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A6885

Sigma-Aldrich

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

≥98.0% (HPLC), powder

Sinônimo(s):

3′,5′-Cyclic AMP sodium salt, cAMP-Na

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About This Item

Fórmula empírica (Notação de Hill):
C10H11N5NaO6P · H2O
Número CAS:
37839-81-9
Peso molecular:
369.20
Beilstein:
54612
Número MDL:
MFCD00069736
Código UNSPSC:
41106305
eCl@ss:
32160414
ID de substância PubChem:
24891151
NACRES:
NA.77

Nível de qualidade

200

Ensaio

≥98.0% (HPLC)

forma

powder

cor

white

solubilidade

H2O: 10 mg/mL

temperatura de armazenamento

−20°C

cadeia de caracteres SMILES

[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

chave InChI

BXJBFCKTIWRKMQ-MCDZGGTQSA-M

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Aplicação

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.

Ações bioquímicas/fisiológicas

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.

Características e benefícios

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.

Código de classe de armazenamento

11 - Combustible Solids

Classe de risco de água (WGK)

WGK 2

Ponto de fulgor (°F)

Not applicable

Ponto de fulgor (°C)

Not applicable

Equipamento de proteção individual

Eyeshields, Gloves, type N95 (US)

Certificados de análise (COA)

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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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Discover Bioactive Small Molecules for Cyclic Nucleotides

Cyclic nucleotides, including cyclic AMP (cAMP), cyclic GMP (cGMP) and cyclic ADP-ribose, have been extensively studied as second messengers of intracellular events initiated by activation of GPCRs. cAMP modifies cell function in all eukaryotic cells, principally through the activation of cAMP-dependent protein kinase (PKA), but also through cAMP-gated ion channels and guanine nucleotide exchange factors directly activated by cAMP.

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