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B1381

Sigma-Aldrich

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

≥98% (HPLC), powder

Sinonimo/i:

8-Br-cGMP, 8-Bromo-cyclic GMP

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About This Item

Formula empirica (notazione di Hill):
C10H10BrN5NaO7P
Numero CAS:
51116-01-9
Peso molecolare:
446.08
Numero CE:
256-993-8
Numero MDL:
MFCD00070128
Codice UNSPSC:
41106305
ID PubChem:
24278021
NACRES:
NA.77

Livello qualitativo

200

Saggio

≥98% (HPLC)

Forma fisica

powder

Solubilità

H2O: 50 mg/mL

Temperatura di conservazione

−20°C

Stringa SMILE

[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
ZJRFCXHKYQVNFK-YEOHUATISA-M

Categorie correlate

Descrizione generale

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.

Applicazioni

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)

Azioni biochim/fisiol

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.

Caratteristiche e vantaggi

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.

Codice della classe di stoccaggio

11 - Combustible Solids

Classe di pericolosità dell'acqua (WGK)

WGK 3

Punto d’infiammabilità (°F)

Not applicable

Punto d’infiammabilità (°C)

Not applicable

Dispositivi di protezione individuale

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)
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.
8-bromo-cGMP reduces the myofilament response to Ca2+ in intact cardiac myocytes.
Shah AM, et al.
Circulation Research, 74(5), 970-978 (1994)
Katarina Špiranec Spes et al.
Arteriosclerosis, thrombosis, and vascular biology, 40(1), 159-174 (2019-10-18)
In proliferative retinopathies, complications derived from neovascularization cause blindness. During early disease, pericyte's apoptosis contributes to endothelial dysfunction and leakage. Hypoxia then drives VEGF (vascular endothelial growth factor) secretion and pathological neoangiogenesis. Cardiac ANP (atrial natriuretic peptide) contributes to systemic
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