M3763

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

Name: Adenosine 5′-(α,β-methylene)diphosphate
Brand: SIGMA

≥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

Beilstein:

633678

EC Number:

223-194-0

MDL number:

MFCD00042991

UNSPSC Code:

41106305

PubChem Substance ID:

24896872

NACRES:

NA.51

Key Documents

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Product Name

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

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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Related Categories

Biochemicals

Nucleosides and Nucleotides

Phosphates

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Show Differences

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This Item	A2252	M8386	A9272
Sigma-Aldrich M3763 Adenosine 5′-(α,β-methylene)diphosphate	Sigma-Aldrich A2252 Adenosine 5′-monophosphate monohydrate	Sigma-Aldrich M8386 α,β-Methyleneadenosine 5′-diphosphate sodium salt	Sigma-Aldrich A9272 Adenosine 3′-monophosphate
biological source synthetic (organic)	biological source yeast	biological source synthetic (organic)	biological source yeast
Quality Level 200	Quality Level 200	Quality Level 200	Quality Level 200
assay ≥99% (HPLC)	assay ≥97%	assay ≥98% (HPLC)	assay ≥98% (HPLC)
form powder	form powder	form powder	form powder
solubility water: 50 mg/mL, clear, colorless	solubility 1 M NH4OH: soluble 50 mg/mL, clear, colorless, H₂O: soluble (with addition of mild alkali)	solubility water: 50 mg/mL, clear to slightly hazy, colorless	solubility 1 N NH₄OH: 50 mg/mL, clear, colorless
storage temp. −20°C	storage temp. −20°C	storage temp. −20°C	storage temp. −20°C

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.[1][2]

Preparation Note

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Regulation of VEGF and bFGF mRNA expression and other proliferative compounds in skeletal muscle cells.

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

Enzyme kinetics and pharmacological characterization of nucleotidases released from the guinea pig isolated vas deferens during nerve stimulation: evidence for a soluble ecto-nucleoside triphosphate diphosphohydrolase-like ATPase and a soluble ecto-5'-nucleotidase-like AMPase.

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

The relationship between constitutive ATP release and its extracellular metabolism in isolated rat kidney glomeruli.

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

CD73 Regulates stemness and epithelial-mesenchymal transition in ovarian cancer-initiating cells

Lupia M, et al.

Stem Cell Reports, 10(4), 1412-1425 (2018)

TGFbeta-induced osteogenic potential of human amniotic fluid stem cells via CD73-generated adenosine production

Hau KL, et al.

Scientific Reports, 7(1) (2017)

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