Sep; 55(18):8075-90. doi: 10.1021/jm300965a. [PMID: 22921089]
  • Sheng Hu, Hailong Dong, Haopeng Zhang, Shiquan Wang, Lichao Hou, Shaoyang Chen, Jinsong Zhang, Lize Xiong. Noninvasive limb remote ischemic preconditioning contributes neuroprotective effects via activation of adenosine A1 receptor and redox status after transient focal cerebral ischemia in rats. Brain research. 2012 Jun; 1459(?):81-90. doi: 10.1016/j.brainres.2012.04.017. [PMID: 22560096]
  • Edwin K Jackson, Dongmei Cheng, Stevan P Tofovic, Zaichuan Mi. Endogenous adenosine contributes to renal sympathetic neurotransmission via postjunctional A1 receptor-mediated coincident signaling. American journal of physiology. Renal physiology. 2012 Feb; 302(4):F466-76. doi: 10.1152/ajprenal.00495.2011. [PMID: 22114202]
  • Ruibo Wang, Maria L Urso, Edward J Zambraski, Erik P Rader, Kevin P Campbell, Bruce T Liang. Adenosine A(3) receptor stimulation induces protection of skeletal muscle from eccentric exercise-mediated injury. American journal of physiology. Regulatory, integrative and comparative physiology. 2010 Jul; 299(1):R259-67. doi: 10.1152/ajpregu.00060.2010. [PMID: 20427727]
  • Dovenia S Ponnoth, Ahmed Nadeem, Stephen Tilley, S Jamal Mustafa. Involvement of A1 adenosine receptors in altered vascular responses and inflammation in an allergic mouse model of asthma. American journal of physiology. Heart and circulatory physiology. 2010 Jul; 299(1):H81-7. doi: 10.1152/ajpheart.01090.2009. [PMID: 20400685]
  • Zhaogang Yang, Wei Sun, Keli Hu. Adenosine A(1) receptors selectively target protein kinase C isoforms to the caveolin-rich plasma membrane in cardiac myocytes. Biochimica et biophysica acta. 2009 Dec; 1793(12):1868-75. doi: 10.1016/j.bbamcr.2009.10.007. [PMID: 19879903]
  • Caijiao Xie, Ke Ran, Jianhua Liu, Junmei Xu, Yetian Chang. [Metallothionein mediates cardioprotection induced by delayed preconditioning with adenosine A1 receptor agonist in rabbits]. Zhong nan da xue xue bao. Yi xue ban = Journal of Central South University. Medical sciences. 2009 Jul; 34(7):603-7. doi: . [PMID: 19648671]
  • Jin Deok Joo, Mihwa Kim, Patrick Horst, Jeehee Kim, Vivette D D'Agati, Charles W Emala, H Thomas Lee. Acute and delayed renal protection against renal ischemia and reperfusion injury with A1 adenosine receptors. American journal of physiology. Renal physiology. 2007 Dec; 293(6):F1847-57. doi: 10.1152/ajprenal.00336.2007. [PMID: 17928414]
  • Agnieszka Walkowska, Leszek Dobrowolski, Elzbieta Kompanowska-Jezierska, Janusz Sadowski. Role of NO and COX pathways in mediation of adenosine A1 receptor-induced renal vasoconstriction. Experimental biology and medicine (Maywood, N.J.). 2007 May; 232(5):690-4. doi: NULL. [PMID: 17463166]
  • V Haktan Ozacmak, Hale Sayan. Pretreatment with adenosine and adenosine A1 receptor agonist protects against intestinal ischemia-reperfusion injury in rat. World journal of gastroenterology. 2007 Jan; 13(4):538-47. doi: 10.3748/wjg.v13.i4.538. [PMID: 17278219]
  • Kenneth A Jacobson, Zhan-Guo Gao. Adenosine receptors as therapeutic targets. Nature reviews. Drug discovery. 2006 Mar; 5(3):247-64. doi: 10.1038/nrd1983. [PMID: 16518376]
  • Kenneth A Jacobson, Zhan-Guo Gao, Susanna Tchilibon, Heng T Duong, Bhalchandra V Joshi, Dmitry Sonin, Bruce T Liang. Semi-rational design of (north)-methanocarba nucleosides as dual acting A(1) and A(3) adenosine receptor agonists: novel prototypes for cardioprotection. Journal of medicinal chemistry. 2005 Dec; 48(26):8103-7. doi: 10.1021/jm050726b. [PMID: 16366590]
  • Wan-Chun Sun, Yan Cao, Lei Jin, Li-Zhen Wang, Fan Meng, Xing-Zu Zhu. Modulating effect of adenosine deaminase on function of adenosine A1 receptors. Acta pharmacologica Sinica. 2005 Feb; 26(2):160-5. doi: 10.1111/j.1745-7254.2005.00524.x. [PMID: 15663892]
  • H Thomas Lee, Hua Xu, Samih H Nasr, Jurgen Schnermann, Charles W Emala. A1 adenosine receptor knockout mice exhibit increased renal injury following ischemia and reperfusion. American journal of physiology. Renal physiology. 2004 Feb; 286(2):F298-306. doi: 10.1152/ajprenal.00185.2003. [PMID: 14600029]
  • Zhan-Guo Gao, Soo-Kyung Kim, Thibaud Biadatti, Wangzhong Chen, Kyeong Lee, Dov Barak, Seong Gon Kim, Carl R Johnson, Kenneth A Jacobson. Structural determinants of A(3) adenosine receptor activation: nucleoside ligands at the agonist/antagonist boundary. Journal of medicinal chemistry. 2002 Sep; 45(20):4471-84. doi: 10.1021/jm020211+. [PMID: 12238926]
  • Zhan-guo Gao, Kenneth A Jacobson. 2-Chloro-N(6)-cyclopentyladenosine, adenosine A(1) receptor agonist, antagonizes the adenosine A(3) receptor. European journal of pharmacology. 2002 May; 443(1-3):39-42. doi: 10.1016/s0014-2999(02)01552-2. [PMID: 12044789]
  • Constance Neely Wilson, Vinod K Batra. Lipopolysaccharide binds to and activates A(1) adenosine receptors on human pulmonary artery endothelial cells. Journal of endotoxin research. 2002; 8(4):263-71. doi: 10.1179/096805102125000470. [PMID: 12230916]
  • V Shneyvays, L Mamedova, T Zinman, K Jacobson, A Shainberg. Activation of A(3)adenosine receptor protects against doxorubicin-induced cardiotoxicity. Journal of molecular and cellular cardiology. 2001 Jun; 33(6):1249-61. doi: 10.1006/jmcc.2001.1387. [PMID: 11444927]
  • A Lorenzen, C Stannek, H Lang, V Andrianov, I Kalvinsh, U Schwabe. Characterization of a G protein-coupled receptor for nicotinic acid. Molecular pharmacology. 2001 Feb; 59(2):349-57. doi: 10.1124/mol.59.2.349. [PMID: 11160872]
  • A Satoh, T Shimosegawa, K Satoh, H Ito, Y Kohno, A Masamune, M Fujita, T Toyota. Activation of adenosine A1-receptor pathway induces edema formation in the pancreas of rats. Gastroenterology. 2000 Sep; 119(3):829-36. doi: 10.1053/gast.2000.16502. [PMID: 10982777]
  • K A Jacobson, X Ji, A H Li, N Melman, M A Siddiqui, K J Shin, V E Marquez, R G Ravi. Methanocarba analogues of purine nucleosides as potent and selective adenosine receptor agonists. Journal of medicinal chemistry. 2000 Jun; 43(11):2196-203. doi: 10.1021/jm9905965. [PMID: 10841798]
  • R D Lasley, P Narayan, A Uittenbogaard, E J Smart. Activated cardiac adenosine A(1) receptors translocate out of caveolae. The Journal of biological chemistry. 2000 Feb; 275(6):4417-21. doi: 10.1074/jbc.275.6.4417. [PMID: 10660613]
  • S Genovesi, F Pieruzzi, P Camisasca, G Ragonesi, G Protasoni, R Golin, A Zanchetti, A Stella. Effects of adenosine receptor agonists on efferent renal nerve activity in anesthetized rats. Journal of cardiovascular pharmacology. 2000 Feb; 35(2):189-94. doi: 10.1097/00005344-200002000-00003. [PMID: 10672849]
  • J Linden, T Thai, H Figler, X Jin, A S Robeva. Characterization of human A(2B) adenosine receptors: radioligand binding, western blotting, and coupling to G(q) in human embryonic kidney 293 cells and HMC-1 mast cells. Molecular pharmacology. 1999 Oct; 56(4):705-13. doi: NULL. [PMID: 10496952]
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  • J S Aguilar, F Tan, I Durand, R D Green. Isolation and characterization of an avian A1 adenosine receptor gene and a related cDNA clone. The Biochemical journal. 1995 May; 307 ( Pt 3)(?):729-34. doi: 10.1042/bj3070729. [PMID: 7741703]
  • H O Kim, X D Ji, S M Siddiqi, M E Olah, G L Stiles, K A Jacobson. 2-Substitution of N6-benzyladenosine-5'-uronamides enhances selectivity for A3 adenosine receptors. Journal of medicinal chemistry. 1994 Oct; 37(21):3614-21. doi: 10.1021/jm00047a018. [PMID: 7932588]
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  • M Massi, A Saija, G Cristalli, C Polidori, M Perfumi, G Costa. Release of atrial natriuretic factor induced by the A1 adenosine receptor agonist 2-chloro-N6-cyclopentyl-adenosine in the rat. Pharmacological research. 1992 May; 25(4):393-402. doi: 10.1016/1043-6618(92)90676-3. [PMID: 1409251]