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Merck

A9376

Sigma-Aldrich

Adenosine 2′:3′-cyclic monophosphate sodium salt

≥93%

Sinónimos:

2′,3′-cAMP sodium salt

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About This Item

Fórmula lineal:
C10H11N5O6PNa
Número de CAS:
Peso molecular:
351.19
EC Number:
MDL number:
UNSPSC Code:
41106305
eCl@ss:
32160414
PubChem Substance ID:
NACRES:
NA.51

biological source

synthetic (organic)

Quality Level

assay

≥93%

form

powder

solubility

water: 50 mg/mL, clear, colorless

storage temp.

−20°C

SMILES string

[Na+].Nc1ncnc2n(cnc12)[C@@H]3O[C@H](CO)[C@H]4OP([O-])(=O)O[C@@H]34

InChI

1S/C10H12N5O6P.Na/c11-8-5-9(13-2-12-8)15(3-14-5)10-7-6(4(1-16)19-10)20-22(17,18)21-7;/h2-4,6-7,10,16H,1H2,(H,17,18)(H2,11,12,13);/q;+1/p-1/t4-,6-,7-,10-;/m1./s1

InChI key

VSDSIACSNXHGOV-MCDZGGTQSA-M

Categorías relacionadas

Application

Adenosine 2′:3′-cyclic monophosphate sodium salt has been used in lysis buffer for affinity purification and also in microscale thermophoresis measurements. It has also been used in electrophysiological studies of Tenebrio tubules.

Biochem/physiol Actions

Adenosine 2′,3′-cyclic monophosphate (2′,3′-cAMP) is believed to serve as an extracellular source of adenosine. The release of extracellular 2′,3′-cAMP occurs in response to injury. 2′,3′-cAMP may be used to study the distribution and specificity of its degrading enzymes in the context of unique biological activities. 2′,3′-cAMP may also be used to study apoptosis induced at the level of mitochondrial permeability transition pores. 2′,3′-cAMP is converted into 2′-AMP and 3′-AMP which inhibit proliferation of preglomerular vascular smooth muscle cells and glomerular mesangial cells via A2B receptors.

Caution

Caution: Do not confuse with the common adenosine 2′(3′)-monophosphate (mixed isomers).

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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S G Srivatsan et al.
Chemistry (Weinheim an der Bergstrasse, Germany), 8(22), 5184-5191 (2003-03-05)
We have synthesized and characterized novel, copper-metalated, polymeric templates that contain adenine nucleobases. These promote hydrolysis of non-natural and natural phosphate ester substrates in a highly efficient and catalytic fashion. The crystal structure of the cooper-containing adenylated monomer reveals the
R P Ballestero et al.
The Journal of biological chemistry, 272(17), 11479-11486 (1997-04-25)
Biochemical characterization of changes in gene expression that accompany optic nerve regeneration has led to the identification of proteins that may play key roles in the regeneration process. In this report, a cDNA encoding gRICH70, a novel isoform of the
Jin Ren et al.
The Journal of pharmacology and experimental therapeutics, 328(3), 855-865 (2008-11-27)
We recently developed a sensitive assay for 3',5'-cAMP using high-performance liquid chromatography-tandem mass spectrometry. Using this assay, we investigated the release of 3',5'-cAMP from isolated, perfused rat kidneys. To our surprise, we observed a dominant chromatographic peak that was because
E I Budowsky et al.
European journal of biochemistry, 220(1), 97-104 (1994-02-15)
The action of the guanylyl-preferring RNase from Bacillus intermedius (binase) on a mixture of oligoadenylates with randomly distributed 2'-5' and 3'-5' internucleotide bonds [(A2'/3'p)n] under conditions sufficient for complete hydrolysis of poly(A) results in a mixture containing a single circular
E Witters et al.
Journal of chromatography. B, Biomedical sciences and applications, 694(1), 55-63 (1997-06-20)
An LC-MS method has been developed combining ion-pair chromatography with an electrospray interface linking microbore and capillary HPLC to mass spectrometry. Separation of cyclic nucleotides on C18 reversed-phase columns, using tetrabutylammonium bromide as an ion pairing agent was evaluated with

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