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ER Subtype Selectivity of M-Carborane-Containing Phenols: C-alkyl Groups on the M-Carborane Cage Enhance ERα Selectivity

ER Subtype Selectivity of M-Carborane-Containing Phenols: C-alkyl Groups on the M-Carborane Cage Enhance ERα Selectivity

Kiminori Ohta, Takumi Ogawa, Koichi Kato, Akifumi Oda, Yasuyuki Endo

Bioorg Med Chem Lett. 2019 Aug 15;29(16):2290-2293.

PMID: 31248773

Abstract:

Estrogen receptor (ER) exhibits two subtypes, ERα and ERβ, whose biological functions are quite different despite expression in the same tissues. We developed diiodo-m-carborane derivative 3a, which showed 14-fold selectivity for ERβ with high binding affinity toward ERβ. Interestingly, introduction of an alkyl group into the carbon atom of the m-carborane cage of 3a markedly enhanced the binding affinity toward ERα and decreased affinity toward ERβ. C-n-propyl derivative 3d showed 28-fold selectivity for ERα in an ER binding assay and promoted proliferation of MCF-7 breast cancer cells. Docking simulation studies suggest that the directions of the n-propyl group and the diiodo substituent introduced on the m-carborane cage play important roles for the control of ER subtype selectivity. As 3a and 3d showed ERβ and ERα selectivity with high binding affinity, respectively, these ligands may be useful as biological tools to aid in understanding the different roles of ER subtypes.

Chemicals Related in the Paper:

Catalog Number	Product Name	Structure	CAS Number	Price
AP16986246	m-Carborane		16986-24-6	Price

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