| Size | Price | Stock | Qty |
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| 10mg |
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| 50mg |
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| 100mg |
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| 250mg |
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| 500mg |
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| Other Sizes |
Purity: =98.9%
| Targets |
- Mitochondrial aldehyde dehydrogenase (Ki = 0.082 μM) [3]
- Serotonin and dopamine metabolism - related enzymes in mitochondria [4] Mitochondrial aldehyde dehydrogenase (ALDH-2). Daidzin is a potent and selective inhibitor of ALDH-2. The inhibition is mixed-type (competitive/noncompetitive). At pH 9.5, the competitive inhibition constant (Ki) for human ALDH-2 is 0.042 μM, and the noncompetitive inhibition constant (αKi) is 0.65 μM. For hamster ALDH-2, Ki is 0.082 μM and αKi is 3.5 μM. For rat ALDH-2, Ki is 0.052 μM. [3] Daidzin also inhibits serotonin (5-HT) and dopamine (DA) metabolism in isolated mitochondria by inhibiting ALDH-2, leading to accumulation of 5-hydroxyindole-3-acetaldehyde (5-HIAL) and 3,4-dihydroxyphenylacetaldehyde (DOPAL). The IC₅₀ for inhibition of 5-HIAA formation in hamster liver mitochondria is approximately 2.7 μM. [4] |
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| ln Vitro |
- Inhibiting mitochondrial enzyme activity: Daidzin inhibits mitochondrial aldehyde dehydrogenase activity, with a Ki value of 0.082 μM. It also inhibits the metabolism of serotonin and dopamine in isolated mitochondria, suppressing the production of 5 - HIAA (IC50 = 2.7 μM) and increasing the content of 5 - HTOL in hamster mitochondrial culture [3][4]
Daidzin had a 0.082 and 0.052 μM Kis inhibitory effect on ALDH-2 and hamster, respectively[1]. Daidzin (500 μM) inhibits phorbol myristyl ester (PMA), which results in antioxidant action. To find out how well 5-HIAL in mitochondria and cells reduces cytochrome c, daidin (0-30 μM, 30 min) suppresses 5-HIAA (IC50 value = 2.7 μM) and increases hamster mitochondrial culture [3]. The 5-HTOL content [4]. Daidzin potently inhibits acetaldehyde oxidation catalyzed by mitochondria isolated from hamster livers. [3] Daidzin inhibits the formation of 5-HIAA from 5-HT in isolated hamster liver mitochondria in a concentration-dependent manner (IC₅₀ ≈ 2.7 μM). Inhibition is accompanied by a concomitant accumulation of 5-HIAL and 5-HTOL. Daidzin, at concentrations that significantly inhibit 5-HIAA formation, has no effect on the rate of 5-HT depletion. [4] Daidzin also inhibits the formation of DOPAC from DA in isolated hamster liver mitochondria in a concentration-dependent manner. [4] Daidzin has no effect on monoamine oxidase (MAO) activity in hamster liver mitochondrial membranes at concentrations up to 30 μM. [4] Daidzin does not compete with NAD⁺ binding at concentrations up to 3 μM. [3] |
| ln Vivo |
- Reducing blood alcohol levels and shortening sleep time: In rats, Daidzin (30 mg/kg, by gavage) can lower the blood alcohol levels caused by 3 g ethanol/kg body weight and shorten the sleep time produced by ethanol intoxication (7 g/kg, by gavage) [1]
- Suppressing ethanol intake: In Syrian golden hamsters, Daidzin can suppress ethanol intake. When administered at a dose of 70 meq/hamster/day by intra - peritoneal injection, it can prevent 62% of ethanol inhalation [3][4] Daidzin (70 meq/hamster/day, intraperitoneal injection) can prevent 62% of ethanol inhalation in rat hamsters [4]. Daidzin (30 mg/kg, gavage) lowers fasting reserve blood alcohol levels (caused by 3 g ethanol/kg weight) and sleep duration (produced by ethanol intoxication, gavage 7 g/kg) [3]. In ethanol-preferring Syrian golden hamsters, intraperitoneal administration of daidzin at a dose of 70 meq/hamster/day suppresses ethanol intake by 62%. [3, 4] In rats employing a two-lever, free-choice (ethanol vs. isocaloric starch solution) self-administration procedure, daidzin suppresses ethanol intake without reflecting an overall suppression of appetite. [3] In Fawn Hooded rats and P rats, daidzin and a crude extract containing daidzin suppress ethanol intake under various conditions, including two-bottle free-choice, limited-access, and alcohol-deprived paradigms. [3] A dose of daidzin that significantly suppresses ethanol intake in hamsters does not affect overall ethanol or acetaldehyde metabolism, indicating it does not act as an ethanol-sensitizing agent. [3] |
| Enzyme Assay |
- Mitochondrial aldehyde dehydrogenase activity assay: Prepare mitochondrial extracts from relevant tissues or cells. Add different concentrations of Daidzin to the reaction system, along with the substrate of mitochondrial aldehyde dehydrogenase. Incubate at an appropriate temperature for a certain period, then use a specific detection method (such as measuring the change of product concentration by spectrophotometry) to determine the enzyme activity, and calculate the inhibitory effect of Daidzin on the enzyme according to the experimental results [3]
- Serotonin and dopamine metabolism - related enzyme activity assay: Isolate mitochondria from hamster tissues. Incubate mitochondria with Daidzin at different concentrations, and add the necessary co - factors and substrates for serotonin and dopamine metabolism. After a certain incubation time, detect the levels of 5 - HIAA and 5 - HTOL in the reaction system by appropriate methods (such as high - performance liquid chromatography), and evaluate the inhibitory effect of Daidzin on the metabolism of these two substances [4] ALDH Activity Assay: ALDH activity was assayed by monitoring the increase in absorbance at 340 nm due to the formation of NADH (ε₃₄₀ = 6.22 mM⁻¹cm⁻¹) in a spectrophotometer using acetaldehyde as the substrate, or by monitoring the increase in fluorescence at 430 nm on formation of 6-dimethylamino-2-naphthaldehyde (λₑₓ = 330 nm) in a spectrofluorimeter when 6-DMA-2-NA was used as the substrate. Assays were performed in 0.1 M sodium pyrophosphate (pH 9.5) or 0.1 M sodium phosphate (pH 7.5) containing 3 mM NAD⁺ and various concentrations of acetaldehyde and daidzin. Kinetic parameters were determined from Lineweaver-Burk plots derived from duplicate determinations of initial velocities for cytosolic ALDHs, and from progress kinetic curves for mitochondrial isozymes. [3] MAO Activity Assay: Mitochondrial membranes were used as a crude preparation of MAO. MAO activity was assayed by the same method described for the 5-HT and DA metabolism assay except that 5 mM semicarbazide was included in the incubation medium as an aldehyde trap. [4] |
| Animal Protocol |
- For the experiment of reducing blood alcohol levels and shortening sleep time, rats are first fasted, and then given 3 g ethanol/kg body weight by gavage. After that, Daidzin is administered at a dose of 30 mg/kg by gavage. Observe and record the blood alcohol levels at different time points, and record the sleep time after giving 7 g/kg ethanol by gavage to induce intoxication [1]
- For the experiment of suppressing ethanol intake, Syrian golden hamsters are used. Daidzin is dissolved in an appropriate solvent and administered to hamsters by intra - peritoneal injection at a dose of 70 meq/hamster/day. Observe and record the ethanol intake of hamsters [3][4] |
| Toxicity/Toxicokinetics |
107971 Intraperitoneal LD50 in mice >2 g/kg, Journal of Medicinal Chemistry, 13(51), 1979
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| References |
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| Additional Infomation |
Daidzein is an antioxidant isoflavone. It has the potential to act as an anti-thirst agent, reducing blood alcohol concentration, shortening sleep time caused by ethanol poisoning, and inhibiting ethanol intake, suggesting its potential value in treating alcohol-related problems [1][3][4]. Daidzein 7-O-β-D-glucoside is a glycosyl isoflavone consisting of daidzein linked to a β-D-glucopyranose residue at position 7 via a glycosidic bond. It is used to treat alcohol dependence (anti-thirst agent). It is a plant metabolite. It is a hydroxy isoflavone, a monosaccharide derivative, and a 7-hydroxy isoflavone 7-O-β-D-glucoside. It is functionally related to daidzein. Daidzein has been reported in Spanish sage, Begonia serrata, and other organisms with available data. See also: Astragalus root (partial).
Daidzin is a major active principle isolated from Radix puerariae (the root of Pueraria lobata, kudzu), a traditional Chinese medicine used for centuries to treat alcohol abuse. It is the first isoflavone recognized to suppress ethanol intake. [3] Daidzin suppresses ethanol intake in all rodent models tested (golden hamsters, Wistar rats, Fawn Hooded rats, and P rats) without affecting overall ethanol or acetaldehyde metabolism, indicating it does not act as an ethanol-sensitizing agent (unlike disulfiram). [3, 4] The antidipsotropic activity of daidzin correlates directly with its ALDH-2 inhibitory activity and its inhibition of 5-HT and DA metabolism in isolated mitochondria. Structural analogs that are stronger ALDH-2 inhibitors (e.g., deczein, hepzein, hexzein) show greater suppression of ethanol intake (up to 84%). [3, 4] Daidzin is proposed to act by inhibiting a physiological pathway catalyzed by ALDH-2, possibly involving serotonin and dopamine metabolism, leading to accumulation of reactive aldehyde intermediates (5-HIAL and DOPAL) that may regulate ethanol drinking behavior. [3, 4] |
| Molecular Formula |
C21H20O9
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|---|---|
| Molecular Weight |
416.3781
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| Exact Mass |
416.11
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| Elemental Analysis |
C, 60.58; H, 4.84; O, 34.58
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| CAS # |
552-66-9
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| PubChem CID |
107971
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| Appearance |
White to off-white solid powder
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| Density |
1.6±0.1 g/cm3
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| Boiling Point |
727.6±60.0 °C at 760 mmHg
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| Melting Point |
234-236°C
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| Flash Point |
259.8±26.4 °C
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| Vapour Pressure |
0.0±2.5 mmHg at 25°C
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| Index of Refraction |
1.695
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| LogP |
0.45
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| Hydrogen Bond Donor Count |
5
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| Hydrogen Bond Acceptor Count |
9
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| Rotatable Bond Count |
4
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| Heavy Atom Count |
30
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| Complexity |
644
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| Defined Atom Stereocenter Count |
5
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| SMILES |
C1=CC(=CC=C1C2=COC3=C(C2=O)C=CC(=C3)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O
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| InChi Key |
KYQZWONCHDNPDP-QNDFHXLGSA-N
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| InChi Code |
InChI=1S/C21H20O9/c22-8-16-18(25)19(26)20(27)21(30-16)29-12-5-6-13-15(7-12)28-9-14(17(13)24)10-1-3-11(23)4-2-10/h1-7,9,16,18-23,25-27H,8H2/t16-,18-,19+,20-,21-/m1/s1
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| Chemical Name |
3-(4-hydroxyphenyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxychromen-4-one
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| Synonyms |
Daidzin; 552-66-9; Daidzoside; Daidzein 7-O-glucoside; Daidzein 7-glucoside; Daidzein-7-glucoside; daidzein 7-O-beta-D-glucoside; CHEBI:42202;
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ~250 mg/mL (~600.41 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.08 mg/mL (5.00 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 (5.00 mM) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), suspension solution; with ultrasonication. 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. View More
Solubility in Formulation 3: ≥ 2.08 mg/mL (5.00 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 2.4017 mL | 12.0083 mL | 24.0165 mL | |
| 5 mM | 0.4803 mL | 2.4017 mL | 4.8033 mL | |
| 10 mM | 0.2402 mL | 1.2008 mL | 2.4017 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.
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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