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(22R,23R)-3β-hydroxy-22,23-epoxy-5α-ergost-8(14)-en-15-one: Improved synthesis and toxicity to MCF-7 cells

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Abstract

The chemical synthesis of (22R,23R)-3β-hydroxy-22,23-epoxy-5α-ergost-8(14)-en-15-one from (22A)-3β-acetoxy-5α-ergosta-7,14,22-triene was improved. The stages of obtaining and isomerization of (22A)-3β-acetoxy-14α15α-epoxy-5α-ergosta-7,22-diene were optimized. The introduction of (22R,23R)-epoxide cycle was carried out by alkaline treatment of intermediate (22S,23R)-3β,23-diacetoxy-22-iodo-5α-ergost-8(14)-en-15-one. In cells of human breast carcinoma MCF-7, (22R,23R)-3β-hydroxy-22,23-epoxy-5α-ergost-8(14)-en-15-one showed a high toxicity (TC50 = 0.4±0.1 μM at 48-h incubation in serum-free medium).

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Abbreviations

FCS:

fetal calf serum

mCBA:

m-chloroperbenzoic acid

MTT:

(3-[4,5-dimethylthiazol-2-yl])-2,5-diphenyltetrazolium bromide

PBS:

phosphate-buffered saline

TFA:

trifluoroacetic acid

THF:

tetrahydrofurane

TosOH:

p-toluenesulfonic acid

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Authors and Affiliations

  1. Orehovich Research Institute of Biomedical Chemistry, Russian Academy of Medical Sciences, Pogodinskaya ul. 10, Moscow, 119992, Russia

    A. R. Mehtiev & A. Yu. Misharin

  2. Engelhardt Institute of Molecular Biology, Russian Academy of Sciences, Moscow, Russia

    V. P. Timofeev

Authors
  1. A. R. Mehtiev
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  2. V. P. Timofeev
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  3. A. Yu. Misharin
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Correspondence to A. Yu. Misharin.

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Original Russian Text © A.R. Mehtiev, V.P. Timofeev, A.Yu. Misharin, 2008, published in Bioorganicheskaya Khimiya, 2008, Vol. 34, No. 6, pp. 840–846.

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Mehtiev, A.R., Timofeev, V.P. & Misharin, A.Y. (22R,23R)-3β-hydroxy-22,23-epoxy-5α-ergost-8(14)-en-15-one: Improved synthesis and toxicity to MCF-7 cells. Russ J Bioorg Chem 34, 755–761 (2008). https://doi.org/10.1134/S1068162008060174

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  • DOI: https://doi.org/10.1134/S1068162008060174

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