Alternative structural projections:
For other salt forms please inquire. Metabolically resistant activator of protein kinase A (cyclic AMP agonist). No metabolic side effects as observed with 8-Cl-cAMP (Cat. No. C 007) and significantly more lipophilic and membrane-permeant. Detailed technical information and updated reference list available on request. Reference: Yokozaki et al., Cancer Res., 52, 2504 - 2508 (1992); Beaver, et al., Nature Neurosci., 4, 159 - 163 (2001).
| Cat. No. | C 004 |
| CAS number | [142754-28-7] |
| Purity | > 99% HPLC |
| Salt form | sodium salt |
| Storage temperature | -20°C / -4°F |
| Molecular formula | C₁₀H₁₀ClN₅O₅PS · Na |
| Molecular weight [g/mol] | 401.7 |
| Modifications | 8-cAMP |
| Target | PKA (cAK) Activator |
| Lipophilicity | 1.64 |
| Absorption max [nm] | 262 |
| Molar extinction coefficient ε [L·mol⁻¹·cm⁻¹] | 17000 |
- 1. Schwede F., Bertinetti D., Langerijs C. N., Hadders M. A., Wienk H., Ellenbroek J. H., de Koning E. J. P., Bos J. L., Herberg F. W., Genieser H.-G., Janssen R. A.Rehmann H., PLoS Biol., 13, 1 - 26 (2015), "Structure-Guided Design of Selective Epac1 and Epac2 Agonists"
- 2. van Bemmelen M. X. P., Szczepanska-Konkel M., Jastorff B., Jankowski M.Angielski S., J. Physiol. Pharmacol., 56, 111 - 120 (2005), "Effect of cAMP Analogues on Glomerular Inulin Space of Isolated Rats Renal Glomeruli"
- 3. Shimegi S., Fischer Q. S., Yang Y. P., Sato H.Daw N. W., J. Neurophysiol., 90, 4027 - 4032 (2003), "Blockade of Cyclic AMP-dependent Protein Kinase does not Prevent the Reverse Ocular Dominance Shift in Kitten Visiual Cortex"
- 4. 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"
- 5. Beaver C. J., Ji Q. H., Fischer Q. S.Daw N. W., Nature Neurosci., 4, 159 - 163 (2001), "Cyclic AMP-dependent Protein Kinase Mediates Ocular Dominance Shifts in Cat Visual Cortex"
- 6. Truss M. C., Stief C. G., Jonas U., Ückert S., Becker A. J.Forssmann W.-G., Deutsche Offenlegungsschrift, 0, 0 - 0 (2001), "Verwendung von Substanzen, die den intrazellulären Gehalt von zyklischem Adenosinmonophosphat (cAMP) erhöhen oder die Aktivität cAMP-bindender Proteine stimulieren, zur Behandlung von Erkrankungen der Harnblase"
- 7. Flores-Hernandez J., Hernandez S., Snyder G. L., Yan Z., Fienberg A. A., Moss S. J., Greengard P.Surmeier D. J., J. Neurophysiol., 83, 2996 - 3004 (2000), "D-1 Dopamine Receptor Activation Reduces GABA(A) Receptor Currents in Neostriatal Neurons through a PKA/DARPP-32/PP1 Signaling Cascade"
- 8. Christensen A., Dao K. K., Doeskeland S. O., Schwede F., Jastorff B., Genieser H.-G., de Rooij J., Bos J. L., Rehmann H., Kraemer A.Wittinghofer A., 12th Protein Kinase Symp. NO/cGMP and Protein Kinase Signaling Bad Brückenau/Germany, 0, 0 - 0 (2000), "8-Modified cAMP Analogs give Insight into the Geometries of the cAMP Binding Sites of RI, RII and EPAC-1"
- 9. Schwede F., Maronde E., Genieser H.-G.Jastorff B., Pharmacol. Ther., 87, 199 - 226 (2000), "Cyclic Nucleotide Analogs as Biochemical Tools and Prospective Drugs"
- 10. Liu S. L., Rao Y.Daw N., Cereb. Cortex., 13, 864 - 69 (2000), "Roles of Protein Kinase A and Protein Kinase G in Synaptic Plasticity in the Visual Cortex"
- 11. 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"
- 12. Sjöholm A., Diabetes, 46, 1141 - 1147 (1997), "Glucose Stimulates Islet ß-Cell Mitogenesis Through GTP Binding Proteins and by Protein Kinase C-Dependent Mechanisms"
- 13. Ückert S., Truss M. C., Stief C. G., Becker A. J.Jonas U., Jahrbuch der Urologie, 0, 0 - 0 (1996), "Beeinflussung des Tonuszustandes Porciner Detrusormuskulatur durch Modulation Intrazellulärer Schlüsselenzyme in Vitro"
- 14. Bayliss M. A., Pereira L., Games D. E., Brenton A. G., Harris F. M., Newton R. P.Walton T. J., Proc. 2. MS-Pharmaday Siena Italy #C 17-67 - 68, 0, 67 - 68 (1996), "Fast-Atom Bombardment Mass Spectrometry of Site-Specific Effectors of Cyclic Nucleotide Dependent Protein Kinases"
- 15. Ruchaud S., Zorn M., Davilar-Villar E., Genieser H.-G., Hoffmann C., Gjertsen B. T., Doeskeland S. O., Jastorff B.Lanotte M., Cell. Pharmacol., 2, 127 - 140 (1995), "Evidence for Several Pathways of Biological Response to Hydrolysable cAMP-Analogues Using a Model System of Apoptosis in IPC-81 Leukaemia Cells"
- 16. Muresan S., Bologa C., Mracec M., Chiriac A., Jastorff B., Simon Z.Naray-Szabo G., J. Mol. Struct., 342, 161 - 171 (1995), "Comparative QSAR Study with Electronic and Steric Parameters for cAMP Derivatives with Large Substituents in Positions 2, 6 and 8"
- 17. Muresan S., Bologa C., Chiriac A., Jastorff B., Kurunczi L.Simon Z., Quant. Struct.-Act. Relat., 13, 242 - 248 (1994), "Comparative Structure-Affinity Relations by MTD for Binding of Cycloadenosine Monophosphate Derivatives to Protein Kinase Receptors"
- 18. Ruchaud S., Duprez E., Gendron M.-C., Houge G., Genieser H.-G., Jastorff B., Doeskeland S. O.Lanotte M., Proc. Natl. Acad. Sci. USA, 91, 8428 - 8432 (1994), "Two Distinctly Regulated Events, Priming and Triggering, During Retinoid-induced Maturation and Resistance of NB4 Promyelocytic Leukemia Cell Line"
- 19. Schaap P., Van Ments-Cohen M., Soede R. D. M., Brandt R., Firtel R. A., Dostmann W., Genieser H.-G., Jastorff B.Van Haastert P. J. M., J. Biol. Chem., 268, 6323 - 6331 (1993), "Cell-permeable Non-hydrolyzable cAMP Derivatives as Tools for Analysis of Signaling Pathways Controlling Gene Regulation in Dictyostelium"
- 20. Naß N., Colling C., Cramer M., Genieser H.-G., Butt E., Winkler E., Jaenicke L.Jastorff B., Biochem. J., 285, 129 - 136 (1992), "Mapping of the Epitope/Paratope Interactions of a Monoclonal Antibody Directed Against Adenosine- 3', 5'- monophosphate"
- 21. Jastorff B., Proceeding of the 8th. Internatl. Conference on Second Messengers & Phosphoproteins UK, 0, 0 - 0 (1992), "A New Generation of Cyclic Nucleotide Analogues : Site Specific, Enzyme Selective, Agonistic or Antagonistic and Resistant to Hydrolysis"
- 22. Yokozaki H., Tortora G., Pepe S., Maronde E., Genieser H.-G., Jastorff B.Cho- Chung Y. S., Cancer Res., 52, 2504 - 2508 (1992), "Unhydrolysable Analogs of Cyclic Adenosine- 3', 5' - Monophosphate Demonstrating Growth Inhibition and Differentiation in Human Cancer Cells"
- 23. Van Lookeren Campagne M. M., Diaz F. V., Jastorff B., Winkler E., Genieser H.-G.Kessin R. W., J. Biol. Chem., 265, 5847 - 5854 (1990), "Characterization of the Yeast Low Km cAMP- Phosphodiesterase With cAMP Analogues"
- 24. Van Ments-Cohen M., Dissertation University of Leiden ( The Netherlands ), 108, 0 - 0 (1990), "cAMP Receptors and Signal Transduction in Dictyostelium Discoideum. A Comparative Study With cAMP Derivatives"
Show more
