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A4386

Sigma-Aldrich

Adenosine 5′-diphosphate bis(cyclohexylammonium) salt

≥95% (HPLC), crystalline, bacterial

Synonym(s):

A2P5P, ADP

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About This Item

Empirical Formula (Hill Notation):
C10H15N5O10P2 · 2C6H13N
CAS Number:
102029-87-8
Molecular Weight:
625.55
MDL number:
MFCD00058338
UNSPSC Code:
41106305
PubChem Substance ID:
329770855
NACRES:
NA.51

biological source

bacterial

Quality Level

200

Assay

≥95% (HPLC)

form

crystalline

solubility

H2O: soluble, clear to slightly hazy, colorless to faintly yellow

storage temp.

−20°C

SMILES string

NC1CCCCC1.NC2CCCCC2.Nc3ncnc4n(cnc34)[C@@H]5O[C@H](COP(O)(=O)OP(O)(O)=O)[C@@H](O)[C@H]5O

InChI

1S/C10H15N5O10P2.2C6H13N/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(24-10)1-23-27(21,22)25-26(18,19)20;2*7-6-4-2-1-3-5-6/h2-4,6-7,10,16-17H,1H2,(H,21,22)(H2,11,12,13)(H2,18,19,20);2*6H,1-5,7H2/t4-,6-,7-,10-;;/m1../s1

InChI key

SCOUEIPNDLFPCX-IDIVVRGQSA-N

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Application

Adenosine 5′-diphosphate (ADP) is an adenine nucleotide involved in energy storage and nucleic acid metabolism via its conversion into ATP by ATP synthases. ADP affects platelet activation through its interaction with ADP receptors P2Y1, P2Y12 and P2X1. Upon its conversion to adenosine by ecto-ADPases, platelet activation is inhibited via adenosine receptors.
Adenosine5′-diphosphate bis(cyclohexylammonium) salt has been used as a standard in luminometry. It has also been used in suramin inhibition assays.

Caution

Stable, non-hygroscopic

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

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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The trypanocidal drug suramin and other trypan blue mimetics are inhibitors of pyruvate kinases and bind to the adenosine site
Morgan HP, et al.
The Journal of Biological Chemistry, 286(36), 31232-31240 (2011)
Effects of anticoagulants used during blood collection on human platelet function
May J A and Heptinstall S
Platelets and megakaryocytes, 3-11 (2004)
Sarah Jones et al.
British journal of haematology, 153(1), 83-91 (2011-02-22)
ADP is considered a weak platelet agonist due to the limited aggregation responses it induces in vitro at physiological concentrations of extracellular Ca(2+) [(Ca(2+) )(o) ]. Lowering [Ca(2+) ](o) paradoxically enhances ADP-evoked aggregation, an effect that has been attributed to
David Erlinge
Advances in pharmacology (San Diego, Calif.), 61, 417-439 (2011-05-19)
The purine- and pyrimidine-sensitive P2Y receptors belong to the large group of G-protein-coupled receptors that are the target of approximately one-third of the pharmaceutical drugs used in the clinic today. It is therefore not unexpected that the P2Y receptors could
David Iyú et al.
Arteriosclerosis, thrombosis, and vascular biology, 31(2), 416-422 (2010-11-26)
To investigate whether adenosine diphosphate (ADP)-derived adenosine might inhibit platelet aggregation, especially in the presence of a P2Y₁₂ antagonist, where the effects of ADP at the P2Y₁₂ receptor would be prevented. Platelet aggregation was measured in response to thrombin receptor
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