IB-MECA (BioDeep_00000706577)

   


代谢物信息卡片


IB-MECA

化学式: C18H19IN6O4 (510.0512484)
中文名称: 匹利诺生
谱图信息: 最多检出来源 () 0%

分子结构信息

SMILES: CNC(=O)C1C(C(C(O1)N2C=NC3=C(N=CN=C32)NCC4=CC(=CC=C4)I)O)O
InChI: InChI=1S/C18H19IN6O4/c1-20-17(28)14-12(26)13(27)18(29-14)25-8-24-11-15(22-7-23-16(11)25)21-6-9-3-2-4-10(19)5-9/h2-5,7-8,12-14,18,26-27H,6H2,1H3,(H,20,28)(H,21,22,23)/t12-,13+,14-,18+/m0/s1

描述信息

C78272 - Agent Affecting Nervous System > C29747 - Adrenergic Agent > C87053 - Adrenergic Agonist
COVID info from clinicaltrial, clinicaltrials, clinical trial, clinical trials
Corona-virus
Coronavirus
SARS-CoV-2
COVID-19
SARS-CoV
COVID19
SARS2
SARS
Piclidenoson (IB-MECA) is a first-in-class, orally active and selective A3 adenosine receptor (A3AR) agonist. Piclidenoson exhibits antiproliferative effect and induces apoptosis in different cancer cell types like melanoma, leukemia. Piclidenoson can be used for the research of autoimmune inflammatory diseases and COVID-19[1][2][3][4].

同义名列表

3 个代谢物同义名

IB-MECA; CF-101; Piclidenoson



数据库引用编号

7 个数据库交叉引用编号

分类词条

相关代谢途径

Reactome(0)

BioCyc(0)

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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)

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

  • Laura Micheli, Mariaconcetta Durante, Elena Lucarini, Silvia Sgambellone, Laura Lucarini, Lorenzo Di Cesare Mannelli, Carla Ghelardini, Emanuela Masini. The Histamine H4 Receptor Participates in the Anti-Neuropathic Effect of the Adenosine A3 Receptor Agonist IB-MECA: Role of CD4+ T Cells. Biomolecules. 2021 10; 11(10):. doi: 10.3390/biom11101447. [PMID: 34680083]
  • 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]
  • 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]
  • 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]
  • Christoph Eisner, SooMi Kim, Alexandra Grill, Yan Qin, Marion Hoerl, Josephine Briggs, Hayo Castrop, Manfred Thiel, Jurgen Schnermann. Profound hypothermia after adenosine kinase inhibition in A1AR-deficient mice suggests a receptor-independent effect of intracellular adenosine. Pflugers Archiv : European journal of physiology. 2017 02; 469(2):339-347. doi: 10.1007/s00424-016-1925-3. [PMID: 27975140]
  • 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]
  • Jo-Anne Baltos, Silvia Paoletta, Anh T N Nguyen, Karen J Gregory, Dilip K Tosh, Arthur Christopoulos, Kenneth A Jacobson, Lauren T May. Structure-Activity Analysis of Biased Agonism at the Human Adenosine A3 Receptor. Molecular pharmacology. 2016 07; 90(1):12-22. doi: 10.1124/mol.116.103283. [PMID: 27136943]
  • Aya Galal, Wesam M El-Bakly, Ekram Nemr Abd Al Haleem, Ebtehal El-Demerdash. Selective A3 adenosine receptor agonist protects against doxorubicin-induced cardiotoxicity. Cancer chemotherapy and pharmacology. 2016 Feb; 77(2):309-22. doi: 10.1007/s00280-015-2937-y. [PMID: 26676227]
  • Caio Maximino, Julliany Gemaque, Rancés Benzecry, Monica Gomes Lima, Evander de Jesus Oliveira Batista, Domingos Wanderley Picanço-Diniz, Karen Renata Matos Oliveira, Anderson Manoel Herculano. Role of nitric oxide in the behavioral and neurochemical effects of IB-MECA in zebrafish. Psychopharmacology. 2015 May; 232(10):1671-80. doi: 10.1007/s00213-014-3799-4. [PMID: 25388291]
  • Amanda Ford, Annie Castonguay, Martin Cottet, Joshua W Little, Zhoumou Chen, Ashley M Symons-Liguori, Timothy Doyle, Terrance M Egan, Todd W Vanderah, Yves De Koninck, Dilip K Tosh, Kenneth A Jacobson, Daniela Salvemini. Engagement of the GABA to KCC2 signaling pathway contributes to the analgesic effects of A3AR agonists in neuropathic pain. The Journal of neuroscience : the official journal of the Society for Neuroscience. 2015 04; 35(15):6057-67. doi: 10.1523/jneurosci.4495-14.2015. [PMID: 25878279]
  • 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]
  • Kali Janes, Emanuela Esposito, Timothy Doyle, Salvatore Cuzzocrea, Dillip K Tosh, Kenneth A Jacobson, Daniela Salvemini. A3 adenosine receptor agonist prevents the development of paclitaxel-induced neuropathic pain by modulating spinal glial-restricted redox-dependent signaling pathways. Pain. 2014 Dec; 155(12):2560-2567. doi: 10.1016/j.pain.2014.09.016. [PMID: 25242567]
  • 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]
  • 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]
  • Athena M Keene, Ramachandran Balasubramanian, John Lloyd, Asher Shainberg, Kenneth A Jacobson. Multivalent dendrimeric and monomeric adenosine agonists attenuate cell death in HL-1 mouse cardiomyocytes expressing the A(3) receptor. Biochemical pharmacology. 2010 Jul; 80(2):188-96. doi: 10.1016/j.bcp.2010.03.020. [PMID: 20346920]
  • Theresa Pang, Xiaohong Tracey Gan, David J Freeman, Michael A Cook, Morris Karmazyn. Compensatory upregulation of the adenosine system following phenylephrine-induced hypertrophy in cultured rat ventricular myocytes. American journal of physiology. Heart and circulatory physiology. 2010 Feb; 298(2):H545-53. doi: 10.1152/ajpheart.00417.2009. [PMID: 19966059]
  • Dilip K Tosh, Moshe Chinn, Lena S Yoo, Dong Wook Kang, Hans Luecke, Zhan-Guo Gao, Kenneth A Jacobson. 2-Dialkynyl derivatives of (N)-methanocarba nucleosides: 'Clickable' A(3) adenosine receptor-selective agonists. Bioorganic & medicinal chemistry. 2010 Jan; 18(2):508-17. doi: 10.1016/j.bmc.2009.12.018. [PMID: 20036562]
  • 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]
  • Chong-Bin Zhu, Jennifer A Steiner, Jaclyn L Munn, Lynette C Daws, William A Hewlett, Randy D Blakely. Rapid stimulation of presynaptic serotonin transport by A(3) adenosine receptors. The Journal of pharmacology and experimental therapeutics. 2007 Jul; 322(1):332-40. doi: 10.1124/jpet.107.121665. [PMID: 17460150]
  • 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]
  • Xiaohong Tracey Gan, Venkatesh Rajapurohitam, James V Haist, Peter Chidiac, Michael A Cook, Morris Karmazyn. Inhibition of phenylephrine-induced cardiomyocyte hypertrophy by activation of multiple adenosine receptor subtypes. The Journal of pharmacology and experimental therapeutics. 2005 Jan; 312(1):27-34. doi: 10.1124/jpet.104.073122. [PMID: 15452191]
  • 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]
  • H Thomas Lee, Ayuko Ota-Setlik, Hua Xu, Vivette D D'Agati, Marlene A Jacobson, Charles W Emala. A3 adenosine receptor knockout mice are protected against ischemia- and myoglobinuria-induced renal failure. American journal of physiology. Renal physiology. 2003 Feb; 284(2):F267-73. doi: 10.1152/ajprenal.00271.2002. [PMID: 12388399]
  • Timothy J Martin, Kenneth J Broadley. Contractile responses to adenosine, R-PIA and ovalbumen in passively sensitized guinea-pig isolated airways. British journal of pharmacology. 2002 Nov; 137(6):729-38. doi: 10.1038/sj.bjp.0704902. [PMID: 12411402]
  • 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]
  • Stefania Gessi, Katia Varani, Stefania Merighi, Elena Cattabriga, Valeria Iannotta, Edward Leung, Pier Giovanni Baraldi, Pier Andrea Borea. A(3) adenosine receptors in human neutrophils and promyelocytic HL60 cells: a pharmacological and biochemical study. Molecular pharmacology. 2002 Feb; 61(2):415-24. doi: 10.1124/mol.61.2.415. [PMID: 11809867]
  • L C Esquisatto, S K Costa, E A Camargo, M T Ribela, S D Brain, G de Nucci, E Antunes. The plasma protein extravasation induced by adenosine and its analogues in the rat dorsal skin: evidence for the involvement of capsaicin sensitive primary afferent neurones and mast cells. British journal of pharmacology. 2001 Sep; 134(1):108-15. doi: 10.1038/sj.bjp.0704245. [PMID: 11522602]
  • 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]
  • 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]
  • K Stambaugh, G T Elliott, K A Jacobson, B T Liang. Additive effects of late preconditioning produced by monophosphoryl lipid A and the early preconditioning mediated by adenosine receptors and KATP channel. Circulation. 1999 Jun; 99(25):3300-7. doi: 10.1161/01.cir.99.25.3300. [PMID: 10385506]
  • G Haskó, Z H Németh, E S Vizi, A L Salzman, C Szabó. An agonist of adenosine A3 receptors decreases interleukin-12 and interferon-gamma production and prevents lethality in endotoxemic mice. European journal of pharmacology. 1998 Oct; 358(3):261-8. doi: 10.1016/s0014-2999(98)00619-0. [PMID: 9822893]
  • 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]
  • J A Auchampach, A Rizvi, Y Qiu, X L Tang, C Maldonado, S Teschner, R Bolli. Selective activation of A3 adenosine receptors with N6-(3-iodobenzyl)adenosine-5'-N-methyluronamide protects against myocardial stunning and infarction without hemodynamic changes in conscious rabbits. Circulation research. 1997 Jun; 80(6):800-9. doi: 10.1161/01.res.80.6.800. [PMID: 9168782]
  • J J Reeves, C A Jones, M J Sheehan, C J Vardey, C J Whelan. Adenosine A3 receptors promote degranulation of rat mast cells both in vitro and in vivo. Inflammation research : official journal of the European Histamine Research Society ... [et al.]. 1997 May; 46(5):180-4. doi: 10.1007/s000110050169. [PMID: 9197988]
  • G Haskó, C Szabó, Z H Németh, V Kvetan, S M Pastores, E S Vizi. Adenosine receptor agonists differentially regulate IL-10, TNF-alpha, and nitric oxide production in RAW 264.7 macrophages and in endotoxemic mice. Journal of immunology (Baltimore, Md. : 1950). 1996 Nov; 157(10):4634-40. doi: NULL. [PMID: 8906843]
  • J Kim, J Wess, A M van Rhee, T Schöneberg, K A Jacobson. Site-directed mutagenesis identifies residues involved in ligand recognition in the human A2a adenosine receptor. The Journal of biological chemistry. 1995 Jun; 270(23):13987-97. doi: 10.1074/jbc.270.23.13987. [PMID: 7775460]
  • K A Jacobson, S M Siddiqi, M E Olah, X D Ji, N Melman, K Bellamkonda, Y Meshulam, G L Stiles, H O Kim. Structure-activity relationships of 9-alkyladenine and ribose-modified adenosine derivatives at rat A3 adenosine receptors. Journal of medicinal chemistry. 1995 May; 38(10):1720-35. doi: 10.1021/jm00010a017. [PMID: 7752196]
  • S M Siddiqi, K A Jacobson, J L Esker, M E Olah, X D Ji, N Melman, K N Tiwari, J A Secrist, S W Schneller, G Cristalli. Search for new purine- and ribose-modified adenosine analogues as selective agonists and antagonists at adenosine receptors. Journal of medicinal chemistry. 1995 Mar; 38(7):1174-88. doi: 10.1021/jm00007a014. [PMID: 7707320]
  • 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]
  • C Gallo-Rodriguez, X D Ji, N Melman, B D Siegman, L H Sanders, J Orlina, B Fischer, Q Pu, M E Olah, P J van Galen. Structure-activity relationships of N6-benzyladenosine-5'-uronamides as A3-selective adenosine agonists. Journal of medicinal chemistry. 1994 Mar; 37(5):636-46. doi: 10.1021/jm00031a014. [PMID: 8126704]
  • K A Jacobson, O Nikodijević, D Shi, C Gallo-Rodriguez, M E Olah, G L Stiles, J W Daly. A role for central A3-adenosine receptors. Mediation of behavioral depressant effects. FEBS letters. 1993 Dec; 336(1):57-60. doi: 10.1016/0014-5793(93)81608-3. [PMID: 8262217]