Δ⁵-7-Ketosterols with Modified Side Chain: The Synthesis and the Effects on Viability and Cholesterol Biosynthesis in Hep G2 Cells

E. A. Piir^a, G. E. Morozevich^a, F. V. Drozdov^a, V. P. Timofeev^b, and A. Yu. Misharin^a,#

^# Phone: +7 (495) 246-3375; e-mail: alexander.misharin@ibmc.msk.ru
^a Orechovich Institute of Biomedical Chemistry, Russian Academy of Medical Sciences, Pogodinskaya ul. 10, Moscow, 119992 Russia
^b Engelhardt Institute of Molecular Biology, Russian Academy of Sciences, ul. Vavilova 32, Moscow, 117984 Russia

Received August 1, 2005; in final form, October 21, 2005

Abstract: (22E)-3β-Hydroxysitosta-5,22-dien-7-one, (22R,23R)-3β,22,23-trihydroxysitost-5-en-7-one, and (22R, 23R)-3β-hydroxy-22,23-isopropylidenedioxysitost-5-en-7-one were synthesized. The cytotoxicity and effects on cholesterol biosynthesis of the resulting 7-ketosterols, 7-ketocholesterol, and (22S,23S)-3β-hydroxy-22,23-oxidositost-5-en-7-one were studied in hepatoblastoma Hep G2 cells.

Key words: oxysterols, synthesis, Hep G2 cells, cholesterol biosynthesis, cytotoxicity

Russian Journal of Bioorganic Chemistry 2006, 32 (5):497-503