Enhanced Drug Skin Permeation by Azone-Mimicking Ionic Liquids: Effects of Fatty Acids Forming Ionic Liquids
<b>Background/Objectives</b>: Laurocapram (Azone) attracted attention 40 years ago as a compound with the highest skin-penetration-enhancing effect at that time; however, its development was shelved due to strong skin irritation. We had already prepared and tested an ante-enhancer (IL-Az...
Saved in:
| Main Authors: | , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2024-12-01
|
| Series: | Pharmaceutics |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1999-4923/17/1/41 |
| Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
| _version_ | 1832587712025067520 |
|---|---|
| author | Takeshi Oshizaka Shunsuke Kodera Rika Kawakubo Issei Takeuchi Kenji Mori Kenji Sugibayashi |
| author_facet | Takeshi Oshizaka Shunsuke Kodera Rika Kawakubo Issei Takeuchi Kenji Mori Kenji Sugibayashi |
| author_sort | Takeshi Oshizaka |
| collection | DOAJ |
| description | <b>Background/Objectives</b>: Laurocapram (Azone) attracted attention 40 years ago as a compound with the highest skin-penetration-enhancing effect at that time; however, its development was shelved due to strong skin irritation. We had already prepared and tested an ante-enhancer (IL-Azone), an ionic liquid (IL) with a similar structure to Azone, consisting of ε-caprolactam and myristic acid, as an enhancer candidate that maintains the high skin-penetration-enhancing effect of Azone with low skin irritation. In the present study, fatty acids with different carbon numbers (caprylic acid: C8, capric acid: C10, lauric acid: C12, myristic acid: C14, and oleic acid: C18:1) were selected and used with ε-caprolactam to prepare various IL-Azones in the search for a more effective IL-Azone. <b>Methods</b>: Excised porcine skin was pretreated with each IL-Azone to assess the in vitro skin permeability of antipyrine (ANP) as a model penetrant. In addition, 1,3-butanediol was selected for the skin permeation test to confirm whether the effect of IL-Azone was due to fatty acids and if this effect differed depending on the concentration of IL-Azone applied. <b>Results</b>: The results obtained showed that C12 IL-Azone exerted the highest skin-penetration-enhancing effect, which was higher than Azone. On the other hand, many of the IL-Azones tested had a lower skin-penetration-enhancing effect. <b>Conclusions</b>: These results suggest the potential of C12 IL-Azone as a strong and useful penetration enhancer. |
| format | Article |
| id | doaj-art-6546e7ad053e4cff85b2512d538fad43 |
| institution | Kabale University |
| issn | 1999-4923 |
| language | English |
| publishDate | 2024-12-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Pharmaceutics |
| spelling | doaj-art-6546e7ad053e4cff85b2512d538fad432025-01-24T13:45:41ZengMDPI AGPharmaceutics1999-49232024-12-011714110.3390/pharmaceutics17010041Enhanced Drug Skin Permeation by Azone-Mimicking Ionic Liquids: Effects of Fatty Acids Forming Ionic LiquidsTakeshi Oshizaka0Shunsuke Kodera1Rika Kawakubo2Issei Takeuchi3Kenji Mori4Kenji Sugibayashi5Faculty of Pharmaceutical Sciences, Josai International University, 1 Gumyo, Togane 283-8555, Chiba, JapanFaculty of Pharmaceutical Sciences, Josai International University, 1 Gumyo, Togane 283-8555, Chiba, JapanFaculty of Pharmaceutical Sciences, Josai International University, 1 Gumyo, Togane 283-8555, Chiba, JapanFaculty of Pharmaceutical Sciences, Josai International University, 1 Gumyo, Togane 283-8555, Chiba, JapanFaculty of Pharmaceutical Sciences, Josai International University, 1 Gumyo, Togane 283-8555, Chiba, JapanFaculty of Pharmaceutical Sciences, Josai International University, 1 Gumyo, Togane 283-8555, Chiba, Japan<b>Background/Objectives</b>: Laurocapram (Azone) attracted attention 40 years ago as a compound with the highest skin-penetration-enhancing effect at that time; however, its development was shelved due to strong skin irritation. We had already prepared and tested an ante-enhancer (IL-Azone), an ionic liquid (IL) with a similar structure to Azone, consisting of ε-caprolactam and myristic acid, as an enhancer candidate that maintains the high skin-penetration-enhancing effect of Azone with low skin irritation. In the present study, fatty acids with different carbon numbers (caprylic acid: C8, capric acid: C10, lauric acid: C12, myristic acid: C14, and oleic acid: C18:1) were selected and used with ε-caprolactam to prepare various IL-Azones in the search for a more effective IL-Azone. <b>Methods</b>: Excised porcine skin was pretreated with each IL-Azone to assess the in vitro skin permeability of antipyrine (ANP) as a model penetrant. In addition, 1,3-butanediol was selected for the skin permeation test to confirm whether the effect of IL-Azone was due to fatty acids and if this effect differed depending on the concentration of IL-Azone applied. <b>Results</b>: The results obtained showed that C12 IL-Azone exerted the highest skin-penetration-enhancing effect, which was higher than Azone. On the other hand, many of the IL-Azones tested had a lower skin-penetration-enhancing effect. <b>Conclusions</b>: These results suggest the potential of C12 IL-Azone as a strong and useful penetration enhancer.https://www.mdpi.com/1999-4923/17/1/41Azoneionic liquidskin permeationchemical enhancerante-enhancerfatty acid |
| spellingShingle | Takeshi Oshizaka Shunsuke Kodera Rika Kawakubo Issei Takeuchi Kenji Mori Kenji Sugibayashi Enhanced Drug Skin Permeation by Azone-Mimicking Ionic Liquids: Effects of Fatty Acids Forming Ionic Liquids Pharmaceutics Azone ionic liquid skin permeation chemical enhancer ante-enhancer fatty acid |
| title | Enhanced Drug Skin Permeation by Azone-Mimicking Ionic Liquids: Effects of Fatty Acids Forming Ionic Liquids |
| title_full | Enhanced Drug Skin Permeation by Azone-Mimicking Ionic Liquids: Effects of Fatty Acids Forming Ionic Liquids |
| title_fullStr | Enhanced Drug Skin Permeation by Azone-Mimicking Ionic Liquids: Effects of Fatty Acids Forming Ionic Liquids |
| title_full_unstemmed | Enhanced Drug Skin Permeation by Azone-Mimicking Ionic Liquids: Effects of Fatty Acids Forming Ionic Liquids |
| title_short | Enhanced Drug Skin Permeation by Azone-Mimicking Ionic Liquids: Effects of Fatty Acids Forming Ionic Liquids |
| title_sort | enhanced drug skin permeation by azone mimicking ionic liquids effects of fatty acids forming ionic liquids |
| topic | Azone ionic liquid skin permeation chemical enhancer ante-enhancer fatty acid |
| url | https://www.mdpi.com/1999-4923/17/1/41 |
| work_keys_str_mv | AT takeshioshizaka enhanceddrugskinpermeationbyazonemimickingionicliquidseffectsoffattyacidsformingionicliquids AT shunsukekodera enhanceddrugskinpermeationbyazonemimickingionicliquidseffectsoffattyacidsformingionicliquids AT rikakawakubo enhanceddrugskinpermeationbyazonemimickingionicliquidseffectsoffattyacidsformingionicliquids AT isseitakeuchi enhanceddrugskinpermeationbyazonemimickingionicliquidseffectsoffattyacidsformingionicliquids AT kenjimori enhanceddrugskinpermeationbyazonemimickingionicliquidseffectsoffattyacidsformingionicliquids AT kenjisugibayashi enhanceddrugskinpermeationbyazonemimickingionicliquidseffectsoffattyacidsformingionicliquids |