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A4233 Sigma

Ara-G hydrate

≥98% (HPLC), solid

Synonym: 9-β-D-Arabinofuranosyl guanine hydrate

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Properties

Related Categories AN-AZ, Apoptosis Inducers, Apoptosis and Cell Cycle, Bioactive Small Molecule Alphabetical Index, Bioactive Small Molecules,
assay   ≥98% (HPLC)
form   solid
solubility   DMSO: >10 mg/mL
  H2O: insoluble
storage temp.   2-8°C

Description

Application

Ara-G is converted by cellular kinases to the active 5′-triphosphate, Ara-GTP. This active form of Ara-G induces apoptosis and inhibits DNA synthesis. Ara-G is also an antineoplastic and antimetabolite.

Biochem/physiol Actions

Ara-G is an inducer of apoptosis; inhibitor of DNA synthesis; antineoplastic; and antimetabolite. Ara-G is converted by cellular kinases to the active 5′-triphosphate, Ara-GTP. Incorporation of Ara-GTP into DNA leads to inhibition of DNA synthesis and apoptosis.

Features and Benefits

This compound is also offered as part of Sigma′s Library of Pharmacologically Active Compounds (LOPAC®,1280), a biologically annotated collection of high-quality, ready-to-screen compounds. Click here to learn more.

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LOPAC is a registered trademark of Sigma-Aldrich Co. LLC

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Safety & Documentation

Safety Information

Symbol 
GHS07  GHS07
Signal word 
Warning
Hazard statements 
Precautionary statements 
Personal Protective Equipment 
Hazard Codes (Europe) 
Xn
Risk Statements (Europe) 
Safety Statements (Europe) 
26
WGK Germany 
3
RTECS 
MF8301000

Documents

Certificate of Analysis

Protocols & Articles

Peer-Reviewed Papers

References

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Nucleoside analogues: mechanisms of drug resistance and reversal stragegies. . Galmarini, C. M. , et al. Leukemia 15, 875, (2001)

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Pharmacokinetics of nelarabine and 9-beta-D-arabinofuranosyl guanine in pediatric and adult patients during a phase I study of nelarabine for the treatment of refractory hematologic malignancies. Kisor DF, Plunkett W, Kurtzberg J, et al. J. Clin. Oncol. 18(5), 995-1003, (2000)

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Enhanced toxicity of purine nucleoside analogs in cells expressing Drosophila melanogaster nucleoside kinase mutants. Solaroli N, Johansson M, Balzarini J, et al. Gene Ther. 14(1), 86-92, (2007)

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Synthesis of 2'-deoxy-2'-[18F]fluoro-9-β-D-arabinofuranosylguanine: a novel agent for imaging T-cell activation with PET. Namavari M, Chang YF, Kusler B, et al. Mol. Imaging Biol. 13(5), 812-8, (2011)

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Arabinosylguanine is phosphorylated by both cytoplasmic deoxycytidine kinase and mitochondrial deoxyguanosine kinase. Rodriguez CO, Mitchell BS, Ayres M, et al. Cancer Res. 62(11), 3100-5, (2002)

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Differential incorporation of 1-beta-D-arabinofuranosylcytosine and 9-beta-D-arabinofuranosylguanine into nuclear and mitochondrial DNA. Zhu C, Johansson M, and Karlsson A FEBS Lett. 474(2-3), 129-32, (2000)

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Reduced levels of mitochondrial DNA increases the toxicity of 9-beta-D-arabinofuranosylguanine (araG). Bjerke M, Balzarini J, and Karlsson A Nucleosides Nucleotides Nucleic Acids 27(6), 746-9, (2008)

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Nelarabine: a new purine analog in the treatment of hematologic malignancies. Curbo S and Karlsson A Rev. Recent Clin. Trials 1(3), 185-92, (2006)

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Nelarabine. Sanford, M., and Lyseng-Williamson, K.A. Drugs 68, 439-447, (2008)

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Nelarabine: a novel purine antimetabolite antineoplastic agent. Luie, L.W., et al. Clin. Ther. 29, 1887-1899, (2007)

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Purine nucleoside analogs as immunosuppressive and antineoplastic agents: mechanism of action and clinical activity. Robak, T., et al. Curr. Med. Chem. 13, 3165-3189, (2006)

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Novel selective human mitochondrial kinase inhibitors: design, synthesis and enzymatic activity. Nunzia Ciliberti et al Bioorg. Med. Chem. 15, 3065-81, (2007)

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Effects of 9-beta-D-arabinofuranosylguanine on mitochondria in CEM T-lymphoblast leukemia cells. Curbo S, Zhivotovsky B, Johansson M, et al. Biochem. Biophys. Res. Commun. 307(4), 942-7, (2003)

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Acute cytotoxicity of arabinofuranosyl nucleoside analogs is not dependent on mitochondrial DNA. Curbo S, Johansson M, Balzarini J, et al. Exp. Cell Res. 315, 2539-2543, (2009)

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In vitro efficacy of forodesine and nelarabine (ara-G) in pediatric leukemia. Homminga I, Zwaan CM, Manz CY, et al. Blood 118(8), 2184-90, (2011)

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Mechanisms for T-cell selective cytotoxicity of arabinosylguanine. Rodriguez CO, Stellrecht CM, and Gandhi V Blood 102(5), 1842-8, (2003)

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Low level of mitochondrial deoxyguanosine kinase is the dominant factor in acquired resistance to 9-beta-D-arabinofuranosylguanine cytotoxicity. Lotfi K, Månsson E, Peterson C, et al. Biochem. Biophys. Res. Commun. 293(5), 1489-96, (2002)

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Induction of fetal hemoglobin and ABCB1 gene expression in 9-β-D-arabinofuranosylguanine-resistant MOLT-4 cells. Fyrberg A, Peterson C, Kågedal B, et al. Cancer Chemother. Pharmacol. 68(3), 583-91, (2011)

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Activation of guanine-β-D-arabinofuranoside and deoxyguanosine to triphosphates by a common pathway blocks T lymphoblasts at different checkpoints. Leanza L, Miazzi C, Ferraro P, et al. Exp. Cell Res. 316(20), 3443-53, (2010)

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Dual mechanisms of 9-beta-D-arabinofuranosylguanine resistance in CEM T-lymphoblast leukemia cells. Curbo S, Zhu C, Johansson M, et al. Biochem. Biophys. Res. Commun. 285(1), 40-5, (2001)

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Resistance to mitochondrial- and Fas-mediated apoptosis in human leukemic cells with acquired resistance to 9-beta-D-arabinofuranosylguanosine. Månsson E, Stridh H, and Albertioni F Biochem. Biophys. Res. Commun. 298(3), 338-44, (2002)

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The novel nucleoside transport system exhibited by NB4 cells, csg, transports deoxyguanosine analogues, including ara-G. Flanagan SA, Gandhi V, Secrist JA, et al. Biochem. Pharmacol. 66(5), 733-7, (2003)

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Plasma and cerebrospinal fluid pharmacokinetics of nelarabine in nonhuman primates. Berg SL, Brueckner C, Nuchtern JG, et al. Cancer Chemother. Pharmacol. 59(6), 743-7, (2007)

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Synthesis of 9-beta-d-arabinofuranosylguanine by combined use of two whole cell biocatalysts. Médici R, Iribarren AM, and Lewkowicz ES Bioorg. Med. Chem. Lett. 19(15), 4210-2, (2009)

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In vitro chemo-sensitivity of B-chronic lymphocytic leukaemia to ara-G. Bromidge T, Frewin R, and Johnson S Leuk. Res. 24(7), 623-6, (2000)

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A potential role of fetal hemoglobin in the development of multidrug resistance. Fyrberg A, Skoglund K, Wolk M, et al. Biochem. Biophys. Res. Commun. 427(3), 456-60, (2012)

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A new high-performance liquid chromatography method determines low production of 9-beta-D-arabinofuranosylguanine triphosphate, an active metabolite of nelarabine, in adult T-cell leukemia cells. Yamauchi T, Nishi R, Kitazumi K, et al. Oncol. Rep. 23(2), 499-504, (2010)

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Combination of guanine arabinoside and Bcl-2 inhibitor YC137 overcomes the cytarabine resistance in HL-60 leukemia cell line. Nishi R, Yamauchi T, Negoro E, et al. Cancer Sci. 104(4), 502-7, (2013)

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