Empirical Equation for Resolution if Ibuprofen Enantiomers by Chiral High-Performance Liquid Chromatography

키랄 고성능 액체 크로마토그래피를 이용하 이부프로펜의 분리도에 관한 실험식

  • 여미순 (초정밀분리기술센터, 인하대학교 공과대학 화학공학과) ;
  • 노경호 (초정밀분리기술센터, 인하대학교 공과대학 화학공학과)
  • Published : 2003.08.01

Abstract

Ibuprofen was analyzed by chiral high performance liquid chromatography. Retention behaviours of the standard mixtures of ibuprofen were investigated to obtain their acceptable resolution. A chromatographic column (3.9 ${\times}$ 300 mm) was packed by Kromasil CHI-TBB packings (10 $\mu\textrm{m}$) and n-hexane was used as a mobile phase with 0.1% acetic acid and tert-butyl methyl ether. Isocratic elution of ibuprofen at 1.0 $m\ell$/min was performed by changing the mobile phase compositions. The experimental variables affecting the resolution were the compositions of mobile phase and chemical buffer (n-hexane and tert-butyl methyl ether). The resolution between the enantiomers were correlated into the several types of empirical equations including linear form, and their agreements between experimental data and calculated values were examined by the regression coefficient.

이부프로펜 중 S-enantiomer는 약물학적 효과를 갖고 있으나 R-enantiomer는 여러 가지 부작용을 갖고 있다. 이런 라세미 혼합물은 키랄 고성능 액체 크로마토그래피를 이용하여 효과적으로 분리 할 수 있었다. 실험에서 이용한 column(3.9 ${\times}$ 300 mm)은 Kromasil 10 $\mu\textrm{m}$를 충진하였고, 이동상으로는 n-hexane/tert-butyl methyl ether/acetic acid를 사용하였다. 유속은 1.0 $m\ell$/min 주입부피는 5 ${\mu}\ell$이고, UV 검출기의 wavelength는 220 nm이며 실온에서 실험하였다. 라세미 형태의 이부프로펜을 키랄 고정상으로 채워진 컬럼을 이용하여 이동상의 조성비를 바꿔가면서 이동상의 조성 변화에 따른 두 물질의 분리도의 상관식을 얻었다. 이 상관식을 이용하여 각 조성에 분리도에 미치는 영향을 정량적으로 표시하였고 보간법 또는 외사법에 의하여 실험이외의 조성에 대한 분리도를 예측할 수 있는 장점이 있다.

Keywords

References

  1. J. Phar. Biomed. Anal. v.8 Importance of enantiomeric purity and its control by thin-layer chromatography Bhushan,R.;J.Martens https://doi.org/10.1016/0731-7085(90)80035-N
  2. Chiral Separations by Chromatography Ahuja,S.
  3. Biomed. Chromatogr. v.12 Resolution of enantiomers of ibuprofen Bhushan,R.;J.Matens https://doi.org/10.1002/(SICI)1099-0801(199811/12)12:6<309::AID-BMC763>3.0.CO;2-K
  4. J. Chromatogr. A v.785 Chiral packed column subcritical fluid chromatography on polysaccharide and macrocyclic antibiotic chiral stationary phases Medvedovici,A.;P.Sandra;L.Toribio;F.David https://doi.org/10.1016/S0021-9673(97)00585-2
  5. J. Phar. Biomed. Anal. v.16 Chiral high performance liquid chromatography resolution of ibuprofen esters Ducret,A.;M.Trani;P.Pepin;R.Lortie
  6. Principles and Applications of Liquid Chromatography Row,K.H.
  7. Excel for Chemical Engineering Row,K.H.
  8. Chromatographic Determination of Molecular Interactions Cserhati,T.;K.Valko
  9. Hwahak Konghak v.38 Optical resolution of racemic ibuprofen by using chiral stationary phase Kim,S.Y.;J.K.Lee;S.S.Suh;M.H.Choi;T.J.Park;D.K.Park
  10. J. Chromatogr. B v.701 Stereospecific analysis of the major metabolites of ibuprofen in urine by sequential achiral-chiral high-peroformance liquid chromatography Tan,S.C.;S.H.D.Jackson;C.G.Swift;A.J.Hutt https://doi.org/10.1016/S0378-4347(97)00338-1
  11. J. Chromatogr. A v.852 Emprical relationship between chiral selectivity and mobile phase modifier properties Blackwell,J.A.;R.W.Stringham;D.Xiang;R.E.Waltermire https://doi.org/10.1016/S0021-9673(99)00637-8
  12. J. Chromatogr. A v.857 Uniform-sized molecularly imprinted polymer for (S)-ibuprofen retention properties in aqueous mobile phases Haginaka,J.;H.Sanbe;H.Takehira https://doi.org/10.1016/S0021-9673(99)00764-5
  13. J. Chromatogr. B v.745 Chiral separation by simultaneous use of vancomycin as stationary phase selector and chiral mobile phase additive Sun,Q.;S.V.Olesik https://doi.org/10.1016/S0378-4347(00)00267-X