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Merck

M152

Sigma-Aldrich

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

≥89% (HPLC), solid

Synonym(e):

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

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About This Item

Empirische Formel (Hill-System):
C11H14N5Na3O10P2S · xH2O
CAS-Nummer:
Molekulargewicht:
539.24 (anhydrous basis)
MDL-Nummer:
UNSPSC-Code:
12352200
PubChem Substanz-ID:

Assay

≥89% (HPLC)

Form

solid

Lagerbedingungen

desiccated

Farbe

white

Löslichkeit

H2O: >20 mg/mL

Lagertemp.

−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

InChIKey

JPTPEMXICPAWKJ-KWIZKVQNSA-K

Biochem./physiol. Wirkung

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.

Leistungsmerkmale und Vorteile

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.

Vorsicht

Hygroscopic, air sensitive

Lagerklassenschlüssel

13 - Non Combustible Solids

WGK

WGK 3

Flammpunkt (°F)

Not applicable

Flammpunkt (°C)

Not applicable

Persönliche Schutzausrüstung

Eyeshields, Gloves, type N95 (US)


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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
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
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
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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