(R)-DPN

CAS# 524047-78-7

(R)-DPN

Catalog No. BCC7939----Order now to get a substantial discount!

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(R)-DPN: 5mg $150 In Stock
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Chemical structure

(R)-DPN

3D structure

Chemical Properties of (R)-DPN

Cas No. 524047-78-7 SDF Download SDF
PubChem ID 6604873 Appearance Powder
Formula C15H13NO2 M.Wt 239.27
Type of Compound N/A Storage Desiccate at -20°C
Solubility Soluble to 25 mM in 1eq. NaOH and to 100 mM in DMSO and to 100 mM in ethanol
Chemical Name (2R)-2,3-bis(4-hydroxyphenyl)propanenitrile
SMILES C1=CC(=CC=C1CC(C#N)C2=CC=C(C=C2)O)O
Standard InChIKey GHZHWDWADLAOIQ-ZDUSSCGKSA-N
Standard InChI 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/t13-/m0/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of (R)-DPN

DescriptionEnantiomer of DPN. Displays higher affinity for estrogen receptor (ER) β over ERα (Ki values are 1.82 and 147 nM respectively).

(R)-DPN Dilution Calculator

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(R)-DPN Molarity Calculator

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Preparing Stock Solutions of (R)-DPN

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 4.1794 mL 20.8969 mL 41.7938 mL 83.5876 mL 104.4845 mL
5 mM 0.8359 mL 4.1794 mL 8.3588 mL 16.7175 mL 20.8969 mL
10 mM 0.4179 mL 2.0897 mL 4.1794 mL 8.3588 mL 10.4484 mL
50 mM 0.0836 mL 0.4179 mL 0.8359 mL 1.6718 mL 2.0897 mL
100 mM 0.0418 mL 0.209 mL 0.4179 mL 0.8359 mL 1.0448 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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References on (R)-DPN

Diarylpropionitrile (DPN) enantiomers: synthesis and evaluation of estrogen receptor beta-selective ligands.[Pubmed:22122563]

J Med Chem. 2012 Jan 12;55(1):528-37.

Two estrogen receptor (ER) subtypes, ERalpha and ERbeta, mediate the actions of estrogens in diverse reproductive and nonreproductive target tissues. ER subtype-selective ligands, which bind to and activate these subtypes differentially, have proved to be useful in elucidating which actions of estrogens proceed through ERalpha vs ERbeta. Some of these ligands show potential as novel therapeutic agents. Diarylpropionitrile (DPN), an ERbeta selective ligand that we developed, is a chiral molecule, but it has been studied almost exclusively as the racemic mixture (rac-DPN, 1). Herein we report the development of an efficient enantioselective synthesis of the two isomers, R-DPN (3) and S-DPN (2), and we have compared the in vitro ligand binding affinities, coactivator binding affinities, recruitment potencies, and cellular transcriptional potencies of these isomers. Both enantiomers show a very high affinity and potency preference for ERbeta over ERalpha, typically in the range of 80-300-fold. Although the enantioselectivity is only modest (3-4-fold), the R-enantiomer is the higher affinity and more potent isomer. While ERbeta can be effectively and selectively stimulated by rac-DPN or by either R-DPN or S-DPN, R-DPN might be the preferred member of this isomeric series for biological studies of ERbeta function.

Estrogen receptor-beta agonist diarylpropionitrile: biological activities of R- and S-enantiomers on behavior and hormonal response to stress.[Pubmed:19074580]

Endocrinology. 2009 Apr;150(4):1817-25.

Estrogens have been shown to have positive and negative effects on anxiety and depressive-like behaviors, perhaps explained by the existence of two distinct estrogen receptor (ER) systems, ERalpha and ERbeta. The ERbeta agonist, diarylpropionitrile (DPN) has been shown to have anxiolytic properties in rats. DPN exists as a racemic mixture of two enantiomers, R-DPN and S-DPN. In this study, we compared R-DPN and S-DPN for their in vitro binding affinity, ability to activate transcription in vitro at an estrogen response element, and in vivo endocrine and behavioral responses. In vitro binding studies using recombinant rat ERbeta revealed that S-DPN has a severalfold greater relative binding affinity for ERbeta than does R-DPN. Furthermore, cotransfection of N-38 immortalized hypothalamic cells with an estrogen response element-luc reporter and ERbeta revealed that S-DPN is a potent activator of transcription in vitro, whereas R-DPN is not. Subsequently, we examined anxiety-like behaviors using the open-field test and elevated plus maze or depressive-like behaviors, using the forced swim test. Ovariectomized young adult female Sprague Dawley rats treated with racemic DPN, S-DPN, and the ERbeta agonist, WAY-200070, showed significantly decreased anxiety-like behaviors in both the open-field and elevated plus maze and significantly less depressive-like behaviors in the forced swim test compared with vehicle-, R-DPN-, or propylpyrazoletriol (ERalpha agonist)-treated animals. In concordance with the relative binding affinity and transcriptional potency, these results demonstrate that the S-enantiomer is the biologically active form of DPN. These studies also indicate that estrogen's positive effects on mood, including its anxiolytic and antidepressive actions, are due to its actions at ERbeta.

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