OrobolCAS# 480-23-9 |
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| Cas No. | 480-23-9 | SDF | Download SDF |
| PubChem ID | 5281801 | Appearance | Yellow powder |
| Formula | C15H10O6 | M.Wt | 286.2 |
| Type of Compound | Flavonoids | Storage | Desiccate at -20°C |
| Solubility | Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc. | ||
| Chemical Name | 3-(3,4-dihydroxyphenyl)-5,7-dihydroxychromen-4-one | ||
| SMILES | C1=CC(=C(C=C1C2=COC3=CC(=CC(=C3C2=O)O)O)O)O | ||
| Standard InChIKey | IOYHCQBYQJQBSK-UHFFFAOYSA-N | ||
| Standard InChI | InChI=1S/C15H10O6/c16-8-4-12(19)14-13(5-8)21-6-9(15(14)20)7-1-2-10(17)11(18)3-7/h1-6,16-19H | ||
| General tips | For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months. We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months. Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it. |
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| About Packaging | 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial. 2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial. 3. Try to avoid loss or contamination during the experiment. |
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| Shipping Condition | Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request. | ||
| Description | 1. Isoflavonoid compounds, orobol, psi-tectorigenin and genistein have been implicated as inhibitors of tyrosine-specific protein kinase and phosphatidylinositol turnover. 2. Orobol has sensitization effect, it can produce produced cisplatin (DDP) sensitivity in human ovarian carcinoma cells by inducing apoptosis through the MT-dependent signaling pathway. 3. Orobol and platelet derived growth factor (PDGF) regulate paclitaxel (PX) sensitivity by reciprocally altering the proportion of tubulin isotype expression and PX-induced apoptotic signaling. 4. Orobol exhibits antiviral effects against some animal viruses, addition of the compound after virus entry inhibits the appearance of late viral protein synthesis in Vesicular Stomatitis Virus, influenza, or vaccinia virus-infected cells, but has no effect on poliovirus protein synthesis. |
| Targets | PI3K | Caspase | Bcl-2/Bax | Calcium Channel | Antifection | Influenza virus |
Orobol Dilution Calculator
Orobol Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 3.4941 mL | 17.4703 mL | 34.9406 mL | 69.8812 mL | 87.3515 mL |
| 5 mM | 0.6988 mL | 3.4941 mL | 6.9881 mL | 13.9762 mL | 17.4703 mL |
| 10 mM | 0.3494 mL | 1.747 mL | 3.4941 mL | 6.9881 mL | 8.7352 mL |
| 50 mM | 0.0699 mL | 0.3494 mL | 0.6988 mL | 1.3976 mL | 1.747 mL |
| 100 mM | 0.0349 mL | 0.1747 mL | 0.3494 mL | 0.6988 mL | 0.8735 mL |
| * Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations. | |||||
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Differential sensitization by orobol in proliferating and quiescent human ovarian carcinoma cells.[Pubmed:11172601]
Int J Oncol. 2001 Feb;18(2):337-42.
The object of this study was to determine how phosphatidylinositol (PI) signaling pathway is involved in the regulation of cisplatin (DDP) sensitivity. Clonogenic survival assay was used to determine the effect of Orobol, a potent PI4-kinase inhibitor, on DDP sensitivity in human ovarian carcinoma 2008 cells. Orobol enhanced sensitivity to DDP in 2008 cells by a factor of 2.1+/-0.4 (SD)-fold (N=3; P<0.01). Sensitization was specific for proliferating cells. Orobol did not alter DDP sensitivity in quiescent cells. Orobol also produced a 2-fold increase in sensitivity to DDP in proliferating 2008/C13*5.25 DDP-resistant variants. Our studies indicated that Orobol-induced sensitization depended on the presence of proliferating cells in G2+M phase of the cell cycle. Orobol did not modulate the cellular accumulation of DDP nor did it alter the CdCl2 sensitivity, suggesting that the amount of platinated-DNA was not changed by Orobol treatment. However, Orobol rendered 2008 cells resistant to rhodamin 123 by 5.7+/-1.7 (SD)-fold (N=3, P<0.01). Since sensitivity to rhodamin 123 is indicative of mitochondrial membrane potential, these results imply that mitochondrial alterations may be an important component of the Orobol sensitization effect in these cells.
Enhancement of sensitivity to cisplatin by orobol is associated with increased mitochondrial cytochrome c release in human ovarian carcinoma cells.[Pubmed:12893210]
Gynecol Oncol. 2003 Aug;90(2):413-20.
OBJECTIVES: Based on our previous report showing that Orobol, a potent phosphatidylinositol 4-kinase (PI4K) inhibitor, produced cisplatin (DDP) sensitivity, we have determined the mechanism of Orobol-sensitization effect. METHODS AND RESULTS: Orobol produced >2-fold DDP sensitivity in human ovarian carcinoma 2008 cells and its DDP-resistant variant 2008/C13*5.25 cells (C13). Because Orobol had no effect on conventional mechanisms such as DDP accumulation or cellular metallothionein and glutathione content, we have focused on the apoptotic signaling pathway. Orobol induced a significant increase in apoptosis in DDP-treated cells, as estimated by frequency of condensed nuclear chromatin with Hoechst 33342 stain, although Orobol alone did not have any effect on apoptotic potential. The caspase-3-inhibiting peptide Ac-DEVD-CHO completely inhibited the Orobol sensitization effect but did not block DDP cell cytotoxicity per se. Orobol rendered both of these cells resistant to rhodamine 123 (Rh) by more than 2.5-fold, indicating significant decrease of mitochondrial membrane potential (DeltaPsim). Confocal laser microscopy of cells stained with the mitochondria (MT)-specific dye Rh revealed that Orobol decreased Rh-fluorescent intensity. Electron microscopy of these cells showed that Orobol induced swelling and condensation of MT. Orobol suppressed both naturally expressed and the DDP-induced Bcl-2 expression significantly. Orobol and DDP treatment reduced cytochrome c level in MT determined by Western blot analysis, indicating increased amount of cytochrome c release from MT, whereas Orobol alone did not alter the amount of cytochrome c in MT. CONCLUSIONS: These results indicate that Orobol produced DDP sensitivity in human ovarian carcinoma cells by inducing apoptosis through the MT-dependent signaling pathway.
Isoflavonoids, genistein, psi-tectorigenin, and orobol, increase cytoplasmic free calcium in isolated rat hepatocytes.[Pubmed:1734888]
Biochem Biophys Res Commun. 1992 Jan 31;182(2):894-9.
Isoflavonoid compounds, genistein, psi-tectorigenin and Orobol have been implicated as inhibitors of tyrosine-specific protein kinase and phosphatidylinositol turnover. These compounds have been frequently used as a pharmacological tool to assess signal transduction pathways in various cell systems. In the course of analyzing signaling pathways in rat hepatocytes, we obtained an unexpected finding that these compounds transiently increase cytoplasmic free calcium. Since the Ca2+ mobilizing effect was observed in 1 microM calcium containing buffer, the source of the Ca2+ may be intracellular stores. Thus, when interpreting data obtained using these compounds, caution is needed.
Differential regulation of the cytotoxicity activity of paclitaxel by orobol and platelet derived growth factor in human ovarian carcinoma cells.[Pubmed:17549368]
Oncol Rep. 2007 Jul;18(1):195-201.
Paclitaxel (PX) binds to and stabilizes tubulin, preventing depolymerization, and resulting in cell death. Based on a previous report showing the activity of phosphatidylinositol kinase (PIK) on tubulin, we investigated the effect of the PI4K inhibitor Orobol and the PI3K activator platelet derived growth factor (PDGF) on PX sensitivity. Drug sensitivity was examined by classical colony forming assay. Tubulin isotype expression was determined by semi-quantitative RT-PCR. Microtubule texture was observed by laser confocal microscope using anti-beta-tubulin antibody. Apoptotic activity was estimated by frequency of condensed nuclear chromatin with Hoechst 33342 stain. Orobol enhanced PX sensitivity of human ovarian carcinoma 2008 cells by 18.9+/-1.2-fold (N=3; P<0.01). In contrast, pretreatment with PDGF rendered cells resistant to PX by 2.3+/-0.4-fold (N=3; P<0.01). Neither Orobol nor PDGF showed any effect on cell growth. Orobol produced a 2.5-fold sensitization in cisplatin-resistant 2008/C13*5.25 (C13) cells, and PDGF rendered the cells 2.3-fold resistant to PX. Orobol suppressed the beta 4a-tubulin isotype expression by 85% and other isotypes by 20%. In contrast, PDGF induced beta 4a-tubulin isotype expression by 1.3-fold, while it supressed all the other isotypes by 20-40%. Orobol produced thick microtubules and PDGF generated ring condensed microtubules. Orobol promoted PX-induced apoptosis, while PDGF caused 50% reduction of apoptosis. These results indicate that Orobol and PDGF regulate PX sensitivity by reciprocally altering the proportion of tubulin isotype expression and PX-induced apoptotic signaling.
