D6392

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

≥95%, powder

• Synonym(s): A(5′)P5(5′)A trilithium salt, Diadenosine pentaphosphate trilithium salt
• Empirical Formula (Hill Notation): C₂₀H₂₆Li₃N₁₀O₂₂P₅
• CAS Number: 75522-97-3
• Molecular Weight: 934.17
• EC Number: 278-237-6
• MDL number: MFCD00044936
• UNSPSC Code: 12352202
• eCl@ss: 32160414
• PubChem Substance ID: 24894024
• NACRES: NA.77

Properties

• biological source: synthetic (organic)
• assay: ≥95%
• form: powder
• color: white to off-white
• solubility: H₂O: 50 mg/mL
• storage temp.: −20°C
• SMILES string: [Li+].[Li+].[Li+].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/C20H29N10O22P5.3Li/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;3*+1/p-3/t7-,8-,11-,12-,13-,14-,19-,20-;;;/m1.../s1
• InChI key: BFBDFBHROZLGEG-JJCYRVQFSA-K

Description

Application

P1,P5-Di(adenosine-5′) pentaphosphate trilithium salt has been used as a adenylate kinase inhibitor and as a component of pre-AMPPNP rigor solution for treating muscle fibres.

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: 11 - Combustible Solids
• wgk_germany: WGK 3
• flash_point_f: Not applicable
• flash_point_c: Not applicable
• ppe: Eyeshields, Gloves, type N95 (US)