| Catalogue number |
C108558 |
| Chemical name | Genipin |
| CAS Number | 6902-77-8 |
| Synonyms | (1R,4aS,7aS)-1-hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-4-carboxylic acid methyl ester |
| Molecular Weight | C11H14O5 |
| Formula | 226.2 |
| Purity | 98% |
| Physical Description | White powder |
| Solvent | Chloroform, Dichloromethane,DMSO |
| Storage | Stored at 2-8°C, Protected from air and light, refrigerate or freeze |
| Applications | Genipin is an excellent natural cross-linker for proteins, collagen, gelatin, and chitosan cross-linking. It has a low acute toxicity, with LD50 i.v. 382 mg/kg in mice, therefore, much less toxic than glutaraldehyde and many other commonly used synthetic cross-linking reagents. Furthermore, genipin can be used as a regulating agent for drug delivery, as the raw material for gardenia blue pigment preparation, and as the intermediate for alkaloid syntheses.
In vitro experiments have shown that genipin blocks the action of the enzyme uncoupling protein 2. Uncoupling protein-2 (UCP2) is known to suppress mitochondrial reactive oxygen species (ROS) production and is employed by drug-resistant cancer cells to mitigate oxidative stress. Using the drug-sensitive HL-60 cells and the drug-resistant MX2 subline as model systems, we show that genipin, a UCP2 inhibitor, sensitizes drug-resistant cells to cytotoxic agents. Increased MX2 cell death was observed upon co-treatment with genipin and different doses of menadione, doxorubicin, and epirubicin. DCFH-DA fluorimetry revealed that the increase in MX2 cell death was accompanied by enhanced cellular ROS levels. The drug-induced increase in ROS was linked to genipin-mediated inhibition of mitochondrial proton leak. State 4 and resting cellular respiratory rates were higher in the MX2 cells in comparison to the HL-60 cells, and the increased respiration was readily suppressed by genipin in the MX2 cells. UCP2 accounted for a remarkable 37% of the resting cellular oxygen consumption indicating that the MX2 cells are functionally reliant on this protein. Higher amounts of UCP2 protein were detected in the MX2 versus the HL-60 mitochondria. The observed effects of genipin were absent in the HL-60 cells pointing to the selectivity of this natural product for drug-resistant cells. The specificity of genipin for UCP2 was confirmed using CHO cells stably expressing UCP2 in which genipin induced an ~22% decrease in state 4 respiration. These effects were absent in empty vector CHO cells expressing no UCP2. Thus, the chemical inhibition of UCP2 with genipin sensitizes multidrug-resistant cancer cells to cytotoxic agents.
It is also used for pharmaceutical purposes, such as choleretic action for liver diseases control.
|
| References | 1. Planta Med., 2001, 67(9), 807-810.
2. Journal of Biomedical Materials Research Part A, 2005, 75A(4), 917-927.
3. Phytochemistry, 1983, 22(8), 1761-1765.
4. J Biomed Mater Res A., 2010, 95(2), 465-475.
|
| Guestbook |
|
The packaging of the product may have turned upside down during transportation, resulting in the product adhering to the neck or cap of the vial. take the vial out of its packaging and gently shake to let the compounds fall to the bottom of the vial. for liquid products, centrifuge at 200-500 RPM to gather the liquid at the bottom of the vial. try to avoid loss or contamination during handling.
| Size | Price(USD) | Discount |
| 5mg | Inquiry | N/A |
| 10mg | Inquiry | N/A |
| 25mg | Inquiry | N/A |
Orders can be placed by Emails. All orders received will be shipped in the next day if the stock is available.
To place an order, please provide the following information.
1) Your name and telephone number
2) Purchase order number
3) Product number, package size, description, and quantity
4) Shipping and billing addresses
Sent to your order to our email: info@coompo.com
If you have any questions about discounts or dealer discount, please send us a message. We will be glad to help.
