| Identification | Back Directory | [Name]
BISPHENOL A-(3-CHLORO-2-HYDROXYPROPYL)-& | [CAS]
227947-06-0 | [Synonyms]
CS-2260
EPI-001
BADGE-HCl-H2O
BISPHENOL A-(3-CHLORO-2-HYDROXYPROPYL)-&
BISPHENOL A 3-CHLORO-2-HYDROXYPROPYL DIH
3-(4-(2-(4-(3-chloro-2-hydroxypropoxy)phenyl)propan-2-yl)phenoxy)propane-1,2-diol
3-[4-[1-[4-(3-Chloro-2-hydroxypropoxy)phenyl]-1-methylethyl]phenoxy]-1,2-propanediol
2-[4-(3-chloro-2-hydroxypropyloxy)phenyl]-2-[4-(2,3-dihydroxypropyloxy)phenyl]propane
1,2-Propanediol, 3-[4-[1-[4-(3-chloro-2-hydroxypropoxy)phenyl]-1-methylethyl]phenoxy]-
BADGE-HCl-H2O, 2-[4-(3-Chloro-2-hydroxypropyloxy)phenyl]-2-[4-(2,3-dihydroxypropyloxy)phenyl]propane
Bisphenol A (3-chloro-2-hydroxypropyl) (2,3-dihydroxypropyl) ether,2-[4-(3-Chloro-2-hydroxypropyloxy)phenyl]-2-[4-(2,3-dihydroxypropyloxy)phenyl]propane, BADGE-HCl-H2O | [EINECS(EC#)]
200-258-5 | [Molecular Formula]
C21H27ClO5 | [MDL Number]
MFCD02683414 | [MOL File]
227947-06-0.mol | [Molecular Weight]
394.892 |
| Chemical Properties | Back Directory | [Melting point ]
67 °C | [Boiling point ]
601.0±55.0 °C(Predicted) | [density ]
1.228±0.06 g/cm3(Predicted) | [storage temp. ]
2-8°C
| [solubility ]
DMSO: soluble15mg/mL, clear | [form ]
powder | [pka]
13.13±0.20(Predicted) | [color ]
white to beige | [Major Application]
cleaning products
cosmetics
food and beverages
personal care | [InChI]
InChI=1S/C21H27ClO5/c1-21(2,15-3-7-19(8-4-15)26-13-17(24)11-22)16-5-9-20(10-6-16)27-14-18(25)12-23/h3-10,17-18,23-25H,11-14H2,1-2H3 | [InChIKey]
HDTYUHNZRYZEEB-UHFFFAOYSA-N | [SMILES]
C(O)C(O)COC1=CC=C(C(C2=CC=C(OCC(O)CCl)C=C2)(C)C)C=C1 |
| Safety Data | Back Directory | [Hazard Codes ]
Xi | [Risk Statements ]
36/37/38 | [Safety Statements ]
26-36 | [WGK Germany ]
3
| [HS Code ]
29072300 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 |
| Hazard Information | Back Directory | [Uses]
EPI-001 is a selective peroxisome proliferator-activated receptor-gamma modulator that inhibits androgen receptor expression and activity in prostate cancer. It is a novel androgen receptor antagonists that has the potential for treating prostate cancer. | [Definition]
ChEBI: Bisphenol A (3-chloro-2-hydroxypropyl) (2,3-dihydroxypropyl) ether is the (3-chloro-2-hydroxypropyl) (2,3-dihydroxypropyl) diether of bisphenol A; a small molecule that inhibits transactivation of the AR amino-terminal domain (NTD). It has a role as an androgen antagonist. It is an organochlorine compound and a diether. It is functionally related to a bisphenol A and a glycerol. | [Biological Activity]
epi-001 is a small-molecule inhibitor of androgen receptor n-terminal domain. epi-001 could target the amino terminal domain of the ar and inhibit the protein-protein interactions which are necessary for ar transcriptional activity. the androgen receptor (ar) is involved in mediating the actions of male sex steroids. amplification and over-expression of androgen receptor gene may result in hormone-refractory prostate cancer [1]. | [in vitro]
epi-001 inhibited the ligand-dependent argal4 transcriptional activity in lncap cells and the ligand-independent argal4 transcriptional activity in the crpc c4-2 cell line. in a panel of cell lines, epi-001 treatment decreased the mrna expression level of ar protein after 8 and 16 h treatment, such as androgen sensitive pca, crpc, lncap, c4-2, and lapc4 cell line. epi-001 dose-dependently inhibited the pca/crpc cell growth [2]. | [in vivo]
intravenous injection of epi-001 significantly reduced the weight of benign prostates and blocked the growth of prostate cancer xenograft from noncastrated mature mice. epi-001 caused tumor regression of crpc. in male mice bearing lncap xenografts, after treated with epi- 001 by i.v. injection for 2 weeks, the tumor size was less than half of the control group [3]. | [References]
andersen r j, mawji n r, wang j, et al. regression of castrate-recurrent prostate cancer by a small-molecule inhibitor of the amino-terminus domain of the androgen receptor[j]. cancer cell, 2010, 17(6): 535-546.brand l j, olson m e, ravindranathan p, et al. epi-001 is a selective peroxisome proliferator-activated receptor-gamma modulator with inhibitory effects on androgen receptor expression and activity in prostate cancer[j]. oncotarget, 2015, 6(6): 3811.sadar m d. small molecule inhibitors targeting the “achilles' heel” of androgen receptor activity[j]. cancer research, 2011, 71(4): 1208-1213. |
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