Influence of pH on Skin Permeation of Amino Acids

Hatanaka, Tomomi; Kamon, Toshihiko; Uozumi, Chisato; Morigaki, Setsuko; Aiba, Tetsuya; Katayama, Kazunori; Koizumi, Tamotsu

doi:10.1111/j.2042-7158.1996.tb03949.x

Cited by 8 publications

(11 citation statements)

References 19 publications

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“…T he formation of zwitterionic structures in amino acids is of fundamental importance in biology [1][2][3][4][5][6]. The resulting electric field plays a crucial role in determining the structure of many proteins and the reactivity enzymes [7][8][9].…”

mentioning

confidence: 99%

Zwitterion formation in gas-phase cyclodextrin complexes

Ahn

Cong

Lebrilla

et al. 2005

J. Am. Soc. Mass Spectrom.

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Protonated complexes of amino acids and underivatized ␤-cyclodextrin, produced by electrospray ionization and trapped in the Fourier transform mass spectrometer, undergo formation of ternary complexes when reacted with alkyl amine. Based on the reactivities of the protonated amino acid complexes with alkylamines, the reactivities of the corresponding amino acid esters, and partially derivatized ␤-cyclodextrin hosts, we conclude that the ternary complexes are salt-bridge zwitterionic species composed of amino acid zwitterions and protonated alkylamine all interacting with the hydroxyl groups on the narrow rim of the cyclodextrin. Molecular modeling calculations and experimental results suggest that the interactions of the amino acids with the rims contribute greatly to the formation of the zwitterionic species. (J Am Soc Mass Spectrom 2005, 16, 166 -175)

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mentioning

confidence: 99%

Zwitterion formation in gas-phase cyclodextrin complexes

Ahn

Cong

Lebrilla

et al. 2005

J. Am. Soc. Mass Spectrom.

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“…The exception is lysine whose permeability is significantly increased by palmitate but for this amino acid, penetration experiments were carried out at pH 9. At pH 9, in spite of ion pair mechanism, the enhanced penetration can be caused by alteration of the membrane at basic pH [3].…”

Section: Resultsmentioning

confidence: 99%

“…In the other studies, small differences in permeability coefficients of amino acids at different pH were observed [3]. For example, the permeability coefficient of valine decreased as cation fraction decreased and zwitterion fraction increased.…”

Section: Introductionmentioning

confidence: 90%

“…Even though amino acids are used in a very wide range of applications, surprisingly only a few experiments on penetration abilities of amino acids have been done [1–5].…”

Section: Introductionmentioning

confidence: 99%

“…1). It was shown that the permeability coefficients through the skin of the unionized species are much more greater than those for the ionized species [6] and the permeability coefficients for the cations are greater than those for anions [3, 7]. It was also demonstrated that the relative contributions of the ionized and unionized species to the total flux as well as total flux vary significantly, depending on the pH of the donor solution.…”

Section: Introductionmentioning

confidence: 99%

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The fatty acids as penetration enhancers of amino acids by ion pairing

Arct

Chelkowska

Kasiura

et al. 2002

Intern J of Cosmetic Sci

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The influence of palmitic acid on n-octanol/water partition coefficient (log P) of selected amino acids, alanine, glycine, proline, hydroxyproline, seine, valine, threonine and lysine, was measured at a wide range of pH. A parabolic shape curve was obtained in every case (pH vs. Deltalog P), with maximum depending on the amino acid. In each case in the presence of palmitic acid, the apparent partition coefficient increased. To check the possible mechanism of extraction of amino acids into n-octanol phase in the presence of palmitate additionally, the influence of an amount of counter ion on partition coefficient of lysine was investigated. The results suggest that the enhanced partitioning of lysine results from the ion pair formation with palmitate. The ion pair stratum corneum-lipid membrane transport of the amino acids was investigated as well, using palmitate as a counter ion. The apparent permeability coefficients were enhanced significantly by palmitic acid at pH 7.4. As many substances (e.g. organic solvents, unsaturated fatty acids, etc.) are penetration enhancers which change the structure of intercellular lipid, the influence of palmitic acid on membrane was investigated. After pretreatment of membrane with palmitic acid, no changes in permeation of alanine were observed. Investigations suggest the enhanced permeation of amino acids via ion pairing. The method for prediction of pH in which the possibility of ion pairing is the highest was developed as well.

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Estimation of skin concentrations of topically applied lidocaine at each depth profile

Oshizaka

Kikuchi

Kadhum

et al. 2014

International Journal of Pharmaceutics

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Skin concentrations of topically administered compounds need to be considered in order to evaluate their efficacies and toxicities. This study investigated the relationship between the skin permeation and concentrations of compounds, and also predicted the skin concentrations of these compounds using their permeation parameters. Full-thickness skin or stripped skin from pig ears was set on a vertical-type diffusion cell, and lidocaine (LID) solution was applied to the stratum corneum (SC) in order to determine in vitro skin permeability. Permeation parameters were obtained based on Fick's second law of diffusion. LID concentrations at each depth of the SC were measured using tape-stripping. Concentration-depth profiles were obtained from viable epidermis and dermis (VED) by analyzing horizontal sections. The corresponding skin concentration at each depth was calculated based on Fick's law using permeation parameters and then compared with the observed value. The steady state LID concentrations decreased linearly as the site became deeper in SC or VED. The calculated concentration-depth profiles of the SC and VED were almost identical to the observed profiles. The compound concentration at each depth could be easily predicted in the skin using diffusion equations and skin permeation data. Thus, this method was considered to be useful for promoting the efficient preparation of topically applied drugs and cosmetics.

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Influence of pH on Skin Permeation of Amino Acids

Cited by 8 publications

References 19 publications

Zwitterion formation in gas-phase cyclodextrin complexes

Zwitterion formation in gas-phase cyclodextrin complexes

The fatty acids as penetration enhancers of amino acids by ion pairing

Estimation of skin concentrations of topically applied lidocaine at each depth profile

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