Vancomycin as chiral selector for enantioselective separation of selected profen nonsteroidal anti-inflammatory drugs in capillary liquid chromatography

Božena Kafková, Zuzana Bosáková, Eva Tesařová, Pavel Coufal, Antonella Messina, Massimo Sinibaldi

Research output: Contribution to journalArticle

25 Citations (Scopus)

Abstract

The chiral selector vancomycin was used either as mobile phase additive or bound as a chiral stationary phase (CSP) for the stereoselective separation of seven racemic nonsteroidal anti-inflammatory drugs (NSAIDs), fenoprofen, carprofen, flurbiprofen, indoprofen, flobufen, ketoprofen, and suprofen, by capillary liquid chromatography. The effect of the type of stationary phase, the chiral column Chirobiotic V or the achiral stationary phases Nucleosil 100 C8 HD and Nucleosil 100 C18 HD, and the concentration of vancomycin in the mobile phase on separation of the drug enantiomers were evaluated. All the drugs, except flobufen, were successfully enantioseparated on Nucleosil 100 C8 HD with 4 mM vancomycin present in the mobile phase (composed of methanol and buffer) in the reversed phase mode. On the vancomycin-bonded chiral stationary phase, it was difficult to gut enantioseparations of the profen NSAIDs. However, flobufen gave better enantioseparation on the vancomycin CSP. The better enantioresolution of the majority of profen derivatives on the achiral columns with vancomycin added to the mobile phase can be attributed in particular to the higher separation efficiency of this capillary chromatographic system. In addition, vancomycin dimers, formed in the mobile phase, seem to offer a better steric arrangement for stereoselective interaction to these analytes than the vancomycin bonded on the CSP. These substantial differences in the CS structure significantly influence the chiral discrimination mechanism.

Original languageEnglish
Pages (from-to)531-538
Number of pages8
JournalChirality
Volume18
Issue number7
DOIs
Publication statusPublished - 2006

Fingerprint

Liquid chromatography
Vancomycin
Liquid Chromatography
flobufen
Anti-Inflammatory Agents
Pharmaceutical Preparations
Enantiomers
Dimers
Methanol
Derivatives
Indoprofen
Suprofen
Fenoprofen
Flurbiprofen
Ketoprofen
Buffers

Keywords

  • Chiral separation
  • cLC
  • Macrocyclic antibiotic
  • Vancomycin chiral mobile phase additive
  • Vancomycin-based chiral stationary phase

ASJC Scopus subject areas

  • Analytical Chemistry
  • Drug Discovery
  • Organic Chemistry
  • Pharmacology

Cite this

Vancomycin as chiral selector for enantioselective separation of selected profen nonsteroidal anti-inflammatory drugs in capillary liquid chromatography. / Kafková, Božena; Bosáková, Zuzana; Tesařová, Eva; Coufal, Pavel; Messina, Antonella; Sinibaldi, Massimo.

In: Chirality, Vol. 18, No. 7, 2006, p. 531-538.

Research output: Contribution to journalArticle

Kafková, Božena ; Bosáková, Zuzana ; Tesařová, Eva ; Coufal, Pavel ; Messina, Antonella ; Sinibaldi, Massimo. / Vancomycin as chiral selector for enantioselective separation of selected profen nonsteroidal anti-inflammatory drugs in capillary liquid chromatography. In: Chirality. 2006 ; Vol. 18, No. 7. pp. 531-538.
@article{288935792b58461ca343b282b7947c98,
title = "Vancomycin as chiral selector for enantioselective separation of selected profen nonsteroidal anti-inflammatory drugs in capillary liquid chromatography",
abstract = "The chiral selector vancomycin was used either as mobile phase additive or bound as a chiral stationary phase (CSP) for the stereoselective separation of seven racemic nonsteroidal anti-inflammatory drugs (NSAIDs), fenoprofen, carprofen, flurbiprofen, indoprofen, flobufen, ketoprofen, and suprofen, by capillary liquid chromatography. The effect of the type of stationary phase, the chiral column Chirobiotic V or the achiral stationary phases Nucleosil 100 C8 HD and Nucleosil 100 C18 HD, and the concentration of vancomycin in the mobile phase on separation of the drug enantiomers were evaluated. All the drugs, except flobufen, were successfully enantioseparated on Nucleosil 100 C8 HD with 4 mM vancomycin present in the mobile phase (composed of methanol and buffer) in the reversed phase mode. On the vancomycin-bonded chiral stationary phase, it was difficult to gut enantioseparations of the profen NSAIDs. However, flobufen gave better enantioseparation on the vancomycin CSP. The better enantioresolution of the majority of profen derivatives on the achiral columns with vancomycin added to the mobile phase can be attributed in particular to the higher separation efficiency of this capillary chromatographic system. In addition, vancomycin dimers, formed in the mobile phase, seem to offer a better steric arrangement for stereoselective interaction to these analytes than the vancomycin bonded on the CSP. These substantial differences in the CS structure significantly influence the chiral discrimination mechanism.",
keywords = "Chiral separation, cLC, Macrocyclic antibiotic, Vancomycin chiral mobile phase additive, Vancomycin-based chiral stationary phase",
author = "Božena Kafkov{\'a} and Zuzana Bos{\'a}kov{\'a} and Eva Tesařov{\'a} and Pavel Coufal and Antonella Messina and Massimo Sinibaldi",
year = "2006",
doi = "10.1002/chir.20284",
language = "English",
volume = "18",
pages = "531--538",
journal = "Chirality",
issn = "0899-0042",
publisher = "Wiley-Liss Inc.",
number = "7",

}

TY - JOUR

T1 - Vancomycin as chiral selector for enantioselective separation of selected profen nonsteroidal anti-inflammatory drugs in capillary liquid chromatography

AU - Kafková, Božena

AU - Bosáková, Zuzana

AU - Tesařová, Eva

AU - Coufal, Pavel

AU - Messina, Antonella

AU - Sinibaldi, Massimo

PY - 2006

Y1 - 2006

N2 - The chiral selector vancomycin was used either as mobile phase additive or bound as a chiral stationary phase (CSP) for the stereoselective separation of seven racemic nonsteroidal anti-inflammatory drugs (NSAIDs), fenoprofen, carprofen, flurbiprofen, indoprofen, flobufen, ketoprofen, and suprofen, by capillary liquid chromatography. The effect of the type of stationary phase, the chiral column Chirobiotic V or the achiral stationary phases Nucleosil 100 C8 HD and Nucleosil 100 C18 HD, and the concentration of vancomycin in the mobile phase on separation of the drug enantiomers were evaluated. All the drugs, except flobufen, were successfully enantioseparated on Nucleosil 100 C8 HD with 4 mM vancomycin present in the mobile phase (composed of methanol and buffer) in the reversed phase mode. On the vancomycin-bonded chiral stationary phase, it was difficult to gut enantioseparations of the profen NSAIDs. However, flobufen gave better enantioseparation on the vancomycin CSP. The better enantioresolution of the majority of profen derivatives on the achiral columns with vancomycin added to the mobile phase can be attributed in particular to the higher separation efficiency of this capillary chromatographic system. In addition, vancomycin dimers, formed in the mobile phase, seem to offer a better steric arrangement for stereoselective interaction to these analytes than the vancomycin bonded on the CSP. These substantial differences in the CS structure significantly influence the chiral discrimination mechanism.

AB - The chiral selector vancomycin was used either as mobile phase additive or bound as a chiral stationary phase (CSP) for the stereoselective separation of seven racemic nonsteroidal anti-inflammatory drugs (NSAIDs), fenoprofen, carprofen, flurbiprofen, indoprofen, flobufen, ketoprofen, and suprofen, by capillary liquid chromatography. The effect of the type of stationary phase, the chiral column Chirobiotic V or the achiral stationary phases Nucleosil 100 C8 HD and Nucleosil 100 C18 HD, and the concentration of vancomycin in the mobile phase on separation of the drug enantiomers were evaluated. All the drugs, except flobufen, were successfully enantioseparated on Nucleosil 100 C8 HD with 4 mM vancomycin present in the mobile phase (composed of methanol and buffer) in the reversed phase mode. On the vancomycin-bonded chiral stationary phase, it was difficult to gut enantioseparations of the profen NSAIDs. However, flobufen gave better enantioseparation on the vancomycin CSP. The better enantioresolution of the majority of profen derivatives on the achiral columns with vancomycin added to the mobile phase can be attributed in particular to the higher separation efficiency of this capillary chromatographic system. In addition, vancomycin dimers, formed in the mobile phase, seem to offer a better steric arrangement for stereoselective interaction to these analytes than the vancomycin bonded on the CSP. These substantial differences in the CS structure significantly influence the chiral discrimination mechanism.

KW - Chiral separation

KW - cLC

KW - Macrocyclic antibiotic

KW - Vancomycin chiral mobile phase additive

KW - Vancomycin-based chiral stationary phase

UR - http://www.scopus.com/inward/record.url?scp=33745408128&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=33745408128&partnerID=8YFLogxK

U2 - 10.1002/chir.20284

DO - 10.1002/chir.20284

M3 - Article

VL - 18

SP - 531

EP - 538

JO - Chirality

JF - Chirality

SN - 0899-0042

IS - 7

ER -