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M152

Sigma-Aldrich

2-(Methylthio)adenosine 5′-diphosphate trisodium salt hydrate

≥89% (HPLC), solid

Synonym(s):

2-(Methylthio)adenosine 5′-trihydrogen diphosphate trisodium salt hydrate, 2-Methylthio-ADP trisodium salt hydrate

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About This Item

Empirical Formula (Hill Notation):
C11H14N5Na3O10P2S · xH2O
CAS Number:
Molecular Weight:
539.24 (anhydrous basis)
MDL number:
UNSPSC Code:
12352200
PubChem Substance ID:

Assay

≥89% (HPLC)

form

solid

storage condition

desiccated

color

white

solubility

H2O: >20 mg/mL

storage temp.

−20°C

SMILES string

O.[Na+].[Na+].[Na+].CSc1nc(N)c2ncn([C@@H]3O[C@H](COP([O-])(=O)OP([O-])([O-])=O)[C@@H](O)[C@H]3O)c2n1

InChI

1S/C11H17N5O10P2S.3Na.H2O/c1-29-11-14-8(12)5-9(15-11)16(3-13-5)10-7(18)6(17)4(25-10)2-24-28(22,23)26-27(19,20)21;;;;/h3-4,6-7,10,17-18H,2H2,1H3,(H,22,23)(H2,12,14,15)(H2,19,20,21);;;;1H2/q;3*+1;/p-3/t4-,6-,7-,10-;;;;/m1..../s1

InChI key

JPTPEMXICPAWKJ-KWIZKVQNSA-K

Biochem/physiol Actions

2-Methylthio-ADP (2-ME-SADP) is a P2 purinoceptor agonist, which induces platelet aggregation and shape change and inhibits cyclic AMP accumulation in platelets exposed to prostaglandin E1. Compared with ADP, 2-methylthio-ADP was 3-5 times as active as an aggregating agent and 150-200 times as active as an inhibitor of cyclic AMP accumulation. Purinergic signaling may be an important factor in TSP-1-mediated cell-matrix and cell-cell interactions such as those occurring during development and repair.

Features and Benefits

This compound is featured on the P2 Receptors: P2Y G-Protein Family page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Caution

Hygroscopic, air sensitive

Storage Class Code

13 - Non 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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D G Satchell et al.
The Journal of pharmacology and experimental therapeutics, 195(3), 540-548 (1975-12-01)
The inhibitory actions of adenosine diphosphate (ADP), adenosine monophosphate (AMP), adenosine and 16 adenine nucleotide and nucleoside analogs on the isolated guinea-pig taenia coli preparation were compared with those of adenosine triphosphate (ATP). Responses were quantitated as magnitude of maximal
D E Macfarlane et al.
The Journal of clinical investigation, 71(3), 420-428 (1983-03-01)
2-Methylthio-ADP and its radioactive analogue [beta-32P]2-methylthio-ADP were synthesized and used to investigate platelet receptors for ADP. 2-Methylthio-ADP induced platelet aggregation and shape change, and inhibited cyclic AMP accumulation in platelets exposed to prostaglandin E1. Compared with ADP, 2-methylthio-ADP was 3-5
N J Cusack et al.
British journal of pharmacology, 77(2), 329-333 (1982-10-01)
1 Adenosine 5'-diphosphate (ADP) induces human platelet aggregation and noncompetitively inhibits stimulated human platelet adenylate cyclase; these two effects are mediated by the same ADP receptor, at which adenosine 5'-triphosphate (ATP) is a competitive antagonist. 2 Two ADP analogues, 2-azidoadenosine
Madelene Lindkvist et al.
Thrombosis research, 174, 5-12 (2018-12-14)
Platelet aggregation and secretion can be induced by a large number of endogenous activators, such as collagen, adenosine diphosphate (ADP) and epinephrine. Conversely, the blood vessel endothelium constitutively release platelet inhibitors including nitric oxide (NO) and prostacyclin. NO and prostacyclin

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