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, Takeshi
AU - Santa, Tomofumi
AU - Homma, Hiroshi
AU - Al-kindy, Salma M.
AU - Imai, Kazuhiro
PY - 1997/5/1
Y1 - 1997/5/1
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)sulfonyl]-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/CH3-CN 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)sulfonyl]-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/CH3-CN 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
C2 - 21639306
AN - SCOPUS:0030917225
SN - 0003-2700
VL - 69
SP - 1793
EP - 1799
JO - Analytical Chemistry
JF - Analytical Chemistry
IS - 9
ER -