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D1262

Sigma-Aldrich

P1,P4-Di(adenosine-5′) tetraphosphate ammonium salt

≥95% (HPLC), powder

Synonym(s):

A(5′)p4(5′)A, Diadenosine tetraphosphate ammonium salt

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About This Item

Empirical Formula (Hill Notation):
C20H28N10O19P4 · xNH3
CAS Number:
102783-36-8
Molecular Weight:
836.39 (free acid basis)
MDL number:
MFCD00058622
UNSPSC Code:
41106305
eCl@ss:
32160414
PubChem Substance ID:
24277711
NACRES:
NA.77

assay

≥95% (HPLC)

form

powder

color

white to off-white

solubility

H2O: 50 mg/mL

storage temp.

−20°C

SMILES string

N.Nc1ncnc2n(cnc12)[C@@H]3O[C@H](COP(O)(=O)OP(O)(=O)OP(O)(=O)OP(O)(=O)OC[C@H]4O[C@H]([C@H](O)[C@@H]4O)n5cnc6c(N)ncnc56)[C@@H](O)[C@H]3O

InChI

1S/C20H28N10O19P4.H3N/c21-15-9-17(25-3-23-15)29(5-27-9)19-13(33)11(31)7(45-19)1-43-50(35,36)47-52(39,40)49-53(41,42)48-51(37,38)44-2-8-12(32)14(34)20(46-8)30-6-28-10-16(22)24-4-26-18(10)30;/h3-8,11-14,19-20,31-34H,1-2H2,(H,35,36)(H,37,38)(H,39,40)(H,41,42)(H2,21,23,25)(H2,22,24,26);1H3/t7-,8-,11-,12-,13-,14-,19-,20-;/m1./s1

InChI key

JTLRVYSRZSPJKJ-AHKIGRPSSA-N

Gene Information

human ... PLD1(5337) , PLD2(5338) , PLD3(23646) , PLD4(122618) , PLD5(200150)

Application

P1,P4-Di(adenosine-5′) tetraphosphate ammonium salt has been used as a substrate for nudix hydrolyse. It has also been used as a ATP analog and nudix substrate for cleavage factor II Im25 subunit.

Biochem/physiol Actions

Diadenosine polyphosphate (Ap4A) functions as a second messenger in pancreatic cells. Diadenosine polyphosphate is majorly stored in neuronal cells, thrombocytes and chromaffin. It stimulates phospholipase D, fluctuates intracellular calcium levels, induces nitric oxide release, activates 5′-nucleotidase, and inhibits adenosine kinase activity in vitro. The membrane-bound ectoenzymes in endothelial cells in blood plasma and smooth muscle cell metabolize Ap4A.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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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M Edgecombe et al.
The Biochemical journal, 323 ( Pt 2), 451-456 (1997-04-15)
Diadenosine polyphosphates released into the extracellular environment influence a variety of metabolic and other cellular activities in a wide range of target tissues. Here we have studied the impact of these novel nucleotides on gluconeogenesis in isolated rat proximal tubules.
Diadenosine polyphosphate-mediated activation of phospholipase D in isolated rat liver cells
Edgecombe M, et al.
Cellular Signalling, 10(7), 505-509 (1998)
Diadenosine polyphosphates in insulin-secreting cells: interaction with specific receptors and degradation.
Verspohl EJ and Johannwille B
Diabetes, 47(11), 1727-1734 (1998)
Adenine dinucleotides: a novel class of signalling molecules.
Ogilvie A, et al.
Journal of Autonomic Pharmacology, 16(6), 325-328 (1996)
S S Wildman et al.
European journal of pharmacology, 367(1), 119-123 (1999-03-19)
The pharmacological activity of diadenosine polyphosphates was investigated at three recombinant P2X receptors (rat P2X1, rat P2X3, rat P2X4) expressed in Xenopus oocytes and studied under voltage-clamp conditions. For the rat P2X1 receptor, only P1,P6-diadenosine hexaphosphate (Ap6A) was a full
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