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Int. J. Mol. Sci. 2016, 17(8), 1349; doi:10.3390/ijms17081349

Effects of Concentrations on the Transdermal Permeation Enhancing Mechanisms of Borneol: A Coarse-Grained Molecular Dynamics Simulation on Mixed-Bilayer Membranes

1,2,3,†
,
1,2,3,†
,
4
,
4
,
1,2,3,* and 1,2,3,*
1
School of Traditional Chinese Medicine, Beijing University of Chinese Medicine, No. 6 of Zhonghuan South Road, Wangjing, Chaoyang District, Beijing 100102, China
2
Key Laboratory of TCM-information Engineer of State Administration of TCM, No. 6 of Zhonghuan South Road, Wangjing, Chaoyang District, Beijing 100102, China
3
Beijing Key Laboratory of Manufacturing Process Control and Quality Evaluation of Chinese Medicine, No. 6 of Zhonghuan South Road, Wangjing, Chaoyang District, Beijing 100102, China
4
School of Traditional Chinese Medicine, Capital Medical University, No. 10 of Xitoutiao Outside Youanmen, Fengtai District, Beijing 100069, China
These authors contributed equally to this work.
*
Authors to whom correspondence should be addressed.
Academic Editor: Ge Zhang
Received: 21 June 2016 / Revised: 22 July 2016 / Accepted: 27 July 2016 / Published: 18 August 2016
(This article belongs to the Section Physical Chemistry, Theoretical and Computational Chemistry)
View Full-Text   |   Download PDF [11262 KB, uploaded 18 August 2016]   |  

Abstract

Borneol is a natural permeation enhancer that is effective in drugs used in traditional clinical practices as well as in modern scientific research. However, its molecular mechanism is not fully understood. In this study, a mixed coarse-grained model of stratum corneum (SC) lipid bilayer comprised of Ceramide-N-sphingosine (CER NS) 24:0, cholesterol (CHOL) and free fatty acids (FFA) 24:0 (2:2:1) was used to examine the permeation enhancing mechanism of borneol on the model drug osthole. We found two different mechanisms that were dependent on concentrations levels of borneol. At low concentrations, the lipid system maintained a bilayer structure. The addition of borneol made the lipid bilayer loosen and improved drug permeation. The “pull” effect of borneol also improved drug permeation. However, for a strongly hydrophobic drug like osthole, the permeation enhancement of borneol was limited. When most borneol molecules permeated into bilayers and were located at the hydrophobic tail region, the spatial competition effect inhibited drug molecules from permeating deeper into the bilayer. At high concentrations, borneol led to the formation of water pores and long-lived reversed micelles. This improved the permeation of osthole and possibly other hydrophobic or hydrophilic drugs through the SC. Our simulation results were supported by Franz diffusion tests and transmission electron microscope (TEM) experiments. View Full-Text
Keywords: molecular dynamics simulation; coarse-grained force field; transdermal drug delivery system; permeation enhancer molecular dynamics simulation; coarse-grained force field; transdermal drug delivery system; permeation enhancer
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Dai, X.; Yin, Q.; Wan, G.; Wang, R.; Shi, X.; Qiao, Y. Effects of Concentrations on the Transdermal Permeation Enhancing Mechanisms of Borneol: A Coarse-Grained Molecular Dynamics Simulation on Mixed-Bilayer Membranes. Int. J. Mol. Sci. 2016, 17, 1349.

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