Enantiomeric separation and detection of 2-arylpropionic acids derivatized with [(N,N-dimethylamino)sulfonyl]benzofurazan reagents on a modified cellulose stationary phase by high-performance liquid chromatography

T. Fukushima, T. Santa, H. Homma, S. M. Al-Kindy, K. Imai

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Abstract

(RS)-2-Arylpropionic acids (2-APAs) were derivatized with the fluorogenic reagents, 4-[(N,N-dimethylamino)sulfonyl]-7-piperazino-2,1,3-benzoxadiazole (DBD-PZ) and 4-[[(N-hydrazinoformyl)methyl]-N-methyl]amino-7-[N,N(dimethylamino)sul fonyl]-2,1,3-benzoxadiazole (DBD-COHz), and their enantiomeric separation by a chiral stationary phase high-performance liquid chromatography was investigated in the reversed-phase mode with H2O/CH3CN or H2O/MeOH as the mobile phase on a column of cellulose tris(3,5-dimethylphenyl carbamate) coated on a silica gel support (Chiralcel OD-R). The derivatives with DBD-PZ were enantiomerically separated well under the elution condition of H2O/MeOH, based on the π-π interaction between the derivatives and the stationary phase. The rigid and bulky structure of DBD-PZ was demonstrated to be more effective as compared to the less rigid ones. The derivatives with DBD-COHz were more efficiently separated into each enantiomer with H2O/CH3CN as the eluent. The effective separation was based on hydrogen-bonding interaction between the acid hydrazide of the derivatives and the carbamoyl moiety of the stationary phase. There was a reversal in the elution order of the enantiomers between the two fluorescent derivatives. The detection limits obtained for each enantiomer were approximately 10-30 fmol on column. The derivatization with the reagent and the concomitant use of the reversed-phase and chiral stationary-phase HPLC were demonstrated to be useful for the enantiomeric quantification in rat plasma after intravenous administration of flurbiprofen racemate, a representative of 2-APAs.

Original languageEnglish
Pages (from-to)1793-1799
Number of pages7
JournalAnalytical Chemistry
Volume69
Issue number9
DOIs
Publication statusPublished - 1997

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High performance liquid chromatography
Cellulose
Enantiomers
Derivatives
Acids
Flurbiprofen
Silica Gel
Rats
Hydrogen bonds
benzofurazan
Plasmas
4-(N,N-dimethylaminosulphonyl)-7-(1-piperazinyl)-2,1,3-benzoxadiazole
cellulose tris-3,5-dimethylphenyl-carbamate

ASJC Scopus subject areas

  • Analytical Chemistry

Cite this

@article{45179c8f494b4878ab92d9c2c0b02e53,
title = "Enantiomeric separation and detection of 2-arylpropionic acids derivatized with [(N,N-dimethylamino)sulfonyl]benzofurazan reagents on a modified cellulose stationary phase by high-performance liquid chromatography",
abstract = "(RS)-2-Arylpropionic acids (2-APAs) were derivatized with the fluorogenic reagents, 4-[(N,N-dimethylamino)sulfonyl]-7-piperazino-2,1,3-benzoxadiazole (DBD-PZ) and 4-[[(N-hydrazinoformyl)methyl]-N-methyl]amino-7-[N,N(dimethylamino)sul fonyl]-2,1,3-benzoxadiazole (DBD-COHz), and their enantiomeric separation by a chiral stationary phase high-performance liquid chromatography was investigated in the reversed-phase mode with H2O/CH3CN or H2O/MeOH as the mobile phase on a column of cellulose tris(3,5-dimethylphenyl carbamate) coated on a silica gel support (Chiralcel OD-R). The derivatives with DBD-PZ were enantiomerically separated well under the elution condition of H2O/MeOH, based on the π-π interaction between the derivatives and the stationary phase. The rigid and bulky structure of DBD-PZ was demonstrated to be more effective as compared to the less rigid ones. The derivatives with DBD-COHz were more efficiently separated into each enantiomer with H2O/CH3CN as the eluent. The effective separation was based on hydrogen-bonding interaction between the acid hydrazide of the derivatives and the carbamoyl moiety of the stationary phase. There was a reversal in the elution order of the enantiomers between the two fluorescent derivatives. The detection limits obtained for each enantiomer were approximately 10-30 fmol on column. The derivatization with the reagent and the concomitant use of the reversed-phase and chiral stationary-phase HPLC were demonstrated to be useful for the enantiomeric quantification in rat plasma after intravenous administration of flurbiprofen racemate, a representative of 2-APAs.",
author = "T. Fukushima and T. Santa and H. Homma and Al-Kindy, {S. M.} and K. Imai",
year = "1997",
doi = "10.1021/ac961105g",
language = "English",
volume = "69",
pages = "1793--1799",
journal = "Analytical Chemistry",
issn = "0003-2700",
publisher = "American Chemical Society",
number = "9",

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TY - JOUR

T1 - Enantiomeric separation and detection of 2-arylpropionic acids derivatized with [(N,N-dimethylamino)sulfonyl]benzofurazan reagents on a modified cellulose stationary phase by high-performance liquid chromatography

AU - Fukushima, T.

AU - Santa, T.

AU - Homma, H.

AU - Al-Kindy, S. M.

AU - Imai, K.

PY - 1997

Y1 - 1997

N2 - (RS)-2-Arylpropionic acids (2-APAs) were derivatized with the fluorogenic reagents, 4-[(N,N-dimethylamino)sulfonyl]-7-piperazino-2,1,3-benzoxadiazole (DBD-PZ) and 4-[[(N-hydrazinoformyl)methyl]-N-methyl]amino-7-[N,N(dimethylamino)sul fonyl]-2,1,3-benzoxadiazole (DBD-COHz), and their enantiomeric separation by a chiral stationary phase high-performance liquid chromatography was investigated in the reversed-phase mode with H2O/CH3CN or H2O/MeOH as the mobile phase on a column of cellulose tris(3,5-dimethylphenyl carbamate) coated on a silica gel support (Chiralcel OD-R). The derivatives with DBD-PZ were enantiomerically separated well under the elution condition of H2O/MeOH, based on the π-π interaction between the derivatives and the stationary phase. The rigid and bulky structure of DBD-PZ was demonstrated to be more effective as compared to the less rigid ones. The derivatives with DBD-COHz were more efficiently separated into each enantiomer with H2O/CH3CN as the eluent. The effective separation was based on hydrogen-bonding interaction between the acid hydrazide of the derivatives and the carbamoyl moiety of the stationary phase. There was a reversal in the elution order of the enantiomers between the two fluorescent derivatives. The detection limits obtained for each enantiomer were approximately 10-30 fmol on column. The derivatization with the reagent and the concomitant use of the reversed-phase and chiral stationary-phase HPLC were demonstrated to be useful for the enantiomeric quantification in rat plasma after intravenous administration of flurbiprofen racemate, a representative of 2-APAs.

AB - (RS)-2-Arylpropionic acids (2-APAs) were derivatized with the fluorogenic reagents, 4-[(N,N-dimethylamino)sulfonyl]-7-piperazino-2,1,3-benzoxadiazole (DBD-PZ) and 4-[[(N-hydrazinoformyl)methyl]-N-methyl]amino-7-[N,N(dimethylamino)sul fonyl]-2,1,3-benzoxadiazole (DBD-COHz), and their enantiomeric separation by a chiral stationary phase high-performance liquid chromatography was investigated in the reversed-phase mode with H2O/CH3CN or H2O/MeOH as the mobile phase on a column of cellulose tris(3,5-dimethylphenyl carbamate) coated on a silica gel support (Chiralcel OD-R). The derivatives with DBD-PZ were enantiomerically separated well under the elution condition of H2O/MeOH, based on the π-π interaction between the derivatives and the stationary phase. The rigid and bulky structure of DBD-PZ was demonstrated to be more effective as compared to the less rigid ones. The derivatives with DBD-COHz were more efficiently separated into each enantiomer with H2O/CH3CN as the eluent. The effective separation was based on hydrogen-bonding interaction between the acid hydrazide of the derivatives and the carbamoyl moiety of the stationary phase. There was a reversal in the elution order of the enantiomers between the two fluorescent derivatives. The detection limits obtained for each enantiomer were approximately 10-30 fmol on column. The derivatization with the reagent and the concomitant use of the reversed-phase and chiral stationary-phase HPLC were demonstrated to be useful for the enantiomeric quantification in rat plasma after intravenous administration of flurbiprofen racemate, a representative of 2-APAs.

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U2 - 10.1021/ac961105g

DO - 10.1021/ac961105g

M3 - Article

VL - 69

SP - 1793

EP - 1799

JO - Analytical Chemistry

JF - Analytical Chemistry

SN - 0003-2700

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