Enantioseparation of vinclozolin by gamma-cyclodextrin-modified micellar electrokinetic chromatography.
Cyclodextrin-modified micellar electrokinetic chromatography was applied to the enantioseparation of vinclozolin, which has been used as a fungicide and has an anti-androgenic activity, using gamma-cyclodextrin together with sodium dodecyl sulfate. Factors affecting the chiral resolution and migration time of vinclozolin were studied. The optimum running conditions were found to be 20 mM phosphate-5 mM borate buffer (pH 8.5) containing 50 mM gamma-cyclodextrin and 100 mM sodium dodecyl sulfate with an effective voltage of 20 kV at 20 degrees C using direct detection at 203 nm. Under these conditions, the resolution (Rs) of racemic vinclozolin was approximately 2.1. The sample was concentrated by solid-phase extraction and was fractionated by HPLC. The peak area ratio of (+)- and (-)-vinclozolins in wine was found to be 2:3, namely, not racemic, suggesting that degradation rates were different between (+)- and (-)-vinclozolins. The anti-androgenic activities of (+)- and (-)-vinclozolins on dihydrotestosterone-induced transcription were also investigated. The anti-androgenic activity of (+)-vinclozolin tended to be stronger than that of (-)-vinclozolin, suggesting the possibility that vinclozolin can act as an enantioselective anti-androgen.
Kodama
Shuji
S
Toyama Institute of Health, 17-1 Nakataikoyama, Kosugi-machi, Toyama 939-0363, Japan. lee07664@nifty.ne.jp
Yamamoto
Atsushi
A
Saitoh
Yukio
Y
Matsunaga
Akinobu
A
Okamura
Kazumasa
K
Kizu
Ryoichi
R
Hayakawa
Kazuichi
K
D002851:Chromatography, High Pressure Liquid; D003505:Cyclodextrins; D019075:Electrophoresis, Capillary / Q000379:methods; D005659:Fungicides, Industrial / Q000737:chemistry* / Q000302:isolation & purification; D007202:Indicators and Reagents; D008823:Micelles; D010080:Oxazoles / Q000737:chemistry* / Q000302:isolation & purification; D013237:Stereoisomerism; D047408:gamma-Cyclodextrins
D003505:Cyclodextrins; D005659:Fungicides, Industrial; D007202:Indicators and Reagents; D008823:Micelles; D010080:Oxazoles; D047408:gamma-Cyclodextrins; C025643:vinclozolin; C023792:gamma-cyclodextrin