A3262

Adenosine 3′,5′-cyclic monophosphate tris salt

≥97% (HPLC), powder

• Synonym(s): cAMP, cyclic AMP
• Empirical Formula (Hill Notation): C₁₀H₁₂N₅O₆P · C₄H₁₁NO₃
• CAS Number: 102029-77-6
• Molecular Weight: 450.34
• MDL number: MFCD00058346
• UNSPSC Code: 41106305
• eCl@ss: 32160414
• PubChem Substance ID: 329770822
• NACRES: NA.51

Properties

• 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.

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 Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves