0 Items - $0.00
Categories
A to Z

Alternative structural projections:

2'-O-MB-cAMP

2'- O- Monobutyryladenosine- 3', 5'- cyclic monophosphate, sodium salt ( 2'-O-MB-cAMP )
Metabolically activatable prodrug form of cyclic AMP
Cat. No.: M 007
    
CAS No.: [55443-13-5]
Shipping: ambient
Product Name Price (net) Qty
Cat. No.: M 007-50
Unit: 50 µmol / ~21 mg
$90.00
For other salt forms or metabolites please inquire. 2'-O-MB-cAMP is a lipophilic precursor of cAMP. During metabolic activation by esterases cAMP and butyrate are released. Caution: Butyrate was shown to have distinct biological effects! Significantly more lipophilic and membrane-permeant compared to cAMP. Detailed technical information and references available. Reference: Schaeffer et al., J. Pharmaceut. Sci., 72, 1255 - 1259 (1983).
Cat. No. M 007
CAS number [55443-13-5]
Purity > 97% HPLC
Salt form Sodium
Storage temperature -20°C / -4°F
Molecular formula C₁₄H₁₇N₅O₇P · Na
Molecular weight [g/mol] 421.3
Modifications 2'-cAMP
Lipophilicity 1.93
Absorption max [nm] 259
Molar extinction coefficient ε [L·mol⁻¹·cm⁻¹] 15000
  • 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. Scott S.-P., Shea P. W.Dryer S. E., Biochem., 46, 9417 - 9431 (2007), "Mapping Ligand Interactions with the Hyperpolarization Activated Cyclic Nucleotide Modulated (HCN) Ion Channel Binding Domain Using a Soluble Construct"
  • 3. 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"
  • 4. Anciaux K., Van Dommelen K., Willems R., Roymans D.Slegers H., FEBS Lett., 400, 75 - 79 (1997), "Inhibition of Nucleoside Diphosphate Kinase (NDPK/NM23) by cAMP Analogues"
  • 5. Anciaux K., Van Dommelen K., Nicolai S., Van Mechelen E.Slegers H., J. Neurosci. Res., 48, 324 - 333 (1997), "Cyclic AMP-Mediated Induction of the Glial Fibrillary Acidic Protein is Independent of Protein Kinase A Activation in Rat C6 Glioma"
  • 6. Nicolai S., Willems J., Zwijsen A., Van Mechelen E.Slegers H., Free Radical Biol. Med., 21, 481 - 486 (1996), "Cyclic AMP-induced Differentiation Increases the Synthesis of Extracellular Superoxide Dismutase in Rat C6 Glioma"
  • 7. Butt E., Beltman J., Becker D. E., Jensen G. S., Rybalkin S. D., Jastorff B.Baevo J. A., Mol. Pharmacol., 47, 340 - 347 (1995), "Characterization of Cyclic Nucleotide Phosphodiesterases with Cyclic AMP Analogs: Topology of the Catalytic Site and Comparison with Other Cyclic AMP-Binding Proteins"
  • 8. Richter-Landsberg C.Jastorff B., NATO ASI Ser. (Glial- Neur. Commun. Dev. Regener.), 2, 339 - 354 (1987), "Effect of Nerve Growth Factor and cAMP Analogs on Neuronal Differentiation in PC12 Cells: Studies with an Inhibitor of cAMP- Dependent Protein Kinases"
  • 9. Braumann T., Jastorff B.Richter-Landsberg C., J. Neurochem., 47, 912 - 919 (1986), "Fate of Cyclic Nucleotides in PC12 Cell Cultures: Uptake, Metabolism, and Effects of Metabolites on Nerve Growth Factor-Induced Neurite Outgrowth"
  • 10. Schaeffer V. L., Masoud A. N.Rubin R. J., J. Pharm. Sci., 72, 1255 - 1259 (1983), "Analysis of Monobutyryl and Dibutyryl Derivates of Adenosine 3´,5´-Monophosphate in Biological Samples Using Isocratic Ion Pair High-Performance Liqiud Chromatography"
  • 11. Yagura T. S.Miller J. P., Biochemistry, 20, 879 - 887 (1981), "Mapping Adenosine Cyclic 3',5'- Phosphate Binding Sites on Type I and Type II Adenosine Cyclic 3',5'- Phosphate Dependent Protein Kinases Using Ribose Ring and Cyclic Phosphate Ring Analogues of Adenosine Cyclic 3', 5'- Phosphate"
  • 12. 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"
  • 13. 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"
  • 14. Bevers M. M., van Rijn J.van Wijk R., FEBS Letters, 72, 275 - 278 (1976), "A Comparative Study on the Metabolism of N6, O2'-Dibutyryl Adenosine 3', 5'-Monophosphate in Various Rat Hepatoma Cell Lines in Culture"
  • 15. O'Neill J. P., Schröder C. H.Hsie A. W., J. Biol. Chem., 250, 990 - 995 (1975), "Hydrolysis of Butyryl Derivatives of Adenosine Cyclic 3',5'-Monophosphate by Chinese Hamster Ovary Cell Extracts and Characterization of the Products"
  • 16. Siggins G. R.Henriksen S. J., Science, 189, 559 - 560 (1975), "Analogs of Cyclic Adenosine Monophosphate: Correlation of Inhibition of Purkinje Neurons with Protein Kinase Activation"
  • 17. Meyer R. B.Miller J. P., Life Sci., 14, 1019 - 1040 (1974), "Analogs of Cyclic AMP and Cyclic GMP: General Methods of Synthesis and the Relationship of Structure to Enzymatic Activity"
  • 18. Antonoff R. S.Ferguson J. J., J. Biol. Chem., 249, 3319 - 3321 (1974), "Photoaffinity Labeling with Cyclic Nucleotides"
  • 19. Kaukel E., Mundhenk K.Hilz H., Eur. J. Biochem., 27, 197 - 200 (1972), "N6-Monobutyryladenosine 3': 5'- Monophosphate as the Biologically Active Derivative of Dibutyryladenosine 3': 5'- Monophosphate in HeLa S3 Cells"
  • 20. Steiner A. L., Parker C. W.Kipnis D. M., J. Biol. Chem., 247, 1106 - 1113 (1972), "Radioimmunoassay for Cyclic Nucleotides. I. Preparation of Antibodies and Iodinated Cyclic Nucleotides"
  • 21. Blecher M., Ro'Ane J. T.Flynn P. D., J. Biol. Chem., 245, 1867 - 1870 (1970), "Metabolism of Dibutyryl Cyclic Adenosine 3', 5'- Monophosphate During its Regulation of Lipolysis and Glucose Oxidation in Isolated Epididymal Adipocytes"
  • 22. Henion W. F., Sutherland E. W.Posternak T. H., Biochim. Biophys. Acta, 148, 106 - 113 (1967), "Effects of Derivatives of Adenosine 3', 5'-Phosphate on Liver Slices and Intact Animals"
  • 23. Falbriard J.-G., Posternak T.Sutherland E. W., BBA, 148, 99 - 105 (1967), "Preparation of Derivatives of Adenosine 3', 5'-Phosphate"
  • 24. Posternak T., Sutherland E. W.Henion W. F., BBA, 65, 558 - 560 (1962), "Derivatives of Cyclic 3',5'- Adenosine Monophosphate"

Show more