M8386

α,β-Methyleneadenosine 5′-diphosphate sodium salt

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

≥98% (HPLC), synthetic (organic), powder

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

Key Documents

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Product Name

α,β-Methyleneadenosine 5′-diphosphate sodium salt, CD73 inhibitor

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

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Show Differences

1 of 4

This Item	M3509	M3763	T9375
Sigma-Aldrich M8386 α,β-Methyleneadenosine 5′-diphosphate sodium salt	Sigma-Aldrich M3509 β,γ-Methyleneguanosine 5′-triphosphate sodium salt	Sigma-Aldrich M3763 Adenosine 5′-(α,β-methylene)diphosphate	Sigma-Aldrich T9375 Thymidine 5′-diphosphate sodium salt
biological source synthetic (organic)	biological source synthetic (organic)	biological source synthetic (organic)	biological source synthetic (organic)
Quality Level 200	Quality Level 200	Quality Level 200	Quality Level 200
form powder	form powder	form powder	form powder
assay ≥98% (HPLC)	assay ≥98% (HPLC)	assay ≥99% (HPLC)	assay ≥96% (HPLC)
solubility water: 50 mg/mL, clear to slightly hazy, colorless	solubility water: 50 mg/mL, clear, colorless	solubility water: 50 mg/mL, clear, colorless	solubility water: 50 mg/mL, clear to very slightly hazy, colorless
storage temp. −20°C	storage temp. −20°C	storage temp. −20°C	storage temp. −20°C

Application

α,β-Methyleneadenosine 5′-diphosphate sodium salt has been used as an ectonucleotidase/CD73 inhibitor to characterize the mode of adenosine production[1] and as an inhibitor for in vitro studies.[2]

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.[1][2]

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number

0000486235

0000450520

0000447101

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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)

CD73 inhibition by purine cytotoxic nucleoside analogue-based diphosphonates.

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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