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M3763

Sigma-Aldrich

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

ADP analog

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
Beilstein/REAXYS Number:
633678
EC Number:
223-194-0
MDL number:
MFCD00042991
UNSPSC Code:
41106305
PubChem Substance ID:
24896872
NACRES:
NA.51

biological source

synthetic (organic)

Quality Level

200

assay

≥99% (HPLC)

form

powder

solubility

water: 50 mg/mL, clear, colorless

storage temp.

−20°C

SMILES string

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

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

InChI key

OLCWZBFDIYXLAA-IOSLPCCCSA-N

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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.

Reconstitution

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

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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.
Caldwell CC, Lentsch AB.
Gastroenterologie Clinique Et Biologique, 135, 1460-1462 (2008)
Daniel Pens Gelain et al.
Molecular and cellular biochemistry, 245(1-2), 1-9 (2003-04-24)
It has been long postulated that extracellular purines can modulate the function of the male reproductive system by interacting with different purinergic receptors of Sertoli and germinative cells. Many authors have described the biological changes induced by extracellular ATP and/or
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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