Partition coefficients of the local anesthetic dibucaine into a lipid bilayer membrane determined with a dibucaine cation sensor

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  • NISHIMOTO Makoto
    Department of Materials Science and Engineering, Kochi National College of Technology
  • MATSUOKA Kazuhiko
    Department of Materials Science and Engineering, Kochi National College of Technology
  • NAGAYAMA Kazuhito
    Department of Materials Science and Engineering, Kochi National College of Technology
  • HATA Takashi
    Department of Materials Science and Engineering, Kochi National College of Technology
  • MATSUKI Hitoshi
    Department of Biological Science and Technology, Faculty of Engineering, The University of Tokushima
  • SATAKE Hiromu
    Center for Cooperative Research, The University of Tokushima
  • KANESHINA Shoji
    Department of Biological Science and Technology, Faculty of Engineering, The University of Tokushima

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Other Title
  • 局所麻酔薬ジブカインカチオンセンサーを用いる脂質二分子膜へのジブカインの分配測定
  • キョクショ マスイヤク ジブカインカチオンセンサー オ モチイル シシツ 2ブンシ マク エ ノ ジブカイン ノ ブンパイ ソクテイ

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Abstract

Local anesthetics are known to be typical drugs which act directly on biomembranes. However, the molecular mechanism of anesthetic action is still uncertain. In order to clarity the action mechanism, the partition coefficient of anesthetics to lipid membranes is necessarily important. Most local anesthetics in clinical use are tertiary amine compounds that exist in neutral and/or positively charged species, depending on the pH of the solution. In this study, we prepared coated wire electrodes sensitive to the local anesthetic dibucaine cation, and determined the partition coefficient of anesthetics into a lipid membrane. Moreover, we focused our attention on the pH-dependence of the partition coefficient in order to elucidate the contribution of charged- and uncharged-dibucaine to the lecithin membrane/buffer partition coefficients. The lecithin membrane/buffer partition coefficient was directly determined by the dibucaine cation sensor as a function of the anesthetic concentration and the pH. The limiting partition coefficient extrapolated to infinite dilution was employed because the values of partition coefficients were dependent upon the dibucaine concentration. The limiting partition coefficient increased with an increase in the pH. This means that uncharged species increased with an increase in the pH because pKa of dibucaine is 8.72 at 25°C. The partition coefficients of charged and uncharged dibucaine into the lecithin membranes were estimated from the pH-dependence of the limiting partition coefficients. The partition coefficients were 1.6×104 and 8.6×106 for charged and uncharged dibucaine, respectively. The electrodes were applied satisfactorily for determining for the partition coefficient of local anesthetic dibucaine into biomembranes.<br>

Journal

  • BUNSEKI KAGAKU

    BUNSEKI KAGAKU 52 (9), 781-785, 2003

    The Japan Society for Analytical Chemistry

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