A new approach to the synthesis of polyunsaturated deuterated isoprostanes: total synthesis of d4-5-epi-8,12-iso-iPF3alpha-VI and d4-8,12-iso-iPF3alpha-VI.
Bioorg Med Chem Lett
; 19(23): 6755-8, 2009 Dec 01.
Article
em En
| MEDLINE
| ID: mdl-19846297
ABSTRACT
The total and stereospecific synthesis of d(4)-5-epi-8,12-iso-iPF(3alpha)-VI 55 and d(4)-8,12-iso-iPF(3alpha)-VI 64, EPA-derived all-syn-isoprostanes (iPs), has been accomplished. Because of issues related to volatility and yield with some of the primary deuterated synthons an improved synthesis is presented. These two deuterated analogs were used to discover and quantify the presence of the corresponding endogenous isoprostanes in human urine. These assays may serve as a valuable index of oxidative stress in population with omega-3 fatty acid enriched diets containing eicosapentaenoic acid (EPA) and docosahexaenoic acid (DHA) and may also be useful as an index of the severity of inflammatory diseases such as atherosclerosis and Alzheimer's disease.
Texto completo:
1
Base de dados:
MEDLINE
Assunto principal:
Ácido Eicosapentaenoico
/
Isoprostanos
Idioma:
En
Ano de publicação:
2009
Tipo de documento:
Article