The effect of the nature of H-bonding groups on diffusion through PDMS membranes saturated with octanol and toluene

被引:25
作者
Du Plessis, J [1 ]
Pugh, WJ
Judefeind, A
Hadgraft, J
机构
[1] Potchefstroom Univ Christian Higher Educ, Sch Pharm, ZA-2520 Potchefstroom, South Africa
[2] Cardiff Univ, Welsh Sch Pharm, Cardiff CF1 3XF, S Glam, Wales
[3] Univ Greenwich, NRI, Chatham ME4 4TB, Kent, England
基金
英国惠康基金;
关键词
hydrogen bonding; silicone; skin; phenols; diffusion; thermodynamic activity; solvatochromic effects;
D O I
10.1016/S0928-0987(01)00212-3
中图分类号
R9 [药学];
学科分类号
1007 ;
摘要
The permeation of a series of structurally related compounds across silicone membranes (PDMS) was studied. The PDMS was saturated either with toluene, to mimic a functionally inert barrier, or octanol, to mimic the polar/hydrogen bonding environment of the stratum corneum lipid barrier. Phenol, salicylic acid, benzoic acid, anisole, phenylethanol and benzyl alcohol were chosen in an attempt to relate permeation to their different H-bonding capabilities. The flux was lower through the octanol system suggesting retardation by polar/H-bonding interactions. Separation of the permeability coefficient into its thermodynamic (partition coefficient) and kinetic (diffusion coefficient) terms suggests that the effect of altering polarity within the membrane has a greater impact on the diffusion of permeant rather than its chemical potential within the membrane. (C) 2002 Elsevier Science B.V. All rights reserved.
引用
收藏
页码:63 / 69
页数:7
相关论文
共 11 条
[2]   HYDROGEN-BONDING .32. AN ANALYSIS OF WATER-OCTANOL AND WATER-ALKANE PARTITIONING AND THE DELTA-LOG-P PARAMETER OF SEILER [J].
ABRAHAM, MH ;
CHADHA, HS ;
WHITING, GS ;
MITCHELL, RC .
JOURNAL OF PHARMACEUTICAL SCIENCES, 1994, 83 (08) :1085-1100
[3]   The effect of hydrogen bonding on diffusion across model membranes: consideration of the number of H-bonding groups [J].
Du Plessis, J ;
Pugh, WJ ;
Judefeind, A ;
Hadgraft, J .
EUROPEAN JOURNAL OF PHARMACEUTICAL SCIENCES, 2001, 13 (02) :135-141
[4]   PERCUTANEOUS PENETRATION OF DRUGS - A QUANTITATIVE STRUCTURE PERMEABILITY RELATIONSHIP STUDY [J].
ELTAYAR, N ;
TSAI, RS ;
TESTA, B ;
CARRUPT, PA ;
HANSCH, C ;
LEO, A .
JOURNAL OF PHARMACEUTICAL SCIENCES, 1991, 80 (08) :744-749
[5]   The relative effect of Azone(R) and Transcutol(R) on permeant diffusivity and solubility in human stratum corneum [J].
Harrison, JE ;
Watkinson, AC ;
Green, DM ;
Hadgraft, J ;
Brain, K .
PHARMACEUTICAL RESEARCH, 1996, 13 (04) :542-546
[6]   PREDICTING SKIN PERMEABILITY [J].
POTTS, RO ;
GUY, RH .
PHARMACEUTICAL RESEARCH, 1992, 9 (05) :663-669
[7]   Epidermal permeability - Penetrant structure relationships .3. The effect of hydrogen bonding interactions and molecular size on diffusion across the stratum corneum [J].
Pugh, WJ ;
Roberts, MS ;
Hadgraft, J .
INTERNATIONAL JOURNAL OF PHARMACEUTICS, 1996, 138 (02) :149-165
[8]   Epidermal permeability: Penetrant structure relationships .2. The effect of H-bonding groups in penetrants on their diffusion through the stratum corneum [J].
Roberts, MS ;
Pugh, WJ ;
Hadgraft, J .
INTERNATIONAL JOURNAL OF PHARMACEUTICS, 1996, 132 (1-2) :23-32
[9]   Epidermal permeability penetrant structure relationships .1. An analysis of methods of predicting penetration of monofunctional solutes from aqueous solutions [J].
Roberts, MS ;
Pugh, WJ ;
Hadgraft, J ;
Watkinson, AC .
INTERNATIONAL JOURNAL OF PHARMACEUTICS, 1995, 126 (1-2) :219-233
[10]  
SCHEUPLEIN RJ, 1971, PHYSIOL REV, V1, P707