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8-Chloroadenosine CAS: 34408-14-5

Category: Inhibitors
Product Name: 8-Chloroadenosine
Cat No: I000117
CAS No: 34408-14-5
Synonyms: 8-Chloroadenosine; 8 Chloroadenosine; 8Chloroadenosine; NSC-354258; NSC 354258; NSC354258; 8-Cl-Ado; 8 Cl Ado; 8ClAdo;(2R,3R,4S,5R)-2-(6-amino-8-chloro-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol
Molecular Formula: C10H12ClN5O4
Molecular Weight: 301.69
SMILES: OC[C@@H]1[C@H]([C@H]([C@H](N2C(Cl)=NC3=C(N=CN=C32)N)O1)O)O
InChI: InChI=1S/C10H12ClN5O4/c11-10-15-4-7(12)13-2-14-8(4)16(10)9-6(19)5(18)3(1-17)20-9/h2-3,5-6,9,17-19H,1H2,(H2,12,13,14)/t3-,5-,6-,9-/m1/s1
InChIKey: MHDPPLULTMGBSI-UUOKFMHZSA-N
Solubility: Soluble in DMSO
Target: DNA Synthesis
Storage: Store at -20°C
CAS 34408-14-5,8-Chloroadenosine
  • Description

8-Chloroadenosine, also known as NSC-354258 and 8-Cl-Ado, is an 5' AMP-activated protein kinase (AMPK) agonist potentially for the treatment of chronic lymphocytic leukemia. 8-Chloroadenosine has shown to deplete ATP and inhibit tumor growth in hematological malignancies as well as in lung and breast cancer cell lines. 8-chloroadenosine activity is associated with inhibition of the mTOR pathway, and that phospho RPS6 and PI3K pathway activation status may determine resistance.

  • Spec

Appearance:Solid powder
Purity: > 98%

  • References


1:8-Chloroadenosine Sensitivity in Renal Cell Carcinoma Is Associated with AMPK Activation and mTOR Pathway Inhibition. Kearney AY, Fan YH, Giri U, Saigal B, Gandhi V, Heymach JV, Zurita AJ.PLoS One. 2015 Aug 27;10(8):e0135962. doi: 10.1371/journal.pone.0135962. eCollection 2015. PMID: 26313261 Free PMC Article
2:8-Chloroadenosine 3',5'-monophosphate induces cell cycle arrest and apoptosis in multiple myeloma cells through multiple mechanisms. Cheng YM, Zhu Q, Yao YY, Tang Y, Wang MM, Zou LF.Oncol Lett. 2012 Dec;4(6):1384-1388. Epub 2012 Sep 11. PMID: 23226809 Free PMC Article
3:Regioselective enzymatic undecylenoylation of 8-chloroadenosine and its analogs with biomass-based 2-methyltetrahydrofuran as solvent. Gao WL, Liu H, Li N, Zong MH.Bioresour Technol. 2012 Aug;118:82-8. doi: 10.1016/j.biortech.2012.04.104. Epub 2012 May 9. PMID: 22705510
4:Intracellular succinylation of 8-chloroadenosine and its effect on fumarate levels. Dennison JB, Ayres ML, Kaluarachchi K, Plunkett W, Gandhi V.J Biol Chem. 2010 Mar 12;285(11):8022-30. doi: 10.1074/jbc.M109.085803. Epub 2010 Jan 11. PMID: 20064937 Free PMC Article
5:Preclinical activity of 8-chloroadenosine with mantle cell lymphoma: roles of energy depletion and inhibition of DNA and RNA synthesis. Dennison JB, Balakrishnan K, Gandhi V.Br J Haematol. 2009 Nov;147(3):297-307. doi: 10.1111/j.1365-2141.2009.07850.x. Epub 2009 Aug 25. PMID: 19709085 Free PMC Article
6:8-chloroadenosine induced HL-60 cell growth inhibition, differentiation, and G(0)/G(1) arrest involves attenuated cyclin D1 and telomerase and up-regulated p21(WAF1/CIP1). Zhu B, Zhang LH, Zhao YM, Cui JR, Strada SJ.J Cell Biochem. 2006 Jan 1;97(1):166-77. PMID: 16173047
7:Inhibition of B16 mouse melanoma cell growth and induction of apoptotic cell death with 8-chloroadenosine-3',5'-monophosphate and tiazofurin. Korićanac LB, Todorović DV, Popović NM, Demajo MA, Ruzdijić SD, Ristić-Fira AM.Ann N Y Acad Sci. 2004 Dec;1030:384-92. PMID: 15659821
8:[Inhibition of 8-chloroadenosine on proteasome activity of HL-60 cells]. Zhang Y, Wu J, Xu B, Zhang LH, Cui JR.Ai Zheng. 2004 Feb;23(2):155-9. Chinese. PMID: 14960234
9:[The inhibitory effect of 8-chloroadenosine on tumor necrosis factor-induced proto-oncogene expression of retinal pigment epithelial cells]. Yang P, Zhang HR.Zhonghua Yan Ke Za Zhi. 2003 Dec;39(12):750-2. Chinese. PMID: 14769229
10:Synthesis and hybridization properties of RNA containing 8-chloroadenosine. Chen LS, Sheppard TL.Nucleosides Nucleotides Nucleic Acids. 2002;21(8-9):599-617. PMID: 12484453


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