B1381

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

≥98% (HPLC), powder

• Sinônimo(s): 8-Br-cGMP, 8-Bromo-cyclic GMP
• Fórmula empírica (Notação de Hill): C₁₀H₁₀BrN₅NaO₇P
• Número CAS: 51116-01-9
• Peso molecular: 446.08
• Número CE: 256-993-8
• Número MDL: MFCD00070128
• Código UNSPSC: 41106305
• ID de substância PubChem: 24278021
• NACRES: NA.77

Propriedades

• Ensaio: ≥98% (HPLC)
• Formulário: powder
• solubilidade: H₂O: 50 mg/mL
• temperatura de armazenamento: −20°C
• cadeia de caracteres 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
• chave InChI: ZJRFCXHKYQVNFK-YEOHUATISA-M

Descrição

Descrição geral

8-Bromoguanosine 3′,5′-cyclic monophosphate is a cell-permeable cGMP analog of cyclic guanosine 3′:5′-monophosphate (cGMP).[1] It is a lipid-soluble analog used in cGMP based contraction studies in cardiomyocytes.[2]

Aplicação

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)

Ações bioquímicas/fisiológicas

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.[1]

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.

Características e benefícios

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.

Informações de segurança

• Código de classe de armazenamento: 11 - Combustible Solids
• Classe de risco de água (WGK): WGK 3
• Ponto de fulgor (°F): Not applicable
• Ponto de fulgor (°C): Not applicable
• Equipamento de proteção individual: Eyeshields, Gloves, type N95 (US)