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A3262

Sigma-Aldrich

Adenosine 3′,5′-cyclic monophosphate tris salt

≥97% (HPLC), powder

Synonyme(s) :

cAMP, cyclic AMP

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About This Item

Formule empirique (notation de Hill):
C10H12N5O6P · C4H11NO3
Numéro CAS:
102029-77-6
Poids moléculaire :
450.34
Numéro MDL:
MFCD00058346
Code UNSPSC :
41106305
eCl@ss :
32160414
ID de substance PubChem :
329770822
Nomenclature NACRES :
NA.51

Source biologique

synthetic

Niveau de qualité

200

Pureté

≥97% (HPLC)

Forme

powder

Couleur

white

Solubilité

H2O: 100 mg/mL

Température de stockage

−20°C

Chaîne SMILES 

NC(CO)(CO)CO.Nc1ncnc2n(cnc12)[C@@H]3O[C@@H]4COP(O)(=O)O[C@H]4[C@H]3O

InChI

1S/C10H12N5O6P.C4H11NO3/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;5-4(1-6,2-7)3-8/h2-4,6-7,10,16H,1H2,(H,17,18)(H2,11,12,13);6-8H,1-3,5H2/t4-,6-,7-,10-;/m1./s1

Clé InChI

CLDDYJFNXTUHIN-MCDZGGTQSA-N

Catégories apparentées

Description générale

Adenosine 3′,5′-cyclic monophosphate (cAMP) is synthesized from ATP in the presence of Adenylate cyclase enzyme. cAMP is majorly used as a marker in immunochemical detection assays. Intracellular levels of cAMP control immune and inflammatory functions. Bacterial infection triggers intracellular cAMP production. Elevated levels of cAMP modulates mitogen-activated protein kinase (MAPK) in cancer. An altered cAMP level is implicated in pathogenesis of cataract and cardiovascular disease. A decrease in cAMP levels triggers impaired insulin secretion in diabetes.

Application

Adenosine 3′,5′-cyclic monophosphate tris salt has been used as a medium supplement for human endometrial stromal cells (hESCs) culture and induced neural stem cells (iNSCs). It has been used in the spectroscopic characterization of pink flamindo, a red cAMP indicator.

Actions biochimiques/physiologiques

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.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

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Yanmin Chen et al.
Planta medica, 85(9-10), 738-744 (2019-06-12)
Chronic heart failure is the terminal stage of various cardiovascular diseases. Despite the availability of several classes of drugs, there is still an unmet need for effective treatment. Based on bench work during the past two decades, we have proposed
Guillaume St-Jean et al.
Biology of reproduction, 100(1), 49-60 (2018-07-17)
Wnt4 and Wnt5a have well-established roles in the embryonic development of the female reproductive tract, as well as in implantation, decidualization, and ovarian function in adult mice. Although these roles appear to overlap, whether Wnt5a and Wnt4 are functionally redundant
Joshua H K Tam et al.
Molecular brain, 7, 54-54 (2014-08-03)
Alzheimer's disease (AD) is characterized by cerebral deposition of β-amyloid peptide (Aβ). Aβ is produced by sequential cleavage of the Amyloid Precursor Protein (APP) by β- and γ-secretases. Many studies have demonstrated that the internalization of APP from the cell
Cyclic AMP: master regulator of innate immune cell function
Serezani CH, et al.
American Journal of Respiratory Cell and Molecular Biology, 39(2), 127-132 (2008)
Conversion of adult human peripheral blood mononuclear cells into induced neural stem cell by using episomal vectors
Tang X, et al.
Stem Cell Research, 16(2), 236-242 (2016)
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