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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 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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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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