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A3262 Sigma-Aldrich

Adenosine 3′,5′-cyclic monophosphate tris salt

≥97% (HPLC), powder

Synonym: cAMP, cyclic AMP

  • CAS Number 102029-77-6

  • Empirical Formula (Hill Notation) C10H12N5O6P · C4H11NO3

  • Molecular Weight 450.34

  •  MDL number MFCD00058346

  •  eCl@ss 32160414

  •  PubChem Substance ID 329770822

  •  NACRES NA.51

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Properties

Related Categories Biochemicals and Reagents, Nucleosides, Nucleotides, Oligonucleotides, Nucleotide Analogs More...
Quality Level   200
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

Description

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.

Safety & Documentation

Safety Information

Personal Protective Equipment 
RIDADR 
NONH for all modes of transport
WGK Germany 
WGK 3
Flash Point(F) 
Not applicable
Flash Point(C) 
Not applicable

Documents

Certificate of Analysis (COA)

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Certificate of Origin (COO)

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Protocols & Articles
Peer-Reviewed Papers
15

References

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