A3262

Adenosine 3′,5′-cyclic monophosphate tris salt

Name: Adenosine 3′,5′-cyclic monophosphate tris salt
Brand: SIGMA
Price: 2029 MYR

≥97% (HPLC), synthetic, powder

Synonym(s):

cAMP, cyclic AMP

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500 MG

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About This Item

Empirical Formula (Hill Notation):

C₁₀H₁₂N₅O₆P · C₄H₁₁NO₃

CAS Number:

102029-77-6

Molecular Weight:

450.34

UNSPSC Code:

41106305

eCl@ss:

32160414

PubChem Substance ID:

329770822

NACRES:

NA.51

MDL number:

MFCD00058346

Key Documents

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Product Name

Adenosine 3′,5′-cyclic monophosphate tris salt, ≥97% (HPLC), powder

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

biological source

synthetic

assay

≥97% (HPLC)

form

powder

color

white

solubility

H₂O: 100 mg/mL

storage temp.

−20°C

Quality Level

200

Related Categories

Phosphates

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1 of 4

This Item	A9376	A0386	A9501
Sigma-Aldrich A3262 Adenosine 3′,5′-cyclic monophosphate tris salt	Sigma-Aldrich A9376 Adenosine 2′:3′-cyclic monophosphate sodium salt	Sigma-Aldrich A0386 Adenosine 3′-monophosphate sodium salt	Sigma-Aldrich A9501 Adenosine 3′,5′-cyclic monophosphate
biological source synthetic	biological source synthetic (organic)	biological source yeast	biological source -
Quality Level 200	Quality Level 200	Quality Level 200	Quality Level 200
assay ≥97% (HPLC)	assay ≥93%	assay ≥98% (HPLC)	assay ≥98.5% (HPLC)
form powder	form powder	form powder	form powder
storage temp. −20°C	storage temp. −20°C	storage temp. −20°C	storage temp. −20°C
color white	color -	color -	color white

Application

Adenosine 3′,5′-cyclic monophosphate tris salt has been used as a medium supplement for human endometrial stromal cells (hESCs) culture[1] and induced neural stem cells (iNSCs).[2] It has been used in the spectroscopic characterization of pink flamindo, a red cAMP indicator.[3]

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.

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.[4] Intracellular levels of cAMP control immune and inflammatory functions. Bacterial infection triggers intracellular cAMP production.[5] 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.[6]

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number

0000425160

0000364881

SLCF8554

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Targeted ablation of Wnt4 and Wnt5a in Müllerian duct mesenchyme impedes endometrial gland development and causes partial Müllerian agenesis.

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

Higenamine, a Dual Agonist for β 1- and β 2-Adrenergic Receptors Identified by Screening a Traditional Chinese Medicine Library.

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

The Amyloid Precursor Protein is rapidly transported from the Golgi apparatus to the lysosome and where it is processed into beta-amyloid.

Joshua H K Tam et al.

Molecular brain, 7, 54-54 (2014-08-03)

Alzheimer's disease (AD) is characterized by cerebral deposition of β-amyloid peptide (Aβ). Aβ is produced by sequential cleavage of the Amyloid Precursor Protein (APP) by β- and γ-secretases. Many studies have demonstrated that the internalization of APP from the cell

cAMP-response element-binding 3-like protein 1 (CREB3L1) is required for decidualization and its expression is decreased in women with endometriosis

Ahn JI, et al.

Current Molecular Medicine, 16(3), 276-287 (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)

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Adenosine 3′,5′-cyclic monophosphate tris salt