0 Items - $0.00
Categories
A to Z

Alternative structural projections:

6-Phe-cAMP

N6- Phenyladenosine- 3', 5'- cyclic monophosphate ( 6-Phe-cAMP ), sodium salt

Site-selective PKA agonist, Epac-negative control
Cat. No.: P 006
    
CAS No.: [34051-30-4]
Shipping: ambient
Product Name Price (net) Qty
Cat. No.: P 006-05
Unit: 5 µmol / ~2.1 mg
$132.00
For other salt forms or metabolites please inquire. Potent site-selective and highly membrane-permeant activator of protein kinase A showing strong preference for site A of both isozymes. Together with e.g. SP-5,6-DCl-cBIMPS (Cat. No. D 014) selective stimulation of type II can be achieved. Highly membrane-permeant analogue. Available with phosphorothioate modification (Cat. No. P 018) as well. Detailed technical information and updated reference list available. Reference: Kloss et al., Mol. Pharmacol., 65, 1440 - 1451 (2004).
Cat. No. P 006
CAS number [34051-30-4]
Purity > 98% HPLC
Salt form Sodium
Storage temperature -20°C / -4°F
Molecular formula C₁₆H₁₅N₅O₆P · Na
Molecular weight [g/mol] 427.3
Target PKA (cAK) Activator
Lipophilicity 2.46
Absorption max [nm] 288
Molar extinction coefficient ε [L·mol⁻¹·cm⁻¹] 20800
  • 1. Lu D., Aroonsakool N., Yokoyama U., Patel H. H.Insel P. A., Mol. Pharmacol., 84, 787 - 793 (2013), "Increase in Cellular Cyclic AMP Concentrations Reverses the Pro-Fibrogenic Phenotype of Cardiac Myofibroblasts: a Novel Therapeutic Approach for Cardiac Fibrosis"
  • 2. Banales J. M., Masyuk T. V., Gradilone S. A., Masyuk A. I.LaRusso N. F., Hepatology, 49, 160 - 174 (2009), "The cAMP Effectors Epac and Protein Kinase A (PKA) are Involved in the Hepatic Cystogenesis of an Animal Model of Autosomal Recessive Polycystic Kidney Disease (ARPKD)"
  • 3. Harper S. M., Wienk H., Wechselberger R. W., Bos J. L., Boelens R.Rehmann H., J. Biol. Chem., 283, 6501 - 6508 (2008), "Structural Dynamics in the Activation of EPAC"
  • 4. Schweinsberg S., Moll D., Burghardt N. C., Hahnefeld C., Schwede F., Zimmermann B., Drewianka S., Werner L., Kleinjung F., Genieser H.-G., Schuchhardt J.Herberg F. W., Proteomics, 8, 1212 - 1220 (2008), "Systematic interpretation of cyclic nucleotide binding studies using KinetXBase"
  • 5. Yokoyama U., Patel H. H., Lai N. C., Aroonsakool N., Roth D. M.Insel P. A., PNAS, 105, 6386 - 6391 (2008), "The cyclic AMP Effector Epac Integrates Pro- and Anti-fibrotic Signals"
  • 6. Schmidt R., Baumann O.Walz B., BMC Physiol., 8, 1 - 27 (2008), "cAMP Potentiates InsP3-induced Ca2+ Release from the Endoplasmic Reticulum in Bowfly Salvary Glands"
  • 7. Li J., O'Connor K. L., Cheng X., Mei F. C., Uchida T., Townsend C. M.Evers B. M., Mol. Endocrinol., 21, 159 - 171 (2007), "Cyclic AMP-stimulated Neurotensin Secretion is Mediated Through Rap1 Downstream of Both Epac and PKA Signaling Pathways"
  • 8. Dao K. K., Teigen K., Kopperud R. K., Hodneland E., Schwede F., Christensen A. E., Martinez A.Doeskeland S. O., J. Biol. Chem., 281, 21500 - 21511 (2006), "Epac1 and cAMP-dependent Protein Kinase Holoenzyme Have Similar cAMP Affinity, but Their cAMP Domains Have Distinct Structural Features and Cyclic Nucleotide Recognition"
  • 9. Sedej S., Rose T.Rupnik M., J. Physiol., 567, 799 - 813 (2005), "cAMP Increases Ca2+-dependent Exocytosis Through Both PKA and Epac2 in Mouse Melantrophs from Pituitary Tissue Slices"
  • 10. Makarevich A. V., Sirotkin A. V.Genieser H.-G., Anim. Reprod. Sci., 81, 125 - 136 (2004), "Action of Protein Kinase A Regulators on Secretory Activity of Porcine Granulosa Cells in Vitro"
  • 11. Genieser H.-G., Bos J. L., Christensen A. E., Doeskeland S. O., Havemann U., Manzau U., Rehmann H.Schwede F., Poster #THP016 Montreal, 12, 0 - 0 (2004), "Analogues of Cyclic AMP to Distinguish Between PKA and Epac"
  • 12. Kloss S., Srivastava R.Mülsch A., Mol. Pharmacol., 65, 1440 - 1451 (2004), "Down-regulation of Soluble Guanylyl Cyclase Expression by Cyclic AMP is Mediated by mRNA-stabilizing Protein HuR"
  • 13. Mutafova-Yambolieva V. N., Smyth L.Bobalova J., Cardiovasc. Res., 57, 217 - 224 (2003), "Involvement of Cyclic AMP-mediated Pathway in Neural Release of Noradrenaline in Canine Isolated Mesenteric Artery and Vein"
  • 14. Rehmann H., Schwede F., Doeskeland S. O., Wittinghofer A.Bos J. L., J. Biol. Chem., 278, 38548 - 38556 (2003), "Ligand-mediated Activation of the cAMP-responsive Guanine Nucleotide Exchange Factor Epac"
  • 15. Christensen A. E., Selheim F., de Rooij J., Dremier S., Schwede F., Dao K. K., Martinez A., Maenhaut C., Bos J. L., Genieser H.-G.Doeskeland S. O., J. Biol. Chem., 278, 35394 - 35402 (2003), "cAMP Analog Mapping of Epac1 and cAMP-Kinase. Discriminating Analogs Demonstrate that Epac and cAMP-Kinase Act Synergistically to Promote PC-12 Cell Neurite Extension"
  • 16. Christensen A. E., de Rooij J., Kopperud R. K., Nilsen O. K., Dao K. K., Schwede F., Bos J. L., Genieser H.-G.Doeskeland S. O., Abstract of the 13th Protein Kinase Symposium, 0, 5 - 5 (2002), "Comparison of the cAMP Binding Sites of EPAC-1 and cAMP-Kinase"
  • 17. Hahnefeld C.Herberg F. W., Abstract of the 13th Protein Kinase Symposium p. 14, 0, 12 - 15 (2002), "cAMP-dependent Protein Kinase: cAMP Analog Screening Using Surface Plasmon Resonance and Fluorescent Methods"
  • 18. 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"
  • 19. Bradbury N. A., J. Cell. Physiol., 185, 408 - 415 (2000), "Protein Kinase-A-mediated Secretion of Mucin from Human Colonic Epithelial Cells"
  • 20. Muhonen W. W.Shabb J. B., Protein Sci., 9, 2446 - 2456 (2000), "Resonant Mirror Biosensor Analysis of Type I(Alpha) cAMP-dependent Protein Kinase B Domain-Cyclic Nucleotide Interactions"
  • 21. Rodriguez P., Snyder S. K., Chiffer R. C.Smith C. L., Manuskript, 0, 0 - 0 (2000), "cAMP Signaling Induces Rapid Dephosphorylation of Histone H3 Independently of Protein Kinase A and Epac"
  • 22. Qi Z., Hao C. M., Salter K., Redha R.Breyer M. D., Amer. J. Physiol., 276, 622 - 628 (1999), "Type II cAMP-Dependent Protein Kinase Regulates Electronic Ion Transport in Rabbit Collecting Duct"
  • 23. Maronde E., Wicht H., Tasken K., Genieser H.-G., Dehghani F., Olcese J.Korf H.-W., J. Pineal Res., 27, 170 - 182 (1999), "CREB Phosphorylation and Melatonin Biosynthesis in the Rat Pineal Gland: Involvement of cyclic AMP-dependent Protein KinaseType II"
  • 24. Pfeifer A., Ruth P., Dostmann W., Sausbier M., Klatt P.Hofmann F., in Rev. Physiol. Biochem. Pharmacol. Berlin / Springer, 135, 105 - 149 (1999), "Structure and Function of cGMP-Dependent Protein Kinases"
  • 25. 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"
  • 26. Singh A. K., Tasken K., Walker W., Frizzell R. A., Watkins S. C., Bridges R. J.Bradbury N. A., Am. J. Physiol., 275, 562 - 570 (1998), "Characterization of PKA Isoforms and Kinase-dependent Activation of Chloride Secretion in T84 Cells"
  • 27. Maronde E., Middendorff R., Telgmann R., Müller D., Hemmings B., Tasken K.Olcese J., J. Neurochem., 68, 770 - 777 (1997), "Melatonin Synthesis in the Bovine Pineal Gland is Regulated by Type II Cyclic AMP-Dependent Protein Kinase"
  • 28. Torgersen K. M., Vaage J. T., Levy F. O., Hansson V., Rolstad B.Tasken K., J. Biol. Chem., 272, 5495 - 5500 (1997), "Selective Activation of cAMP-Dependent Protein Kinase Type I Inhibits Rat Natural Killer Cell Cytotoxicity"
  • 29. Sirotkin A. V., Makarevic A. V.Genieser H.-G., 3rd Intl. Conf. Cyclic Nucleotide Phosphodiesterases ( From Genes to Therapies ) Scotland, 0, 0 - 0 (1996), "The Effect of PDE Inhibitors and Other Regulators of PKA on the Secretory Activity of Porcine Ovarian Granulosa Cells"
  • 30. Huq I., Dostmann W. R. G.Oegreid D., Biochem. J., 316, 337 - 343 (1996), "Isoleucine 368 is Involved in Low-Affinity Binding of N6-Modified cAMP Analogues to Site B of the Regulatory Subunit of cAMP-Dependent Protein Kinase I"
  • 31. Sirotkin A. V., Makarevich A. V.Genieser H.-G., J. Physiol. Pharmacol., 47, 134 - 0 (1996), "Effect of Regulators of Protein Kinase A on IGF-I and Steroid Secretion by Porcine Granulosa Cells in Vitro"
  • 32. Gjertsen B. T., Mellgren G., Otten A., Maronde E., Genieser H.-G., Jastorff B., Vintermyr O. K., McKnight G. S.Doeskeland S. O., J. Biol. Chem., 270, 20599 - 20607 (1995), "Novel (Rp)-cAMPS Analogs as Tools for Inhibition of cAMP-Kinase in Cell Culture"
  • 33. 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"
  • 34. 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"
  • 35. Connolly B. J., Willits P. B., Warrington B. H.Murray K. J., Biochem. Pharmacol., 44, 2303 - 2306 (1992), "8-(4-Chlorophenyl)thio-cyclic AMP is a Potent Inhibitor of the cyclic GMP-specific Phosphodiesterase (PDEV )"
  • 36. Steinberg R. A., Gorman K. B., Oegreid D., Doeskeland S. O.Weber I. T., J. Biol. Chem., 266, 3547 - 3553 (1991), "Mutations that Alter the Charge of Type I Regulatory Subunit and Modify Activation Properties of Cyclic AMP-dependent Protein Kinase from S49 Mouse Lymphoma Cells"
  • 37. Houge G., Steinberg R. A., Oegreid D.Doeskeland S. O., J. Biol. Chem., 265, 19507 - 19516 (1990), "The Interaction of Catalytic Subunit (C) of cAMP-dependent Protein Kinase with Regulatory Subunit (RI) Having One or Both cAMP Sites Occupied"
  • 38. Oegreid D., Ekanger R., Suva R. H., Miller J. P.Doeskeland S. O., Eur. J. Biochem., 181, 19 - 31 (1989), "Comparison of the Two Classes of Binding Sites ( A and B ) of Type I and Type II Cyclic AMP-dependent Protein Kinases Using Cyclic Nucleotide Analogs"
  • 39. Oegreid D., Doeskeland S. O., Gorman K. B.Steinberg R. A., J. Biol. Chem., 263, 17397 - 17404 (1988), "Mutations That Prevent Cyclic Nucleotide Binding to Binding Sites A or B of Type I Cyclic AMP- dependent Protein Kinase"
  • 40. Oegreid D., Ekanger R., Suva R. H., Miller J. P., Sturm P., Corbin J. D.Doeskeland S. O., Eur. J. Biochem., 150, 219 - 227 (1985), "Activation of Protein Kinase Isozymes by Cyclic Nucleotide Analogs Used Singly or in Combination"
  • 41. Ebright R. H., Le Grice S. F. J., Miller J. P.Krakow J. S., J. Mol. Biol., 182, 91 - 107 (1985), "Analogs of Cyclic AMP that Elicit the Biochemically Defined Conformational Change in Catabolite Gene Activator Protein (CAP) but do not Stimulate Binding to DNA"
  • 42. Hong C. I., Tritsch G. L., Mittelman A., Hebborn P.Chheda G. B., J. Med. Chem., 18, 465 - 473 (1975), "Synthesis and Antitumor Activity of 5'-Phosphates and Cyclic 3', 5' -Phosphates Derived from Biologically Active Nucleosides"

Show more