| Chemical & Physical Properties | |
|---|---|
| CAS Number | 84573-16-0 |
| Catalog No. | 2A-9066655 |
| Chinese Name | 楝酰胺 |
| Synonyms | Rocaglamide |
| Molecular Formula | C29H31NO7 |
| Molecular Weight | 505.56 |
| Purity | ≥96 (HPLC) |
| Density | 1.3±0.1 g/cm3 |
| Boiling Point | 667.3±55.0 °C at 760 mmHg |
| Appearance | film |
| Storage Condition | Sealed in a cool, dry environment |
| Application | Rocaglamide is a potent inhibitor of NF-κB activation. |
| SMILES | N(C)(C)C(=O)[C@H]1[C@H]([C@@]2([C@@](Oc5c2c(cc(c5)OC)OC)([C@@H]1c4ccccc4)c3ccc(cc3)OC)O)O |
| InChI | 1S/C29H31NO7/c1-30(2)27(32)23-24(17-9-7-6-8-10-17)29(18-11-13-19(34-3)14-12-18)28(33,26(23)31)25-21(36-5)15-20(35-4)16-22(25)37-29/h6-16,23-24,26,31,33H,1-5H3/t23-,24-,26-,28+,29+/m1/s1 |
| InChI Key | DAPAQENNNINUPW-IDAMAFBJSA-N |
| NACRES Code | NA.77 |
| UNSPSC | 12352200 |
| Hazard Symbols | transportation |
| MSDS | msds/66655_1_84573_16_0.pdf |
| Bioactivity | Rocaglamide is a potent NF-κB activation inhibitor. Related Catalog Signaling Pathways >> NF-κB >> NF-κB Research Areas >> Others Target HSF1:50 nM (IC50) In Vitro Rocaglamide enhances TRAIL-induced apoptosis in resistant HCC cells. Treatment with Rocaglamide alone leads to apoptosis in 9% HepG2 and 11% Huh-7 cells and treatment with TRAIL induces apoptosis in 16% HepG2 and 17% Huh-7 cells. However, the combination of Rocaglamide and TRAIL induces apoptosis in 55% HepG2 and 57% Huh-7 cells, which is evidently more than an additive effect. A similar result is obtained by measurement of cell viability using crystal violet staining. Rocaglamide has the potential to sensitize highly chemoresistant HepG2 and Huh-7 cells to TRAIL-based therapy[2]. In Vivo Tumor volumes in the Rocaglamide-treated group are 45±12% compared with the control group. Rocaglamide significantly suppresses tumor growth compared with that in the control group. Treatment with Rocaglamide does not lead to any reduction in body weight and no apparent signs of toxicity are observed in the mice during the treatment, suggesting that Rocaglamide is generally tolerated well[2]. Cell Assay HepG2 and Huh-7 cells (1×104/well) are seeded in 96-well plates in complete culture medium and incubated for 24 h. The cells are then exposed to 100 nM Rocaglamide and/or 100 ng/mL TRAIL for 24 h. The control cells are treated with DMSO at a concentration equal to that used for the drug-treated cells. The complete culture medium is then removed and MTT (200 μL, 0.5 mg/mL in 10% FBS-containing DMEM) is added to each well and the plate is incubated for 2 h at 37°C in a humidified incubator. The solution is then removed from the wells and 200 μL DMSO is added to each well prior to agitation. The absorbance at 570 nm is read using a microplate reader (Bio-Tek ELx800). The value for the vehicle-treated cells is considered to indicate 100% viability. Furthermore, a crystal violet assay is carried out. Briefly, the cells (1×105/mL) are seeded in a 12 well plate for 12 h, and treated with TRAIL (0-100 ng/mL) and/or RocA(1-100 nM) for 12 h. The treated cells are washed with phosphate-buffered saline (PBS), fixed with 4% paraformaldehyde for 15 min, and stained using crystal violet for a further 30 min[2]. Animal Admin Mice[2] The Huh-7 cells (3×106), suspended in 100 μL mix (equal volumes of DMEM and Matrigel), are implanted subcutaneously into the right flank of 10 female SCID mice (6-week-old) and then randomly divided into two equal groups, one of which received an intraperitoneal injection of Rocaglamide (2.5 mg/kg in 80 μL olive oil; n=5) and the other, used as a vehicle control, received olive oil alone (n=5). These treatments are performed once daily for 32 days and the tumor volumes and body weights of the animals are measured twice a week. The tumor volumes (mm3) are calculated using the following formula: Tumor volume=LS2/2, where L is the longest diameter and S is the shortest. At the end of the experiments, the mice are sacrificed and tumor samples are harvested, fixed in formalin and embedded in paraffin as tissue sections for immunohistochemical analysis. References [1]. Santagata S, et al. Tight coordination of protein translation and heat shock factor 1 activation supports the anabolic malignant state. Science. 2013 Jul 19; 341(6143): 1238303. [2]. Luan Z, et al. Rocaglamide overcomes tumor necrosis factor-related apoptosis-inducing ligand resistance in hepatocellular carcinoma cells by attenuating the inhibition of caspase-8 through cellular FLICE-like-inhibitory protein downregulation. Mol Med Rep Chemical & Physical Properties Density 1.3±0.1 g/cm3 Boiling Point 667.3±55.0 °C at 760 mmHg Molecular Formula C29H31NO7 Molecular Weight 505.559 Flash Point 357.4±31.5 °C Exact Mass 505.210052 PSA 97.69000 LogP 3.10 Appearance of Characters colorless Vapour Pressure 0.0±2.1 mmHg at 25°C Index of Refraction 1.634 InChIKey DAPAQENNNINUPW-IDAMAFBJSA-N SMILES COc1ccc(C23Oc4cc(OC)cc(OC)c4C2(O)C(O)C(C(=O)N(C)C)C3c2ccccc2)cc1 Storage condition ?20°C |
| Use of | Rocaglamide is a potent NF-κB activation inhibitor. Properties Articles25 Name rocaglamide Synonym More Synonyms Rocaglamide Biological Activity Description Rocaglamide is a potent NF-κB activation inhibitor. Related Catalog Signaling Pathways >> NF-κB >> NF-κB Research Areas >> Others HSF1:50 nM (IC50) References [1]. Santagata S, et al. Tight coordination of protein translation and heat shock factor 1 activation supports the anabolic malignant state. Science. 2013 Jul 19; 341(6143): 1238303. [2]. Luan Z, et al. Rocaglamide overcomes tumor necrosis factor-related apoptosis-inducing ligand resistance in hepatocellular carcinoma cells by attenuating the inhibition of caspase-8 through cellular FLICE-like-inhibitory protein downregulation. Mol Med Rep Chemical & Physical Properties Molecular Formula C29H31NO7 Exact Mass 505.210052 PSA 97.69000 Appearance of Characters colorless Index of Refraction 1.634 InChIKey DAPAQENNNINUPW-IDAMAFBJSA-N |
| Transport Info | Shipping Name: UN |
| MSDS Transport Info | Module 14. Shipping information 14.1 UN dangerous goods number European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.2 United Nations shipping name European Land Transport Dangerous Regulations: Non-dangerous goods IMDG Code: Non-dangerous goods International air transport dangerous goods regulations: non-dangerous goods 14.3 Transport hazard categories European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.4 Package group European Land Transport Dangerous Regulations: -International Maritime Dangerous Regulations: -International Air Transport Dangerous Regulations: - 14.5 Environmental hazards European Land Transport Danger Regulations: No International Maritime Danger Regulations International Air Transport Danger Regulations: No Marine pollutants (yes/no): No 14.6 Special reminder to users No data available The above information is believed to be correct, but is not all-inclusive and should be used as a guide only. The information in this document is based on our current knowledge and is Correct safety instructions apply to this product. This information does not represent a warranty as to the properties of this product. See reverse side of invoice or packing slip. |
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