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Alternative structural projections:

2'-O-MB-cGMP

2'- O- Monobutyrylguanosine- 3', 5'- cyclic monophosphate, sodium salt (2'-O-MB-cGMP)
Metabolically activatable PKG agonist
Cat. No.: M 006
    
CAS No.: [58329-72-9]
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Product Name Price (net) Qty
Cat. No.: M 006-10
Unit: 10 µmol / ~4.4 mg
$56.00
For other salt forms or metabolites please inquire. 2'-O-MB-cGMP is a lipophilic precursor of cyclic GMP. During metabolic activation by esterases cGMP and butyrate are released. Caution: Butyrate was shown to have distinct biological effects. Significantly more lipophilic and membrane-permeant compared to cGMP. Detailed technical information available. Reference: Hebert et al., J. Biol. Chem., 273, 5557 - 5565 (1998).
Cat. No. M 006
CAS number [58329-72-9]
Purity > 97% HPLC
Salt form Sodium
Storage temperature -20°C / -4°F
Molecular formula C₁₄H₁₇N₅O₈P · Na
Molecular weight [g/mol] 437,3
Modifications 2'-cAMP
Target PKG (cGK) Activator
Absorption max [nm] 252
Molar extinction coefficient ε [L·mol⁻¹·cm⁻¹] 13500
  • 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. 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"
  • 3. Hebert M. C., Schwede F., Jastorff B.Cote R. H., J. Biol. Chem., 273, 5557 - 5565 (1998), "Structural Features of the Noncatalytic cGMP Binding Sites of Frog Photoreceptor Phoshodiesterase Using cGMP Analogs"
  • 4. 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"
  • 5. Sugiyama K., Takada K.Yamamoto I., European Patent Application Filing date 10.08.87, 87111542, 1 - 36 (1987), "Cosmetic Agent for Application to Skin"
  • 6. Braumann T., Erneux C., Petridis G., Stohrer W.-D.Jastorff B., Biochim. Biophys. Acta, 871, 199 - 206 (1986), "Hydrolysis of Cyclic Nucleotides by a Purified cGMP- stimulated Phosphodiesterase: Structural Requirements for Hydrolysis"
  • 7. 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"
  • 8. 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"
  • 9. 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"
  • 10. Miller J. P., Shuman D. A., Scholten M. B., Dimmitt M. K., Stewart C. M., Khwaja T. A., Robins R. K.Simon L. N., Biochemistry, 12, 1010 - 1016 (1973), "Synthesis and Biological Activity of Some 2' Derivatives of Adenosin 3',5' - Cyclic Phosphate"