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A6885

Sigma-Aldrich

Adenosine 3′,5′-cyclic monophosphate sodium salt monohydrate

≥98.0% (HPLC), cyclic-AMP-dependent protein kinase (PKA) activator, powder

Synonym(s):

3′,5′-Cyclic AMP sodium salt, cAMP-Na

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About This Item

Empirical Formula (Hill Notation):
C10H11N5NaO6P · H2O
CAS Number:
37839-81-9
Molecular Weight:
369.20
Beilstein/REAXYS Number:
54612
MDL number:
MFCD00069736
UNSPSC Code:
41106305
eCl@ss:
32160414
PubChem Substance ID:
24891151
NACRES:
NA.77

Key Documents

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Product Name

Adenosine 3′,5′-cyclic monophosphate sodium salt monohydrate, ≥98.0% (HPLC), powder

Quality Level

200

assay

≥98.0% (HPLC)

form

powder

color

white

solubility

H2O: 10 mg/mL

storage temp.

−20°C

SMILES string

[Na+].Nc1ncnc2n(cnc12)[C@@H]3O[C@@H]4COP([O-])(=O)O[C@H]4[C@H]3O

InChI

1S/C10H12N5O6P.Na/c11-8-5-9(13-2-12-8)15(3-14-5)10-6(16)7-4(20-10)1-19-22(17,18)21-7;/h2-4,6-7,10,16H,1H2,(H,17,18)(H2,11,12,13);/q;+1/p-1/t4-,6-,7-,10-;/m1./s1

InChI key

BXJBFCKTIWRKMQ-MCDZGGTQSA-M

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Application

Adenosine-3′,5′-cyclic monophosphate (cAMP) is an activator of cyclic-AMP-dependent protein kinase A (PKA). The cAMP/PKA signaling pathway has been shown to inhibit cell proliferation, induce differentiation and lead to apoptosis. Exogneous cAMP plays a role in the spontaneous activity and contraction of the heart muscle.

Biochem/physiol Actions

Naturally-occurring activator of cyclic-AMP-dependent protein kinase (PKA).
Naturally-occurring activator of cyclic-AMP-dependent protein kinase (PKA). cAMP is an important second messenger that is linked in many systems to neurotransmitter- or hormone-induced receptor stimulation. The cAMP/PKA signaling pathway has been shown to inhibit cell proliferation, induce differentiation and lead to apoptosis.

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 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
SLCK5310
SLCF4511
SLBZ9078
SLBR7851V
SLBJ8361V

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U Dunzendorfer et al.
European urology, 8(6), 363-366 (1982-01-01)
Patients with a history of idiopathic calcium oxalate stones, but without current stone formation, show distinctly higher levels of serum cAMP (cyclic adenosine 3',5'-monophosphate) after rapid injection of an extreme concentration of parathyroid extract (PTE). Extreme parathyroid hormone (PTH) levels
W Tuganowski et al.
Polish journal of pharmacology and pharmacy, 30(4), 451-454 (1978-07-01)
Isotonic solution of cAMP-Na was applied into spontaneously beating auricular fibres by a cut-end method. Cyclic AMP enhanced the spontaneous rate (mean 48%) and increased the contractile tension (mean 297%). These results provided direct evidence that cAMP is involved in
Michaela Beese et al.
BMC cell biology, 11, 68-68 (2010-09-09)
Endothelial tight and adherens junctions control a variety of physiological processes like adhesion, paracellular transport of solutes or trafficking of activated leukocytes. Formation and maintenance of endothelial junctions largely depend on the microenvironment of the specific vascular bed and on
Corinne Giusti et al.
Experimental cell research, 315(1), 26-38 (2008-10-28)
Dictyostelium atg1- mutant cells provide an experimentally and genetically favorable model to study necrotic cell death (NCD) with no interference from apoptosis or autophagy. In such cells subjected to starvation and cAMP, induction by the differentiation-inducing factor DIF or by
Logan A Collier et al.
mBio, 11(6) (2020-11-26)
The filamentous fungus Neurospora crassa decomposes lignocellulosic biomass to generate soluble sugars as carbon sources. In this study, we investigated a role for heterotrimeric G-protein signaling in cellulose degradation. Loss of the Gα subunit genes gna-1 and gna-3, the Gβ
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Cyclic nucleotides like cAMP modulate cell function via PKA activation and ion channels.

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