Skip to Content
Merck
All Photos(1)

Documents

M8386

Sigma-Aldrich

α,β-Methyleneadenosine 5′-diphosphate sodium salt

CD73 inhibitor

Synonym(s):

AMP-CP

Sign Into View Organizational & Contract Pricing
All Photos(1)

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)

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 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’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

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)
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)
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
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
View All Related Papers

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service