Citation: Chu Tianzhe, Wang Heping, Zhao Ligang. Construction and Penetration Evaluation of d-4-methyl-1-(1-methylethyl)-3-cyclohexen-1-yl Butanoate as Novel Percutaneous Absorption Enhancer[J]. Chemistry, ;2020, 83(10): 929-934. shu

Construction and Penetration Evaluation of d-4-methyl-1-(1-methylethyl)-3-cyclohexen-1-yl Butanoate as Novel Percutaneous Absorption Enhancer

1.
School of Pharmacy, North China University of Science and Technology, Tangshan, 063210
2.
Tangshan key laboratory of novel preparations and drug release technology, Tangshan, 063210

Corresponding author: Zhao Ligang, tsyxzlg@163.com
Received Date: 4 April 2020
Accepted Date: 3 July 2020

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In this paper, d-4-terpineol (d-4-TER) and butyric acid were used as raw materials to synthesize d-4-methyl-1-(1-methylethyl)-3-cyclohexen-1-yl butanoate (d-4-T-C4) by esterification method, and the structure of the product was characterized by MS and ¹H NMR. The penetration promoting activity of d-4-T-C4 on SR-FP was investigated, and its penetration mechanism was studied using infrared spectroscopy and molecular docking technology. When d-4-T-C4 was added, the accumulative 24h premeation amount (Q_24h) of SR-FP was 383.5±48.75 μg·cm^-2, which was 3.12 and 1.34 times of the control group and d-4-TER group, respectively. However, the promoting ability of d-4-T-C4 on S-FP and R-FP were almost identical. Mechanism research showed that d-4-T-C4 insertes into the stratum corneum lipid domain, disrupting the hydrogen bonding interaction between the drug and ceramide, increasing lipid mobility and the free energy of the drug, thereby promoting drug penetration. d-4-T-C4 had a significant enhancing effect on the permeation of SR-FP through the skin and is expected to be widely used as a new type of penetration enhancer in transdermal drug delivery system.
- d-4-methyl-1-(1-methylethyl)-3-cyclohexen-1-yl butanoate,
- Esterification,
- Penetration enhancer,
- Penetration mechanism
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1.
沈阳化工大学材料科学与工程学院沈阳 110142