EBPCAldose reductase inhibitor CAS# 4450-98-0 |
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Quality Control & MSDS
Number of papers citing our products
Chemical structure
3D structure
| Cas No. | 4450-98-0 | SDF | Download SDF |
| PubChem ID | 54677973 | Appearance | Powder |
| Formula | C14H15NO4 | M.Wt | 261.28 |
| Type of Compound | N/A | Storage | Desiccate at -20°C |
| Solubility | Soluble to 100 mM in DMSO and to 50 mM in ethanol | ||
| Chemical Name | ethyl 1-benzyl-4-hydroxy-5-oxo-2H-pyrrole-3-carboxylate | ||
| SMILES | CCOC(=O)C1=C(C(=O)N(C1)CC2=CC=CC=C2)O | ||
| Standard InChIKey | IGYRPDIWSYGHMY-UHFFFAOYSA-N | ||
| Standard InChI | InChI=1S/C14H15NO4/c1-2-19-14(18)11-9-15(13(17)12(11)16)8-10-6-4-3-5-7-10/h3-7,16H,2,8-9H2,1H3 | ||
| 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 | Potent aldose reductase inhibitor. Improves the cytotoxicity of anticancer reagents such as cisplatin and doxorubicin in HeLa cervical carcinoma cells through an increase in ERK activity. |
EBPC Dilution Calculator
EBPC Molarity Calculator
| 1 mg | 5 mg | 10 mg | 20 mg | 25 mg | |
| 1 mM | 3.8273 mL | 19.1366 mL | 38.2731 mL | 76.5462 mL | 95.6828 mL |
| 5 mM | 0.7655 mL | 3.8273 mL | 7.6546 mL | 15.3092 mL | 19.1366 mL |
| 10 mM | 0.3827 mL | 1.9137 mL | 3.8273 mL | 7.6546 mL | 9.5683 mL |
| 50 mM | 0.0765 mL | 0.3827 mL | 0.7655 mL | 1.5309 mL | 1.9137 mL |
| 100 mM | 0.0383 mL | 0.1914 mL | 0.3827 mL | 0.7655 mL | 0.9568 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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Barriers to the evidence-based patient choice (EBPC) consultation.[Pubmed:12191542]
Patient Educ Couns. 2002 Jun;47(2):179-85.
This study was conducted to explore barriers to the implementation of the 'evidence-based patient choice' (EBPC) consultation in medical practice. The theory behind EBPC encompasses the idea that patients should be provided with evidence-based information in a way that facilitates their ability to make choices or decisions about their health care. Semi-structured interviews were conducted with purposively selected general practitioners (GPs) (n=11), hospital doctors (n=10), practice nurses (n=5), academics (n=11) and lay people (n=8). Qualitative analyses of participants' responses were conducted to identify key themes and categories. Lack of medical evidence per se and evidence relevant to individual patients were the most commonly reported barriers to the EBPC consultation. Other barriers included: doctors' attitudes, limited time for doctors to keep up with the evidence and to introduce evidence into the consultation; economic and resource constraints and a lack of technical resources and training to enable doctors to practice this type of approach.
Inhibition of aldose reductase enhances HeLa cell sensitivity to chemotherapeutic drugs and involves activation of extracellular signal-regulated kinases.[Pubmed:12394272]
Anticancer Drugs. 2002 Sep;13(8):859-68.
Changes in glucose metabolism during diabetes are linked to an increased risk for the development of cancer. Increased activity of aldose reductase, the rate-limiting polyol pathway enzyme that converts glucose into sorbitol, mediates pathologies associated with diabetes and is thought to be involved in increased resistance to chemotherapeutic drugs. Thus, increased intracellular sorbitol levels may serve a protective function in cancer cells. In these studies we determined whether an inhibitor of aldose reductase could enhance the effectiveness of anticancer agents. Our findings indicate that treatment with the aldose reductase inhibitor, ethyl 1-benzyl-3-hydroxy-2(5H)-oxopyrrole-4-carboxylate (EBPC), enhances the cytotoxic effects of the anticancer agents doxorubicin and cisplatin in HeLa cervical carcinoma cells. To establish a mechanistic basis for the increased cytotoxicity by EBPC, we examined the activity of the extracellular signal-regulated kinase (ERK) pathway, which is an important regulator of cell growth. Interestingly, treatment with EBPC in combination with the chemotherapeutic drugs increased ERK activity as compared to treatment with the chemotherapeutic drugs, suggesting a possible role for the ERK pathway in mediating doxorubicin- or cisplatin-induced cell death. Consistent with this possibility, inhibition of ERK activation by the MEK inhibitor, U0126, reversed the EBPC-mediated enhancement of cell death. In summary, these data provide evidence that adjuvant therapy with aldose reductase inhibitors improves the effectiveness of chemotherapeutic drugs, possibly through an ERK pathway-mediated mechanism.
A highly specific aldose reductase inhibitor, ethyl 1-benzyl-3-hydroxy-2(5H)-oxopyrrole-4-carboxylate, and its congeners.[Pubmed:1900532]
J Med Chem. 1991 Mar;34(3):1011-8.
Ethyl 1-benzyl-3-hydroxy-2(5H)-oxopyrrole-4-carboxylate (1, EBPC) is a potent and specific inhibitor of aldose reductase. It was greater than 4000X more potent in its inhibition of rat lens aldose reductase than the closely related rat or pig kidney aldehyde reductase, thus making it the most selective inhibitor of a NADPH-dependent carbonyl reductase identified to date. In agreement with this observation, it was found to be a highly potent inhibitor of aldose reductase from rat sciatic nerve with greater than 98% inhibition at 1 microM, but it was practically devoid of activity against aldehyde reductases from rat liver and brain. Inhibition of aldose reductase was mixed type for glyceraldehyde (Ki = 8.0 x 10(-8) M) and noncompetitive for NADPH (Ki = 1.70 x 10(-8) M). Its potential as an in vitro tool to quantitate monomeric aldo/keto reductase activities in crude tissue extracts is presented. Structure-activity relationships emerging from synthetic modifications of EBPC are discussed. Several modifications were found to be active in vitro against aldose reductase from human placenta and in vivo in a rat model of diabetic complications, but none was more potent than EBPC.
