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

SIGMA/B1381 - ≥98% (HPLC), powder

Synonym: 8-Br-cGMP; 8-Bromo-cyclic GMP

CAS Number: 51116-01-9
Empirical Formula (Hill Notation): C₁₀H₁₀BrN₅NaO₇P
Molecular Weight: 446.08
EC Number: 256-993-8
MDL Number: MFCD00070128
Linear Formula: C₁₀H₁₀BrN₅NaO₇P
Product Type: Chemical

Catalog Number	PKG Qty.	Price


45-B1381-10MG	10 mg	$91.90 1/EA	Add To Favorites
45-B1381-25MG	25 mg	$184.00 1/EA	Add To Favorites
45-B1381-100MG	100 mg	$702.00 1/EA	Add To Favorites

This picture is provided solely for illustration purposes. Optical properties of the actual product may deviate. Relevant product information is printed on labeled products and other accompanying or available information material. This image depicts SKU: B1381-100MG

Properties
Descriptions
Safety Info.
Basic Data

assay	≥98% (HPLC)
form	powder
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
Quality Level	200
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
solubility	H₂O: 50 mg/mL
storage temp.	−20°C

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.
Biochem/physiol Actions:	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 .
Features and Benefits:	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 .
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.
Packaging:	10 mg in glass bottle
Packaging:	25, 100 mg in poly bottle

RIDADR	NONH for all modes of transport
WGK Germany	WGK 3
Flash Point(F)	Not applicable
Flash Point(C)	Not applicable

Purity	≥98% (HPLC)
Storage Temp.	−20°C
UNSPSC	41106305

To Order From a Quote