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A3262

Sigma-Aldrich

Adenosine 3′,5′-cyclic monophosphate tris salt

≥97% (HPLC), powder

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Synonym(s):
cAMP, cyclic AMP
Empirical Formula (Hill Notation):
C10H12N5O6P · C4H11NO3
CAS Number:
Molecular Weight:
450.34
MDL number:
eCl@ss:
32160414
PubChem Substance ID:
NACRES:
NA.51

biological source

synthetic

Quality Level

assay

≥97% (HPLC)

form

powder

color

white

solubility

H2O: 100 mg/mL

storage temp.

−20°C

SMILES string

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

InChI key

CLDDYJFNXTUHIN-MCDZGGTQSA-N

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This Item
A9376A0386A9501
Quality Level

200

Quality Level

200

Quality Level

200

Quality Level

200

form

powder

form

powder

form

powder

form

powder

assay

≥97% (HPLC)

assay

≥93%

assay

≥98% (HPLC)

assay

≥98.5% (HPLC)

color

white

color

-

color

-

color

white

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

General description

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.

Biochem/physiol Actions

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.

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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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.
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