B1381
8-Bromoguanosine 3′,5′-cyclic monophosphate sodium salt
≥98% (HPLC), cGMP analog, powder
Synonym(s):
8-Br-cGMP, 8-Bromo-cyclic GMP
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About This Item
Empirical Formula (Hill Notation):
C10H10BrN5NaO7P
CAS Number:
Molecular Weight:
446.08
NACRES:
NA.77
PubChem Substance ID:
UNSPSC Code:
41106305
EC Number:
256-993-8
MDL number:
Product Name
8-Bromoguanosine 3′,5′-cyclic monophosphate sodium salt, ≥98% (HPLC), powder
InChI key
ZJRFCXHKYQVNFK-YEOHUATISA-M
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
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
assay
≥98% (HPLC)
form
powder
solubility
H2O: 50 mg/mL
storage temp.
−20°C
Quality Level
Related Categories
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.
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.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
ppe
Eyeshields, Gloves, type N95 (US)
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U C Garg et al.
The Journal of clinical investigation, 83(5), 1774-1777 (1989-05-01)
Endothelium-derived relaxing factor has been recently identified as nitric oxide. The purpose of this study was to determine if vasodilator drugs that generate nitric oxide inhibit vascular smooth muscle mitogenesis and proliferation in culture. Three chemically dissimilar vasodilators, sodium nitroprusside
Cyclic guanosine 3': 5'-monophosphate mimics the effects of light on a circadian pacemaker in the eye of aplysia
Eskin A, et al.
The Journal of Neuroscience, 4(10), 2466-2471 (1984)
8-bromo-cGMP reduces the myofilament response to Ca2+ in intact cardiac myocytes.
Shah AM, et al.
Circulation Research, 74(5), 970-978 (1994)
Arun Govindapillai et al.
Scientific reports, 8(1), 6939-6939 (2018-05-04)
Patients born with congenital heart defects frequently encounter arrhythmias due to defects in the ventricular conduction system (VCS) development. Although recent studies identified transcriptional networks essential for the heart development, there is scant information on the mechanisms regulating VCS development.
Nadine Suffee et al.
Proceedings of the National Academy of Sciences of the United States of America, 114(5), E771-E780 (2017-01-18)
The abundance of epicardial adipose tissue (EAT) is associated with atrial fibrillation (AF), the most frequent cardiac arrhythmia. However, both the origin and the factors involved in EAT expansion are unknown. Here, we found that adult human atrial epicardial cells
Articles
Cyclic nucleotides like cAMP modulate cell function via PKA activation and ion channels.
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