D4022

P¹,P⁵-Di(adenosine-5′) pentaphosphate pentasodium salt

≥95% (HPLC), powder

• Synonym(s): A(5′)P5(5′)A, Diadenosine pentaphosphate pentasodium salt
• Linear Formula: C₂₀H₂₉N₁₀O₂₂P₅ · 5 Na
• CAS Number: 4097-04-5
• Molecular Weight: 1026.28
• Beilstein: 4949216
• EC Number: 223-852-7
• MDL number: MFCD00077718
• UNSPSC Code: 12352202
• eCl@ss: 32160414
• PubChem Substance ID: 24893808
• NACRES: NA.51

Properties

• biological source: synthetic (organic)
• Assay: ≥95% (HPLC)
• form: powder
• mol wt: ~_1.0 kDa
• color: white to yellow-white
• solubility: H₂O: 50 mg/mL
• storage temp.: −20°C
• SMILES string: [Na+].[Na+].[Na+].[Na+].[Na+].Nc1ncnc2n(cnc12)[C@@H]3O[C@H](COP([O-])(=O)OP([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/C20H29N10O22P5.5Na/c21-15-9-17(25-3-23-15)29(5-27-9)19-13(33)11(31)7(47-19)1-45-53(35,36)49-55(39,40)51-57(43,44)52-56(41,42)50-54(37,38)46-2-8-12(32)14(34)20(48-8)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)(H,43,44)(H2,21,23,25)(H2,22,24,26);;;;;/q;5*+1/p-5/t7-,8-,11-,12-,13-,14-,19-,20-;;;;;/m1...../s1
• InChI key: NNMFUJJMJIYTSP-CSMIRWGRSA-I

Description

General description

P¹,P⁵-Di(adenosine-5′) pentaphosphate (Ap5A) is a diadenosine polyphosphate, which has a tail-to-tail dimer structure. Ap5A is synthesized in a twostep process involving the formation of adenosine 5′-tetraphosphate (P4A) from the ATP and trimeta-phosphate (P3). In the second step, P4A is converted to Ap5A. The synthesis of Ap5A requires a pH optimum in the range of 7.5 to 8.5 and is modulated by metal ions.

Application

P¹,P⁵-Di(adenosine-5′) pentaphosphate pentasodium salt has been used as:

• an adenylate kinase (AK) inhibitor in: sarcoma osteogenic (Saos-2) cells
• mitochondrial lysates during ATP synthesis
• tetramethylrhodamine methyl ester (TMRM) based membrane potential assay
• chromoplasts

Biochem/physiol Actions

A diadenosine polyphosphate stored in secretory granules of thrombocytes, chromaffin and neuronal cells. After release into the extracellular space, it affects a variety of biological activities in a wide range of target tissues. In the nervous system it acts through various purinergic receptors. It also activates 5′-nucleotidase and inhibits adenosine kinase activity in vitro. Ap5A is metabolized by soluble enzymes in the blood plasma and by membrane-bound ectoenzymes of a number of cell types including endothelial and smooth muscle cells. In cardiac muscle, pM to nM concentrations significantly increase the open-probability of ryanodine-receptor (RyR2) gates, with prolonged action due to slow dissociation from the receptor.

Safety Information

• 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