0 Items - $0.00
Categories
A to Z

8-Cl-Ado

8- Chloroadenosine ( 8-Cl-Ado )
Metabolite of 8-Cl-cAMP
Cat. No.: C 006
    
CAS No.: [34408-14-5]
Shipping: ambient
Product Name Price (net) Qty
Cat. No.: C 006-10
Unit: 10 µmol / ~3 mg
$101.00
Cytotoxic metabolite of 8-chloro cyclic AMP (Cat. No. C 007). Detailed technical information and updated reference list available. References: Cho-Chung et al., Cancer Invest., 7, 161 - 177 (1989); Gu et al., Biochem. Pharmacol., 72, 541 - 550 (2006).
This compound is also part of the Ko-Libri compound library (K 001).
Cat. No. C 006
CAS number [34408-14-5]
Purity > 98% HPLC
Storage temperature -20°C / -4°F
Molecular formula C₁₀H₁₂ClN₅O₄
Molecular weight [g/mol] 301.7
Absorption max [nm] 262
Molar extinction coefficient ε [L·mol⁻¹·cm⁻¹] 17000
  • 1. Stellrecht C. M., Vangapandu H. V., Le X.-F., Mao W.Shentu S., J. Hematol. Oncol., 7:23, 7, 0 - 0 (2014), "ATP Directed Agent, 8-Chloro-adenosine, Induces AMP Activated Protein Kinase Activity, Leading to Autophagic Cell Death in Breast Cancer Cells"
  • 2. Jiao Y.-Y., Wang X.-Q., Lu W.-L., Yang Z.-J.Zhang Q., Eur. J. Pharmacol. Sci., 48, 249 - 258 (2013), "A Novel Approach to Improve the Pharmacokinetic Properties of 8-chloro-adenosine by the Dual Combination of Lipophilic Derivatisation and Liposome Formulation"
  • 3. Dennison J. B., Ayres M., Kaluarachchi K., Plunkett W.Gandhi V., J. Biol. Chem., 285, 8022 - 8030 (2010), "Intracellular Succinylation of 8-Chloroadenosine and its Effect on Fumarate Levels"
  • 4. Stanley N. R., Pattison D. I.Hawkins C. L., Chem. Res. Toxicol., 23, 1293 - 1302 (2010), "Ability of Hypochlorous Acid and N-Chloramines to Chlorinate DNA and Its Constituents"
  • 5. Waidmann O., Pleli T., Dvorak K., Baehr C., Mondorf U., Plotz G., Biondi R. M., Zeuzem S.Piiper A., J.Biol.Chem., 284, 32256 - 32263 (2009), "Inhibition of the Equilibrative Nucleoside Transporter 1 and Activation of A2A Adenosine Receptors by 8-(4-Chlorophenylthio)-modified cAMP Analogs and their Hydrolytic Products"
  • 6. Gu Y. Y., Zhang H. Y., Zhang H. J., Li S. Y., Ni J. H.Jia H. T., Biochem. Pharmacol., 72, 541 - 550 (2006), "8-Chloro-adenosine Inhibits Growth at Least Partly by Interfering with Actin Polymerization in Cultured Human Lung Cancer Cells"
  • 7. Jankovic D., Pesic M., Markovic J., Kanazir S., Markovic I., Rakic L.Ruzdijic S., Invest. New Drug., 24, 15 - 25 (2006), "The Combination of Sulfinosine and 8-Cl-cAMP Induces Synergistic Cell Growth Inhibition of the Human Neuroblastoma Cell Line In Vitro"
  • 8. Long M. C.Parker W. B., Biochem. Pharmacol., 71, 1671 - 1682 (2006), "Structure-activity Relationship for Nucleoside Analogs as Inhibitors or Substrates of Adenosine Kinase from Mycobacterium Tuberculosis I. Modifications to the Adenine Moiety"
  • 9. Balakrishnan K., Stellrecht C. M., Genini D., Ayres M., Wierda W. G., Keating M. J., Leoni L. M.Gandhi V., Blood, 105, 4455 - 4462 (2005), "Cell Death of Bioenergetically Compromised and Transcriptionally Challenged CLL Lymphocytes by Chlorinated ATP"
  • 10. Ahn Y. H., Jung J. M.Hong S. H., Cancer Res., 65, 4896 - 4901 (2005), "8-Chloro-Cyclic AMP-Induced Growth Inhibition and Apoptosis is Mediated by p38 Mitogen-Activated Protein Kinase Activation in HL60 Cells"
  • 11. Badouard C., Masuda M., Nishino H., Cadet J., Favier A.Ravanat J.-L., J. Chromatogr., 827, 26 - 31 (2005), "Detection of Chlorinated DNA and RNA Nucleosides by HPLC Coupled to Tandem Mass Spectrometry as Potential Biomarkers of Inflammation"
  • 12. Zhang H. Y., Gu Y. Y., Li Z. G., Jia Y. H., Yuan L., Li S. Y., An G. S., Ni J. H.Jia H. T., Neoplasia, 6, 802 - 812 (2004), "Exposure of Human Lung Cancer Cells to 8-Chloro-Adenosine Induces G(2)/M Arrest and Mitotic Catastrophe"
  • 13. Christensen A. E.Doeskeland S. O., Handbook of Cell Signaling Academic Press/Elsevier Science San Diego CA, 2, 549 - 554 (2003), "Cyclic Nucleotide Analogs as Tools to Investigate Cyclic Nucleotide Signaling"
  • 14. Lamb D.Steinberg R. A., J. Cell. Physiol., 192, 216 - 224 (2002), "Anti-Proliferative Effects of 8-Chloro-cAMP and other cAMP Analogs Are Unrelated to Their Effects on Protein Kinase A Regulatory Subunit Expression"
  • 15. Gandhi V., Chen W., Ayres M., Rhie J. K., Madden T. L.Newman R. A., Cancer Chemother. Pharmacol., 50, 85 - 94 (2002), "Plasma and Cellular Pharmacology of 8-Chloro-Adenosine in Mice and Rats"
  • 16. Carlson C. C., Burnham L. L., Shanks R. A.Dransfield D. T., Digest. Dis. Sci., 46, 757 - 764 (2001), "8-Cl-Adenosine Induces Differentiation in LS174T Cells"
  • 17. Yin Y. Z., Allen P. D., Jia L., Kelsey S. M.Newland A. C., Leuk. Res., 25, 423 - 431 (2001), "8-Cl-Adenosine Mediated Cytotoxicity and Sensitization of T-Lymphoblastic Leukemia Cells to TNF Alpha-induced Apoptosis is via Inactivation of NF-kappa B"
  • 18. Gandhi V., Ayres M., Halgren R. G., Krett N. L., Newman R. A.Rosen S. T., Cancer Res., 61, 5474 - 5479 (2001), "8-Chloro-cAMP and 8-Chloro-Adenosine Act by the Same Mechanism in Multiple Myeloma Cells"
  • 19. Dransfield D. T., Griner R. D., Ray S., Keskintepe M.Bollag W. B., J. Invest. Dermatol., 117, 1588 - 1593 (2001), "8-Cl-Adenosine Induces Growth Arrest without Differentiation of Primary Mouse Epidermal Keratinocytes"
  • 20. Robbins S. K., Houlbrook S., Priddle J. D.Harris A. L., Cancer Chemother. Pharmacol., 48, 451 - 458 (2001), "8-Cl-Adenosine is an Active Metabolite of 8-Cl-cAMP Responsible for its In Vitro Anti Proliferative Effects on CHO Mutants Hypersensitive to Cytostatic Drugs"
  • 21. Davydova N. N., Glisic J.Wainer I. W., J. Pharmaceut. Biomed. Anal., 24, 857 - 862 (2001), "Determination of 8-Chloroadenosine 3',5'-Monophosphate in Dog Plasma by Capillary Electrophoresis"
  • 22. Yin Y., Allen P. D., Jia L., Macey M. G., Kelsey S. M.Newland A. C., Br. J. Haematol., 108, 565 - 573 (2000), "Constitutive Levels of cAMP-Dependent Protein Kinase Activity Determine Sensitivity of Human Multidrug-Resistant Leukaemic Cell Lines to Growth Inhibition and Apoptosis by Forskolin and Tumour Nekrosis Factor Alpha"
  • 23. Schwede F., Maronde E., Genieser H.-G.Jastorff B., Pharmacol. Ther., 87, 199 - 226 (2000), "Cyclic Nucleotide Analogs as Biochemical Tools and Prospective Drugs"
  • 24. Carlson C. C., Chinery R., Burnham L. L.Dransfield D. T., Neoplasia, 2, 441 - 448 (2000), "8-Cl-Adenosine-Induced Inhibition of Colorectal Cancer Growth In Vitro and In Vivo"
  • 25. Budillon A., Di Gennaro E., Caraglia M., Barbarulo D., Abbruzzese A.Tagliaferri P., Brit. J. Cancer, 81, 1134 - 1141 (1999), "8-Cl-cAMP Antagonizes Mitogen-Activated Protein Kinase Activation and Cell Growth Stimulation Induced by Epidermal Growth Factor"
  • 26. Parissenti A. M., Gannon B. R., Villeneuve D. J., Kirwan-Rhude A. F., Chadderton A.Glück S., Int. J. Cancer, 82, 893 - 900 (1999), "Lack of Modulation of MDR1 Gene Expression by Dominant Inhibition of cAMP-Dependent Protein Kinase in Doxorubicin-Resistant MCF-7 Breast Cancer Cells"
  • 27. Kozlowska M., Smolenski R. T., Makarewicz W., Hoffmann C., Jastorff B.Swierczynski J., Toxicol. Lett., 104, 171 - 181 (1999), "ATP Depletion, Purine Riboside Triphosphate Accumulation and Rat Thymocyte Death Induced by Purine Riboside"
  • 28. Cho-Chung Y. S., Jastorff B.Genieser H.-G., USA patent 5916, 843, 0 - 0 (1998), "Cyclic AMP Analogues, Individually and in Pairs, to Inhibit Neoplastic Cell Growth"
  • 29. Halgren R. G., Traynor A. E., Pillay S., Zell J. L., Heller K. F., Krett N. L.Rosen S. T., Blood, 92, 2893 - 2898 (1998), "8-Cl-cAMP Cytotoxicity in both Steroid Sensitive and Insensitive Multiple Myeloma Cell Lines is Mediated by 8-Cl-Adenosine"
  • 30. Noguchi K., Murata T.Cho-Chung Y. S., Eur. J. Cancer, 34, 1260 - 1267 (1998), "8-Chloroadenosine 3',5'-monophosphate (8-Cl-cAMP) Selectively Eliminates Protein Kinase A Type I to Induce Growth Inhibition in c-ras-transformed Fibroblasts"
  • 31. Cho-Chung Y. S.Robins R. K., United States Patent 5752 of August 11, 792, 0 - 0 (1998), "8-Chloro cAMP and Related cAMP Compounds as Antineoplastic Agents"
  • 32. Langeveld C. H., Jongenelen C. A. M., Theeuwes J. W. M., Baak J. P. A., Heimans J. J., Stoof J. C.Peters G. J., Biochem. Pharmacol., 53, 141 - 148 (1997), "The Antiproliferative Effect of 8-Chloro-Adenosine, an Active Metabolite of 8-Chloro-Cyclic Adenosine Monophosphate, and Disturbances in Nucleic Acid Synthesis and Cell Cycle Kinetics"
  • 33. Bosanquet A. G., Burlton A. R., Bell P. B.Harris A. L., Brit. J. Cancer, 76, 511 - 518 (1997), "Ex Vivo Cytotoxic Drug Evaluation by DiSC Assay to Expedite Identification of Clinical Targets - Results with 8-Chloro-cAMP"
  • 34. Sandnes D., Jacobson F. W., Refsnes M.Christoffersen T., Pharmacol. Toxicol., 79, 15 - 22 (1996), "8-Bromo-cAMP and 8-CPT-cAMP Increase the Density of ß-Adrenoceptors in Hepatocytes by a Mechanism Not Mimicking the Effect of cAMP"
  • 35. Barajas-Lopez C., Peres A. L.Espinosaluna R., Amer. J. Physiol., 40, 264 - 275 (1996), "Cellular Mechanisms Underlying Adenosine Actions on Cholinergic Transmission in Enteric Neurons"
  • 36. Budillon A., Clair T., Hartmann N., Strong J., Sobukawa Y., Miki K., Worby A., Murray K. J.Cho-Chung Y. S., Int. J. Oncol., 9, 1113 - 1120 (1996), "Novel Growth Inhibitory Effect of 8-Cl-cAMP is Dependent on Serum Factors that Modulate Protein Kinase A Expression But Not the Hydrolysis of 8-Cl-cAMP"
  • 37. Cummings J., Langdon S. P., Ritchie A. A., Burns D. J., Mackay J., Stockman P., Leonard R. C. F.Miller W. R., Ann. Oncol., 7, 291 - 296 (1996), "Pharmacokinetics, Metabolism and Tumour Disposition of 8-Chloroadenosine 3',5'-Monophosphate in Breast Cancer Patients and Xenograft Bearing Mice"
  • 38. Han Z. Y., Chatterjee D., Early J., Pantazis P., Hendrickson E. A.Wyche J. H., Cancer Res., 56, 1621 - 1628 (1996), "Isolation and Characterization of an Apoptosis-Resistant Variant of Human Leukemia HL-60 Cells that has Switched Expression from Bcl-2 to Bcl-X(L)"
  • 39. Boe R., Gjertsen B. T., Doeskeland S. O.Vintermyr O. K., Br. J. Cancer, 72, 1151 - 1159 (1995), "8-Chloro-cAMP Induces Apoptotic Cell Death in a Human Mammary Carcinoma Cell (MCF-7) Line"
  • 40. Scala S., Budillon A., Zhan Z. R., Cho-Chung Y. S., Jefferson J., Tsokos M.Bates S. E., J. Clin. Invest., 96, 1026 - 1034 (1995), "Downregulation of MDR-1 Expression by 8-Cl-cAMP in Multidrug Resistant MCF-7 Human Breast Cancer Cells"
  • 41. Vintermyr O. K., Böe R., Brustugun O. T., Maronde E., Aakvaag A.Doeskeland S. O., Endocrinology, 136, 2513 - 2520 (1995), "Cyclic Adenosine Monophosphate (cAMP) Analogs 8-Cl- and 8-NH(2)-cAMP Induce Cell Death Independently of cAMP Kinase-Mediated Inhibition of the G(1)/S Transition in Mammary Carcinoma Cells (MCF-7)"
  • 42. Schultz C., Vajanaphanich M., Genieser H.-G., Jastorff B., Barrett K. E.Tsien R. Y., Mol. Pharmacol., 46, 702 - 708 (1994), "Membrane-permeant Derivatives of Cyclic AMP Optimized for High Potency, Prolonged Activity, or Rapid Reversibility"
  • 43. Cummings J., Leonard R. C. F.Miller W. R., J. Chromatogr., 658, 183 - 188 (1994), "Sensitive Determination of 8-Chloroadenosine 3',5'- Monophosphate and 8-Chloroadenosine in Plasma by High-Performance Liquid Chromatography"
  • 44. Rohlff C., Safa B., Rahman A., Cho-Chung Y. S., Klecker R. W.Glazer R. I., Mol. Pharmacol., 43, 372 - 379 (1993), "Reversal of Resistance to Adriamycin by 8-Cl-cyclic AMP in Adriamycin-resistant HL-60 Leukemia Cells is Associated with Reduction of Type I Cyclic AMP-dependent Protein Kinase and Cyclic AMP Response Element-binding Protein DNA-binding Activity"
  • 45. Langeveld C. H., Jongenelen C. A. M., Heimans J. J.Stoof J. C., Cancer Res., 52, 3994 - 3999 (1992), "Growth Inhibition of Human Glioma Cells Induced by 8-Chloroadenosine, an Active Metabolite of 8-Chloro Cyclic Adenosine 3':5'- Monophosphate"
  • 46. Taylor C. W.Yeoman L. C., Anti-Cancer Drug, 3, 485 - 491 (1992), "Inhibition of Colon Tumor Cell Growth by 8 Chloro cAMP is Independent Upon its Conversion to 8-Chloroadenosine"
  • 47. Lange-Carter C. A., Vuillequez J. J.Malkinson A. M., Cancer Res., 53, 393 - 400 (1992), "8-Chloroadenosine Mediates 8-Chloro-Cyclic AMP-Induced Down- Regulation of Cyclic AMP-dependent Protein Kinase in Normal and Neoplastic Mouse Lung Epithelial Cells by a Cyclic AMP-independent Mechanism"
  • 48. Han Z., Chatterjee D.Wyche J. H., J. Pharmacol. Exp. Ther., 265, 790 - 794 (1992), "Proliferation of Nontransformed Cells is Inhibited by Adenosine Metabolite of But Not by Parental 8-Cl-Cyclic AMP"
  • 49. Van Lookeren Campagne M. M., Diaz F. V., Jastorff B.Kessin R. H., Cancer Res., 51, 1600 - 1605 (1991), "8-Chloroadenosine 3',5'-Monophosphate Inhibits the Growth of Chinese Hamster Ovary and Molt-4 Cells Through its Adenosine Metabolite"
  • 50. Cho-Chung Y. S., Cancer Res., 51, 6206 - 6208 (1991), "Correspondence re.: Van Lookeren Campagne et al.: Cancer Res., 51, 6100 - 6105 (1991) ( Letter to the Editor )"
  • 51. Kessin R. H., Cancer Res., 51, 6206 - 6208 (1991), "Correspondence re.: Van Lookeren Campagne et al.: Cancer Res., 51, 6100 - 6105 (1991)( Reply )"
  • 52. Pepe S., Tortora G., Noguchi P. D., Marti G. E., Washington G. C.Cho-Chung Y. S., Cancer Res., 51, 6263 - 6267 (1991), "Effects of 8-Chloradenosine 3´,5´-Monophosphate and N6-Benzyl-Cyclic Adenosine 5´-Monophosphate on Cell Cycle Kinetics of HL-60 Leukemia Cells"
  • 53. Cho-Chung Y. S., Clair T., Tagliaferri P., Ally S., Katsaros D., Tortora G., Neckers L. M., Avery T. L., Crabtree G. W.Robins R. K., Cancer Invest., 7, 161 - 177 (1989), "Site-selective Cyclic AMP Analogs as New Biological Tools in Growth Control, Differentiation, and Proto-oncogene Regulation"
  • 54. Tagliaferri P., Katsaros D., Clair T., Ally S., Tortora G., Neckers L. M., Rubalcava B., Parandoosh Z., Chang Y.-A., Revankar G. R., Crabtree G. W., Robins R. K.Cho-Chung Y. S., Cancer Res., 48, 1642 - 1650 (1988), "Synergistic Inhibition of Growth of Breast and Colon Human Cancer Cell Lines by Site-selective Cyclic AMP Analogs"

Show more