B1381

8-Bromoguanosine 3′,5′-cyclic monophosphate sodium salt

≥98% (HPLC), powder

• Synonyme(s) : 8-Br-cGMP, 8-Bromo-cyclic GMP
• Formule empirique (notation de Hill): C₁₀H₁₀BrN₅NaO₇P
• Numéro CAS: 51116-01-9
• Poids moléculaire : 446.08
• Numéro CE : 256-993-8
• Numéro MDL: MFCD00070128
• Code UNSPSC : 41106305
• ID de substance PubChem : 24278021
• Nomenclature NACRES : NA.77

Propriétés

• Pureté: ≥98% (HPLC)
• Forme: powder
• Solubilité: H₂O: 50 mg/mL
• Température de stockage: −20°C
• Chaîne SMILES: [Na+].NC1=Nc2c(nc(Br)n2[C@@H]3O[C@@H]4COP([O-])(=O)O[C@H]4[C@H]3O)C(=O)N1
• InChI: 1S/C10H11BrN5O7P.Na/c11-9-13-3-6(14-10(12)15-7(3)18)16(9)8-4(17)5-2(22-8)1-21-24(19,20)23-5;/h2,4-5,8,17H,1H2,(H,19,20)(H3,12,14,15,18);/q;+1/p-1/t2-,4-,5-,8-;/m1./s1
• Clé InChI: ZJRFCXHKYQVNFK-YEOHUATISA-M

Description

Description générale

8-Bromoguanosine 3′,5′-cyclic monophosphate is a cell-permeable cGMP analog of cyclic guanosine 3′:5′-monophosphate (cGMP). It is a lipid-soluble analog used in cGMP based contraction studies in cardiomyocytes.

Application

8-Bromoguanosine 3′,5′-cyclic monophosphate sodium salt has been used:

• as a cyclic guanosine 3′:5′-monophosphate (cGMP) agonist in the collapse assay in retinal ganglion axons(10)
• as a component of reaction buffer in in vitro kinase activity assay of recombinant protein kinase (PKG)(11)
• as a cyclic nucleotide analog for the induction of cyclic nucleotide-gated channel (CNGA and CNGC) expression in human embryonic kidney cells(12)

Actions biochimiques/physiologiques

8-Bromoguanosine 3′,5′-cyclic monophosphate has greater resistance to hydrolysis by phosphodiesterases than cGMP. Activates cGMP-dependent protein kinase. It slows or inhibits the intracellular calcium oscillations of tracheal smooth muscle cells in response to acetylcholine. 8-Bromoguanosine 3′,5′-cyclic monophosphate sodium salt mimics the effect of nitric oxide generating drugs. It modulates circadian rhythms and increases optic nerve impulses. In the eye 8-Bromoguanosine 3′,5′-cyclic monophosphate may favour transduction of non-R-type photoreceptors.

Cell-permeable cGMP analog having greater resistance to hydrolysis by phosphodiesterases than cGMP. Activates cGMP-dependent protein kinase. Slows or inhibits the intracellular calcium oscillations of tracheal smooth muscle cells in response to acetylcholine. Reported to mimic the effect of nitric oxide generating drugs.

Caractéristiques et avantages

This compound is a featured product for Cyclic Nucleotide research. Click here to discover more featured Cyclic Nucleotide products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.

This compound is featured on the PKA & PKG page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Informations sur la sécurité

• Code de la classe de stockage: 11 - Combustible Solids
• Classe de danger pour l'eau (WGK): WGK 3
• Point d'éclair (°F): Not applicable
• Point d'éclair (°C): Not applicable
• Équipement de protection individuelle: Eyeshields, Gloves, type N95 (US)