ChemicalBook Product Catalog Natural Products Flavonoids 2'-Hydroxy-2,4,4',5,6'-pentamethoxychalcone

2'-Hydroxy-2,4,4',5,6'-pentamethoxychalcone

Product Name2'-Hydroxy-2,4,4',5,6'-pentamethoxychalcone
CAS73694-15-2
MFC20H22O7
MW374.39
EINECS
MOL File73694-15-2.mol

Chemical Properties

Boiling point	586.1±50.0 °C(Predicted)
Density	1.214±0.06 g/cm3(Predicted)
storage temp.	2-8°C
solubility	DMSO: 2mg/mL, clear (warmed)
pka	6.79±0.40(Predicted)
form	powder
color	yellow to orange
InChI	1S/C20H22O7/c1-23-13-9-15(22)20(19(10-13)27-5)14(21)7-6-12-8-17(25-3)18(26-4)11-16(12)24-2/h6-11,22H,1-5H3/b7-6+
InChIKey	VHCQVGQULWFQTM-VOTSOKGWSA-N
SMILES	O(C)c1c(cc(c(c1)OC)\C=C\C(=O)c2c(cc(cc2O)OC)OC)OC

Safety Information

WGK Germany	WGK 3
Storage Class	11 - Combustible Solids

Usage And Synthesis

Uses

Rubone, a chalcone analog, is a modulator of miR-34a. Rubone upregulates miR-34a expression in a p53 dependent manner, downregulates the downstream target Bcl-2 and Cyclin D1 expression, and suppresses hepatocellular carcinoma (HCC) growth in vivo. Rubone enhances the anticancer effect of Paclitaxel (PTX; HY-B0015) in PTX-resistant prostate cancer cell lines by reversing the expression of miR-34a downstream targets[1][2][3].

Definition

ChEBI: Rubone is a member of chalcones.

Biological Activity

Rubone has strong anticancer activity. Rubone and paclitaxel (PTX) combination therapy retarded cancer cell growth, migration and cancer stem-like cells (CSC) population growth.', 'Rubone is a miR34a modulator th at specifically restores miR34a in hepatocellular carcinoma cells with wild-type or mutated p53. Rubone potently inhibits growth of hepatocellular carcinoma in a mouse xenograft model. Rubone does not effect the growth of nontumorigenic human hepatocytes.', 'Rubone is a miR34a modulator th at specifically restores miR34a in hepatocellular carcinoma cells.

in vivo

Rubone monotherapy (20 mg/kg loaded PEG-PCD micelles; iv for five doses every other day) or combination therapy with PTX (10 mg/kg for each drug loaded PEG-PCD micelles) significantly upregulates miR-34a expression in tumor. The combination therapy inhibits tumor growth. Rubone monotherapy failed to suppress tumor cell proliferation^[3].

Animal Model:	8 weeks old male nude mice transfected prostate cancer cells^[3]
Dosage:	20 mg/kg or 10 mg/kg for each drug (PTX and Rubone) loaded PEG-PCD micelles
Administration:	Intravenously for five doses every other day
Result:	Had little effect on body weight loss and inhibited tumor growth. Monotherapy or combination therapy with PTX significantly upregulated miR-34a expression in tumor. Alone or with PTX significantly reversed E-cadherin, Cyclin D1, and SIRT1 expression.

References

[1] Zhangang Xiao, et al. Small molecule targeting miR-34a for cancer therapy. Mol Cell Oncol. 2015 Feb 24;2(1):e977160. DOI:10.4161/23723556.2014.977160
[2] Lu Zhang, et al. MicroRNA-34 family: a potential tumor suppressor and therapeutic candidate in cancer. J Exp Clin Cancer Res. 2019 Feb 4;38(1):53. DOI:10.1186/s13046-019-1059-5
[3] Di Wen, et al. Micellar Delivery of miR-34a Modulator Rubone and Paclitaxel in Resistant Prostate Cancer. Cancer Res. 2017 Jun 15;77(12):3244-3254. DOI:10.1158/0008-5472.CAN-16-2355

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