0 Items - $0.00
Categories
A to Z

Alternative structural projections:

DB-cGMP / Dibutyryl-cGMP

N², 2'- O- Dibutyrylguanosine- 3', 5'- cyclic monophosphate ( DB-cGMP / Dibutyryl-cGMP ), sodium salt

Metabolically activatable PKG agonist
Cat. No.: D 010
    
CAS No.: [51116-00-8]
Shipping: ambient
Product Name Price (net) Qty
Cat. No.: D 010-50
Unit: 50 µmol / ~25 mg
$227.00
For other salt forms please inquire. Caution: We do not recommend this cGMP analogue due to its lacking potency and selectivity. The metabolically released N2-monobutyryl cGMP is only a poor activator of cGMP- dependent protein kinase, and released butyrate can have its own side effects leading to misinterpretation of experimental results. Ref.: Butt et al., Biochem. Pharmacol., 43, 2591 - 2600 (1992). We offer numerous more recommendable cGMP agonists; e.g. 8-pCPT-cGMP (Cat. No. C 009), is a much better choice. Detailed technical information available.
Cat. No. D 010
CAS number [51116-00-8]
Purity > 97% HPLC
Salt form Sodium
Storage temperature -20°C / -4°F
Molecular formula C₁₈H₂₃N₅O₉P · Na
Molecular weight [g/mol] 507.4
Modifications 2-cGMP, 2'-cGMP
Target PKG (cGK) Activator
Lipophilicity 2.58
Absorption max [nm] 256
Molar extinction coefficient ε [L·mol⁻¹·cm⁻¹] 16700
  • 1. Wolter S., Dove S., Golombek M., Schwede F.Seifert R., Naunyn-Schmiedeberg's Arch. Pharmacol., 387, 1163 - 1175 (2014), "N4-monobutyryl-cCMP Activates PKA RIalpha and PKA RIIalpha more Potently and with Higher Efficacy than PKG Ialpha in Vitro but not in Vivo"
  • 2. Jäger R., Schwede F., Genieser H.-G., Koesling D.Russwurm M., Br. J. Pharmacol., 161, 1645 - 1660 (2010), "Activation of PDE2 and PDE5 cy Specific GAF Ligands: Delayed Activation of PDE5"
  • 3. Christen M., Christen B., Folcher M., Schauerte A.Jenal U., J. Biol. Chem., 280, 30829 - 30837 (2005), "Identification and Characterization of a Cyclic di-GMP-specific Phosphodiesterase and Its Allosteric Control by GTP"
  • 4. Bhatt D. H., Otto S. J., Depoister B.Fetcho J. R., Science, 305, 254 - 258 (2004), "Cyclic AMP-Induced Repair of Zebrafish Spinal Circuits"
  • 5. Gainey L. F.Greenberg M. J., J. Exp. Biol., 206, 3507 - 3520 (2003), "Nitric Oxide Mediates Seasonal Muscle Potentation in Clam Gills"
  • 6. Manderscheid M., Pereda-Fernandez C.Pfeilschifter J., Kidney Int., 61, 797 - 803 (2002), "Cyclic AMP Increases Rat Inhibitor of Apoptosis Protein (RIAP1) mRNA in Renal Mesangial Cells"
  • 7. Matuszyk J., Cebrat M., Kalas W.Strzadala L., Int. Immunopharmacol., 2, 435 - 442 (2002), "HA1004, an Inhibitor of Serine/Threonine Protein Kinases, Restores the Sensitivity of Thymic Lymphomas to Ca2+-mediated Apoptosis through a Protein Kinase A-independent Mechanism"
  • 8. Boadu E., Vaskinn S., Sundkvist E., Jaeger R.Sager G., Biochem. Pharmacol., 62, 425 - 429 (2001), "Inhibition by Guanosine Cyclic Monophosphate (cGMP) Analogues of Uptake of [H-3]3', 5'-cGMP without Stimulation of ATPase Activity in Human Erythrocyte Inside-out Vesicles"
  • 9. Takuma K., Lee E., Enomoto R., Mori K., Baba A.Matsuda T., Br. J. Pharmacol., 133, 841 - 848 (2001), "Ibudilast Attenuates Astrocyte Apoptosis via Cyclic GMP Signalling Pathway in an In Vitro Reperfusion Model"
  • 10. Brophy C. M., Woodrum D. A., Pollock J., Dickinson M., Komalavilas P., Cornwell T. L.Lincoln T. M., J. Vasc. Res., 39, 95 - 103 (2001), "cGMP-dependent Protein Kinase Expression Restores Contractile Function in Cultured Vascular Smooth Muscle Cells"
  • 11. Yoshioka A., Yamaya Y., Saiki S., Kanemoto M., Hirose G.Pleasure D., J. Neurochem., 74, 633 - 640 (2000), "Cyclic GMP/Cyclic GMP-Dependent Protein Kinase System Prevents Excitotoxicity in an Immortalized Oligodendroglial Cell Line"
  • 12. Vicentini G. E., Constantin J., Lopez C. H.Bracht A., Biochem. Pharmacol., 59, 1187 - 1201 (2000), "Transport of Cyclic AMP and Synthetic Analogs in the Perfused Rat Liver"
  • 13. Wang A., Martin J. A., Lembke L. A.Midura R. J., J. Biol. Chem., 275, 11082 - 11091 (2000), "Reversible Suppression of In Vitro Biomineralization by Activation of Protein Kinase A"
  • 14. Li J., Yang S.Billiar T. R., J. Biol. Chem., 275, 13026 - 13034 (2000), "Cyclic Nucleotides Suppress Tumor Necrosis Factor Alpha-Mediated Apoptosis by Inhibiting Caspase Activation and Cytochrome c Release in Primary Hepatocytes via a Mechanism Independent of Akt Activation"
  • 15. Lei S., Jackson M. F., Jia Z., Roder J., Bai D., Orser B. A.MacDonald J. F., Nature Neurosci., 3, 559 - 565 (2000), "Cyclic GMP-dependent Feedback Inhibition of AMPA Receptors is Independent of PKG"
  • 16. Ho A. K., Hashimoto K.Chik C. L., J. Neurochem., 73, 598 - 604 (1999), "3', 5'-Cyclic Guanosine Monophosphate Activates Mitogen-Activated Protein Kinase in Rat Pinealocytes"
  • 17. Waniishi Y., Inoue R., Morita H., Teramoto N., Abe K.Ito Y., J. Physiol., 511, 719 - 731 (1998), "Cyclic GMP-dependent but G-Kinase-independent Inhibition of Ca2+-dependent Cl-currents by NO Donors in Cat Tracheal Smooth Muscle"
  • 18. Xu X., Zeng W. Z., Diaz J., Lau K. S., Gukovskaya A. C., Brown R. J., Pandol S. J.Muallem S., Cell Calcium, 22, 217 - 28 (1997), "NNOS and CA2+ Influx in Rat Pacreatic Acinar and Submandibular Salivary Gland Cells"
  • 19. Ingram S. L.Williams J. T., J. Physiol., 492, 97 - 106 (1996), "Modulation of the Hyperpolarization-activated Current (Ih) by Cyclic Nucleotides in Guinea-pig Primary Afferent Neurons"
  • 20. Nakamura A., Fujita M.Shiomi H., Brit. J. Pharmacol., 117, 407 - 412 (1996), "Involvement of Endogenous Nitric Oxide in the Mechanism of Bradykinin-induced Peripheral Hyperalgesia"
  • 21. Hichami A., Boichot E., Germain N., Coqueret O.Lagente V., Life Sci., 59, 255 - 261 (1996), "Interactions Between cAMP- and cGMP-dependent Protein Kinase Inhibitors and Phosphodiesterase IV Inhibitors on Arachidonate Release from Human Monocytes"
  • 22. Rooney T. A., Joseph S. K., Queen C.Thomas A. P., J. Biol. Chem., 271, 19817 - 19825 (1996), "Cyclic GMP Induces Oscillatory Calcium Signals in Rat Hepatocytes"
  • 23. Pilar G., Gray D. B.Meriney S. D., Life Sci., 58, 1979 - 1986 (1996), "Membrane Delimited and Intracellular Soluble Pathways in the Somatostatin Modulation of ACH Release"
  • 24. Sadighi Akha A. A., Willmott N. J., Brickley K., Dolphin A. C., Galione A.Hunt S. V., J. Biol. Chem., 271, 7297 - 7300 (1996), "Anti-Ig-induced Calcium Influx in Rat B Lymphocytes Mediated by cGMP Through a Dihydropyridine-sensitive Channel"
  • 25. Tamir H., Liu K.-P., Adlersberg M., Hsiung S.-C.Gershon M. D., J. Biol. Chem., 271, 6441 - 6450 (1996), "Acidification of Serotonin-containing Secretory Vesicles Induced by a Plasma Membrane Calcium Receptor"
  • 26. Anciaux K., Roymans D.Slegers H., Arch. Physiol. Biochem., 104, 32 - 0 (1996), "Effect of cAMP- and cGMP-Analogues on the Enzymatic Activity of the Nucleoside Diphosphate Kinase of Rat C6 Glioma"
  • 27. Chik C. L., Liu Q.-Y., Li B., Karpinski E.Ho A. K., J. Neurosci., 15, 3104 - 3109 (1995), "cGMP Inhibits L-Type Ca2+ Channel Currents Through Protein Phosphorylation in Rat Pinealocytes"
  • 28. Sidhu J. S.Omiecinski C. J., J. Biol. Chem., 270, 12762 - 12773 (1995), "cAMP-associated Inhibition of Phenobarbital-inducible Cytochrome P450 Gene Expression in Primary Rat Hepatocyte Cultures"
  • 29. Rodriguez-Pascual F., Miras-Portugal M. T.Torres M., Neuroscience, 67, 149 - 157 (1995), "Cyclic GMP-dependent Protein Kinase Activation Mediates Inhibition of Catecholamines Secretion and Ca 2+ Influx in Bovine Chromaffin Cells"
  • 30. Schuman E. M., Meffert M. K., Schulmann H.Madison D. V., Proc. Natl. Acad. Sci. USA, 91, 11958 - 11962 (1994), "An ADP-ribosyltransferase as a Potential Target for Nitric Oxide Action in Hippocampal Long-term Potentiation"
  • 31. Butt E., Nolte C., Schulz S., Beltman J., Beavo J. A., Jastorff B.Walter U., Biochem. Pharmacol., 43, 2591 - 2600 (1992), "Analysis of the Functional Role of cGMP-dependent Protein Kinase in Intact Human Platelets Using a Specific Activator 8-pCPT-cGMP"
  • 32. Newton R. P., Salih S. G.Khan J. A., Cyclic Nucleotide Phosphodiesterases: Structure M.D. Houslay ed., Wiley Interscience Chichester UK, 17, 141 - 159 (1990), "Cyclic CMP-Specific Phosphodiesterase Activity"
  • 33. Newton R. P., Walton T. J., Basaif S. A., Jenkins A. M., Brenton A. G., Ghosh D.Harris F. M., Org. Mass Spectrom., 24, 679 - 688 (1989), "Identification of Butyryl Derivatives of Cyclic Nucleotides by Positive Ion Fast Atom Bombardment Mass Spectrometry and Mass-analysed Ion Kinetic Energy Spectrometry"
  • 34. Francis S. H., Noblett B. D., Todd B. W., Wells J. N.Corbin J. D., Mol. Pharmacol., 34, 506 - 517 (1988), "Relaxation of Vascular and Tracheal Smooth Muscle by Cyclic Nucleotide Analogs That Preferentially Activate Purified cGMP-Dependent Protein Kinase"
  • 35. Sugiyama K., Takada K.Yamamoto I., European Patent Application Filing date 10.08.87, 87111542, 1 - 36 (1987), "Cosmetic Agent for Application to Skin"
  • 36. Corbin J. D., Oegreid D., Miller J. P., Suva R. H., Jastorff B.Doeskeland S. O., J. Biol. Chem., 261, 1208 - 1214 (1986), "Studies of cGMP Analog Specificity and Function of the Two Intrasubunit Binding Sites of cGMP-dependent Protein Kinase"
  • 37. Zimmerman A. L., Yamanaka G., Eckstein F., Baylor D. A.Stryer L., Proc. Natl. Acad. Sci. USA, 82, 8813 - 8817 (1985), "Interaction of Hydrolysis-resistant Analogs of Cyclic GMP with the Phosphodiesterase and Light - sensitive Channel of Retinal Rod Outer Segments"
  • 38. Miller L. J., Reilly W. M., Rosenzweig S. A., Jamieson J. D.Go V. L. W., Gastroenterology, 84, 1505 - 1511 (1983), "A Soluble Interaction Between Dibutyryl Cyclic Guanosine 3':5'- Monophosphate and Cholecystokinin: A Possible Mechanism for the Inhibition of Cholecystokinin Activity"
  • 39. Gardner J. D., Gastroenterology, 84, 1619 - 1621 (1983), "Mechanism by Which Dibutyryl Cyclic Guanosine Monophosphate Antagonizes the Action of Cholecystokinin"
  • 40. Robberecht P., Deschodt-Lanckman M., Woussen-Colle M.-C., De Neef P., Camus J. C.Christophe J., Mol. Pharmacol., 17, 268 - 274 (1980), "Butyryl Derivatives of Cyclic GMP Interfere With the Biological and the Immunological Properties of the Pancreozymin-Gastrin Family of Peptides"
  • 41. Peikin S. R., Costenbader C. L.Gardner J. D., J. Biol. Chem., 254, 5321 - 5327 (1979), "Actions of Derivatives of Cyclic Nucleotides on Dispersed Acini from Guinea Pig Pancreas - Discovery of a Competitive Antagonist of the Action of Cholecystokinin"
  • 42. O'Neill J. P., Li A. P.Hsie A. W., BBA, 497, 35 - 45 (1977), "Action of Cyclic Nucleotide Analogues in Chinese Hamster Ovary Cells"
  • 43. Miller J. P., Boswell K. H., Mian A. M., Meyer R. B., Robins R. K.Khwaja T. A., Biochemistry, 15, 217 - 223 (1976), "2'- Derivatives of Guanosine and Inosine Cyclic 3', 5'- Phosphates. Synthesis, Enzymic Activity, and the Effect of 8- Substituents"
  • 44. Kneer N. M., Bosch A. L., Clark M. G.Lardy H. A., Proc. Natl. Acad. Sci. USA, 71, 4523 - 4527 (1974), "Glucose Inhibition of Epinephrine Stimulation of Hepatic Gluconeogenesis by Blockade of the alpha-Receptor Function"
  • 45. Michal G., Mühlegger K., Nelboeck M., Thiessen C.Weimann G., Pharmacol. Res. Commun., 6, 203 - 252 (1974), "Cyclophosphates VI. Cyclophosphates as Substrates and Effectors of Phosphodiesterase"
  • 46. Kuo J. F., Miyamoto E.Reyes P. L., Biochem. Pharmacol., 23, 2011 - 2021 (1974), "Activation and Dissociation of Adenosine 3', 5'- Monophosphate-dependent and Guanosine 3', 5'- monophosphate-dependent Protein Kinases by Various Cyclic Nucleotide Analogs"
  • 47. Nelböck M., Michal G.Weimann G., Pure Appl. Chem., 35, 411 - 437 (1973), "Analogues of Cyclic AMP and their Physiological Response"
  • 48. Anderson W. B., Perlman R. L.Pastan I., J. Biol. Chem., 247, 2717 - 2722 (1972), "Effect of Adenosine 3', 5'- Monophosphate Analogues on the Activity of the Cyclic Adenosine 3', 5'- Monophosphate Receptor in Escherichia coli"
  • 49. Szaduykis-Szadurski L., Weimann G.Berti F., Pharmacol. Res. Commun., 4, 63 - 69 (1972), "Pharmacological Effects of Cyclic Nucleotides and their Derivatives on Tracheal Smooth Muscle"

Show more