EBPC - CAS 4450-98-0
Category: Inhibitor
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Molecular Formula:
C14H15NO4
Molecular Weight:
261.28
COA:
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Targets:
Aldose Reductase
Description:
EBPC is a potent and selective aldose reductase inhibitor. It is used to improve the cytotoxicity of anticancer reagents such as cisplatin and doxorubicin in HeLa cervical carcinoma cells via an increase in ERK activity.
Brife Description:
aldose reductase inhibitor
Purity:
≥99% by HPLC
Appearance:
Pale Pink Solid
Synonyms:
Ethyl 1-benzyl-3-hydroxy-2(5H)-oxopyrrole-4-carboxylate; 1-Benzyl-4-hydroxy-5-oxo-2,5-dihydro-1H-pyrrole-3-carboxylic acid ethyl ester; MFCD00179167; 1-benzyl-4-[ethoxy(hydroxy)methylidene]pyrrolidine-2,3-dione
MSDS:
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Melting Point:
132-134°C
InChIKey:
IGYRPDIWSYGHMY-UHFFFAOYSA-N
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
Canonical SMILES:
CCOC(=O)C1=C(C(=O)N(C1)CC2=CC=CC=C2)O
1.Antioxidant capacity and in vitro prevention of dental plaque formation by extracts and condensed tannins of Paullinia cupana.
Yamaguti-Sasaki E;Ito LA;Canteli VC;Ushirobira TM;Ueda-Nakamura T;Dias Filho BP;Nakamura CV;de Mello JC Molecules. 2007 Aug 20;12(8):1950-63.
Chemical evaluation of the semi-purified fraction from the seeds of guaraná, Paullinia cupana H.B.K. var. sorbilis (Mart.) Ducke, yielded the following compounds: caffeine, catechin, epicatechin, ent-epicatechin, and procyanidins B1, B2, B3, B4, A2, and C1. Measurement of the antioxidant activity by reduction of the DPPH radical confirmed the anti-radical properties of the aqueous (AqE) and crude (EBPC) extracts and semi-purified (EPA and EPB) fractions. The EPA fraction showed radical-scavenging activity (RSA) and protected DPPH from discoloration at 5.23 +/- 0.08 (RSD% = 1.49) microg/mL, and for the phosphomolybdenum complex showed a higher Relative Antioxidant Capacity (RAC) at 0.75 +/- 0.01 (1.75). The EPA fraction had a total polyphenolics content of 65.80% +/- 0.62 (RSD% = 0.93). The plant drug showed 5.47% +/- 0.19 (RSD% = 3.51) and 6.19% +/- 0.08 (RSD% = 1.29) for total polyphenolics and methylxanthines, respectively. In vitro assessment of the antibacterial potential of the Paullinia cupana extracts against Streptococcus mutans showed that these could be used in the prevention of bacterial dental plaque.
2.Occurrence, Molecular Characterization, and Assessment of Zoonotic Risk of Cryptosporidium spp., Giardia duodenalis, and Enterocytozoon bieneusi in Pigs in Henan, Central China.
Wang H;Zhang Y;Wu Y;Li J;Qi M;Li T;Wang J;Wang R;Zhang S;Jian F;Ning C;Zhang L J Eukaryot Microbiol. 2018 May 12. doi: 10.1111/jeu.12634. [Epub ahead of print]
Cryptosporidium spp., Giardia duodenalis, and Enterocytozoon bieneusi are common gastrointestinal pathogens in humans and animals. Little is known about them and the range of species/assemblages/genotypes occurring in domestic pigs in China. Here, we present data on the occurrence and molecular diversity of these pathogens detected in the feces from farms in Henan, central China. Of 897 fecal samples tested, 28 (3.1%), 15 (1.7%), and 408 (45.5%) samples were positive for Cryptosporidium, G. duodenalis, and E. bieneusi, respectively. Cryptosporidium and G. duodenalis were most frequently detected in piglets, while E. bieneusi was markedly more prevalent in fattening pigs. Sequence analysis of SSU rRNA gene revealed that positive Cryptosporidium strains belonged to C. suis (n = 18) and C. scrofarum (n = 10). Giardia duodenalis assemblages E (n = 9), assemblages A (n = 3), and assemblages C (n = 3) were characterized based on the sequence analysis of tpi gene. Thirteen E. bieneusi genotypes comprising four novel (pigHN-I to pigHN-IV) and nine known (EbpC, EbpA, pigEbITS5, LW1, H, CM8, G, CHG19, and CHS5) genotypes were identified by ITS sequence analysis of a large proportion (n = 200) of E.
3.Inhibition of aldose reductase enhances HeLa cell sensitivity to chemotherapeutic drugs and involves activation of extracellular signal-regulated kinases.
Lee EK;Regenold WT;Shapiro P 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.
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CAS 4450-98-0 EBPC

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