Epanorin
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| Category | Enzyme inhibitors |
| Catalog number | BBF-05012 |
| CAS | 18463-10-0 |
| Molecular Weight | 435.47 |
| Molecular Formula | C25H25NO6 |
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Description
Epanorin is a lichen metabolite that can inhibit the proliferation of MCF-7 breast cancer cells.
Specification
| Synonyms | L-Leucine, N-[(3-hydroxy-5-oxo-4-phenyl-2(5H)-furanylidene)phenylacetyl]-, methyl ester; N-[2-(3-Hydroxy-5-oxo-4-phenyl-2(5H)-furanylidene)-2-phenylacetyl]-L-leucine methyl ester; (-)-Epanorin |
| IUPAC Name | methyl (2S)-2-[[(2Z)-2-(3-hydroxy-5-oxo-4-phenylfuran-2-ylidene)-2-phenylacetyl]amino]-4-methylpentanoate |
| Canonical SMILES | CC(C)CC(C(=O)OC)NC(=O)C(=C1C(=C(C(=O)O1)C2=CC=CC=C2)O)C3=CC=CC=C3 |
| InChI | InChI=1S/C25H25NO6/c1-15(2)14-18(24(29)31-3)26-23(28)20(17-12-8-5-9-13-17)22-21(27)19(25(30)32-22)16-10-6-4-7-11-16/h4-13,15,18,27H,14H2,1-3H3,(H,26,28)/b22-20-/t18-/m0/s1 |
| InChI Key | IBSRGCBHIASQMQ-BKBKCADHSA-N |
Properties
| Boiling Point | 608.6±55.0°C (Predicted) |
| Density | 1.280±0.06 g/cm3 (Predicted) |
Reference Reading
1. Epanorin, a lichen secondary metabolite, inhibits proliferation of MCF-7 breast cancer cells
Juan Palacios-Moreno, Cecilia Rubio, Wanda Quilhot, M Fernanda Cavieres, Eduardo de la Peña, Natalia V Quiñones, Hugo Díaz, Flavio Carrión, Carlos F Henríquez-Roldán, Caroline R Weinstein-Oppenheimer Biol Res. 2019 Oct 10;52(1):55. doi: 10.1186/s40659-019-0261-4.
Background: Epanorin (EP) is a secondary metabolite of the Acarospora lichenic species. EP has been found in lichenic extracts with antimicrobial activity, and UV-absorption properties have been described for closely related molecules; however, its antiproliferative activity in cancer cells has not yet been explored. It has been hypothesized that EP inhibits cancer cell growth. MCF-7 breast cancer cells, normal fibroblasts, and the non-transformed HEK-293 cell line were exposed to increasing concentrations of EP, and proliferation was assessed by the sulforhodamine-B assay. Results: MCF-7 cells exposed to EP were examined for cell cycle progression using flow cytometry, and DNA fragmentation was examined using the TUNEL assay. In addition, EP's mutagenic activity was assessed using the Salmonella typhimurium reverse mutation assay. The data showed that EP inhibits proliferation of MCF-7 cells, and it induces cell cycle arrest in G0/G1 through a DNA fragmentation-independent mechanism. Furthermore, EP's lack of overt cytotoxicity in the normal cell line HEK-293 and human fibroblasts in cell culture is supported by the absence of mutagenic activity of EP. Conclusion: EP emerges as a suitable molecule for further studies as a potential antineoplastic agent.
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
