HOMEPRODUCTSCOMPANYCONTACTFAQResearchDictionaryPharmaSign Up FREE or Login

Degradation chemistry of a Vitamin D analogue (ecalcidene) investigated by HPLC-MS, HPLC-NMR and chemical derivatization.

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.
AuthorsFa Zhang, Mathews Nunes, Brigitte Segmuller, Richard Dunphy, Robert Henry Hesse, Sundara Katugam Srinivasetty Setty
JournalJournal of pharmaceutical and biomedical analysis (J Pharm Biomed Anal) Vol. 40 Issue 4 Pg. 850-63 (Mar 03 2006) ISSN: 0731-7085 [Print] England
PMID16242878 (Publication Type: Journal Article)
Chemical References
  • Bone Density Conservation Agents
  • Vitamin D
  • ecalcidene
  • Iodine
Topics
  • Bone Density Conservation Agents (chemistry)
  • Chromatography, High Pressure Liquid (methods)
  • Drug Stability
  • Hydrogen-Ion Concentration
  • Iodine
  • Isomerism
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Spectrophotometry, Ultraviolet
  • Temperature
  • Vitamin D (analogs & derivatives, chemistry)

Join CureHunter, for free Research Interface BASIC access!

Take advantage of free CureHunter research engine access to explore the best drug and treatment options for any disease. Find out why thousands of doctors, pharma researchers and patient activists around the world use CureHunter every day.
Realize the full power of the drug-disease research graph!


Choose Username:
Email:
Password:
Verify Password:
Enter Code Shown: