Effects of Fatty Acids, Fatty Amines and Propylene Glycol on Rat Stratum Corneum Lipids and Proteins in Vitro Measured by Fourier Transform Infrared/Attenuated Total Reflection(FT-IR/ATR) Spectroscopy.

Takeuchi, Yoshikazu; Yasukawa, Hidehito; Yamaoka, Yumiko; Kato, Yuichi; Morimoto, Yosuke; Fukumori, Yoshinobu; Fukuda, Takayuki

doi:10.1248/cpb.40.1887

Cited by 42 publications

(19 citation statements)

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“…[36][37][38][39] Barry has proposed that the mechanism of action may be explained using the lipid-protein-partitioning (LPP) theory. 40,41 This states that enhancers act by one of three primary means.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and in Vitro Transdermal Penetration Enhancing Activity of Lactam N-Acetic Acid Esters

Michniak¹,

Player²,

Sowell³

1996

Journal of Pharmaceutical Sciences

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A homologous series of N-acetic acid esters of 2-pyrrolidinone and 2-piperidinone has been prepared and evaluated for its ability to enhance the skin content and flux of hydrocortisone 21-acetate in hairless mouse skin in vitro. Enhancement ratios (ER) were determined for flux (J), 24-hour diffusion cell receptor cell concentrations (Q24), and 24-h full-thickness mouse skin steroid content (SC) and compared to control values (no enhancer present). In addition, in an attempt to abrogate toxicity, these dermal penetration enhancers were designed to have the potential for biodegradation by dermal esterases. 2-Oxopyrrolidine-alpha acetic acid dodecyl ester (5) showed the highest enhancement ratios for J (ER 67.33) and Q24 (ER 180.66). 2-Oxopiperidine-alpha-acetic acid decyl ester (10) showed a high Q24 (ER 162.07) but a lower J (ER 12.67). 2-Oxopyrrolidine-alpha-acetic acid decyl ester (3) showed the highest enhancement ratio for SC (ER 8.7). The ER Q24 for 3, 5 and 10, as well as other lactam N-acetic acid esters in this work, were significantly higher than the ER found using Azone as enhancer.

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Section: Resultsmentioning

confidence: 99%

Synthesis and in Vitro Transdermal Penetration Enhancing Activity of Lactam N-Acetic Acid Esters

Michniak¹,

Player²,

Sowell³

1996

Journal of Pharmaceutical Sciences

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“…Protein order was also disrupted, as indicated by an increase in C-O stretching consistent with conformational transformation of keratin from α-helix to β-sheet structure [23]. This conformational change of keratin may be a secondary effect of the disruption of stratum corneum lipid structure [31].…”

Section: Magainin Can Increase Skin Permeability By Disrupting Stratumentioning

confidence: 92%

Transdermal delivery enhanced by magainin pore-forming peptide

Kim

Ludovice

Prausnitz

2007

Journal of Controlled Release

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In this study we tested the hypothesis that magainin, a peptide known to form pores in bacterial cell membranes, can increase skin permeability by disrupting stratum corneum lipid structure. We further hypothesized that magainin's enhancement requires co-administration with a surfactant chemical enhancer to increase magainin penetration into the skin. In support of these hypotheses, exposure to a known surfactant chemical enhancer, N-lauroyl sarcosine (NLS), in 50% ethanol solution increased in vitro skin permeability to fluorescein 15 fold and the combination of magainin and NLS-ethanol synergistically increased skin permeability 47 fold. In contrast, skin permeability was unaffected by exposure to magainin without co-enhancement by NLS-ethanol. Furthermore, confocal microscopy showed that magainin in the presence of NLS-ethanol penetrated deeply and extensively into stratum corneum, whereas magainin alone penetrated poorly into the skin. Additional analysis by Fouriertransform infrared spectroscopy, X-ray diffraction, and differential scanning calorimetry showed that NLS-ethanol disrupted stratum corneum lipid structure and that the combination of magainin and NLS-ethanol disrupted stratum corneum lipids even further. Altogether, these data suggest that NLSethanol increased magainin penetration into stratum corneum, which further increased stratum corneum lipid disruption and skin permeability. We believe this is the first study to demonstrate the use of a pore-forming peptide to increase skin permeability. This study also introduces the novel concept of using a first chemical enhancer to increase penetration of a second chemical enhancer into the skin to synergistically increase skin permeability to a model drug.

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“…44,45 On the other hand, OAm is a cationic lipid and known penetration enhancer that readily interacts with negatively charged skin surface and cell membrane as well as induces conformation changes in surface protein conformation. 46 In this example, the hydrophilic chain interacts with the polar lipid region, and the hydrophobic chain themselves are inserted into the SC to disrupt the lipid bilayer structure. 47,48 The functionalized nanoparticles also accumulated in hair follicles in greater amounts, which provided an additional route for transdermal passage.…”

Section: In Vivo Skin Permeation Assessmentmentioning

confidence: 99%

Enhancing the in vivo transdermal delivery of gold nanoparticles using poly(ethylene glycol) and its oleylamine conjugate

Hsiao

Peng

Tang

et al. 2016

IJN

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In this study, we investigated the effect of (ethylene glycol) (PEG) and PEG–oleylamine (OAm) functionalization on the skin permeation property of gold nanoparticles (GNS) in vivo. Chemisorption of polymers onto GNS was verified by a red shift in the ultraviolet–visible spectrum as well as by a change in the nanoparticle surface charge. The physicochemical properties of pristine and functionalized nanoparticles were analyzed by ultraviolet–visible spectroscopy, zeta potential analyzer, and transmission electron microscopy. Transmission electron microscopy revealed that the interparticle distance between nanoparticles increased after GNS functionalization. Comparing the skin permeation profile of pristine and functionalized GNS, the follicular deposition of GNS increased twofold after PEG–OAm functionalization. Moreover, PEG- and PEG–OAm-functionalized nanoparticles were able to overcome the skin barrier and deposit in the deeper subcutaneous adipose tissue. These findings demonstrate the potential of PEG- and PEG–OAm-functionalized GNS in serving a multitude of applications in transdermal pharmaceuticals.

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Effects of Fatty Acids, Fatty Amines and Propylene Glycol on Rat Stratum Corneum Lipids and Proteins in Vitro Measured by Fourier Transform Infrared/Attenuated Total Reflection(FT-IR/ATR) Spectroscopy.

Cited by 42 publications

References 1 publication

Synthesis and in Vitro Transdermal Penetration Enhancing Activity of Lactam N-Acetic Acid Esters

Synthesis and in Vitro Transdermal Penetration Enhancing Activity of Lactam N-Acetic Acid Esters

Transdermal delivery enhanced by magainin pore-forming peptide

Enhancing the in vivo transdermal delivery of gold nanoparticles using poly(ethylene glycol) and its oleylamine conjugate

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