A3262

Sigma-Aldrich

Adenosine 3′,5′-cyclic monophosphate tris salt

≥97% (HPLC), powder

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

Quality Level

biological source

synthetic

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

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.

Packaging

500 mg in poly bottle

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.

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis

Certificate of Origin

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)
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)
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...
Local cAMP signaling in disease at a glance
Gold MG, et al.
Journal of Cell Science, 126(20), 4537-4542 (2013)

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