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G6129

Sigma-Aldrich

Guanosine 3′,5′-cyclic monophosphate sodium salt

≥99% (HPLC), powder

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Synonym(s):
3′,5′-Cyclic GMP monosodium salt, 3′,5′-cGMP-Na, Guanosine 3′,5′-cyclophosphate monosodium salt, cGMP, cyclic GMP
Empirical Formula (Hill Notation):
C10H11N5NaO7P
CAS Number:
Molecular Weight:
367.19
Beilstein/REAXYS Number:
6467425
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

assay

≥99% (HPLC)

form

powder

color

white

solubility

H2O: 50 mg/mL

storage temp.

−20°C

SMILES string

[Na+].NC1=Nc2c(ncn2[C@@H]3O[C@@H]4COP([O-])(=O)O[C@H]4[C@H]3O)C(=O)N1

InChI

1S/C10H12N5O7P.Na/c11-10-13-7-4(8(17)14-10)12-2-15(7)9-5(16)6-3(21-9)1-20-23(18,19)22-6;/h2-3,5-6,9,16H,1H2,(H,18,19)(H3,11,13,14,17);/q;+1/p-1/t3-,5-,6-,9-;/m1./s1

InChI key

KMPIYXNEROUNOG-GWTDSMLYSA-M

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1 of 4

This Item
G7504A6885C9630
form

powder

form

powder

form

powder

form

powder

Quality Level

200

Quality Level

-

Quality Level

200

Quality Level

-

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

solubility

H2O: 50 mg/mL

solubility

0.2 M NaHCO3: 50 mg/mL

solubility

H2O: 10 mg/mL

solubility

water: 50 mg/mL, clear, colorless

color

white

color

white

color

white

color

-

Biochem/physiol Actions

An important second messenger, cGMP is a major intracellular mediator of extracellular signals such as nitric oxide and natriuretic peptides. Cyclic GMP interacts with three types of intracellular receptor proteins: cGMP-dependent protein kinases, cGMP-regulated channels, and cGMP-regulated cyclic nucleotide phosphodiesterases. A primary action of elevated cGMP levels in vivo is the stimulation of cGMP-dependent protein kinase (PKG).

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 Phosphodiesterases and PKA & PKG pages of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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C Picco et al.
The Journal of physiology, 460, 741-758 (1993-01-01)
1. The permeability of the channel activated by guanosine 3',5'-cyclic monophosphate (cGMP) to many organic monovalent cations was determined by recording macroscopic currents in excised inside-out patches of plasma membrane from isolated retinal rod outer segments of the tiger salamander.
G Colamartino et al.
The Journal of physiology, 440, 189-206 (1991-01-01)
1. Blockage and permeation of divalent cations through channels activated by guanosine 3',5'-cyclic monophosphate (cyclic GMP) were studied in membrane patches excised from retinal rods of the tiger salamander Ambystoma tigrinum by rapidly changing the ionic medium bathing the intracellular
Katja S Kroker et al.
Neurobiology of aging, 35(9), 2072-2078 (2014-04-22)
The cyclic nucleotide cGMP is an important intracellular messenger for synaptic plasticity and memory function in rodents. Therefore, inhibition of cGMP degrading phosphodiesterases, like PDE9A, has gained interest as potential target for treatment of cognition deficits in indications like Alzheimer's
You-Lin Tain et al.
Biology of reproduction, 92(1), 7-7 (2014-11-15)
Nitric oxide (NO) deficiency induced by the NO synthase (NOS) inhibitor N(G)-nitro-L-arginine-methyl ester (L-NAME) resulted in hypertension. L-citrulline (CIT) can be converted to L-arginine to generate NO. We examined whether maternal CIT supplementation can prevent L-NAME-induced programmed hypertension. Pregnant Sprague-Dawley
Milton Packer et al.
Circulation, 131(1), 54-61 (2014-11-19)
Clinical trials in heart failure have focused on the improvement in symptoms or decreases in the risk of death and other cardiovascular events. Little is known about the effect of drugs on the risk of clinical deterioration in surviving patients.

Articles

Cyclic nucleotides like cAMP modulate cell function via PKA activation and ion channels.

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