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D1262

Sigma-Aldrich

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

≥95% (HPLC), powder

Synonyme(s) :

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

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About This Item

Formule empirique (notation de Hill):
C20H28N10O19P4 · xNH3
Numéro CAS:
102783-36-8
Poids moléculaire :
836.39 (free acid basis)
Numéro MDL:
MFCD00058622
Code UNSPSC :
41106305
eCl@ss :
32160414
ID de substance PubChem :
24277711
Nomenclature NACRES :
NA.77

Pureté

≥95% (HPLC)

Forme

powder

Couleur

white to off-white

Solubilité

H2O: 50 mg/mL

Température de stockage

−20°C

Chaîne SMILES 

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

Clé InChI

JTLRVYSRZSPJKJ-AHKIGRPSSA-N

Informations sur le gène

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.

Actions biochimiques/physiologiques

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.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

Eyeshields, Gloves, type N95 (US)

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Consulter la Bibliothèque de documents

E J Verspohl et al.
Diabetes, 47(11), 1727-1734 (1998-10-29)
A role of diadenosine polyphosphates as second messengers was suggested for insulin-secreting cells. It has not yet been investigated whether specific receptors for these compounds exist and how these extracellular compounds and their degradation products may contribute to insulin release.
A Ogilvie et al.
Journal of autonomic pharmacology, 16(6), 325-328 (1996-12-01)
1. Adenine dinucleotides (Ap3A, Ap4A, Ap5A, Ap6A) are stored in secretory granules of thrombocytes, chromaffin cells and neuronal cells. After release into the extracellular space, the dinucleotides exhibit divergent biological effects on a variety of target cells and organs. The
M Edgecombe et al.
Cellular signalling, 10(7), 505-509 (1998-10-01)
Diadenosine polyphosphates (ApnAs) can, through interaction with appropriate purinoceptors, affect a range of cellular activities. Ap4A, the most prominent naturally occurring diadenosine polyphosphate, stimulates alterations in intracellular calcium homeostasis and subsequent activation of glycogen breakdown in isolated liver cells. Here
G E Blouse et al.
Biochimica et biophysica acta, 1375(1-2), 61-72 (1998-10-10)
P1,P4-Diadenosine 5'-tetraphosphate (Ap4A) acts as an extracellular modulator through its interaction with purinoceptors. Our laboratory has demonstrated the presence of an Ap4A receptor in cardiac tissue [1,2]. Due to the rapid hydrolysis of ATP by cardiac membranes the relationship of
The Ralstonia solanacearum effector RipN suppresses plant PAMP-triggered immunity, localizes to the endoplasmic reticulum and nucleus, and alters the NADH/NAD+ ratio in Arabidopsis
Sun Y, et al.
Molecular Plant Pathology, 20(4), 533-546 (2019)
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