Chiral high-performance liquid chromatographic separation and circular dichroism spectra of the enantiomers of cytotoxic aristocularine alkaloids

The HPLC enantiomeric separation of the racemic cularinoid alkaloids N- p-methoxy-1,α-dihydroaristoyagonine ( 1) and 4′,5′-demethoxy-1,α-dihydroaristoyagonine ( 2) was accomplished using five chiral stationary phases (CSPs), some of them polysaccharide-derived ones. The molecular size and conjugativ...

Full description

Saved in:
Bibliographic Details
Published in:Journal of Chromatography A 2006-09, Vol.1129 (1), p.140-144
Main Authors: Caccamese, Salvatore, Scivoli, Giovanna, Bianca, Salvatore, López-Romero, Juan Manuel, Ortiz-López, Francisco Javier
Format: Article
Language:English
Subjects:
Alkaloids - analysis
Alkaloids - chemistry
Alkaloids - pharmacology
Analysis
Antineoplastic agents
Biological and medical sciences
Cell Survival - drug effects
Chromatography, High Pressure Liquid - methods
Circular Dichroism - methods
Circular dichroism spectra
Cularine alkaloids
Cytotoxicity of enantiomers
Enantioselective chromatography
General aspects
General pharmacology
HT29 Cells
Humans
Isoquinolines - analysis
Isoquinolines - chemistry
Isoquinolines - pharmacology
Medical sciences
Pharmacology. Drug treatments
Polysaccharide and Pirkle-type chiral stationary phases
Reproducibility of Results
Stereoisomerism
Citations: Items that this one cites
Items that cite this one
Online Access:Get full text
Tags: Add Tag
No Tags, Be the first to tag this record!
Description
Summary:The HPLC enantiomeric separation of the racemic cularinoid alkaloids N- p-methoxy-1,α-dihydroaristoyagonine ( 1) and 4′,5′-demethoxy-1,α-dihydroaristoyagonine ( 2) was accomplished using five chiral stationary phases (CSPs), some of them polysaccharide-derived ones. The molecular size and conjugative effect strongly affect the different enantioselectivity of the compounds 1 and 2 on the various CSPs investigated. Single enantiomers of 1 were isolated by repeated injections on an analytical HPLC column, and their circular dichroism spectra and optical rotations were measured. The cytotoxicity of the isolated enantiomers was measured on a human colon carcinoma cell line and compared with that of the racemic compound.
ISSN:0021-9673
DOI:10.1016/j.chroma.2006.07.077