2,3-BIS(4-HYDROXYPHENYL)-PROPIONITRILE Chemical Properties

Melting point:

200.0 to 204.0 °C

Boiling point:

449.4±35.0 °C(Predicted)

Density 

1.256±0.06 g/cm3(Predicted)

RTECS 

UG0900000

storage temp. 

-20°C

solubility 

DMSO: soluble10mg/mL, clear

pka

9.41±0.26(Predicted)

form 

powder

color 

white to beige

Water Solubility 

Soluble in 1eq. NaOH (30 mM), ethanol (100 mM), DMSO (100 mM), DMF (~30 mg/ml), and water (0.5 mg/ml at 25°C).

Stability:

Stable for 1 year from date of purchase as supplied. Solutions in DMSO or ethanol may be stored at -20°C for up to 1 month.

Safety Information

Hazard Codes 

Xi,N

Risk Statements 

36-50

Safety Statements 

26-61

RIDADR 

UN 3077 9 / PGIII

WGK Germany 

3

HS Code 

2926.90.4801

HazardClass 

9

2,3-BIS(4-HYDROXYPHENYL)-PROPIONITRILE Usage And Synthesis

Description

DPN (1428-67-7) is a potent estrogen ERβ receptor agonist. Displays a 70-fold selectivity over ERα, EC50 = 0.85 and 66 nM, respectively.1 Regulates expression of GluR1, 2 and 3 in rat hippocampus.2 Ameliorates portal hypertension in a carbon tetrachloride-induced liver cirrhosis rat model.3 Stimulates proliferation of androgen-independent prostate cancer cell line PC-3 via a novel pathway involving ERβ-mediated activation of β-catenin.4 A useful tool for elucidating the biological function of ERβ.5

Uses

2,3-Bis(4-hydroxyphenyl)propionitrile is an estrogen receptor β and α specific with pro- and anti-nociceptive actions in mice.

Definition

ChEBI: A nitrile that is acetonitrile in which one of the hydrogens is replaced by a 4-hydroxyphenyl group while a second hydrogen is replaced by a 4-hydroxybenzyl group. It is a specific agonist for estrogen receptor beta (ERbeta).

Biological Activity

Highly potent estrogen ER β receptor agonist with a 70-fold selectivity over ER α (EC 50 values are 0.85 and 66 nM respectively). Relaxes mesenteric arteries in vitro .

Biochem/physiol Actions

2,3-Bis(4-hydroxyphenyl)-propionitrile (Diarylprepionitrile, DPN) is an ERβ-selective agonist; IC50 = 15nM. DPN protects WT and ARKO mice and significantly decreases IL-1β following LPS treatment in young adult-derived microglia. PPT (Cat. No.H6036, ERa agonist) enhances cell proliferation, while DPN inhibits it. PPT increases Bcl-2 expression, while DPN decreases it. DPN also elevates Bax expression. DPN induces a dose-dependent increase on vitellogenin synthesis. PPT and DPN are effective in dynamically, but differentially regulating intracellular calcium signaling in hippocampal neurons. DPN is more efficacious than PPT in potentiating a physiological concentration of glutamate-induced intracellular Ca2+ rise in these neurons. DPN prevents the development of prostatic hyperplasia and inflammation in testosterone-treated LuRKO mice.

storage

-20°C (desiccate)

References

[1] MARVIN J. MEYERS. Estrogen Receptor-β Potency-Selective Ligands: Structure−Activity Relationship Studies of Diarylpropionitriles and Their Acetylene and Polar Analogues[J]. Journal of Medicinal Chemistry, 2001, 44 24: 4230-4251. DOI:10.1021/jm010254a
[2] ELIZABETH M. WATERS . Estrogen receptor alpha and beta specific agonists regulate expression of synaptic proteins in rat hippocampus[J]. Brain Research, 2009, 1290: Pages 1-11. DOI:10.1016/j.brainres.2009.06.090
[3] CHENG-GANG ZHANG. Role of estrogen receptor β selective agonist in ameliorating portal hypertension in rats with CCl4-induced liver cirrhosis.[J]. World Journal of Gastroenterology, 2016, 22 18: 4484-4500. DOI:10.3748/wjg.v22.i18.4484
[4] ANA PAOLA G. LOMBARDI. Estrogen receptor beta (ERβ) mediates expression of β-catenin and proliferation in prostate cancer cell line PC-3[J]. Molecular and Cellular Endocrinology, 2016, 430: Pages 12-24. DOI:10.1016/j.mce.2016.04.012
[5] WILLIAM R. HARRINGTON . Activities of estrogen receptor alpha- and beta-selective ligands at diverse estrogen responsive gene sites mediating transactivation or transrepression[J]. Molecular and Cellular Endocrinology, 2003, 206 1: Pages 13-22. DOI:10.1016/s0303-7207(03)00255-7

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