| Size | Price | Stock | Qty |
|---|---|---|---|
| 10mg |
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| 50mg |
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| 100mg |
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| 250mg | |||
| 500mg | |||
| Other Sizes |
| Targets |
Estrogen receptor alpha (ERα) (Relative Binding Affinity (RBA) = 0.25% compared to estradiol)
Estrogen receptor beta (ERβ) (RBA = 18% compared to estradiol; β/α selectivity = 72-fold; Transcriptional EC50 for ERβ = 0.85 nM, for ERα = 66 nM; β/α potency selectivity = 78-fold) [1] |
|---|---|
| ln Vitro |
DPN is a full ERα agonist with 78-fold selectivity for ERα potency (EC50 for ERβ=0.85 nM; EC50 for ERα=66 nM) and a 70-fold relative binding affinity selectivity for ERα [1]. In cultured cortical neurons, Aβ1-42 (10 μM)-induced toxicity is prevented from causing morphological changes by DPN (10 nM) [2]. ROS levels are lowered by DPN (0.1–100 nM) in a non-dose-responsive way [2]. In a dose-independent manner, DPN (0.1-100 nM) significantly reduces Aβ1-42-stimulated Bax expression [2]. In cultured cortical neurons, DPN (0.1-100 nM) lowers activated IL-1 levels induced by Aβ1-42 treatment [2]. Aβ1-42-upregulated JNK and p38 phosphorylation are inhibited by DPN (0.1-100 nM) [2].
DPN acts as a full agonist on both ERα and ERβ but shows strong selectivity for ERβ, with a 70-fold higher relative binding affinity and 170-fold higher relative potency in transcription assays compared to ERα. It demonstrates higher affinity and potency for ERβ than the phytoestrogen genistein. [1] |
| ln Vivo |
In an 11-day period, DPN (10 μg) administered subcutaneously improved swimming capacity, decreased FST immobility, and elevated TPH protein expression in the dorsal raphe nucleus (DR) in a rat model [3].
|
| Enzyme Assay |
A competitive radiometric binding assay was used to determine the binding affinities of DPN for purified, recombinant full-length human ERα and ERβ. The assay was performed using 10 nM [³H]estradiol as the tracer. Incubations were carried out at 0°C for 18–24 hours, and hydroxyapatite was used to absorb the purified receptor-ligand complexes. Binding affinities are expressed as relative binding affinity (RBA) values, with the RBA of estradiol set at 100%. [1]
|
| Cell Assay |
Transcriptional activation was assessed in human endometrial cancer (HEC-1) cells transfected with expression plasmids for ERα and ERβ and an estrogen-responsive reporter gene (chloramphenicol acetyltransferase (CAT) or luciferase (Luc)). For the CAT assay, cells in 60 mm dishes were transfected with a calcium phosphate precipitate containing the reporter plasmid, ER expression vector, and internal control (pCMVβGal). After 24 hours of ligand treatment, CAT activity was measured and normalized to β-galactosidase activity. For the Luc assay, HEC-1 cells in 24-well plates were transfected using lipofectin-transferrin with the reporter plasmid, ER expression vector, and internal control (pRL-CMV). After 6 hours, the medium was replaced with media containing ligands, and incubation continued for 24 hours. Luciferase activity was measured using a dual-luciferase reporter assay system, normalized to transfection efficiency, and expressed as a percentage of the activity induced by 10⁻⁸ M estradiol. [1]
|
| Animal Protocol |
Animal/Disease Models: Adult SD (SD (Sprague-Dawley)) female rat (220-250 g), ovariectomized animal model [3]
Doses: 10 μg/rat Route of Administration: daily subcutaneous injection for 11 days Experimental Results: increased number of swimming times in FST, diminished immobility. |
| References |
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| Additional Infomation |
2,3-bis(4-hydroxyphenyl)propionitrile is a nitrile compound with the structure of acetonitrile, in which one hydrogen atom is replaced by 4-hydroxyphenyl and the other hydrogen atom is replaced by 4-hydroxybenzyl. It is a specific agonist of estrogen receptor β (ERβ). It has the function of an estrogen receptor agonist. It belongs to the phenol and nitrile classes.
DPN (2,3-bis(4-hydroxyphenyl)propionitrile) is a diarylpropionitrile that has been identified as a potent and selective ERβ agonist. Its nitrile functional group is crucial for ERβ selectivity, providing an optimal combination of linear geometry and polarity. Structural modifications, such as the addition of a second nitrile group or ortho-methyl group to the β-aryl ring, can enhance its affinity and selectivity for ERβ. DPN and its analogues are useful tools for studying the structural and functional differences between ERα and ERβ. [1] |
| Molecular Formula |
C15H13NO2
|
|---|---|
| Molecular Weight |
239.2692
|
| Exact Mass |
239.094
|
| CAS # |
1428-67-7
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| Related CAS # |
(R)-DPN;524047-78-7
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| PubChem CID |
102614
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| Appearance |
White to off-white solid powder
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| Density |
1.3±0.1 g/cm3
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| Boiling Point |
449.4±35.0 °C at 760 mmHg
|
| Melting Point |
203°C
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| Flash Point |
225.6±25.9 °C
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| Vapour Pressure |
0.0±1.1 mmHg at 25°C
|
| Index of Refraction |
1.640
|
| LogP |
2.06
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| Hydrogen Bond Donor Count |
2
|
| Hydrogen Bond Acceptor Count |
3
|
| Rotatable Bond Count |
3
|
| Heavy Atom Count |
18
|
| Complexity |
293
|
| Defined Atom Stereocenter Count |
0
|
| InChi Key |
GHZHWDWADLAOIQ-UHFFFAOYSA-N
|
| InChi Code |
InChI=1S/C15H13NO2/c16-10-13(12-3-7-15(18)8-4-12)9-11-1-5-14(17)6-2-11/h1-8,13,17-18H,9H2
|
| Chemical Name |
2,3-bis(4-hydroxyphenyl)propanenitrile
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| 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 |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
|
| Solubility (In Vitro) |
DMSO : ~100 mg/mL (~417.94 mM)
H2O : ~0.67 mg/mL (~2.80 mM) |
|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (10.45 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 (10.45 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 (10.45 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 | 4.1794 mL | 20.8969 mL | 41.7938 mL | |
| 5 mM | 0.8359 mL | 4.1794 mL | 8.3588 mL | |
| 10 mM | 0.4179 mL | 2.0897 mL | 4.1794 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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