MIBE

MIBE
Identifiers
IUPAC name
  • Ethyl 3-[5-(2-ethoxycarbonyl-1-methylvinyloxy)-1-methyl-1H-indol-3-yl]but-2-enoate
Chemical and physical data
FormulaC21H25NO5
Molar mass371.433 g·mol−1
3D model (JSmol)
SMILES
  • C(OC(/C=C(/OC1=CC=C2C(C(/C(/C)=C/C(OCC)=O)=CN2C)=C1)\C)=O)C
InChI
  • InChI=1S/C21H25NO5/c1-6-25-20(23)10-14(3)18-13-22(5)19-9-8-16(12-17(18)19)27-15(4)11-21(24)26-7-2/h8-13H,6-7H2,1-5H3/b14-10+,15-11+
  • Key:VFEAHZYKQWLUSD-WFYKWJGLSA-N

MIBE is a synthetic, nonsteroidal antiestrogen that acts as a dual antagonist of the ERα and the GPER.[1][2] It was found to prevent estradiol-induced proliferation of MCF-7 breast cancer cells, an action that was mediated via inhibition of both receptors.[1][2] The drug was synthesized in 2012.[1] It has been suggested that drugs like MIBE might be superior agents in the treatment of breast cancer compared to current antiestrogens like tamoxifen and fulvestrant, which are antagonistic at the ERα but were found in 2005 to be GPER agonists.[1][2]

References

  1. 1 2 3 4 Lappano R, Santolla MF, Pupo M, Sinicropi MS, Caruso A, Rosano C, Maggiolini M (2012). "MIBE acts as antagonist ligand of both estrogen receptor α and GPER in breast cancer cells". Breast Cancer Res. 14 (1): R12. doi:10.1186/bcr3096. PMC 3496129. PMID 22251451.
  2. 1 2 3 Rosano C, Lappano R, Santolla MF, Ponassi M, Donadini A, Maggiolini M (2012). "Recent advances in the rationale design of GPER ligands". Curr. Med. Chem. 19 (36): 6199–206. doi:10.2174/092986712804485755. PMID 23116143.



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