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2-O-Acetyl-20-hydroxyecdysone

Cat No.:V31996 Purity: ≥98%
2-O-Acetyl-20-hydroxyecdysone, an ecdysone present in insects and terrestrial plants, inhibits amyloid-β42-induced cell toxicity/cytotoxicity.
2-O-Acetyl-20-hydroxyecdysone
2-O-Acetyl-20-hydroxyecdysone Chemical Structure CAS No.: 19536-25-5
Product category: New2
This product is for research use only, not for human use. We do not sell to patients.
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5mg
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Product Description
2-O-Acetyl-20-hydroxyecdysone, an ecdysone present in insects and terrestrial plants, inhibits amyloid-β42-induced cell toxicity/cytotoxicity. 2-O-Acetyl-20-hydroxyecdysone can reduce the formation of Aβ oligomers by promoting fibrogenesis and converting Aβ oligomers into low-toxic fibers.
Biological Activity I Assay Protocols (From Reference)
Targets
1. Amyloid-β42 (Aβ42, the key target related to Alzheimer’s disease pathogenesis) [1]
ln Vitro
1. Effect on Aβ42 aggregation: 2-O-Acetyl-20-hydroxyecdysone, as an ecdysterone with an acetoxyl group at the 2-position and saturated side chain, could promote Aβ42 fibrilization in vitro; this promotion led to a significant reduction in the level of toxic Aβ42 oligomers in the reaction system [1]
2. Inhibition of Aβ42-induced cytotoxicity: In tumor cell lines treated with Aβ42, 2-O-Acetyl-20-hydroxyecdysone uniformly inhibited Aβ42-induced cytotoxicity. MTT assay results showed that the cell viability of Aβ42-treated cells was restored by the compound, with no significant cytotoxicity of the compound itself at experimental concentrations [1]
3. Amelioration of oxidative stress: 2-O-Acetyl-20-hydroxyecdysone could ameliorate Aβ42-induced release of reactive oxygen species (ROS) in cells, which was one of the key mechanisms for its protective effect against Aβ42-mediated cytotoxicity [1]
Cell Assay
1. Aβ42-induced cytotoxicity detection assay: Tumor cells were seeded in 96-well plates at an appropriate density and incubated for 24 h to attach. The cells were then co-treated with Aβ42 and different concentrations of 2-O-Acetyl-20-hydroxyecdysone for a set period. MTT reagent was added to each well and incubated for several hours, followed by absorbance measurement at the corresponding wavelength to calculate cell viability and evaluate the compound’s protective effect against Aβ42-induced cytotoxicity [1]
2. ROS level detection assay: Cells were seeded in culture plates and treated with Aβ42 alone or in combination with 2-O-Acetyl-20-hydroxyecdysone for a specific time. After incubation, ROS detection reagent was added, and the fluorescence intensity of the cells was measured using a fluorescence detector; the fluorescence intensity was positively correlated with the intracellular ROS level, thus reflecting the compound’s effect on Aβ42-induced ROS release [1]
References

[1]. Diverse ecdysterones show different effects on amyloid-β42 aggregation but all uniformly inhibit amyloid-β42-induced cytotoxicity. J Alzheimers Dis. 2010;22(1):107-17.

Additional Infomation
There have been reports that 2-O-acetyl-20-hydroxy ecdysone has been found in sea anemones (Zoanthus) and red sea anemones (Rhaponticum carthamoides), and related data have been reported.
1. 2-O-acetyl-20-hydroxy ecdysone is an ecdysone, a steroid hormone found in insects and terrestrial plants, with structural diversity and a variety of beneficial pharmacological activities [1]
2. The structure of 2-O-acetyl-20-hydroxy ecdysone (acetoxy group at position 2 and saturated side chain) determines its unique role in Aβ42 aggregation (promoting fibrosis and reducing oligomer levels), and this structural feature is one of the key foundations of the structure-activity relationship of ecdysone in regulating Aβ42 aggregation and cytotoxicity [1]
3. 2-O-acetyl-20-hydroxy ecdysone has the potential to treat Alzheimer's disease (AD) and other amyloidosis diseases because it can inhibit Aβ42-induced cytotoxicity, and its structure-activity relationship can provide a reference for designing anti-AD drugs that target Aβ aggregation and toxicity [1]
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C29H46O8
Molecular Weight
522.671
Exact Mass
522.319
CAS #
19536-25-5
PubChem CID
11060408
Appearance
White to off-white solid powder
Density
1.26±0.1 g/cm3
Boiling Point
707.3±60.0 °C
Melting Point
218-220 ºC
LogP
2.424
Hydrogen Bond Donor Count
5
Hydrogen Bond Acceptor Count
8
Rotatable Bond Count
7
Heavy Atom Count
37
Complexity
975
Defined Atom Stereocenter Count
10
SMILES
CC(=O)O[C@H]1C[C@@]2([C@H]3CC[C@@]4([C@H](CC[C@]4(C3=CC(=O)[C@@H]2C[C@H]1O)O)[C@](C)([C@@H](CCC(C)(C)O)O)O)C)C
InChi Key
TXLUXHSVMYTTCI-FORVDKSSSA-N
InChi Code
InChI=1S/C29H46O8/c1-16(30)37-22-15-26(4)17-7-11-27(5)23(28(6,35)24(33)9-10-25(2,3)34)8-12-29(27,36)18(17)13-20(31)19(26)14-21(22)32/h13,17,19,21-24,32-36H,7-12,14-15H2,1-6H3/t17-,19-,21+,22-,23-,24+,26+,27+,28+,29+/m0/s1
Chemical Name
[(2S,3R,5R,9R,10R,13R,14S,17S)-3,14-dihydroxy-10,13-dimethyl-6-oxo-17-[(2R,3R)-2,3,6-trihydroxy-6-methylheptan-2-yl]-2,3,4,5,9,11,12,15,16,17-decahydro-1H-cyclopenta[a]phenanthren-2-yl] acetate
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: This product requires protection from light (avoid light exposure) during transportation and storage.
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 : ~100 mg/mL (~191.33 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.5 mg/mL (4.78 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 25.0 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: ≥ 2.5 mg/mL (4.78 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 25.0 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: ≥ 2.5 mg/mL (4.78 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 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


 (Please use freshly prepared in vivo formulations for optimal results.)
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 1.9133 mL 9.5663 mL 19.1325 mL
5 mM 0.3827 mL 1.9133 mL 3.8265 mL
10 mM 0.1913 mL 0.9566 mL 1.9133 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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What volume of a given 10 mM stock solution is required to make 25 ml of a 25 μM solution?
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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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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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