Degradation chemistry of a Vitamin D analogue (ecalcidene) investigated by HPLC-MS, HPLC-NMR and chemical derivatization.
J Pharm Biomed Anal
; 40(4): 850-63, 2006 Mar 03.
Article
em En
| MEDLINE
| ID: mdl-16242878
ABSTRACT
Ecalcidene (1-[(1alpha,3beta,5Z,7E,20S)-1,3-dihydroxy-24-oxo-9,10-secochola-5,7,10(19)-trien-24-yl]-piperidine) is a new 1-hydroxyvitamin D analogue. In this report, the thermal degradation, acid induced degradation and iodine induced degradation of ecalcidene were investigated using HPLC-MS, HPLC-NMR and chemical derivatization. In solution ecalcidene was thermally and reversibly transformed to a pre-Vitamin D type isomer 1 which subsequently produced the dehydrated pyrocalciferol and isopyrocalciferol type isomers 2 and 3 by cyclization and dehydration at elevated temperatures. Acidic conditions resulted in the formation of a novel C9-hydroxylated isomer 4 of ecalcidene, possibly via a tachysterol type intermediate, followed by the acid facilitated nucleophilic addition of water. In the presence of iodine, cis/trans isomerization of both ecalcidene and its pre-Vitamin D type isomer 1 occurred. The results may shed light on the stability and metabolism of ecalcidene, provide useful information for its potential pharmaceutical development, and enrich the knowledge of Vitamin D chemistry.
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Coleções:
01-internacional
Base de dados:
MEDLINE
Assunto principal:
Vitamina D
/
Conservadores da Densidade Óssea
Idioma:
En
Revista:
J Pharm Biomed Anal
Ano de publicação:
2006
Tipo de documento:
Article
País de afiliação:
Estados Unidos