[(22R,23R)-3beta-Hydroxy-22,23-epoxy-5alpha-ergost-8(14)-en-15-one: improved synthesis and toxicity to MCF-7 cells].
The chemical synthesis of (22R,23R)-3beta-hydroxy-22,23-epoxy-5alpha-ergost-8(14)-en-15-one from (22E)-3beta-acetoxy-5alpha-ergosta-7,14,22-triene was improved. The stages of obtaining and isomerizing (22E)-3beta-acetoxy-14alpha,15alpha-epoxy-5alpha-ergosta-7,22-diene were optimized. The introduction of the (22R,23R)-epoxide cycle was carried out by a basic treatment of intermediate (22S,23R)-3beta,23-diacetoxy-22-iodo-5alpha-ergost-8(14)-en-15-one. In cells of human mammary gland carcinoma MCF-7 (22R,23R)-3beta-hydroxy-22,23-epoxy-5alpha-ergost-8(14)-en-15-one showed a high toxicity (TC(50) = 0.4 +/- 0.1 microM for 48-h incubation in serum-free medium).
Mekhtiev
A R
AR
Orekhovich Research Institute of Biomedical Chemistry, Russian Academy of Medical Sciences, Pogodinskaya ul. 10, Moscow, 119992 Russia.
Timofeev
V P
VP
Misharin
A Iu
AIu
D001943:Breast Neoplasms / Q000188:drug therapy; D045744:Cell Line, Tumor; D003603:Cytotoxins / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D004354:Drug Screening Assays, Antitumor; D004875:Ergosterol / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology; D005260:Female; D006801:Humans; D013261:Sterols / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*
C522916:3beta-hydroxy-22,23-oxido-5alpha-ergost-8(14)-en-15-one; D003603:Cytotoxins; D013261:Sterols; C015190:ergostane; D004875:Ergosterol