| Identification | Back Directory | [Name]
2'-HYDROXY-2,4,4',5,6'-PENTAMETHOXYCHALCONE | [CAS]
73694-15-2 | [Synonyms]
RUBONE
Rubone >=98% (HPLC)
2'-HYDROXY-2,4,4',5,6'-PENTAMETHOXYCHALCONE
2'-HYDROXY-2,4,5,4',6'-PENTAMETHOXYCHALCONE
2,4,5-Trimethoxybenzylidene(2-hydroxy-4,6-dimethoxyacetophenone)
Rubone~2,4,5-Trimethoxybenzylidene(2-hydroxy-4,6-dimethoxyacetophenone)
2-Propen-1-one, 1-(2-hydroxy-4,6-dimethoxyphenyl)-3-(2,4,5-trimethoxyphenyl)-, (2E)- | [Molecular Formula]
C20H22O7 | [MDL Number]
MFCD00274772 | [MOL File]
73694-15-2.mol | [Molecular Weight]
374.38 |
| Chemical Properties | Back Directory | [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) | [form ]
powder | [pka]
6.79±0.40(Predicted) | [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 |
| Hazard Information | Back Directory | [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 growthmigration 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.
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| [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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| Company Name: |
Synchem OHG
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+49 5662 408730 |
| Website: |
www.synchem.de |
| Company Name: |
Energy Chemical
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021-58432009 400-005-6266 |
| Website: |
http://www.energy-chemical.com |
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