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Conjugated methyl sulfide and phenyl sulfide derivatives of oxidosqualene as inhibitors of oxidosqualene and squalene‐hopene cyclases
Author(s) -
Rocco Flavio,
Bosso Simonetta Oliaro,
Viola Franca,
Milla Paola,
Roma Giorgio,
Grossi Giancarlo,
Ceruti Maurizio
Publication year - 2003
Publication title -
lipids
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.601
H-Index - 120
eISSN - 1558-9307
pISSN - 0024-4201
DOI - 10.1007/s11745-003-1052-6
Subject(s) - conjugated system , chemistry , squalene , saccharomyces cerevisiae , cyclase , lanosterol , stereochemistry , biochemistry , yeast , organic chemistry , enzyme , sterol , cholesterol , polymer
Abstract Various (1 E ,3 E )‐ and (1 Z ,3 E )‐conjugated methylthio derivatives of oxidosqualene (OS) and conjugated and non‐conjugated phenylthio derivatives of OS were obtained. These compounds, designed as inhibitors of pig liver and Saccharomyces cerevisiae 2,3‐oxidosqualene‐lanosterol cyclases (OSC) (EC 5.4.99.7) and of Alicyclobacillus acidocaldarius squalenehopene cyclase (SHC) (EC 5.4.99.‐), contain the reactive function adjacent to carbons involved in the formation of the third and the fourth cycle during OS cyclization. All the new compounds are inhibitors of OSC and SHC, with various degrees of selectivity. The conjugated methylthio derivatives behaved as potent inhibitors of S. cerevisiae OSC, whereas most of the phenylthio derivatives were especially active toward SHC.