Synthesis and evaluation of AKR1C inhibitory properties of A-ring halogenated oestrone derivatives Article Swipe

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Maša Sinreih , Rebeka Jójárt , Zoltán Kele , Tomaž Büdefeld , Gábor Paragi , Erzsébet Mernyák , Tea Lanišnik Rižner ·

YOU? · · 2021 · Open Access · · DOI: https://doi.org/10.1080/14756366.2021.1937142

Enzymes AKR1C regulate the action of oestrogens, androgens, and progesterone at the pre-receptor level and are also associated with chemo-resistance. The activities of these oestrone halides were investigated on recombinant AKR1C enzymes. The oestrone halides with halogen atoms at both C-2 and C-4 positions (13β-, 13α-methyl-17-keto halogen derivatives) were the most potent inhibitors of AKR1C1. The lowest IC₅₀ values were for the 13α-epimers 2_2I,4Br and 2_2I,4Cl (IC₅₀, 0.7 μM, 0.8 μM, respectively), both of which selectively inhibited the AKR1C1 isoform. The 13α-methyl-17-keto halogen derivatives 2_2Br and 2_4Cl were the most potent inhibitors of AKR1C2 (IC₅₀, 1.5 μM, 1.8 μM, respectively), with high selectivity for the AKR1C2 isoform. Compound 1_2Cl,4Cl showed the best AKR1C3 inhibition, and it also inhibited AKR1C1 (Ki: AKR1C1, 0.69 μM; AKR1C3, 1.43 μM). These data show that halogenated derivatives of oestrone represent a new class of potent and selective AKR1C inhibitors as lead compounds for further optimisations.

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Epimer Chemistry Gene isoform Enzyme IC50 Halogen Stereochemistry Ring (chemistry) Halide In vitro Biochemistry Gene Organic chemistry Alkyl

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Type: article
Language: en
Landing Page: https://doi.org/10.1080/14756366.2021.1937142
PDF: https://www.tandfonline.com/doi/pdf/10.1080/14756366.2021.1937142?needAccess=true
OA Status: gold
Cited By: 5
References: 31
Related Works: 10
OpenAlex ID: https://openalex.org/W3179538943

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DOI: https://doi.org/10.1080/14756366.2021.1937142

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Title: Synthesis and evaluation of AKR1C inhibitory properties of A-ring halogenated oestrone derivatives

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Type: article

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Language: en

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Publication year: 2021

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Publication date: 2021-01-01

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Authors: Maša Sinreih, Rebeka Jójárt, Zoltán Kele, Tomaž Büdefeld, Gábor Paragi, Erzsébet Mernyák, Tea Lanišnik Rižner

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Landing page: https://doi.org/10.1080/14756366.2021.1937142

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Concepts: Epimer, Chemistry, Gene isoform, Enzyme, IC50, Halogen, Stereochemistry, Ring (chemistry), Halide, In vitro, Biochemistry, Gene, Organic chemistry, Alkyl

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Cited by: 5

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