| Size | Price | Stock | Qty |
|---|---|---|---|
| 5mg |
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| 10mg |
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| Other Sizes |
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| Targets |
ERα (Ki = 27.4 nM), ERβ (Ki = 15.4 nM)[1]
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|---|---|
| ln Vitro |
(R)-Equol has a Kis of 15.4 nM for ERβ and 27.4 nM for ERβ, making it an agonist for both receptors [1]. The invasive ability of MDA-MB-231 cells was inhibited by (R)-Equol in a dose-dependent manner; this impact was noteworthy even at the highest tested concentration of 50 μM. 50 μM (R)-equol decreased invasion by 62% (p=0.009 compared to untreated cells) after 48 hours of exposure to (R)-equol. Following treatment with 50 μM (R)-Equol, there was a substantial down-regulation of matrix metalloproteinase-2 (MMP-2) expression (p=0.035)[2].
The invasive capacity of MDA-MB-231 cells was significantly reduced (by approximately 50-60 %) following treatment with 50 μM daidzein, R- or S-equol. Anti-invasive effects were also observed with R-equol at 2.5 and 10 μM though overall equipotent effects were induced by all compounds. Inhibition of invasion induced by all three compounds at 50 μM was associated with the down-regulation of MMP-2, while none of the compounds tested significantly affected the expression levels of MMP-9, TIMP-1 or TIMP-2 at this concentration. Following exposure to media containing 50 μM R- or S-equol for 48-h intracellular concentrations of R- and S-equol were 4.38 ± 1.17 and 3.22 ± 0.47 nM, respectively. Conclusion: Daidzein, R- and S-equol inhibit the invasion of MDA-MB-231 human breast cancer cells in part via the down-regulation of MMP-2 expression, with equipotent effects observed for the parent isoflavone daidzein and the equol enantiomers.[1] |
| ln Vivo |
Over time, palpable tumors were considerably less common in animals fed (R)-equol than in controls (P=0.002). Additionally, compared to rats fed S-(-)equol, the number of palpable tumors produced per rat in the (R)-equol-fed group was considerably fewer (P=0.008). There were 43% fewer tumors in animals fed (R)-equol than in controls, a highly significant difference (P=0.004). When comparing animals fed (R)-equol to the control group, the number of tumors/tumor-bearing animals was considerably lower (3.3±0.4 vs. 5.5±0.5, P=0.004). Rats fed on equol had a considerably lower mean (±SEM) tumor weight per animal at necropsy (5.3±1.1 mg) than the controls (9.9±1.4 mg) (P= 0.04). There was a significant increase in tumor latency (P=0.003) after feeding the (R)-equol diet [3].
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| Enzyme Assay |
In this study, researchers describe for the first time the chemopreventive effects of S-(-)equol and R-(+)equol, diastereoisomers with contrasting affinities for estrogen receptors (ERs). S-(-)equol, a ligand for ERbeta, is an intestinally derived metabolite formed by many humans and by rodents consuming diets containing soy isoflavones. [2]
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| Cell Assay |
The anti-invasive effects of daidzein, R- and S-equol (0, 2.5, 10, 50 μM) on MDA-MB-231 cells were determined using the Matrigel invasion assay following 48-h exposure. Effects on MMP-2, MMP-9, TIMP-1 and TIMP-2 expression were assessed using real-time PCR. Chiral HPLC analysis was used to determine intracellular concentrations of R- and S-equol.[1]
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| Animal Protocol |
Whether the well-documented chemopreventive effect of a soy diet could be explained by equol's action was unclear because neither diastereoisomers had been tested in animal models of chemoprevention. Sprague-Dawley rats (n = 40-41 per group) were fed a soy-free AIN-93G diet or an AIN-93G diet supplemented with 250 mg/kg of S-(-)equol or R-(+)equol beginning day 35. On day 50, mammary tumors were induced by dimethylbenz[a]anthracene and thereafter, animals were palpated for number and location of tumors. On day 190, animals were killed and mammary tumors were removed and verified by histology, and the degree of invasiveness and differentiation was determined. S-(-)equol and R-(+)equol plasma concentrations measured on days 35, 100 and 190 by tandem mass spectrometry confirmed diet compliance and no biotransformation of either diastereoisomer. In this model, S-(-)equol had no chemopreventive action, nor was it stimulatory. In contrast, R-(+)equol compared with Controls reduced palpable tumors (P = 0.002), resulted in 43% fewer tumors (P = 0.004), increased tumor latency (88.5 versus 66 days, P = 0.003), and tumors were less invasive but showed no difference in pattern grade or mitosis. Both enantiomers had no effect on absolute uterine weight but caused a significant reduction in body weight gain. In conclusion, the novel finding that the unnatural enantiomer, R-(+)equol, was potently chemopreventive warrants investigation of its potential for breast cancer prevention and treatment.[2]
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| References |
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| Additional Infomation |
(R)-Equol is a member of hydroxyisoflavans.
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| Molecular Formula |
C15H14O3
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|---|---|
| Molecular Weight |
242.26986
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| Exact Mass |
242.094
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| Elemental Analysis |
C, 74.36; H, 5.82; O, 19.81
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| CAS # |
221054-79-1
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| Related CAS # |
(-)-(S)-Equol;531-95-3;(±)-Equol;94105-90-5
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| PubChem CID |
6950272
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| Appearance |
White to yellow solid powder
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| Density |
1.3±0.1 g/cm3
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| Boiling Point |
441.7±45.0 °C at 760 mmHg
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| Melting Point |
189-190ºC
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| Flash Point |
220.9±28.7 °C
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| Vapour Pressure |
0.0±1.1 mmHg at 25°C
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| Index of Refraction |
1.645
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| LogP |
2.98
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
1
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| Heavy Atom Count |
18
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| Complexity |
273
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| Defined Atom Stereocenter Count |
1
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| SMILES |
C1[C@@H](COC2=C1C=CC(=C2)O)C3=CC=C(C=C3)O
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| InChi Key |
ADFCQWZHKCXPAJ-LBPRGKRZSA-N
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| InChi Code |
InChI=1S/C15H14O3/c16-13-4-1-10(2-5-13)12-7-11-3-6-14(17)8-15(11)18-9-12/h1-6,8,12,16-17H,7,9H2/t12-/m0/s1
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| Chemical Name |
(3R)-3-(4-hydroxyphenyl)-3,4-dihydro-2H-chromen-7-ol
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| Synonyms |
(R)-Equol; 221054-79-1; (+)-Equol; (R)-3-(4-hydroxyphenyl)chroman-7-ol; R-Equol; Isoequol; (3R)-3-(4-hydroxyphenyl)-3,4-dihydro-2H-chromen-7-ol; Equol, (+)-;
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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 : ~100 mg/mL (~412.76 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (10.32 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 (10.32 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. View More
Solubility in Formulation 3: ≥ 2.5 mg/mL (10.32 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 | 4.1276 mL | 20.6381 mL | 41.2763 mL | |
| 5 mM | 0.8255 mL | 4.1276 mL | 8.2553 mL | |
| 10 mM | 0.4128 mL | 2.0638 mL | 4.1276 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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