Single-chain bolalipids PC-C24-PC and PC-C32-PC: impact on skin permeation and penetration of caffeine ex vivo, structural organization of the stratum corneum and corneocyte morphology
•synthetic symmetric single-chain bolalipids (SSCBs) do not promote the skin penetration of caffeine ex vivo using the porcine ear model.•both quantitative confocal Raman spectroscopy ex vivo and classic diffusion cell studies support this observation.•SSCBs can be tracked after penetration into por...
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| Published in: | European journal of pharmaceutical sciences Vol. 212; p. 107205 |
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| Main Authors: | , , , , , , |
| Format: | Journal Article |
| Language: | English |
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Elsevier B.V
01.09.2025
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| ISSN: | 0928-0987, 1879-0720, 1879-0720 |
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| Abstract | •synthetic symmetric single-chain bolalipids (SSCBs) do not promote the skin penetration of caffeine ex vivo using the porcine ear model.•both quantitative confocal Raman spectroscopy ex vivo and classic diffusion cell studies support this observation.•SSCBs can be tracked after penetration into porcine stratum corneum through ATR-FTIR spectroscopy.•atomic force microscopy (AFM) confirmed corneocyte surface alterations caused by surfactant dispersions.
Synthetic symmetric single-chain bolalipids (SSCBs) are of interest as new pharmaceutical excipients and might offer new prospects to modulate dermal drug delivery. In contrast to classic anionic surfactants and conventional amphiphilic phospholipids, they have been found to hinder drug penetration of charged permeants into the skin rather than acting as enhancers. However, since only a limited number of permeants have been investigated to date and the underlying mechanism is still unknown, this study aims to investigate the effect of two SSCBs with different alkyl chain length, PC-C24-PC and PC-C32-PC, on ex vivo skin permeation/penetration of an uncharged hydrophilic drug, caffeine, using diffusion cells with dermatomed porcine ear skin as membrane and a quantitative confocal Raman spectroscopy (CRS) approach. In addition, both CRS and attenuated total reflection FTIR spectroscopy (ATR-FTIR) were used to evaluate the effect of the SSCBs on stratum corneum (SC) proteins and the lipid matrix. A novel method was also employed using atomic force microscopy (AFM) to visualize potential SSCB effects on corneocyte surface morphology. Results showed that SSCBs (5 % w/w) reduced skin permeation of caffeine through dermatomed porcine ear skin in comparison to water and 5 % w/w sodium dodecyl sulfate (SDS) solutions as comparator vehicles. Quantitative CRS confirmed these observations. ATR-FTIR studies demonstrated the presence of SSCBs within the SC surface and indicated effects on SC lipid order and protein conformation. AFM revealed trends towards altered corneocyte surface topography after surfactant treatment when compared to the effect of water as solvent. In conclusion, while SSCB formulations interacted with the SC, they did not promote the penetration of caffeine into deeper layers of the epidermis.
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| AbstractList | Synthetic symmetric single-chain bolalipids (SSCBs) are of interest as new pharmaceutical excipients and might offer new prospects to modulate dermal drug delivery. In contrast to classic anionic surfactants and conventional amphiphilic phospholipids, they have been found to hinder drug penetration of charged permeants into the skin rather than acting as enhancers. However, since only a limited number of permeants have been investigated to date and the underlying mechanism is still unknown, this study aims to investigate the effect of two SSCBs with different alkyl chain length, PC-C24-PC and PC-C32-PC, on ex vivo skin permeation/penetration of an uncharged hydrophilic drug, caffeine, using diffusion cells with dermatomed porcine ear skin as membrane and a quantitative confocal Raman spectroscopy (CRS) approach. In addition, both CRS and attenuated total reflection FTIR spectroscopy (ATR-FTIR) were used to evaluate the effect of the SSCBs on stratum corneum (SC) proteins and the lipid matrix. A novel method was also employed using atomic force microscopy (AFM) to visualize potential SSCB effects on corneocyte surface morphology. Results showed that SSCBs (5 % w/w) reduced skin permeation of caffeine through dermatomed porcine ear skin in comparison to water and 5 % w/w sodium dodecyl sulfate (SDS) solutions as comparator vehicles. Quantitative CRS confirmed these observations. ATR-FTIR studies demonstrated the presence of SSCBs within the SC surface and indicated effects on SC lipid order and protein conformation. AFM revealed trends towards altered corneocyte surface topography after surfactant treatment when compared to the effect of water as solvent. In conclusion, while SSCB formulations interacted with the SC, they did not promote the penetration of caffeine into deeper layers of the epidermis.Synthetic symmetric single-chain bolalipids (SSCBs) are of interest as new pharmaceutical excipients and might offer new prospects to modulate dermal drug delivery. In contrast to classic anionic surfactants and conventional amphiphilic phospholipids, they have been found to hinder drug penetration of charged permeants into the skin rather than acting as enhancers. However, since only a limited number of permeants have been investigated to date and the underlying mechanism is still unknown, this study aims to investigate the effect of two SSCBs with different alkyl chain length, PC-C24-PC and PC-C32-PC, on ex vivo skin permeation/penetration of an uncharged hydrophilic drug, caffeine, using diffusion cells with dermatomed porcine ear skin as membrane and a quantitative confocal Raman spectroscopy (CRS) approach. In addition, both CRS and attenuated total reflection FTIR spectroscopy (ATR-FTIR) were used to evaluate the effect of the SSCBs on stratum corneum (SC) proteins and the lipid matrix. A novel method was also employed using atomic force microscopy (AFM) to visualize potential SSCB effects on corneocyte surface morphology. Results showed that SSCBs (5 % w/w) reduced skin permeation of caffeine through dermatomed porcine ear skin in comparison to water and 5 % w/w sodium dodecyl sulfate (SDS) solutions as comparator vehicles. Quantitative CRS confirmed these observations. ATR-FTIR studies demonstrated the presence of SSCBs within the SC surface and indicated effects on SC lipid order and protein conformation. AFM revealed trends towards altered corneocyte surface topography after surfactant treatment when compared to the effect of water as solvent. In conclusion, while SSCB formulations interacted with the SC, they did not promote the penetration of caffeine into deeper layers of the epidermis. Synthetic symmetric single-chain bolalipids (SSCBs) are of interest as new pharmaceutical excipients and might offer new prospects to modulate dermal drug delivery. In contrast to classic anionic surfactants and conventional amphiphilic phospholipids, they have been found to hinder drug penetration of charged permeants into the skin rather than acting as enhancers. However, since only a limited number of permeants have been investigated to date and the underlying mechanism is still unknown, this study aims to investigate the effect of two SSCBs with different alkyl chain length, PC-C24-PC and PC-C32-PC, on ex vivo skin permeation/penetration of an uncharged hydrophilic drug, caffeine, using diffusion cells with dermatomed porcine ear skin as membrane and a quantitative confocal Raman spectroscopy (CRS) approach. In addition, both CRS and attenuated total reflection FTIR spectroscopy (ATR-FTIR) were used to evaluate the effect of the SSCBs on stratum corneum (SC) proteins and the lipid matrix. A novel method was also employed using atomic force microscopy (AFM) to visualize potential SSCB effects on corneocyte surface morphology. Results showed that SSCBs (5 % w/w) reduced skin permeation of caffeine through dermatomed porcine ear skin in comparison to water and 5 % w/w sodium dodecyl sulfate (SDS) solutions as comparator vehicles. Quantitative CRS confirmed these observations. ATR-FTIR studies demonstrated the presence of SSCBs within the SC surface and indicated effects on SC lipid order and protein conformation. AFM revealed trends towards altered corneocyte surface topography after surfactant treatment when compared to the effect of water as solvent. In conclusion, while SSCB formulations interacted with the SC, they did not promote the penetration of caffeine into deeper layers of the epidermis. •synthetic symmetric single-chain bolalipids (SSCBs) do not promote the skin penetration of caffeine ex vivo using the porcine ear model.•both quantitative confocal Raman spectroscopy ex vivo and classic diffusion cell studies support this observation.•SSCBs can be tracked after penetration into porcine stratum corneum through ATR-FTIR spectroscopy.•atomic force microscopy (AFM) confirmed corneocyte surface alterations caused by surfactant dispersions. Synthetic symmetric single-chain bolalipids (SSCBs) are of interest as new pharmaceutical excipients and might offer new prospects to modulate dermal drug delivery. In contrast to classic anionic surfactants and conventional amphiphilic phospholipids, they have been found to hinder drug penetration of charged permeants into the skin rather than acting as enhancers. However, since only a limited number of permeants have been investigated to date and the underlying mechanism is still unknown, this study aims to investigate the effect of two SSCBs with different alkyl chain length, PC-C24-PC and PC-C32-PC, on ex vivo skin permeation/penetration of an uncharged hydrophilic drug, caffeine, using diffusion cells with dermatomed porcine ear skin as membrane and a quantitative confocal Raman spectroscopy (CRS) approach. In addition, both CRS and attenuated total reflection FTIR spectroscopy (ATR-FTIR) were used to evaluate the effect of the SSCBs on stratum corneum (SC) proteins and the lipid matrix. A novel method was also employed using atomic force microscopy (AFM) to visualize potential SSCB effects on corneocyte surface morphology. Results showed that SSCBs (5 % w/w) reduced skin permeation of caffeine through dermatomed porcine ear skin in comparison to water and 5 % w/w sodium dodecyl sulfate (SDS) solutions as comparator vehicles. Quantitative CRS confirmed these observations. ATR-FTIR studies demonstrated the presence of SSCBs within the SC surface and indicated effects on SC lipid order and protein conformation. AFM revealed trends towards altered corneocyte surface topography after surfactant treatment when compared to the effect of water as solvent. In conclusion, while SSCB formulations interacted with the SC, they did not promote the penetration of caffeine into deeper layers of the epidermis. [Display omitted] |
| ArticleNumber | 107205 |
| Author | Klang, Victoria Drescher, Simon Riethmüller, Christoph Dailey, Lea Ann Schwarzinger, Jacqueline Schmolz, Jakob Abdelrahman, Namarig |
| Author_xml | – sequence: 1 givenname: Namarig surname: Abdelrahman fullname: Abdelrahman, Namarig organization: University of Vienna, Doctoral School of Pharmaceutical, Nutritional and Sport Sciences, Vienna 1090, Austria – sequence: 2 givenname: Jakob surname: Schmolz fullname: Schmolz, Jakob organization: University of Vienna, Doctoral School of Pharmaceutical, Nutritional and Sport Sciences, Vienna 1090, Austria – sequence: 3 givenname: Jacqueline surname: Schwarzinger fullname: Schwarzinger, Jacqueline organization: University of Vienna, Doctoral School of Pharmaceutical, Nutritional and Sport Sciences, Vienna 1090, Austria – sequence: 4 givenname: Simon surname: Drescher fullname: Drescher, Simon organization: Phospholipid Research Center, Im Neuenheimer Feld 515, Heidelberg 69120, Germany – sequence: 5 givenname: Christoph surname: Riethmüller fullname: Riethmüller, Christoph organization: Serend-ip GmbH, Centre for Nanotechnology, 48149 Münster, Germany – sequence: 6 givenname: Lea Ann surname: Dailey fullname: Dailey, Lea Ann email: leaann.dailey@univie.ac.at organization: University of Vienna, Department of Pharmaceutical Sciences, Division of Pharmaceutical Technology, Josef-Holaubek-Platz 2, Vienna 1090, Austria – sequence: 7 givenname: Victoria orcidid: 0000-0003-2561-4378 surname: Klang fullname: Klang, Victoria email: victoria.klang@univie.ac.at organization: University of Vienna, Department of Pharmaceutical Sciences, Division of Pharmaceutical Technology, Josef-Holaubek-Platz 2, Vienna 1090, Austria |
| BackLink | https://www.ncbi.nlm.nih.gov/pubmed/40675345$$D View this record in MEDLINE/PubMed |
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| Keywords | Penetration, permeation Bolalipids Confocal Raman spectroscopy ATR-FTIR Caffeine |
| Language | English |
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| Snippet | •synthetic symmetric single-chain bolalipids (SSCBs) do not promote the skin penetration of caffeine ex vivo using the porcine ear model.•both quantitative... Synthetic symmetric single-chain bolalipids (SSCBs) are of interest as new pharmaceutical excipients and might offer new prospects to modulate dermal drug... |
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| SubjectTerms | Administration, Cutaneous Animals ATR-FTIR Bolalipids Caffeine Caffeine - administration & dosage Caffeine - chemistry Caffeine - pharmacokinetics Confocal Raman spectroscopy Epidermis - metabolism Penetration, permeation Permeability Skin - drug effects Skin - metabolism Skin Absorption - drug effects Spectroscopy, Fourier Transform Infrared Spectrum Analysis, Raman Swine |
| Title | Single-chain bolalipids PC-C24-PC and PC-C32-PC: impact on skin permeation and penetration of caffeine ex vivo, structural organization of the stratum corneum and corneocyte morphology |
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