B1381

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

≥98% (HPLC), powder

• Synonym(s): 8-Br-cGMP, 8-Bromo-cyclic GMP
• Empirical Formula (Hill Notation): C₁₀H₁₀BrN₅NaO₇P
• CAS Number: 51116-01-9
• Molecular Weight: 446.08
• EC Number: 256-993-8
• MDL number: MFCD00070128
• UNSPSC Code: 41106305
• PubChem Substance ID: 24278021
• NACRES: NA.77

Properties

• Assay: ≥98% (HPLC)
• form: powder
• solubility: H₂O: 50 mg/mL
• storage temp.: −20°C
• SMILES string: [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
• InChI key: ZJRFCXHKYQVNFK-YEOHUATISA-M

Description

General description

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)

Biochem/physiol Actions

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.

Features and Benefits

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.

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves