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Atractyloside Potassium Salt

Alias: Atractyloside Potassium Atractyloside Potassium Salt
Cat No.:V11858 Purity: ≥98%
Atractyloside potassium salt is a toxic diterpene glycoside compound that can be extracted from the fruits of Atractylodes rhizome.
Atractyloside Potassium Salt
Atractyloside Potassium Salt Chemical Structure CAS No.: 102130-43-8
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
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Product Description
Atractyloside potassium salt is a toxic diterpene glycoside compound that can be extracted from the fruits of Atractylodes rhizome. Atractyloside potassium salt is a highly efficient and specific inhibitor of mitochondrial ADP/ATP transport. Atractyloside potassium salt inhibits chloride channels in the mitochondrial membrane of rat heart.
Atractyloside Potassium Salt (CAS# 102130-43-8) is a highly toxic diterpene glycoside compound that can be extracted from the fruits of Atractylodes rhizome. It is a potent and specific inhibitor of mitochondrial ADP/ATP transport, also known as the adenine nucleotide translocator (ANT). Atractyloside Potassium Salt inhibits oxidative phosphorylation by blocking the transfer of adenosine nucleotides through the mitochondrial membrane.
Biological Activity I Assay Protocols (From Reference)
Targets
Atractyloside Potassium Salt targets the mitochondrial ADP/ATP translocase (ANT), also known as the adenine nucleotide translocator. It is a high-affinity, specific inhibitor of this carrier protein. Atractyloside binds to the ATP-ADP translocase after the protein has off-loaded its ATP into the cytosol and before it binds an ADP for transport into the mitochondrial matrix space. It also inhibits chloride channels in the mitochondrial membrane of rat heart.
ln Vitro
In vitro, Atractyloside Potassium Salt is a powerful and specific inhibitor of mitochondrial ADP/ATP transport. It inhibits oxidative phosphorylation by blocking the transfer of adenosine nucleotides through the mitochondrial membrane. The compound is widely utilized to probe bioenergetic pathways and mitochondrial function. It also inhibits chloride channels from mitochondrial membranes of rat heart. Atractyloside has been used to probe the source of procaspase 8 in human fibroblasts and mouse clonal striatal cells, as related to death receptor-mediated apoptosis.
ln Vivo
In vivo, Atractyloside Potassium Salt is an extremely toxic glucoside. Atractyloside induces the release of a hyaluronidase-induced murine WW domain-containing oxidoreductase from cultured COS-7 cells. It is used as a tool to induce apoptosis in cells and isolated mitochondria. A protocol for the measurement of mitochondrial transmembrane potential in cells and in isolated mitochondria includes the use of atractyloside as one example of apoptotic induction.
Enzyme Assay
The activity of Atractyloside Potassium Salt can be assessed using cell-free assays with isolated mitochondria. Mitochondria are incubated with the compound, and the inhibition of ADP/ATP transport is measured using radiolabeled nucleotides or by monitoring oxygen consumption rates. The binding affinity of atractyloside to the adenine nucleotide translocator can be determined using binding assays with isolated mitochondrial membranes.
Cell Assay
To evaluate the cellular effects of Atractyloside Potassium Salt, cells are treated with the compound, and mitochondrial function is assessed. Parameters such as mitochondrial membrane potential (ΔΨm), ATP levels, and oxygen consumption rate (OCR) are measured. The induction of apoptosis is assessed by measuring caspase activation, cytochrome c release, and DNA fragmentation. The compound's effects on mitochondrial permeability transition and cell death are evaluated.
Animal Protocol
In vivo studies with Atractyloside Potassium Salt typically involve administration to animal models to study its toxic effects or to induce apoptosis in specific tissues. However, due to its high toxicity, such studies are limited. The compound is primarily used as a research tool in isolated mitochondria and cell-based assays to investigate mitochondrial function and apoptosis.
ADME/Pharmacokinetics
Atractyloside Potassium Salt has a molecular formula of C₃₀H₄₄O₁₆S₂K₂ and a molecular weight of 803.0 g/mol. Its CAS number is 102130-43-8. The product is soluble in water (20 mg/ml), yielding a clear, very faint yellow solution, with a maximum solubility of approximately 25 mg/ml at 40 °C. It should be stored at room temperature.
Toxicity/Toxicokinetics
Atractyloside Potassium Salt is an extremely toxic compound. It is highly toxic by ingestion and causes severe poisoning. The inhibition of the adenine nucleotide translocator leads to the collapse of mitochondrial membrane potential, depletion of ATP, and cell death. Atractyloside is used as a research tool to study mitochondrial toxicity and apoptosis. It is not suitable for human consumption and should be handled with extreme caution.
References

[1]. Bongkrekic acid and atractyloside inhibits chloride channels from mitochondrial membranes of rat heart. Biochim Biophys Acta. 2007 Jan;1767(1):31-44.

[2]. Influence of Processing on the Content of Toxic Carboxyatractyloside and Atractyloside and the Microbiological Status of Xanthium sibiricum Fruits (Cang'erzi). Planta Med. 2015 Aug;81(12-13):1213-20.

[3]. Phosphate dependence and atractyloside inhibition of mitochondrial oxidative phosphorylation. The ADP-ATP carrier is rate-limiting. J Biol Chem. 1979 Feb 25;254(4):1248-51.

[4]. Bongkrekic acid and atractyloside inhibits chloride channels from mitochondrial membranes of rat heart. Biochim Biophys Acta. 2007 Jan;1767(1):31-44.

Additional Infomation
Kaurene-type diterpenoid glycosides found in certain plants, including Atractylis gummifera, coffee, Xanthium, and Callilepis. Their toxicity is due to inhibition of adenine nucleotide translocases.
See also: Atractylodesin (note moved to).
Atractyloside Potassium Salt is a potent and specific inhibitor of the mitochondrial adenine nucleotide translocator (ANT) used as a research tool in bioenergetics and apoptosis studies. It is obtained from the Mediterranean thistle Atractylis gummifera and is known for its high toxicity. Atractyloside Potassium Salt is used to probe mitochondrial function, study the mechanisms of apoptosis, and investigate the role of the adenine nucleotide translocator in cellular energy metabolism. It is not a therapeutic agent.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C30H44K2O16S2
Molecular Weight
802.98
Exact Mass
802.134
CAS #
102130-43-8
PubChem CID
5702200
Appearance
White to light yellow solid powder
LogP
3.143
Hydrogen Bond Donor Count
3
Hydrogen Bond Acceptor Count
16
Rotatable Bond Count
10
Heavy Atom Count
50
Complexity
1440
Defined Atom Stereocenter Count
7
SMILES
CC(C)CC(=O)OC1C(C(C(OC1O[C@@H]2C[C@H]([C@H]3CC[C@@]45CC(CC[C@H]4[C@@]3(C2)C)C(=C)[C@@H]5O)C(=O)O)CO)OS(=O)(=O)[O-])OS(=O)(=O)[O-].[K+].[K+]
InChi Key
IUCNQFHEWLYECJ-UAPRPQGYSA-L
InChi Code
InChI=1S/C30H46O16S2.2K/c1-14(2)9-22(32)44-25-24(46-48(39,40)41)23(45-47(36,37)38)20(13-31)43-28(25)42-17-10-18(27(34)35)19-7-8-30-11-16(15(3)26(30)33)5-6-21(30)29(19,4)12-17;;/h14,16-21,23-26,28,31,33H,3,5-13H2,1-2,4H3,(H,34,35)(H,36,37,38)(H,39,40,41);;/q;2*+1/p-2/t16?,17-,18-,19-,20?,21+,23?,24?,25?,26+,28?,29-,30-;;/m1../s1
Chemical Name
Potassium (2R,3R,4R,5R,6S)-6-(((2aR,3R,5R,6aR,6bS,9R,11S,11aR)-3-carboxy-11-hydroxy-6a-methyl-10-methylenetetradecahydro-9,11a-methanocyclohepta[a]naphthalen-5-yl)oxy)-2-(hydroxymethyl)-5-((3-methylbutanoyl)oxy)tetrahydro-2H-pyran-3,4-diyl bis(sulfate)
Synonyms
Atractyloside Potassium Atractyloside Potassium Salt
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture and light.
Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : ~250 mg/mL (~311.34 mM)
H2O : ~66.67 mg/mL (~83.03 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.08 mg/mL (2.59 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.08 mg/mL (2.59 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.08 mg/mL (2.59 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


Solubility in Formulation 4: 50 mg/mL (62.27 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with ultrasonication.

 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 1.2454 mL 6.2268 mL 12.4536 mL
5 mM 0.2491 mL 1.2454 mL 2.4907 mL
10 mM 0.1245 mL 0.6227 mL 1.2454 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

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