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M8386

α,β-Methyleneadenosine 5′-diphosphate sodium salt

Name: α,β-Methyleneadenosine 5′-diphosphate sodium salt
Brand: SIGMA

CD73 inhibitor

Synonym(s):

AMP-CP

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About This Item

Empirical Formula (Hill Notation):

C₁₁H₁₇N₅O₉P₂

CAS Number:

104835-70-3

Molecular Weight:

425.23

MDL number:

MFCD00070019

UNSPSC Code:

41106305

PubChem Substance ID:

24897249

NACRES:

NA.51

biological source

synthetic (organic)

Quality Level

200

Assay

≥98% (HPLC)

form

powder

solubility

water: 50 mg/mL, clear to slightly hazy, colorless

storage temp.

−20°C

SMILES string

[Na].Nc1ncnc2n(cnc12)C3OC(COP(O)(=O)CP(O)(O)=O)C(O)C3O

InChI

1S/C11H17N5O9P2.Na.H/c12-9-6-10(14-2-13-9)16(3-15-6)11-8(18)7(17)5(25-11)1-24-27(22,23)4-26(19,20)21;;/h2-3,5,7-8,11,17-18H,1,4H2,(H,22,23)(H2,12,13,14)(H2,19,20,21);;

InChI key

HEBWZOPLDYDXPJ-UHFFFAOYSA-N

Related Categories

Phosphates

Application

α,β-Methyleneadenosine 5′-diphosphate sodium salt has been used as an ectonucleotidase/CD73 inhibitor to characterize the mode of adenosine production and as an inhibitor for in vitro studies.

Biochem/physiol Actions

α, β-Methyleneadenosine 5′-diphosphate (AMP-CP) is an ADP analog that as an ability to inhibit ectonucleotidase/ CD73 inhibitor and is used to study adenosinergic signaling regulation via CD73/ecto-5′-nucleotidase.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Ischemia-driven expression of CD73 confers tissue protection during liver ischemia/reperfusion.

Charles C Caldwell et al.

Gastroenterology, 135(5), 1460-1462 (2008-10-14)

Studies of the extracellular ATP-adenosine pathway in human urinary tract epithelial cells.

Camilla Mohlin et al.

Pharmacology, 84(4), 196-202 (2009-09-05)

Extracellular ATP may be metabolized to AMP and adenosine by the ectonucleotidases CD39 and CD73 and, in this study, we characterized the pathways for adenosine formation in human urinary tract epithelial cells. Bladder (RT4) and kidney (A498) epithelial cells were

Adenosine A3 receptor elicits chemoresistance mediated by multiple resistance-associated protein-1 in human glioblastoma stem-like cells.

Torres A

Oncotarget, 7, 67373-67386 (2016)

Altered purinergic signaling in CD73-deficient mice inhibits tumor progression.

Gennady G Yegutkin et al.

European journal of immunology, 41(5), 1231-1241 (2011-04-07)

CD73/ecto-5'-nucleotidase dephosphorylates extracellular AMP into adenosine, and it is a key enzyme in the regulation of adenosinergic signaling. The contribution of host CD73 to tumor growth and anti-tumor immunity has not been studied. Here, we show that under physiological conditions

Adenosine enhances progenitor cell recruitment and nerve growth via its A2B receptor during adult fin regeneration

Rampon C, et al.

Purinergic Signaling, 10(4), 595-602 (2014)

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