Partitioning of uncharged local anesthetic benzocaine into model biomembranes

Hitoshi Matsuki, Takashi Hata, Michio Yamanaka, Shoji Kaneshina

Research output: Contribution to journalArticle

7 Citations (Scopus)

Abstract

The partitioning of uncharged local anesthetic benzocaine (BzC) into molecular aggregates formed by cationic surfactant decylammonium chloride (DeAC) and phospholipid dipalmitoylphosphatidylcholine (DPPC) was studied from the surface tension and light transmittance measurements. The quantities concerning the partitioning of BzC, the compositions of BzC in the surface-adsorbed film and micelle and three kinds of differential partition coefficients corresponding to phase transitions of the DPPC bilayer membrane were evaluated from thermodynamic analysis of the experimental data. The surface-adsorbed film and micelle were more abundant in BzC than the aqueous solution and significantly large differential partition coefficients for the DPPC membranes were observed. The results clearly showed that the BzC molecules greatly partitioned into hydrophobic environments produced by surfactant-monolayer and phospholipid-bilayer membranes. The partitioning behavior of BzC was also compared with that of charged local anesthetic procaine hydrochloride (PC·HCl). It was shown that the PC·HCl molecule did not or hardly partition into such hydrophobic environments. The contrasting results of the partitioning between BzC and PC·HCl are attributable to the drastic decrease of hydrophilicity of BzC due to the lacking of ionic polar head group in comparison with PC·HCl.

Original languageEnglish
Pages (from-to)69-76
Number of pages8
JournalColloids and Surfaces B: Biointerfaces
Volume22
Issue number1
DOIs
Publication statusPublished - Jul 12 2001

Fingerprint

Benzocaine
anesthetics
Anesthetics
hydrochlorides
Local Anesthetics
Phospholipids
Membranes
partitions
Micelles
Procaine
membranes
1,2-Dipalmitoylphosphatidylcholine
micelles
Molecules
Cationic surfactants
surfactants
Hydrophilicity
Surface tension
Monolayers
Surface active agents

All Science Journal Classification (ASJC) codes

  • Biotechnology
  • Surfaces and Interfaces
  • Physical and Theoretical Chemistry
  • Colloid and Surface Chemistry

Cite this

Partitioning of uncharged local anesthetic benzocaine into model biomembranes. / Matsuki, Hitoshi; Hata, Takashi; Yamanaka, Michio; Kaneshina, Shoji.

In: Colloids and Surfaces B: Biointerfaces, Vol. 22, No. 1, 12.07.2001, p. 69-76.

Research output: Contribution to journalArticle

Matsuki, Hitoshi ; Hata, Takashi ; Yamanaka, Michio ; Kaneshina, Shoji. / Partitioning of uncharged local anesthetic benzocaine into model biomembranes. In: Colloids and Surfaces B: Biointerfaces. 2001 ; Vol. 22, No. 1. pp. 69-76.
@article{606eaf7eb46a4f5eb74ad48cef7419f5,
title = "Partitioning of uncharged local anesthetic benzocaine into model biomembranes",
abstract = "The partitioning of uncharged local anesthetic benzocaine (BzC) into molecular aggregates formed by cationic surfactant decylammonium chloride (DeAC) and phospholipid dipalmitoylphosphatidylcholine (DPPC) was studied from the surface tension and light transmittance measurements. The quantities concerning the partitioning of BzC, the compositions of BzC in the surface-adsorbed film and micelle and three kinds of differential partition coefficients corresponding to phase transitions of the DPPC bilayer membrane were evaluated from thermodynamic analysis of the experimental data. The surface-adsorbed film and micelle were more abundant in BzC than the aqueous solution and significantly large differential partition coefficients for the DPPC membranes were observed. The results clearly showed that the BzC molecules greatly partitioned into hydrophobic environments produced by surfactant-monolayer and phospholipid-bilayer membranes. The partitioning behavior of BzC was also compared with that of charged local anesthetic procaine hydrochloride (PC·HCl). It was shown that the PC·HCl molecule did not or hardly partition into such hydrophobic environments. The contrasting results of the partitioning between BzC and PC·HCl are attributable to the drastic decrease of hydrophilicity of BzC due to the lacking of ionic polar head group in comparison with PC·HCl.",
author = "Hitoshi Matsuki and Takashi Hata and Michio Yamanaka and Shoji Kaneshina",
year = "2001",
month = "7",
day = "12",
doi = "10.1016/S0927-7765(01)00159-X",
language = "English",
volume = "22",
pages = "69--76",
journal = "Colloids and Surfaces B: Biointerfaces",
issn = "0927-7765",
publisher = "Elsevier",
number = "1",

}

TY - JOUR

T1 - Partitioning of uncharged local anesthetic benzocaine into model biomembranes

AU - Matsuki, Hitoshi

AU - Hata, Takashi

AU - Yamanaka, Michio

AU - Kaneshina, Shoji

PY - 2001/7/12

Y1 - 2001/7/12

N2 - The partitioning of uncharged local anesthetic benzocaine (BzC) into molecular aggregates formed by cationic surfactant decylammonium chloride (DeAC) and phospholipid dipalmitoylphosphatidylcholine (DPPC) was studied from the surface tension and light transmittance measurements. The quantities concerning the partitioning of BzC, the compositions of BzC in the surface-adsorbed film and micelle and three kinds of differential partition coefficients corresponding to phase transitions of the DPPC bilayer membrane were evaluated from thermodynamic analysis of the experimental data. The surface-adsorbed film and micelle were more abundant in BzC than the aqueous solution and significantly large differential partition coefficients for the DPPC membranes were observed. The results clearly showed that the BzC molecules greatly partitioned into hydrophobic environments produced by surfactant-monolayer and phospholipid-bilayer membranes. The partitioning behavior of BzC was also compared with that of charged local anesthetic procaine hydrochloride (PC·HCl). It was shown that the PC·HCl molecule did not or hardly partition into such hydrophobic environments. The contrasting results of the partitioning between BzC and PC·HCl are attributable to the drastic decrease of hydrophilicity of BzC due to the lacking of ionic polar head group in comparison with PC·HCl.

AB - The partitioning of uncharged local anesthetic benzocaine (BzC) into molecular aggregates formed by cationic surfactant decylammonium chloride (DeAC) and phospholipid dipalmitoylphosphatidylcholine (DPPC) was studied from the surface tension and light transmittance measurements. The quantities concerning the partitioning of BzC, the compositions of BzC in the surface-adsorbed film and micelle and three kinds of differential partition coefficients corresponding to phase transitions of the DPPC bilayer membrane were evaluated from thermodynamic analysis of the experimental data. The surface-adsorbed film and micelle were more abundant in BzC than the aqueous solution and significantly large differential partition coefficients for the DPPC membranes were observed. The results clearly showed that the BzC molecules greatly partitioned into hydrophobic environments produced by surfactant-monolayer and phospholipid-bilayer membranes. The partitioning behavior of BzC was also compared with that of charged local anesthetic procaine hydrochloride (PC·HCl). It was shown that the PC·HCl molecule did not or hardly partition into such hydrophobic environments. The contrasting results of the partitioning between BzC and PC·HCl are attributable to the drastic decrease of hydrophilicity of BzC due to the lacking of ionic polar head group in comparison with PC·HCl.

UR - http://www.scopus.com/inward/record.url?scp=0034959202&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0034959202&partnerID=8YFLogxK

U2 - 10.1016/S0927-7765(01)00159-X

DO - 10.1016/S0927-7765(01)00159-X

M3 - Article

AN - SCOPUS:0034959202

VL - 22

SP - 69

EP - 76

JO - Colloids and Surfaces B: Biointerfaces

JF - Colloids and Surfaces B: Biointerfaces

SN - 0927-7765

IS - 1

ER -