Diadenosine pentaphosphate
Diadenosine pentaphosphate (Ap5A; P1,P5-Di(adenosine-5'-)pentaphosphate) is an endogenous generated diadenosine polyphosphate, possessing the dual identities of intracellular alarm signal and extracellular signaling molecule. Diadenosine pentaphosphate regulates calcium signaling in the nervous, cardiac and peripheral sensory systems by activating P2X1/P2X3/P2Y receptor and RyR2 channels (EC50 = 140 μM). Diadenosine pentaphosphate can be used in studies related to intracellular calcium release channels, cardiovascular diseases and nociception (pain).
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- CAS. Nr.: 41708-91-2
- Formel: C20H29N10O22P5
- Molecular Weight:916.37
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Speicherung:
Please store the product under the recommended conditions in the Certificate of Analysis.
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Biologische Aktivität
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Human Endogenous Metabolite |
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Cell Line
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Type | Value | Description | References |
|---|---|---|---|---|
| HEK293 | EC50 |
>=5 μM
Compound: Ap5A
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Activity against rat P2Y1-GFP transfected in HEK293 cells by intracellular calcium increase
Activity against rat P2Y1-GFP transfected in HEK293 cells by intracellular calcium increase
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[PMID: 16539385] |
| PC-12 | IC50 |
29 μM
Compound: 4
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Antioxidant activity in rat PC12 cells assessed as inhibition of Fe2+-induced ROS production after 1 hr by DCFH-DA staining-based fluorometric analysis
Antioxidant activity in rat PC12 cells assessed as inhibition of Fe2+-induced ROS production after 1 hr by DCFH-DA staining-based fluorometric analysis
|
[PMID: 23751098] |
Diadenosine pentaphosphate (100 μM) elevates the intracellular calcium level of cultured human fetal astrocytes to 980 nM via P2 purinergic receptor-mediated extracellular calcium influx, as well as calcium release from IP3-sensitive and ryanodine-sensitive intracellular calcium stores[1].
Diadenosine pentaphosphate (100 μM; 5 sec) increases the production of IP3 in cultured human fetal astrocytes by approximately 2-fold[1].
Diadenosine pentaphosphate (10 μM) activates the IKACh current in isolated guinea pig atrial myocytes by stimulating P1 receptors[2].
Diadenosine pentaphosphate (100 μM) induces local, transient increases in intracellular calcium in distal dendrites and dendritic growth cones of E18 mouse hippocampal neurons cultured in vitro, with no effect on calcium levels in axons or somatodendritic regions[5].
Diadenosine pentaphosphate (100 μM; 72 h) exerts a negative regulatory effect on dendrite growth and quantity in E18 mouse hippocampal neurons cultured in vitro (in phenol red-free medium). After treatment with 100 μM for 72 h, it reduces the total dendrite length by 28.7% and the number of dendrites by 28.1%, but has no effect on axon length[5].
Diadenosine pentaphosphate (100 μM) reduces dendritic length and number in cultured E18 mouse hippocampal neurons. Overexpression of P2X1 mimics this effect, while shRNA knockdown of P2X1 reverses the reduction in dendrite number but fails to rescue the decrease in dendrite length[5].
MedChemExpress (MCE) has not independently confirmed the accuracy of these methods. They are for reference only.
Chemical Information
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CAS. Nr. 41708-91-2
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Molecular Weight 916.37
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Formel C20H29N10O22P5
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SMILES
O[C@@H]1[C@H](O)[C@@H](COP(OP(OP(OP(OP(OC[C@@H](O2)[C@@H](O)[C@@H](O)[C@@H]2N3C=NC4=C(N)N=CN=C43)(O)=O)(O)=O)(O)=O)(O)=O)(O)=O)O[C@H]1N5C6=NC=NC(N)=C6N=C5
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Synonyms
Ap5A; P1,P5-Di(adenosine-5'-)pentaphosphate
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Versand
Room temperature in continental US; may vary elsewhere.
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Speicherung
Please store the product under the recommended conditions in the Certificate of Analysis.
Reinheit & Dokumentation
Verweise
[1].
Holden CP, et al. Diadenosine pentaphosphate increases levels of intracellular calcium in astrocytes by a mechanism involving release from caffeine/ryanodine- and IP3-sensitive stores. J Neurosci Res. 2000 Jan 15;59(2):276-82.
[Content Brief]
[2]. Abramochkin DV, et al. Diadenosine pentaphosphate affects electrical activity in guinea pig atrium via activation of potassium acetylcholine-dependent inward rectifier. The journal of physiological sciences : JPS. 2017 Jul;67(4):523-529. [Content Brief]
[3]. Song L, et al. Diadenosine pentaphosphate is a potent activator of cardiac ryanodine receptors revealing a novel high-affinity binding site for adenine nucleotides. British journal of pharmacology. 2009 Mar;156(5):857-67. [Content Brief]
[4]. Burgstahler R, et al. Diadenosine pentaphosphate is more potent than ATP at P2X receptors in isolated rat vagus nerve. Neuroreport. 2001 Mar 26;12(4):679-82. [Content Brief]
[5]. Diez-Zaera M, et al. Diadenosine pentaphosphate regulates dendrite growth and number in cultured hippocampal neurons. Purinergic signalling. 2024 Apr;20(2):115-125. [Content Brief]
Calculators
Konzentration (Stammlösung) × Volumen (Stammlösung) = Konzentration (Ziellösung) × Volumen (Ziellösung)
- Diadenosine pentaphosphate
- 41708-91-2
- Ap5A
- P1,P5-Di(adenosine-5'-)pentaphosphate
- Endogenous Metabolite
- P2X Receptor
- P2Y Receptor
- Calcium Channel
- RyR2
- P2-type purinoceptors
- P1 purinoceptors
- P2X3
- IP3-sensitive intracellular stores
- I_KAch channels
- sheep cardiac ryanodine receptor
- heteromeric P2X2/3 purinoceptors
- ryanodine-sensitive intracellular stores
- P2X1
- Inhibitor
- inhibitor
- inhibit