Evaluation and comparison of three different ...
Type de document :
Article dans une revue scientifique
PMID :
URL permanente :
Titre :
Evaluation and comparison of three different separation techniques for analysis of retroamide enantiomers and their biological evaluation against h-P2X7 receptor
Auteur(s) :
Baudelet, Davy [Auteur]
Furman, Christophe [Auteur]
Lille Inflammation Research International Center - U 995 [LIRIC]
Ghinet, Alina [Auteur]
Lille Inflammation Research International Center - U 995 [LIRIC]
Dezitter, Xavier [Auteur]
Lille Inflammation Research International Center - U 995 [LIRIC]
Adriouch, Sahil [Auteur]
Capet, Frederic [Auteur]
Unité de Catalyse et Chimie du Solide - UMR 8181 [UCCS]
Rogez-Florent, Tiphaine [Auteur]
Gautret, Philippe [Auteur]
Lille Inflammation Research International Center - U 995 [LIRIC]
Rigo, Benoit [Auteur]
MILLET, Régis [Auteur]
Lille Inflammation Research International Center - U 995 [LIRIC]
Vaccher, Claude [Auteur]
Groupe de Recherche sur les formes Injectables et les Technologies Associées - ULR 7365 [GRITA]
Lipka, Emmanuelle [Auteur]
Lille Inflammation Research International Center - U 995 [LIRIC]
Furman, Christophe [Auteur]
Lille Inflammation Research International Center - U 995 [LIRIC]
Ghinet, Alina [Auteur]
Lille Inflammation Research International Center - U 995 [LIRIC]
Dezitter, Xavier [Auteur]
Lille Inflammation Research International Center - U 995 [LIRIC]
Adriouch, Sahil [Auteur]
Capet, Frederic [Auteur]
Unité de Catalyse et Chimie du Solide - UMR 8181 [UCCS]
Rogez-Florent, Tiphaine [Auteur]
Gautret, Philippe [Auteur]
Lille Inflammation Research International Center - U 995 [LIRIC]
Rigo, Benoit [Auteur]
MILLET, Régis [Auteur]
Lille Inflammation Research International Center - U 995 [LIRIC]
Vaccher, Claude [Auteur]
Groupe de Recherche sur les formes Injectables et les Technologies Associées - ULR 7365 [GRITA]
Lipka, Emmanuelle [Auteur]
Lille Inflammation Research International Center - U 995 [LIRIC]
Titre de la revue :
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences
Nom court de la revue :
J. Chromatogr. B
Numéro :
986
Pagination :
35-43
Date de publication :
2015-04-01
ISSN :
1570-0232
Mot(s)-clé(s) en anglais :
Amy lose tris (3
5-dimethylphenylcarbamate)
Supercritical fluid chromatography
Dual cyclodextrins system
N-[1-(2
4-Dichlorobenzyl)-5-oxopyrrolidin-2-yl]-2-(2
4-dichlorophenyl) acetamide
High performance liquid chromatography
Capillary electrophoresis
Mesh:Phenylcarbamates/chemistry*
Mesh: Purinergic P2X Receptor Antagonists/chemistry*
Mesh: Purinergic P2X Receptor Antagonists/isolation & purification*
Mesh: Reproducibility of Results
Mesh: Sensitivity and Specificity
Mesh: Stereoisomerism
Mesh: Amylose/analogs & derivatives*
Mesh: Amylose/chemistry
Mesh: Cellulose/analogs & derivatives*
Mesh: Cellulose/chemistry
Mesh: Chromatography
Mesh: High Pressure Liquid/methods*
Mesh: Linear Models
Mesh: Purinergic P2X Receptor Antagonists/analysis
5-dimethylphenylcarbamate)
Supercritical fluid chromatography
Dual cyclodextrins system
N-[1-(2
4-Dichlorobenzyl)-5-oxopyrrolidin-2-yl]-2-(2
4-dichlorophenyl) acetamide
High performance liquid chromatography
Capillary electrophoresis
Mesh:Phenylcarbamates/chemistry*
Mesh: Purinergic P2X Receptor Antagonists/chemistry*
Mesh: Purinergic P2X Receptor Antagonists/isolation & purification*
Mesh: Reproducibility of Results
Mesh: Sensitivity and Specificity
Mesh: Stereoisomerism
Mesh: Amylose/analogs & derivatives*
Mesh: Amylose/chemistry
Mesh: Cellulose/analogs & derivatives*
Mesh: Cellulose/chemistry
Mesh: Chromatography
Mesh: High Pressure Liquid/methods*
Mesh: Linear Models
Mesh: Purinergic P2X Receptor Antagonists/analysis
Discipline(s) HAL :
Sciences du Vivant [q-bio]
Résumé en anglais : [en]
The P2X receptors are seven-transmembrane domain G protein-coupled receptors and the 7 subtypes of P2X receptors identified in humans, and named P2X1 to P2X7, are channel receptors whose endogenous ligand is ATP. New ...
Lire la suite >The P2X receptors are seven-transmembrane domain G protein-coupled receptors and the 7 subtypes of P2X receptors identified in humans, and named P2X1 to P2X7, are channel receptors whose endogenous ligand is ATP. New antagonists of the P2X7 receptor were developed, since this purinergic receptor was highlighted to be involved in many diseases such as different types of pain, cancer, ischemia, neurodegenerative diseases (including Parkinson's and Alzheimer's diseases) characterized by inflammatory processes. With the aim of evaluate the impact of chirality on the pharmacological activity of a new P2X7R antagonist, a semi-preparative method was developed in supercritical fluid chromatography (SFC). Among four polysaccharide based chiral stationary phases: Chiralcel OD-H and OJ-H and Chiralpak AS-H and AD-H, the last one namely amylose tris (3,5-dimethylphenylcarbamate) with a mobile phase consisted of carbon dioxide-ethanol (80:20, v/v), led to the successful separation of the enantiomers in short run time and with good resolution. Limits of detection and quantification were calculated and were found equal for compound 1, to 1.37 μM and 4.57 μM respectively, for peak 1 and were equal to 1.60 μM and 5.30 μM respectively, for peak 2 at λ=210 nm. Before carrying out the pharmacological evaluation of each enantiomer, two complementary methodologies, e.g. liquid chromatography and capillary electrophoresis were performed in parallel to improve the limits of detection and quantification to assess the enantiomeric purity. HPLC using a Chiralpak AD stationary phase led to four times lower limits of detection and quantification with regard to SFC. In the same time, capillary electrophoresis involving dual cyclodextrins system constituted of a SBE-β-CD and a MM-β-CD mixture enhanced the signal-to-noise ratio and led to similar limits of detection and quantification with regard to SFC. No trace of the other enantiomer was found in the isolated one. Biological activities of individual enantiomers were then evaluated and revealed no cytotoxicity against cell lines and a significant difference in terms of their IC50 values with respect to the investigated racemate (6.43 μM): 3.49 μM for the (R)-enantiomer and >10(-4)μM for the (S)-enantiomer, for compound 1, showing that, this antagonist activity is stereospecific.Lire moins >
Lire la suite >The P2X receptors are seven-transmembrane domain G protein-coupled receptors and the 7 subtypes of P2X receptors identified in humans, and named P2X1 to P2X7, are channel receptors whose endogenous ligand is ATP. New antagonists of the P2X7 receptor were developed, since this purinergic receptor was highlighted to be involved in many diseases such as different types of pain, cancer, ischemia, neurodegenerative diseases (including Parkinson's and Alzheimer's diseases) characterized by inflammatory processes. With the aim of evaluate the impact of chirality on the pharmacological activity of a new P2X7R antagonist, a semi-preparative method was developed in supercritical fluid chromatography (SFC). Among four polysaccharide based chiral stationary phases: Chiralcel OD-H and OJ-H and Chiralpak AS-H and AD-H, the last one namely amylose tris (3,5-dimethylphenylcarbamate) with a mobile phase consisted of carbon dioxide-ethanol (80:20, v/v), led to the successful separation of the enantiomers in short run time and with good resolution. Limits of detection and quantification were calculated and were found equal for compound 1, to 1.37 μM and 4.57 μM respectively, for peak 1 and were equal to 1.60 μM and 5.30 μM respectively, for peak 2 at λ=210 nm. Before carrying out the pharmacological evaluation of each enantiomer, two complementary methodologies, e.g. liquid chromatography and capillary electrophoresis were performed in parallel to improve the limits of detection and quantification to assess the enantiomeric purity. HPLC using a Chiralpak AD stationary phase led to four times lower limits of detection and quantification with regard to SFC. In the same time, capillary electrophoresis involving dual cyclodextrins system constituted of a SBE-β-CD and a MM-β-CD mixture enhanced the signal-to-noise ratio and led to similar limits of detection and quantification with regard to SFC. No trace of the other enantiomer was found in the isolated one. Biological activities of individual enantiomers were then evaluated and revealed no cytotoxicity against cell lines and a significant difference in terms of their IC50 values with respect to the investigated racemate (6.43 μM): 3.49 μM for the (R)-enantiomer and >10(-4)μM for the (S)-enantiomer, for compound 1, showing that, this antagonist activity is stereospecific.Lire moins >
Langue :
Anglais
Audience :
Internationale
Vulgarisation :
Non
Établissement(s) :
Université de Lille
CHU Lille
ENSCL
CNRS
Inserm
Centrale Lille
Univ. Artois
CHU Lille
ENSCL
CNRS
Inserm
Centrale Lille
Univ. Artois
Collections :
Date de dépôt :
2019-02-26T17:11:50Z
2020-01-30T13:03:33Z
2020-01-30T13:06:17Z
2020-01-30T13:03:33Z
2020-01-30T13:06:17Z