4097-04-5

Basic information

• Product Name: A[5']P5[5']A SODIUM SALT
• Synonyms: A[5']P5[5']A SODIUM SALT;P1,P5-DI(ADENOSINE-5') PENTAPHOSPHATE SODIUM SALT;A(5′)P5(5′)A;Diadenosine pentaphosphate pentasodium salt ;P1,P5-Di(adenosine-5′) pentaphosphate pentasodium;Adenosine 5'-(hexahydrogen pentaphosphate), 5'->5'-ester with adenosine, pentasodium salt;P1,P5-DI(ADENOSINE-5') PENTAPHOSPHATESOD IUM;P1,P5-di(adenosine-5')pentaphosphate pentasodium salt 5H2O
• CAS NO: 4097-04-5
• Molecular Formula: C₂₀H₂₄N₁₀O₂₂P₅*5Na
• Molecular Weight: 1026.28
• EINECS: 223-852-7
• Mol File: 4097-04-5.mol
• Article Data: 3

Chemical Properties

• Appearance: white to white with yellow cast/powder
• Storage Temp.: −20°C
• Solubility: H2O: 50 mg/mL
• BRN: 4949216
• CAS DataBase Reference: A[5']P5[5']A SODIUM SALT(CAS DataBase Reference)
• NIST Chemistry Reference: A[5']P5[5']A SODIUM SALT(4097-04-5)
• EPA Substance Registry System: A[5']P5[5']A SODIUM SALT(4097-04-5)

Safety Data

• WGK Germany: 3
• F: 10-21
• Hazardous Substances Data: 4097-04-5(Hazardous Substances Data)

Usage

Description

A[5']P5[5']A SODIUM SALT, also known as P1,P5-Di(adenosine-5′) pentaphosphate (Ap5A), is a diadenosine polyphosphate with a tail-to-tail dimer structure. It is synthesized through a two-step process involving the formation of adenosine 5′-tetraphosphate (P4A) from ATP and trimeta-phosphate (P3), followed by the conversion of P4A 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.

Uses

Used in Biochemical Research:
A[5']P5[5']A SODIUM SALT is used as an adenylate kinase (AK) inhibitor for various applications in biochemical research.
Used in Sarcoma Osteogenic (Saos-2) Cells:
A[5']P5[5']A SODIUM SALT is used as an AK inhibitor in Saos-2 cells, which are a type of osteosarcoma cell line. This application helps in studying the role of AK in these cells and its potential as a therapeutic target.
Used in Mitochondrial Lysates:
A[5']P5[5']A SODIUM SALT is used as an AK inhibitor in mitochondrial lysates during ATP synthesis. This application aids in understanding the role of AK in ATP production and its regulation in mitochondria.
Used in TMRM Based Membrane Potential Assay:
A[5']P5[5']A SODIUM SALT is used as an AK inhibitor in tetramethylrhodamine methyl ester (TMRM) based membrane potential assays. This application helps in studying the effects of AK inhibition on membrane potential and its implications in cellular processes.
Used in Chromoplasts:
A[5']P5[5']A SODIUM SALT is used as an AK inhibitor in chromoplasts, which are specialized plastids found in plants. This application assists in understanding the role of AK in chromoplast function and its potential impact on plant development and metabolism.

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.

Upstream product

• 41708-91-2 p¹,p⁵-di(adenosine 5'-)pentaphosphate 
• 1577254-51-3 adenosine 5′-phosphoropiperidate triethylammonium salt 

Relevant articles and documents

One-pot synthesis of symmetrical dinucleoside polyphosphates and analogs via 4,5-dicyanoimidazole-promoted tandem P-O coupling reactions

A novel one-pot protocol for the synthesis of symmetrical dinucleoside tri-, tetra-, and pentaphosphates, and their phosphonate analogs simply from nucleoside 5′-phosphoropiperidates has been developed by utilizing 4,5-dicyanoimidazole-promoted tandem P-O coupling reactions.

What is the conformation of physiologically-active dinucleoside polyphosphates in solution? Conformational analysis of free dinucleoside polyphosphates by NMR and molecular dynamics simulations

Dinucleoside polyphosphates, or dinucleotides (NpnN′; N, N′ = A, U, G, C; n = 2-7), are naturally occurring ubiquitous physiologically active compounds. Despite the interest in dinucleotides, and the relevance of their conformation to their biological function, the conformation of dinucleotides has been insufficiently studied. Therefore, here we performed conformational analysis of a series of NpnN′ Na+ salts (N = A, G, U, C; N′ = A, G, U, C; n = 2-5) by various NMR techniques. All studied dinucleotides, except for Up4/5U, formed intramolecular base stacking interactions in aqueous solutions as indicated by NMR. The conformation around the glycosidic angle in NpnN′s was found to be anti/high anti and the preferred conformation around the C4′-C5′, C5′-O5′ bonds was found to be gauche-gauche (gg). The ribose moiety in NpnN′s showed a small preference for the S conformation, but when attached to cytosine the ribose ring preferred the N conformation. However, no predominant conformation was observed for the ribose moiety in any of the dinucleotides. Molecular dynamics simulations of Ap2A and Ap4A Na+ salts supported the experimental results. In addition, three modes of base-stacking were found for Ap2/4A: α-α, β-β and α-β, which exist in equilibrium, while none is dominant. We conclude that natural, free NpnN′s (n = 2-5) at physiological pH exist mostly in a folded (stacked), rather than extended conformation, in several interconverting stacking modes. Intramolecular base stacking of NpnN′s does not alter the conformation of each of the nucleotide moieties, which remains the same as that of the mononucleotides in solution.