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Merck

M8386

Sigma-Aldrich

α,β-Methyleneadenosine 5′-diphosphate sodium salt

CD73 inhibitor

Sinónimos:

AMP-CP

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About This Item

Fórmula empírica (notación de Hill):
C11H17N5O9P2
Número de CAS:
Peso molecular:
425.23
MDL number:
UNSPSC Code:
41106305
PubChem Substance ID:
NACRES:
NA.51

biological source

synthetic (organic)

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

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

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


Certificados de análisis (COA)

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Visite la Librería de documentos

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)
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)
Charles Dumontet et al.
European journal of medicinal chemistry, 157, 1051-1055 (2018-09-04)
The ecto-5'-nucleotidase CD73 has emerged as an important drug target in oncoimmunology as well as in other diseases. We describe new ADP analogues as CD73 inhibitors based on the replacement of the adenosine moiety, in the reference inhibitor APCP, by
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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