CAS 51116-00-8|Dibutyryl-cGMP sodium
Introduction：Basic information about CAS 51116-00-8|Dibutyryl-cGMP sodium, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
| Common Name | Dibutyryl-cGMP sodium | ||
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| CAS Number | 51116-00-8 | Molecular Weight | 507.367 |
| Density | / | Boiling Point | / |
| Molecular Formula | C18H23N5NaO9P | Melting Point | / |
| MSDS | / | Flash Point | / |
Names
| Name | N2,2′-O-Dibutyrylguanosine 3′,5′-cyclic monophosphate sodium salt hydrate |
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| Synonym | More Synonyms |
Dibutyryl-cGMP sodium BiologicalActivity
| Description | Dibutyryl-cGMP sodium (Bt2cGMP sodium) is a cell-permeable cGMP analogue. Dibutyryl-cGMP sodium preferentially activates cGMP-dependent protein kinase (PKG). Dibutyryl-cGMP sodium inhibits the release of [3H]-arachidonic acid from γ thrombin-stimulated human platelets. Dibutyryl-cGMP sodium induces peripheral antinociception via activation of ATP-sensitive K+ channels[1][2][3]. |
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| Related Catalog | Research Areas >>Cardiovascular DiseaseSignaling Pathways >>Membrane Transporter/Ion Channel >>Potassium Channel |
| Target | cGMP-dependent protein kinase (PKG)[1]; ATP-sensitive K+ channels[3] |
| In Vitro | Dibutyryl-cGMP is able to induce process elongation and branching in astrocytes resulting from a rapid, reversible and concentration-dependent redistribution of glial fibrillary acidic protein (GFAP) and actin filaments without significant change in protein levels[1]. When cells are co-incubated with Dibutyryl-cGMP (100 μM) stress fibre formation is prevented and cells acquired a stellate morphology in cerebellar astrocytes[1]. In cells treated with Dibutyryl-cGMP (100 μM, 2 h) the particulate fraction is nearly devoid of RhoA protein. Dibutyryl-cGMP prevents RhoA-membrane association[1]. Using the scratchwound model, the size of the wound is significantly smaller in cells treated with Dibutyryl-cGMP after the wound indicating that dbcGMP accelerates wound closure[1]. |
| In Vivo | Dibutyryl-cGMP (50-200 μg/paw; subcutaneous injection; male Wistar rats) treatment antagonizes the hyperalgesic effect of PGE2 in a dose-dependent manner. Maximal antinociceptive effect of DbcGMP is at 1 h after administration and last for plus 2 h[3]. Animal Model: Male Wistar rats (180- 250 g) injection with Prostaglandin E2 (PGE2)[3] Dosage: 50 μg/paw, 75 μg/paw, 100 μg/paw and 200 μg/paw Administration: Subcutaneous injection Result: Antagonized the hyperalgesic effect of PGE2 (2 μg/paw), in a dose-dependent manner. |
| References | [1]. Borán MS, et al. The cyclic GMP-protein kinase G pathway regulates cytoskeleton dynamics and motility in astrocytes. J Neurochem. 2007 Jul;102(1):216-30. [2]. Sane DC, et al. Cyclic GMP analogs inhibit gamma thrombin-induced arachidonic acid release in human platelets. Biochem Biophys Res Commun. 1989 Dec 15;165(2):708-14. [3]. Soares AC, et al. Dibutyryl-cyclic GMP induces peripheral antinociception via activation of ATP-sensitive K(+) channels in the rat PGE2-induced hyperalgesic paw. Br J Pharmacol. 2001 Sep;134(1):127-31. |
Chemical & Physical Properties
| Molecular Formula | C18H23N5NaO9P |
|---|---|
| Molecular Weight | 507.367 |
| Exact Mass | 507.113098 |
| PSA | 196.60000 |
| LogP | 1.49450 |
| InChIKey | MGBPJXVWDGGLKI-GBIKJYCISA-M |
| SMILES | CCCC(=O)Nc1nc2c(ncn2C2OC3COP(=O)([O-])OC3C2OC(=O)CCC)c(=O)[nH]1.[Na+] |
Synonyms
| sodium,[6-[2-(butanoylamino)-6-oxo-3H-purin-9-yl]-2-oxido-2-oxo-4a,6,7,7a-tetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-7-yl] butanoate |
| Butanoic acid, (4aR,6R,7R,7aR)-6-[1,6-dihydro-6-oxo-2-[(1-oxobutyl)amino]-9H-purin-9-yl]tetrahydro-2-hydroxy-2-oxido-4H-furo[3,2-d]-1,3,2-dioxaphosphorin-7-yl ester, sodium salt (1:1) |
| Sodium (4aR,6R,7R,7aR)-6-[2-(butyrylamino)-6-oxo-1,6-dihydro-9H-purin-9-yl]-7-(butyryloxy)tetrahydro-4H-furo[3,2-d][1,3,2]dioxaphosphinin-2-olate 2-oxide |
