Human skin permeation of neutral species and ionic species: Extended linear free‐energy relationship analyses
Identifieur interne : 003A62 ( Main/Exploration ); précédent : 003A61; suivant : 003A63Human skin permeation of neutral species and ionic species: Extended linear free‐energy relationship analyses
Auteurs : Keda Zhang [Allemagne] ; Ming Chen [Allemagne] ; Gerhard K. E. Scriba [Allemagne] ; Michael H. Abraham [Royaume-Uni] ; Alfred Fahr [Allemagne] ; Xiangli Liu [Allemagne]Source :
- Journal of Pharmaceutical Sciences [ 0022-3549 ] ; 2012-06.
English descriptors
- KwdEn :
- Abraham, Anion, Base cations, Cation, Cerasome, Chem, Compound, Cooh, Descriptor, Donor solution, Donor solutions, Epidermis, Ethylene glycol, Experimental values, Franz cell, Hplc, Human epidermis, Human skin, Human skin permeation, Ionic, Ionic species, Ionizable compounds, Ionization, June, Lfer, Lfer model, Lipid, Liposome electrokinetic chromatography, Membrane partitions, Neutral acids, Neutral form, Neutral molecules, Neutral solutes, Neutral species, Nicotinate, Partition, Partitioning, Passive permeation, Permeability, Permeation, Permeation studies, Pharm, Pharmaceutical, Pharmaceutical sciences, Phosphate buffer, Physicochemical, Piroxicam, Poct, Poor permeability, Receptor, Receptor medium, Singh, Skin permeability, Skin permeation, Slow diffusion, Solute, Solute descriptors, Stratum corneum, Zhang.
- Teeft :
- Abraham, Anion, Base cations, Cation, Cerasome, Chem, Compound, Cooh, Descriptor, Donor solution, Donor solutions, Epidermis, Ethylene glycol, Experimental values, Franz cell, Hplc, Human epidermis, Human skin, Human skin permeation, Ionic, Ionic species, Ionizable compounds, Ionization, June, Lfer, Lfer model, Lipid, Liposome electrokinetic chromatography, Membrane partitions, Neutral acids, Neutral form, Neutral molecules, Neutral solutes, Neutral species, Nicotinate, Partition, Partitioning, Passive permeation, Permeability, Permeation, Permeation studies, Pharm, Pharmaceutical, Pharmaceutical sciences, Phosphate buffer, Physicochemical, Piroxicam, Poct, Poor permeability, Receptor, Receptor medium, Singh, Skin permeability, Skin permeation, Slow diffusion, Solute, Solute descriptors, Stratum corneum, Zhang.
Abstract
The permeability, Kp, of some ionized solutes (including nine acids and nine bases) through human epidermis membrane was measured in this work. Combined with the experimental Kp data set for neutral species created by Abraham and Martins and reliable Kp data for ionic species from the literature, a linear free‐energy relationship (LFER) analysis was conducted. The values of log Kp for 118 compounds have been correlated with solute descriptors to yield an LFER equation that incorporates neutral species and ionic species, with R2 = 0.861 and SD = 0.462 log units. The equation can be used to predict Kp for neutral species and ionic species, as well as partly ionized solutes. Predicted values for the passive permeation of the sodium ion and the tetraethylammonium ion are in good accord with the experimental values. It was observed that neutral acids and bases are more permeable than their ionized forms, and that the ratio depends on the actual structure. The correlation between human skin permeation and water–organic solvent/artificial membrane partitions was investigated by comparison of the coefficients in the LFER equations. Partition into cerasome is a reasonable model for partition into skin, and using cerasome as a surrogate for the partitioning process, we separate permeation into partition and diffusion processes. We show that the poor permeability of ionic species is largely due to slow diffusion through the stratum corneum. This is especially marked for a number of protonated base cations. © 2012 Wiley Periodicals, Inc. and the American Pharmacists Association J Pharm Sci 101:2034–2044, 2012
Url:
DOI: 10.1002/jps.23086
Affiliations:
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sortKey="Liu, Xiangli" sort="Liu, Xiangli" uniqKey="Liu X" first="Xiangli" last="Liu">Xiangli Liu</name><affiliation wicri:level="1"><country xml:lang="fr">Allemagne</country><wicri:regionArea>Department of Pharmaceutical Technology, Friedrich‐Schiller‐Universität Jena, 07743 Jena</wicri:regionArea><wicri:noRegion>07743 Jena</wicri:noRegion><wicri:noRegion>07743 Jena</wicri:noRegion></affiliation><affiliation wicri:level="1"><country wicri:rule="url">Allemagne</country></affiliation><affiliation></affiliation></author></analytic><monogr></monogr><series><title level="j" type="main">Journal of Pharmaceutical Sciences</title><title level="j" type="alt">JOURNAL OF PHARMACEUTICAL SCIENCES</title><idno type="ISSN">0022-3549</idno><idno type="eISSN">1520-6017</idno><imprint><biblScope unit="vol">101</biblScope><biblScope unit="issue">6</biblScope><biblScope unit="page" from="2034">2034</biblScope><biblScope unit="page" to="2044">2044</biblScope><biblScope unit="page-count">11</biblScope><publisher>Wiley Subscription Services, Inc., A Wiley Company</publisher><pubPlace>Hoboken</pubPlace><date type="published" when="2012-06">2012-06</date></imprint><idno type="ISSN">0022-3549</idno></series></biblStruct></sourceDesc><seriesStmt><idno type="ISSN">0022-3549</idno></seriesStmt></fileDesc><profileDesc><textClass><keywords scheme="KwdEn" xml:lang="en"><term>Abraham</term><term>Anion</term><term>Base cations</term><term>Cation</term><term>Cerasome</term><term>Chem</term><term>Compound</term><term>Cooh</term><term>Descriptor</term><term>Donor solution</term><term>Donor solutions</term><term>Epidermis</term><term>Ethylene glycol</term><term>Experimental values</term><term>Franz cell</term><term>Hplc</term><term>Human epidermis</term><term>Human skin</term><term>Human skin permeation</term><term>Ionic</term><term>Ionic species</term><term>Ionizable compounds</term><term>Ionization</term><term>June</term><term>Lfer</term><term>Lfer model</term><term>Lipid</term><term>Liposome electrokinetic chromatography</term><term>Membrane partitions</term><term>Neutral acids</term><term>Neutral form</term><term>Neutral molecules</term><term>Neutral solutes</term><term>Neutral species</term><term>Nicotinate</term><term>Partition</term><term>Partitioning</term><term>Passive permeation</term><term>Permeability</term><term>Permeation</term><term>Permeation studies</term><term>Pharm</term><term>Pharmaceutical</term><term>Pharmaceutical sciences</term><term>Phosphate buffer</term><term>Physicochemical</term><term>Piroxicam</term><term>Poct</term><term>Poor permeability</term><term>Receptor</term><term>Receptor medium</term><term>Singh</term><term>Skin permeability</term><term>Skin permeation</term><term>Slow diffusion</term><term>Solute</term><term>Solute descriptors</term><term>Stratum corneum</term><term>Zhang</term></keywords><keywords scheme="Teeft" xml:lang="en"><term>Abraham</term><term>Anion</term><term>Base cations</term><term>Cation</term><term>Cerasome</term><term>Chem</term><term>Compound</term><term>Cooh</term><term>Descriptor</term><term>Donor solution</term><term>Donor solutions</term><term>Epidermis</term><term>Ethylene glycol</term><term>Experimental values</term><term>Franz cell</term><term>Hplc</term><term>Human epidermis</term><term>Human skin</term><term>Human skin permeation</term><term>Ionic</term><term>Ionic species</term><term>Ionizable compounds</term><term>Ionization</term><term>June</term><term>Lfer</term><term>Lfer model</term><term>Lipid</term><term>Liposome electrokinetic chromatography</term><term>Membrane partitions</term><term>Neutral acids</term><term>Neutral form</term><term>Neutral molecules</term><term>Neutral solutes</term><term>Neutral species</term><term>Nicotinate</term><term>Partition</term><term>Partitioning</term><term>Passive permeation</term><term>Permeability</term><term>Permeation</term><term>Permeation studies</term><term>Pharm</term><term>Pharmaceutical</term><term>Pharmaceutical sciences</term><term>Phosphate buffer</term><term>Physicochemical</term><term>Piroxicam</term><term>Poct</term><term>Poor permeability</term><term>Receptor</term><term>Receptor medium</term><term>Singh</term><term>Skin permeability</term><term>Skin permeation</term><term>Slow diffusion</term><term>Solute</term><term>Solute descriptors</term><term>Stratum corneum</term><term>Zhang</term></keywords></textClass></profileDesc></teiHeader><front><div type="abstract" xml:lang="en">The permeability, Kp, of some ionized solutes (including nine acids and nine bases) through human epidermis membrane was measured in this work. Combined with the experimental Kp data set for neutral species created by Abraham and Martins and reliable Kp data for ionic species from the literature, a linear free‐energy relationship (LFER) analysis was conducted. The values of log Kp for 118 compounds have been correlated with solute descriptors to yield an LFER equation that incorporates neutral species and ionic species, with R2 = 0.861 and SD = 0.462 log units. The equation can be used to predict Kp for neutral species and ionic species, as well as partly ionized solutes. Predicted values for the passive permeation of the sodium ion and the tetraethylammonium ion are in good accord with the experimental values. It was observed that neutral acids and bases are more permeable than their ionized forms, and that the ratio depends on the actual structure. The correlation between human skin permeation and water–organic solvent/artificial membrane partitions was investigated by comparison of the coefficients in the LFER equations. Partition into cerasome is a reasonable model for partition into skin, and using cerasome as a surrogate for the partitioning process, we separate permeation into partition and diffusion processes. We show that the poor permeability of ionic species is largely due to slow diffusion through the stratum corneum. This is especially marked for a number of protonated base cations. © 2012 Wiley Periodicals, Inc. and the American Pharmacists Association J Pharm Sci 101:2034–2044, 2012</div></front></TEI><affiliations><list><country><li>Allemagne</li><li>Royaume-Uni</li></country><region><li>Angleterre</li><li>Grand Londres</li></region><settlement><li>Londres</li></settlement><orgName><li>University College de Londres</li></orgName></list><tree><country name="Allemagne"><noRegion><name sortKey="Zhang, Keda" sort="Zhang, Keda" uniqKey="Zhang K" first="Keda" last="Zhang">Keda Zhang</name></noRegion><name sortKey="Chen, Ming" sort="Chen, Ming" uniqKey="Chen M" first="Ming" last="Chen">Ming Chen</name><name sortKey="Fahr, Alfred" sort="Fahr, Alfred" uniqKey="Fahr A" first="Alfred" last="Fahr">Alfred Fahr</name><name sortKey="Liu, Xiangli" sort="Liu, Xiangli" uniqKey="Liu X" first="Xiangli" last="Liu">Xiangli Liu</name><name sortKey="Liu, Xiangli" sort="Liu, Xiangli" uniqKey="Liu X" first="Xiangli" last="Liu">Xiangli Liu</name><name sortKey="Scriba, Gerhard K E" sort="Scriba, Gerhard K E" uniqKey="Scriba G" first="Gerhard K. E." last="Scriba">Gerhard K. E. Scriba</name></country><country name="Royaume-Uni"><region name="Angleterre"><name sortKey="Abraham, Michael H" sort="Abraham, Michael H" uniqKey="Abraham M" first="Michael H." last="Abraham">Michael H. Abraham</name></region><name sortKey="Abraham, Michael H" sort="Abraham, Michael H" uniqKey="Abraham M" first="Michael H." last="Abraham">Michael H. Abraham</name></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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