Linked Life Data

2769687

Source:http://linkedlifedata.com/resource/pubmed/id/2769687

Statements in which the resource exists as a subject.
PredicateObject
rdf:type
lifeskim:mentions
pubmed:issue
9
pubmed:dateCreated
1989-10-12
pubmed:abstractText
Several squalene analogues containing 1,1-dihaloalkene, acetylene, allene, diene, and cyclopropane functionalities were synthesized and evaluated as potential inhibitors of pig liver squalene epoxidase and oxidosqualene cyclase. Both monofunctionalized and bisfunctionalized analogues were prepared. Poor inhibition of squalene epoxidase and oxidosqualene cyclase was found for most compounds (IC50 much greater than 400 microM), with the exception of the monofunctionalized alkynol (IC50 = 300 microM). This alkynol showed mixed-function inhibition with KI = 0.95 mM. Oxidation of the alcohol to the alkynone resulted in loss of epoxidase activity, indicating that the hydroxyl group is necessary for inhibition and that the alkynol is not a proinhibitor. Molecular mechanics calculations indicated that a good inhibitor should possess hydrophobic substituents on an unpolarized, unsaturated system; additionally, the presence of a pro-C-3 hydroxyl group can confer inhibitory potency.
pubmed:language
eng
pubmed:journal
pubmed:citationSubset
IM
pubmed:chemical
pubmed:status
MEDLINE
pubmed:month
Sep
pubmed:issn
0022-2623
pubmed:author
pubmed:issnType
Print
pubmed:volume
32
pubmed:owner
NLM
pubmed:authorsComplete
Y
pubmed:pagination
2152-8
pubmed:dateRevised
2006-11-15
pubmed:meshHeading
pubmed:year
1989
pubmed:articleTitle
Squalene analogues containing isopropylidene mimics as potential inhibitors of pig liver squalene epoxidase and oxidosqualene cyclase.
pubmed:affiliation
Department of Chemistry, State University of New York, Stony Brook 11794-3400.
pubmed:publicationType
Journal Article, Research Support, Non-U.S. Gov't