Citation: TIAN Qing-Ping, SONG Shu-Qin, SHI Wen-Jing, XIE Yin, SONG Yan-Hong, TANG Hai-Fei, GONG Ming-Xing, ZHONG Hua, ZHANG Ling-Ling, REN Fu-De. Investigation on the Percutaneous Enhancing Permeation Mechanism of Azone for Ketoprofen Based on the Intermolecular Hydrogen-bonding Interaction[J]. Chinese Journal of Structural Chemistry, ;2014, 33(2): 304-318. shu

Investigation on the Percutaneous Enhancing Permeation Mechanism of Azone for Ketoprofen Based on the Intermolecular Hydrogen-bonding Interaction

1.
a Department of Pharmacy, Shanxi Medical University, Taiyuan 030001, China;
2.
b The Third Hospital of Shanxi Medical University, Taiyuan 030053, China;
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c Feedstuff and Veterinary Drugs Watch Office, Department of Agriculture Shanxi Province, Taiyuan 030027, China;
4.
d College of Chemical Engineering and Environment, North University of China, Taiyuan 030051, China

Received Date: 10 July 2013
Available Online: 17 January 2014
Fund Project: Supported by the Natural Science Foundation of Shanxi Province (No.2012011007-5) (No.2012011007-5)

The permeation enhancing activity of Azone for ketoprofen through excised cavia skins was investigated using Franz diffusion cell. The possible hydrogen-bonded complexes formed between ketoprofen and the model molecule of Azone as azacyclopentane-2-one were fully optimized at the B3LYP/6-311++G^** level. The intermolecular hydrogen-bonding interactions were calculated using the B3LYP/6-311++G^**, B3LYP/6-311++G (2df, 2p), MP2 (full)/6-311++G^** and MP2 (full)/6-311++G (2df, 2p) methods, respectively. The results show that the steady-state permeation rate of ketoprofen through excised cavia skins enhances over 9 times in the solvent with 2% Azone as compared with the solvent without Azone. The stable O-H…O=C and N-H…O=C hydrogen-bonded complexes could exist between azacyclopentane and ketoprofen. The hydrogen-bonding interaction energy follows the order of (a) >(b) >(c) >(d) >(g) >(e) >(h) >(f). The formation of the complexes leads to the change of the conformation and molecular polarity of ketoprofen, and thus causes a better percutaneous permeation for the drug. The analyses of AIM (atom in molecule) and shift of electron density were used to further reveal the nature of the enhancing permeation activity of Azone for ketoprofen. The investigations of the temperature and solvent effects confirm that ketoprofen might enter into the skin by means of the Azone complex.
- intermolecular hydrogen-bonding interaction,
- Azone,
- ketoprofen,
- transdermal delivery,
- MP2
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