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20-(B)-20,25-dihydroperoxy-3beta-hydroxycholest-5-ene and 20-(S)-20,25-dihydroperoxy-3beta-hydroxycholest-5-ene

a technology of dihydroperoxy and cholest5ene, which is applied in the field of medicine agents and methods for combatting atherogenesis, can solve the problems of low blood cholesterol, ineffective atherosclerosis treatment, and ineffective chemically reduced hydroperoxides in reducing atherosclerosis, and achieves suppressing atherogenesis and high activity

Inactive Publication Date: 2003-02-18
IOWA STATE UNIV RES FOUND
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Medicinal agents reported as reducing development of athersclerotic lesions typically result in the lowering of blood cholesterol levels.
Chlorpromazine may function as an inhibitor of calmodulin (Gietzen, 1986) but it is classified pharmacologically as a tranquilizer and sedative (Merck Index, 1976), and therefore is not likely to be useful as a treatment for atherosclerosis.
In a related experiment, it was found that the chemically reduced hydroperoxides were not effective in reducing atheroma formation.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment Construction

The effects of cholesterol hydroperoxides on the esterification of cholesterol in mouse peritoneal macrophages was tested as follows:

Monolayers of mouse peritoneal macrophages were pretreated with various concentration of .[.20-(S)-hydroperoxy-cholest-5-ene-3.beta.,25-diol hydroxycholesterol (A) or 20-(R)-hydroperoxycholest-5-ene-3.beta.,25 diol (B).]. .Iadd.20-(S)-20,25-dihydroperoxy-3.beta.-hydroxycholest-5-ene-(A) or 20-(R)-20,25-dihydroperoxy-3.beta.-hydroxycholest-5-ene (B) .Iaddend.at 37.degree. C. After 15 min preincubation, medium M199 providing 2.5% fetal calf serum, acetyl-LDL (25 .mu.g protein / ml) and .sup.3 H-oleate (0.25 .mu.Ci / ml) was added to the culture dishes. After 6 hr of incubation with 5% CO.sub.2 at 37.degree. C. the cellular lipids were extracted. This layer chromatography was used to separate cholesteryl ester from other lipid classes before the radioactivity was determined. The activities reported have been corrected for losses during chromatography and elut...

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Abstract

A method is provided for suppressing atherogenesis in which <DEL-S DATE="20030218" ID="DEL-S-00001" / >a cholesterol 20-hydroperoxide is administered, which is preferably one or both of the novel compounds: 20(R)-hydroperoxy-25-hydrocholesterol and 29(S)-hydroperoxy-25-hydrocholesterol<DEL-E ID="DEL-S-00001" / > <INS-S DATE="20030218" ID="INS-S-00001" / >20(R)-hydroperoxy-25 hydrocholesterol and 20(S)-hydroperoxy-25-hydrocholesterol are administered. The compositions 20(R)-hydroperoxy-25-hydrocholesterol and 20(S)-hydroperoxy-25-hydrocholesterol are also provided<INS-E ID="INS-S-00001" / >.

Description

FIELD OF INVENTIONThe field of the invention is medicine agents and methods for combatting atherogenesis.BACKGROUND OF INVENTIONThe role of cholesterol oxidation products in atherogenesis has long been a controversial topic. Peng and Taylor (1983), for example, hypothesized that cholesterol oxidation products may be responsible for an initial arterial cell injury that eventually results in atherosclerosis. On the other hand, Higley et al. (1986) disputed that hypothesis, claiming instead that oxidized cholesterol is substantially less atherogenic than purified cholesterol. The analysis of the oxidized cholesterol shown in Table 1 of Higley et al. indicated the presence of diols and epoxides (78%) as the major oxidized compounds with a minor amount of hydroperoxide (18%) identified as 7.alpha.-hydroperoxide.Hypercholesteroloemia is widely considered to be a major risk factor for the development of atherosclerosis. The lowering of blood cholesterol levels has therefore been an importa...

Claims

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Application Information

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Patent Type & Authority Patents(United States)
IPC IPC(8): C07J9/00
CPCC07J9/00
Inventor TIPTON, CARL L.SHIH, MEILING
Owner IOWA STATE UNIV RES FOUND