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Merck

M3763

Adenosine 5′-(α,β-methylene)diphosphate

≥99% (HPLC), synthetic (organic), powder

Synonym(s):

α,β-Methyleneadenosine 5′-diphosphate, ADP[α,β-CH2], AMP-CP

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About This Item

Empirical Formula (Hill Notation):
C11H17N5O9P2
CAS Number:
3768-14-7
Molecular Weight:
425.23
NACRES:
NA.51
PubChem Substance ID:
24896872
UNSPSC Code:
41106305
EC Number:
223-194-0
MDL number:
MFCD00042991
Beilstein/REAXYS Number:
633678

Key Documents

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Product Name

Adenosine 5′-(α,β-methylene)diphosphate, ADP analog

InChI key

OLCWZBFDIYXLAA-IOSLPCCCSA-N

InChI

1S/C11H17N5O9P2/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)/t5-,7-,8-,11-/m1/s1

SMILES string

Nc1ncnc2n(cnc12)[C@@H]3O[C@H](COP(O)(=O)CP(O)(O)=O)[C@@H](O)[C@H]3O

biological source

synthetic (organic)

assay

≥99% (HPLC)

form

powder

solubility

water: 50 mg/mL, clear, colorless

storage temp.

−20°C

Quality Level

200

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Application

Adenosine 5′-(α,β-methylene)diphosphate has been used as a component of culture media, to study its effects as an inhibitor of cluster of differentiation 73 (CD73) and adenosinergic signaling regulation via CD73 or ecto-5′-nucleotidase.

Preparation Note

soluble in water up to Approx. 50 mg/ml with heating

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
0000514795
0000514794
0000514794
0000514795
0000443472

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Ischemia-driven expression of CD73 confers tissue protection during liver ischemia/reperfusion.
Caldwell CC, Lentsch AB.
Gastroenterologie Clinique Et Biologique, 135, 1460-1462 (2008)
L Jensen et al.
Angiogenesis, 7(3), 255-267 (2004-12-21)
The role of muscle contraction, prostanoids, nitric oxide and adenosine in the regulation of vascular endothelial growth factor (VEGF), basic fibroblast growth factor (bFGF) and endothelial cell proliferative compounds in skeletal muscle cell cultures was examined. VEGF and bFGF mRNA
J Karczewska et al.
Journal of physiology and pharmacology : an official journal of the Polish Physiological Society, 58(2), 321-333 (2007-07-12)
ATP and adenosine are important extracellular regulators of glomerular functions. In this study, ATP release from glomeruli suspension and its extracellular metabolism were investigated. Basal extraglomerular ATP concentration (1nM) increased several fold during inhibition of ecto-ATPase activity, reflecting the basal
Svetlana T Mihaylova-Todorova et al.
The Journal of pharmacology and experimental therapeutics, 302(3), 992-1001 (2002-08-17)
Previously, we have demonstrated that stimulation of the sympathetic nerves of the guinea pig vas deferens evokes release not only of the cotransmitters ATP and norepinephrine but also of soluble nucleotidases that break down extracellular ATP, ADP, and AMP into
CD73 Regulates stemness and epithelial-mesenchymal transition in ovarian cancer-initiating cells
Lupia M, et al.
Stem Cell Reports, 10(4), 1412-1425 (2018)
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