Monte Carlo simulations of the chiral recognition of fenoprofen enantiomers by cyclomaltoheptaose (β-cyclodextrin)

被引:15
作者
Choi, YH
Yang, CH
Kim, HW
Jung, S
机构
[1] Konkuk Univ, Dept Microbial Engn, Kwangjin Ku, Seoul 143701, South Korea
[2] Seoul Natl Univ, Dept Chem, Seoul 151742, South Korea
[3] Yonsei Univ, Dept Biochem, Wonju Coll Med, Wonju 220701, South Korea
关键词
Monte Carlo simulation; chiral recognition; fenoprofen; beta-cyclodextrin;
D O I
10.1016/S0008-6215(00)00101-4
中图分类号
Q5 [生物化学]; Q7 [分子生物学];
学科分类号
071010 ; 081704 ;
摘要
Differential complexation of fenoprofen enantiomers by cyclomaltoheptaose (beta-cyclodextrin) was investigated by Monte Carlo docking simulations. The chiral discrimination of (R)- and (S)-fenoprofen by beta-cyclodextrin was discussed in terms of the difference in the interaction energies and the patterns of molecular interactions. The interaction energies between each enantiomer of fenoprofen and beta-cyclodextrin were consistent with the reported experimental results that showed that the S isomer interacted preferentially with beta-cyclodextrin and was retained longer in a separation process than the R isomer. The thermodynamic preference of inclusion complex formation of (S)-fenoprofen could be explained by the orientation of the phenyl group attached to the chiral carbon, which provided closer contact and thus more favorable intermolecular interactions between the host and guest molecule. The results presented here would be very useful for the prediction of chiral recognition ability of beta-cyclodextrin. (C) 2000 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:393 / 397
页数:5
相关论文
共 15 条
  • [1] SEPARATION OF DRUG STEREOISOMERS BY THE FORMATION OF BETA-CYCLODEXTRIN INCLUSION COMPLEXES
    ARMSTRONG, DW
    WARD, TJ
    ARMSTRONG, RD
    BEESLEY, TE
    [J]. SCIENCE, 1986, 232 (4754) : 1132 - 1135
  • [2] CYCLODEXTRIN CHIRAL STATIONARY PHASES FOR LIQUID-CHROMATOGRAPHIC SEPARATIONS OF DRUG STEREOISOMERS
    BERTHOD, A
    JIN, HL
    BEESLEY, TE
    DUNCAN, JD
    ARMSTRONG, DW
    [J]. JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS, 1990, 8 (02) : 123 - 130
  • [3] TOPOGRAPHY OF CYCLODEXTRIN INCLUSION COMPLEXES .20. CIRCULAR AND FLIP-FLOP HYDROGEN-BONDING IN BETA-CYCLODEXTRIN UNDECAHYDRATE - A NEUTRON-DIFFRACTION STUDY
    BETZEL, C
    SAENGER, W
    HINGERTY, BE
    BROWN, GM
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1984, 106 (24) : 7545 - 7557
  • [4] Separation of profen enantiomers by capillary electrophoresis using cyclodextrins as chiral selectors
    Blanco, M
    Coello, J
    Iturriaga, H
    Maspoch, S
    Pérez-Maseda, C
    [J]. JOURNAL OF CHROMATOGRAPHY A, 1998, 793 (01) : 165 - 175
  • [5] FENOPROFEN - REVIEW OF ITS PHARMACOLOGICAL PROPERTIES AND THERAPEUTIC EFFICACY IN RHEUMATIC DISEASES
    BROGDEN, RN
    PINDER, RM
    SPEIGHT, TM
    AVERY, GS
    [J]. DRUGS, 1977, 13 (04) : 241 - 265
  • [6] Choi YH, 1999, B KOREAN CHEM SOC, V20, P753
  • [7] STRUCTURE AND ENERGETICS OF LIGAND-BINDING TO PROTEINS - ESCHERICHIA-COLI DIHYDROFOLATE REDUCTASE TRIMETHOPRIM, A DRUG-RECEPTOR SYSTEM
    DAUBEROSGUTHORPE, P
    ROBERTS, VA
    OSGUTHORPE, DJ
    WOLFF, J
    GENEST, M
    HAGLER, AT
    [J]. PROTEINS-STRUCTURE FUNCTION AND GENETICS, 1988, 4 (01): : 31 - 47
  • [8] MOLECULAR MODELING OF THE INCLUSION COMPLEXES BETWEEN BETA-CYCLODEXTRIN AND (R)/(S)-METHYLPHENOBARBITONE AND ITS APPLICATION TO HPLC
    DURHAM, DG
    LIANG, HX
    [J]. CHIRALITY, 1994, 6 (04) : 239 - 244
  • [9] KRISTULOVIC AM, 1989, CHIRAL SEPARATIONS H, P147
  • [10] Complex forming ability of a family of isolated cyclosophoraoses with ergosterol and its Monte Carlo docking computational analysis
    Kwon, C
    Choi, YH
    Kim, N
    Yoo, JS
    Yang, CH
    Kim, HW
    Jung, S
    [J]. JOURNAL OF INCLUSION PHENOMENA AND MACROCYCLIC CHEMISTRY, 2000, 36 (01) : 55 - 65