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A8016

Sigma-Aldrich

Adenosine 5′-[β-thio]diphosphate trilithium salt

≥80% (HPLC)

Synonym(s):

ADP-β-S, Adenosine-5′-0-(2-thiodiphosphate) trilithium salt, Ado-5′-PP[S]

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About This Item

Empirical Formula (Hill Notation):
C10H12Li3N5O9P2S
CAS Number:
73536-95-5
Molecular Weight:
461.07
MDL number:
MFCD00077314
UNSPSC Code:
41106305
eCl@ss:
32160414
PubChem Substance ID:
24891307
NACRES:
NA.77

Assay

≥80% (HPLC)

form

powder

storage temp.

−20°C

SMILES string

[Li+].[Li+].[Li+].Nc1ncnc2n(cnc12)[C@@H]3O[C@H](COP([O-])(=O)OP([O-])([O-])=S)[C@@H](O)[C@H]3O

InChI

1S/C10H15N5O9P2S.3Li/c11-8-5-9(13-2-12-8)15(3-14-5)10-7(17)6(16)4(23-10)1-22-25(18,19)24-26(20,21)27;;;/h2-4,6-7,10,16-17H,1H2,(H,18,19)(H2,11,12,13)(H2,20,21,27);;;/q;3*+1/p-3/t4-,6-,7-,10-;;;/m1.../s1

InChI key

CPKFUAYUUSSFFZ-MSQVLRTGSA-K

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Application

Adenosine 5′-[β-thio]diphosphate is a substrate and inhibitor for AMP dependent enzyme systems. Adenosine 5′-[β-thio]diphosphate has been used to explore the myenteric control mechanisms of human esophageal motility and the effect of nitrergic and nonnitrergic neurotransmitters.
Adenosine 5′-[β-thio]diphosphate trilithium salt has been used to induce neuropathic pain in rats to study the effect of dorsal horn cannabinoid CB2 receptor activation on the expression of P2Y12 and P2Y13 (purinoceptors) receptors.

Biochem/physiol Actions

P2Y receptor agonist.

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.

Other Notes

Non-hydrolyzable ADP analog

Substrates

Substrate and inhibitor for AMP dependent enzyme systems.

Pictograms

Health hazardExclamation mark
GHS08,GHS07

Signal Word

Warning

Hazard Statements

H302,H371

Hazard Classifications

Acute Tox. 4 Oral - STOT SE 2

Target Organs

Eyes,Central nervous system

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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B Lecea et al.
American journal of physiology. Gastrointestinal and liver physiology, 300(5), G782-G794 (2011-02-19)
The aim of this study was to explore the myenteric mechanisms of control of human esophageal motility and the effect of nitrergic and nonnitrergic neurotransmitters. Human circular esophageal strips were studied in organ baths and with microelectrodes. Responses following electrical
Tibor Kiss
The European journal of neuroscience, 21(8), 2177-2185 (2005-05-05)
Members of the mytilus inhibitory peptide (MIP) family play an important role in the modulation of many physiological processes in molluscs. The signal transduction pathways affected by the MIP effect have not, however, been elucidated. Application of guanosine 5'-[gamma-thio]triphosphate tetralithium
Alexander K Filippov et al.
The Journal of neuroscience : the official journal of the Society for Neuroscience, 26(36), 9340-9348 (2006-09-08)
We have shown previously that stimulation of heterologously expressed P2Y1 nucleotide receptors inhibits M-type K+ currents in sympathetic neurons. We now report that activation of endogenous P2Y1 receptors induces inhibition of the M-current in rat CA1/CA3 hippocampal pyramidal cells in
Gilles Kauffenstein et al.
British journal of pharmacology, 159(3), 576-585 (2010-01-14)
Extracellular nucleotides produce vasodilatation through endothelial P2 receptor activation. As these autacoids are actively metabolized by the ecto-nucleotidase nucleoside triphosphate diphosphohydrolase-1 (NTPDase1), we studied the effects of this cell surface enzyme on nucleotide-dependent vasodilatation. Vascular NTPDase expression and activity were
Bronagh McDonnell et al.
American journal of physiology. Gastrointestinal and liver physiology, 294(4), G1041-G1051 (2008-03-01)
The neurotransmitter(s) underlying nitric oxide synthase (NOS)-independent neural inhibition in the internal anal sphincter (IAS) is still uncertain. The present study investigated the role of purinergic transmission. Contractile and electrical responses to electrical field stimulation of nerves (0.1-5 Hz for
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