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N6, 2'- O-Dibutyryladenosine- 3', 5'- cyclic monophosphate, acetoxymethyl ester (DB-cAMP-AM)

Metabolically activatable prodrug form of dibutyryl cAMP
Cat. No.: D 008
CAS No.: [159910-48-2]
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Cat. No.: D 008-01
Unit: 1 µmol / ~0.5 mg
Highly potent and membrane-permeant precursor of DB-cAMP. Releases dibutyryl cAMP after metabolic activation by esterases. Due to further degradation to the much more polar monobutyryl cAMP and cAMP the kinase activators are trapped inside the cell. Detailed technical information and references available. Reference: Schultz et al., J. Biol. Chem., 268, 6316 - 6322 (1993).
Caution: This analogue releases butyrate due to intracellular and extracellular esterase action. Butyrate was shown to have distinct biological effects!
Biolog also offers Phosphate tris(acetoxymethyl)ester (PO4-AM3, Cat. No. P 030) which is recommended as control reagent in nucleotide-AM ester applications.
Cat. No. D 008
CAS number [159910-48-2]
Purity > 97% HPLC for mixture of isomers
Storage temperature -20°C / -4°F
Molecular formula C₂₁H₂₈N₅O₁₀P
Molecular weight [g/mol] 541,5
Modifications 2'-cAMP
Target PKA (cAK) Activator
Absorption max [nm] 273
Molar extinction coefficient ε [L·mol⁻¹·cm⁻¹] 17000
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  • 2. Dzhura I., Chepurny O. G., Leech C. A., Roe M. W., Dzhura E., Xu X., Lu Y., Schwede F., Genieser H.-G., Smrcka A. V.Holz G. G., Islets, 3, 121 - 128 (2011), "Phospholipase C-epsilon Links Epac2 Activation to the Potentiation of Glucose-stimulated Insulin Secretion from Mouse Islets of Langerhans"
  • 3. Chepurny O. G., Leech C. A., Kelley G. G., Dzhura I., Dzhura E., Li X., Rindler M. J., Schwede F., Genieser H.-G.Holz G. G., J. Biol. Chem., 284, 10728 - 10736 (2009), "Enhanced Rap1 activation and insulin secretagogue properties of an acetoxymethyl ester of an Epac-selective cyclic AMP analog in rat INS-1 cells: Studies with 8-pCPT-2'-O-Me-cAMP-AM."
  • 4. Kelley G. G., Chepurny O. G., Schwede F., Genieser H.-G., Leech C. A., Roe M. W., Li X., Dzhura I., Dzhura E., Afshari P.Holz G. G., Islets, 1, 260 - 265 (2009), "Glucose-dependent Potentation of Mouse Islet Insulin Secretion by Epac Activator 8-pCPT-2'-O-Me-cAMP-AM"
  • 5. Bertelsen L. S., Barrett K. E.Keely S. J., J. Biol. Chem., 279, 6271 - 6279 (2004), "Gs Protein-coupled Receptor Agonists Induce Transactivation of the Epidermal Growth Factor Receptor in T84 Cells"
  • 6. Bartsch M., Zorn-Kruppa M., Kühl N., Genieser H.-G., Schwede F.Jastorff B., Biol. Chem., 384, 1321 - 1326 (2003), "Bioactivatable, Membrane-permeant Analogs of Cyclic Nucleotides as Biological Tools for Growth Control of C6 Glioma Cells"
  • 7. Schultz C., Bioorg. Med. Chem., 11, 885 - 898 (2003), "Prodrugs of Biologically Active Phosphate Esters"
  • 8. Orlic T., Loomis W. H., Shreve A., Namiki S.Junger W. G., Am. J. Physiol. - Cell Physiol., 282, 1261 - 1269 (2002), "Hypertonicity Increases cAMP in PMN and Blocks Oxidative Burst by PKA-dependent and -independent Mechanisms"
  • 9. 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"
  • 10. Schultz C., Vajanaphanich M., Harootunian A. T., Sammak P. J., Barrett K. E.Tsien R. Y., J. Biol. Chem., 268, 6316 - 6322 (1993), "Acetoxymethyl Esters of Phosphates: Enhancement of the Permeability and Potency of cAMP"