Prinaberel

Names

[ Name ]:
Prinaberel

[Synonym ]:
BIDD:ER0139
SDZ 205-557 hydrochloride
UNII-A9C8MNF7CA
2-(3-Fluoro-4-hydroxyphenyl)-7-vinyl-1,3-benzoxazol-5-ol
1x7b
5-Benzoxazolol, 7-ethenyl-2-(3-fluoro-4-hydroxyphenyl)-
Prinaberel
ERB 041

Biological Activity

[Description]:

Prinaberel(ERB-041) is a potent and selective ERbeta agonist; being >200-fold selective for ERbeta.IC50 value:Target: ERbeta agonistin vitro: Treatment with ERβ selective estrogen agonists liquiritigenin and ERB-041 reduced the ability to invade a reconstituted basement membrane and to migrate in response to the cellular stimulus [1]. Pretreatment the PMs with ERB-041 resulted in a significant inhibition of LPS-induced iNOS expression and NF-kappaB activation by preventing its nuclear translocation [3].in vivo: Tumor numbers and volume were reduced by 60% and 84%, respectively, in the Erb-041-treated group as compared with UVB (alone) control. This inhibition in tumorigenesis was accompanied by the decrease in proliferating cell nuclear antigen (PCNA), cyclin D1, VEGF, and CD31, and an increase in apoptosis [2].

[Related Catalog]:

Signaling Pathways >> Others >> Estrogen Receptor/ERR

Research Areas >> Cancer

[References]

[1]. Hinsche O, et al. Estrogen receptor β selective agonists reduce invasiveness of triple-negative breast cancer cells. Int J Oncol. 2015 Feb;46(2):878-84.

[2]. Chaudhary SC, et al. Erb-041, an estrogen receptor-β agonist, inhibits skin photocarcinogenesis in SKH-1 hairless mice by downregulating the WNT signaling pathway. Cancer Prev Res (Phila). 2014 Feb;7(2):186-98.

[3]. Xiu-li W, et al. ERB-041, a selective ER beta agonist, inhibits iNOS production in LPS-activated peritoneal macrophages of endometriosis via suppression of NF-kappaB activation. Mol Immunol. 2009 Jul;46(11-12):2413-8.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
451.6±45.0 °C at 760 mmHg

[ Melting Point ]:
250-252ºC

[ Molecular Formula ]:
C₁₅H₁₀FNO₃

[ Molecular Weight ]:
271.243

[ Flash Point ]:
226.9±28.7 °C

[ Exact Mass ]:
271.064484

[ PSA ]:
66.49000

[ LogP ]:
3.97

[ Vapour Pressure ]:
0.0±1.1 mmHg at 25°C

[ Index of Refraction ]:
1.695

[ Storage condition ]:
2-8℃

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302-H319

[ Precautionary Statements ]:
P305 + P351 + P338

[ RIDADR ]:
NONH for all modes of transport

Synthetic Route

Click to get detail synthetic route

Articles

Genistein increases estrogen receptor beta expression in prostate cancer via reducing its promoter methylation.

J. Steroid Biochem. Mol. Biol. 152 , 62-75, (2015)

Genistein has protective effects against prostate cancer (PCa) but whether this protection involves an estrogen receptor (ER) β dependent mechanism has yet to be elucidated. ER-β has a tumor suppresso...

Drug and cell type-specific regulation of genes with different classes of estrogen receptor beta-selective agonists.

PLoS ONE 7 , (2009)

Estrogens produce biological effects by interacting with two estrogen receptors, ERalpha and ERbeta. Drugs that selectively target ERalpha or ERbeta might be safer for conditions that have been tradit...

Mouse leydig cells with different androgen production potential are resistant to estrogenic stimuli but responsive to bisphenol a which attenuates testosterone metabolism.

PLoS ONE 8 , e71722, (2013)

It is well known that estrogens and estrogen-like endocrine disruptors can suppress steroidogenic gene expression, attenuate androgen production and decrease differentiation of adult Leydig cell linea...