Chloro-IB-MECA (BioDeep_00000719697)

   


代谢物信息卡片


Chloro-IB-MECA

化学式: C18H18ClIN6O4 (544.0122768)
中文名称: 氯-IB-MECA
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: ClC1=NC(NCC2=CC=CC(I)=C2)=C3N=CN([C@@H]4O[C@H](C(NC)=O)[C@@H](O)[C@H]4O)C3=N1
InChI: InChI=1S/C18H18ClIN6O4/c1-21-16(29)13-11(27)12(28)17(30-13)26-7-23-10-14(24-18(19)25-15(10)26)22-6-8-3-2-4-9(20)5-8/h2-5,7,11-13,17,27-28H,6H2,1H3,(H,21,29)(H,22,24,25)/t11-,12+,13-,17+/m0/s1

描述信息

D018377 - Neurotransmitter Agents > D058905 - Purinergic Agents > D058913 - Purinergic Agonists
C274 - Antineoplastic Agent > C2189 - Signal Transduction Inhibitor
Namodenoson (CF-102) is a selective A3 adenosine receptor (A3AR) agonist (Ki=0.33 nM). Namodenoson displays 2500- and 1400-fold selectivity over A1 and A2A receptors respectively[1][2].
Namodenoson (CF-102) is a selective A3 adenosine receptor (A3AR) agonist (Ki=0.33 nM). Namodenoson displays 2500- and 1400-fold selectivity over A1 and A2A receptors respectively[1][2].

同义名列表

4 个代谢物同义名

Chloro-IB-MECA; 2-CL-IB-MECA; CF-102; Namodenoson



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

  • Dilip K Tosh, Veronica Salmaso, Harsha Rao, Ryan Campbell, Amelia Bitant, Zhan-Guo Gao, John A Auchampach, Kenneth A Jacobson. Direct Comparison of (N)-Methanocarba and Ribose-Containing 2-Arylalkynyladenosine Derivatives as A3 Receptor Agonists. ACS medicinal chemistry letters. 2020 Oct; 11(10):1935-1941. doi: 10.1021/acsmedchemlett.9b00637. [PMID: 33062176]
  • R Rama Suresh, Shanu Jain, Zhoumou Chen, Dilip K Tosh, Yanling Ma, Maren C Podszun, Yaron Rotman, Daniela Salvemini, Kenneth A Jacobson. Design and in vivo activity of A3 adenosine receptor agonist prodrugs. Purinergic signalling. 2020 09; 16(3):367-377. doi: 10.1007/s11302-020-09715-0. [PMID: 32720036]
  • 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]
  • Riccardo Petrelli, Mirko Scortichini, Sonja Kachler, Serena Boccella, Carmen Cerchia, Ilaria Torquati, Fabio Del Bello, Daniela Salvemini, Ettore Novellino, Livio Luongo, Sabatino Maione, Kenneth A Jacobson, Antonio Lavecchia, Karl-Norbert Klotz, Loredana Cappellacci. Exploring the Role of N6-Substituents in Potent Dual Acting 5'-C-Ethyltetrazolyladenosine Derivatives: Synthesis, Binding, Functional Assays, and Antinociceptive Effects in Mice ∇. Journal of medicinal chemistry. 2017 05; 60(10):4327-4341. doi: 10.1021/acs.jmedchem.7b00291. [PMID: 28447789]
  • Jinha Yu, Long Xuan Zhao, Jongmi Park, Hyuk Woo Lee, Pramod K Sahu, Minghua Cui, Steven M Moss, Eva Hammes, Eugene Warnick, Zhan-Guo Gao, Minsoo Noh, Sun Choi, Hee-Chul Ahn, Jungwon Choi, Kenneth A Jacobson, Lak Shin Jeong. N6-Substituted 5'-N-Methylcarbamoyl-4'-selenoadenosines as Potent and Selective A3 Adenosine Receptor Agonists with Unusual Sugar Puckering and Nucleobase Orientation. Journal of medicinal chemistry. 2017 04; 60(8):3422-3437. doi: 10.1021/acs.jmedchem.7b00241. [PMID: 28380296]
  • Lucia de Stephanis, Anna Bonon, Katia Varani, Giovanni Lanza, Roberta Gafà, Paolo Pinton, Monika Pema, Stefan Somlo, Alessandra Boletta, Gianluca Aguiari. Double inhibition of cAMP and mTOR signalling may potentiate the reduction of cell growth in ADPKD cells. Clinical and experimental nephrology. 2017 Apr; 21(2):203-211. doi: 10.1007/s10157-016-1289-1. [PMID: 27278932]
  • Dilip K Tosh, Antonella Ciancetta, Eugene Warnick, Steven Crane, Zhan-Guo Gao, Kenneth A Jacobson. Structure-Based Scaffold Repurposing for G Protein-Coupled Receptors: Transformation of Adenosine Derivatives into 5HT2B/5HT2C Serotonin Receptor Antagonists. Journal of medicinal chemistry. 2016 12; 59(24):11006-11026. doi: 10.1021/acs.jmedchem.6b01183. [PMID: 27933810]
  • Dilip K Tosh, Antonella Ciancetta, Eugene Warnick, Robert O'Connor, Zhoumou Chen, Elizabeth Gizewski, Steven Crane, Zhan-Guo Gao, John A Auchampach, Daniela Salvemini, Kenneth A Jacobson. Purine (N)-Methanocarba Nucleoside Derivatives Lacking an Exocyclic Amine as Selective A3 Adenosine Receptor Agonists. Journal of medicinal chemistry. 2016 Apr; 59(7):3249-63. doi: 10.1021/acs.jmedchem.5b01998. [PMID: 26890707]
  • Dilip K Tosh, Amanda Finley, Silvia Paoletta, Steven M Moss, Zhan-Guo Gao, Elizabeth T Gizewski, John A Auchampach, Daniela Salvemini, Kenneth A Jacobson. In vivo phenotypic screening for treating chronic neuropathic pain: modification of C2-arylethynyl group of conformationally constrained A3 adenosine receptor agonists. Journal of medicinal chemistry. 2014 Dec; 57(23):9901-14. doi: 10.1021/jm501021n. [PMID: 25422861]
  • Shamama Nishat, Anna Klinke, Stephan Baldus, Luqman Ahmad Khan, Seemi Farhat Basir. Increased A3AR-dependent vasoconstriction in diabetic mice is promoted by myeloperoxidase. Journal of cardiovascular pharmacology. 2014 Nov; 64(5):465-72. doi: 10.1097/fjc.0000000000000139. [PMID: 25000478]
  • Kiran S Toti, Steven M Moss, Silvia Paoletta, Zhan-Guo Gao, Kenneth A Jacobson, Serge Van Calenbergh. Synthesis and evaluation of N⁶-substituted apioadenosines as potential adenosine A₃ receptor modulators. Bioorganic & medicinal chemistry. 2014 Aug; 22(15):4257-68. doi: 10.1016/j.bmc.2014.05.036. [PMID: 24931275]
  • Elena Polycarpou, Lisiane B Meira, Simon Carrington, Elizabeth Tyrrell, Helmout Modjtahedi, Mark A Carew. Resveratrol 3-O-D-glucuronide and resveratrol 4'-O-D-glucuronide inhibit colon cancer cell growth: evidence for a role of A3 adenosine receptors, cyclin D1 depletion, and G1 cell cycle arrest. Molecular nutrition & food research. 2013 Oct; 57(10):1708-17. doi: 10.1002/mnfr.201200742. [PMID: 23650147]
  • 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]
  • Endre G Mikus, Kinga Boér, Géza Timári, Katalin Urbán-Szabó, Zoltán Kapui, Judit Szeredi, Katalin Gerber, Tibor Szabó, Sándor Bátori, Michel Finet, Péter Arányi, Anne-Marie Galzin. Interaction of SSR161421, a novel specific adenosine A(3) receptor antagonist with adenosine A(3) receptor agonists both in vitro and in vivo. European journal of pharmacology. 2013 Jan; 699(1-3):62-6. doi: 10.1016/j.ejphar.2012.11.046. [PMID: 23219789]
  • Eszter Kozma, P Suresh Jayasekara, Lucia Squarcialupi, Silvia Paoletta, Stefano Moro, Stephanie Federico, Giampiero Spalluto, Kenneth A Jacobson. Fluorescent ligands for adenosine receptors. Bioorganic & medicinal chemistry letters. 2013 Jan; 23(1):26-36. doi: 10.1016/j.bmcl.2012.10.112. [PMID: 23200243]
  • S Cohen, S M Stemmer, G Zozulya, A Ochaion, R Patoka, F Barer, S Bar-Yehuda, L Rath-Wolfson, K A Jacobson, P Fishman. CF102 an A3 adenosine receptor agonist mediates anti-tumor and anti-inflammatory effects in the liver. Journal of cellular physiology. 2011 Sep; 226(9):2438-47. doi: 10.1002/jcp.22593. [PMID: 21660967]
  • Yoonkyung Kim, Sonia de Castro, Zhan-Guo Gao, Adriaan P Ijzerman, Kenneth A Jacobson. Novel 2- and 4-substituted 1H-imidazo[4,5-c]quinolin-4-amine derivatives as allosteric modulators of the A3 adenosine receptor. Journal of medicinal chemistry. 2009 Apr; 52(7):2098-108. doi: 10.1021/jm801659w. [PMID: 19284749]
  • Zhan-Guo Gao, Kai Ye, Anikó Göblyös, Adriaan P Ijzerman, Kenneth A Jacobson. Flexible modulation of agonist efficacy at the human A3 adenosine receptor by the imidazoquinoline allosteric enhancer LUF6000. BMC pharmacology. 2008 Dec; 8(?):20. doi: 10.1186/1471-2210-8-20. [PMID: 19077268]
  • Artem Melman, Ben Wang, Bhalchandra V Joshi, Zhan-Guo Gao, Sonia de Castro, Cara L Heller, Soo-Kyung Kim, Lak Shin Jeong, Kenneth A Jacobson. Selective A(3) adenosine receptor antagonists derived from nucleosides containing a bicyclo[3.1.0]hexane ring system. Bioorganic & medicinal chemistry. 2008 Sep; 16(18):8546-56. doi: 10.1016/j.bmc.2008.08.007. [PMID: 18752961]
  • Francesca Di Sole, Robert Cerull, Victor Babich, Valeria Casavola, Corinna Helmle-Roth, Gerhard Burckhardt. Short- and long-term A3 adenosine receptor activation inhibits the Na+/H+ exchanger NHE3 activity and expression in opossum kidney cells. Journal of cellular physiology. 2008 Jul; 216(1):221-33. doi: 10.1002/jcp.21399. [PMID: 18286509]
  • Artem Melman, Zhan-Guo Gao, Deepmala Kumar, Tina C Wan, Elizabeth Gizewski, John A Auchampach, Kenneth A Jacobson. Design of (N)-methanocarba adenosine 5'-uronamides as species-independent A3 receptor-selective agonists. Bioorganic & medicinal chemistry letters. 2008 May; 18(9):2813-9. doi: 10.1016/j.bmcl.2008.04.001. [PMID: 18424135]
  • Natarajan V Bhanu, Wulin Aerbajinai, Nicole M Gantt, Edwin K Jackson, Sung-Ho Goh, Y Terry Lee, Jeffery L Miller. Cl-IB-MECA inhibits human erythropoiesis. British journal of haematology. 2007 May; 137(3):233-6. doi: 10.1111/j.1365-2141.2007.06540.x. [PMID: 17408462]
  • D Rüsing, C E Müller, E J Verspohl. The impact of adenosine and A(2B) receptors on glucose homoeostasis. The Journal of pharmacy and pharmacology. 2006 Dec; 58(12):1639-45. doi: 10.1211/jpp.58.12.0011. [PMID: 17331328]
  • Soo-Kyung Kim, Zhan-Guo Gao, Lak Shin Jeong, Kenneth A Jacobson. Docking studies of agonists and antagonists suggest an activation pathway of the A3 adenosine receptor. Journal of molecular graphics & modelling. 2006 Dec; 25(4):562-77. doi: 10.1016/j.jmgm.2006.05.004. [PMID: 16793299]
  • 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]
  • Susanna Tchilibon, Bhalchandra V Joshi, Soo-Kyung Kim, Heng T Duong, Zhan-Guo Gao, Kenneth A Jacobson. (N)-methanocarba 2,N6-disubstituted adenine nucleosides as highly potent and selective A3 adenosine receptor agonists. Journal of medicinal chemistry. 2005 Mar; 48(6):1745-58. doi: 10.1021/jm049580r. [PMID: 15771421]
  • James Fossetta, James Jackson, Gregory Deno, Xuedong Fan, Xixuan Karen Du, Loretta Bober, Anne Soudé-Bermejo, Odette de Bouteiller, Christophe Caux, Charles Lunn, Daniel Lundell, R Kyle Palmer. Pharmacological analysis of calcium responses mediated by the human A3 adenosine receptor in monocyte-derived dendritic cells and recombinant cells. Molecular pharmacology. 2003 Feb; 63(2):342-50. doi: 10.1124/mol.63.2.342. [PMID: 12527805]
  • Sidney R Smith, Georgetta Denhardt, Carol Terminelli. A role for histamine in cytokine modulation by the adenosine A(3) receptor agonist, 2-Cl-IB-MECA. European journal of pharmacology. 2002 Dec; 457(1):57-69. doi: 10.1016/s0014-2999(02)02645-6. [PMID: 12460644]
  • 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]
  • Seong Gon Kim, Gnana Ravi, Carsten Hoffmann, Yun Jin Jung, Min Kim, Aishe Chen, Kenneth A Jacobson. p53-Independent induction of Fas and apoptosis in leukemic cells by an adenosine derivative, Cl-IB-MECA. Biochemical pharmacology. 2002 Mar; 63(5):871-80. doi: 10.1016/s0006-2952(02)00839-0. [PMID: 11911839]
  • K A Jacobson, Z G Gao, A Chen, D Barak, S A Kim, K Lee, A Link, P V Rompaey, S van Calenbergh, B T Liang. Neoceptor concept based on molecular complementarity in GPCRs: a mutant adenosine A(3) receptor with selectively enhanced affinity for amine-modified nucleosides. Journal of medicinal chemistry. 2001 Nov; 44(24):4125-36. doi: 10.1021/jm010232o. [PMID: 11708915]
  • A Chen, Z G Gao, D Barak, B T Liang, K A Jacobson. Constitutive activation of A(3) adenosine receptors by site-directed mutagenesis. Biochemical and biophysical research communications. 2001 Jun; 284(3):596-601. doi: 10.1006/bbrc.2001.5027. [PMID: 11396942]
  • 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]
  • S J Reshkin, L Guerra, A Bagorda, L Debellis, R Cardone, A H Li, K A Jacobson, V Casavola. Activation of A(3) adenosine receptor induces calcium entry and chloride secretion in A(6) cells. The Journal of membrane biology. 2000 Nov; 178(2):103-13. doi: 10.1007/s002320010018. [PMID: 11083899]
  • A H Li, S Moro, N Melman, X D Ji, K A Jacobson. Structure-activity relationships and molecular modeling of 3, 5-diacyl-2,4-dialkylpyridine derivatives as selective A3 adenosine receptor antagonists. Journal of medicinal chemistry. 1998 Aug; 41(17):3186-201. doi: 10.1021/jm980093j. [PMID: 9703464]
  • K A Jacobson, K S Park, J L Jiang, Y C Kim, M E Olah, G L Stiles, X D Ji. Pharmacological characterization of novel A3 adenosine receptor-selective antagonists. Neuropharmacology. 1997 Sep; 36(9):1157-65. doi: 10.1016/s0028-3908(97)00104-4. [PMID: 9364471]
  • E A Van Schaick, K A Jacobson, H O Kim, A P IJzerman, M Danhof. Hemodynamic effects and histamine release elicited by the selective adenosine A3 receptor agonist 2-Cl-IB-MECA in conscious rats. European journal of pharmacology. 1996 Jul; 308(3):311-4. doi: 10.1016/0014-2999(96)00373-1. [PMID: 8858305]
  • 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]
  • S M Duboise, B E Moore, B P Sagik. Poliovirus survival and movement in a sandy forest soil. Applied and environmental microbiology. 1976 Apr; 31(4):536-43. doi: 10.1128/aem.31.4.536-543.1976. [PMID: 5057]