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A theoretical investigation on the synergetic effect of hydrogen-bonding interactions and thermodynamic property in the 1: 2 (azacyclopentane-2-one: N-methylolacetamide) ternary complex

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Abstract

Context

Using chemical penetration enhancers to improve the penetration effect is one kind of important strategies in transdermal drug delivery system. Azone is a widely used transdermal absorption enhancer for transdermal drug delivery. To shed light on the permeation-promoting mechanism of azone, we selected ternary systems formed by azacyclopentane-2-one and N-methylolacetamide (1: 2) and explored the synergetic effect of hydrogen-bonding interactions among them and their thermodynamic properties. The findings indicate that the synergetic effects can enhance the ability of azone to change the original conformation of ceramides and even break the original hydrogen bonds, which is more beneficial for azone to destroy the 3D network structure of ceramides. When azone interacts with ceramide, the order of action tends to interact with one molecule of ceramide first and then with another molecule of ceramide.

Methods

The synergetic effects of hydrogen-bonding interactions in ternary systems were computed at the B3LYP/6–311 +  + G** and MP2(full)/6–311 +  + G** levels. Thermodynamic parameters for two ternary-complex routes were worked out at the B3LYP/aug-cc-pVDZ level. The shift of the electron density occurring simultaneously with trimer formation was analyzed at the MP2(full)/6–311 +  + G** level. The above calculations were carried out using the Gaussian 03 program packages. Atoms in molecules (AIM) method and the AIMPAC program showed the topological charge density at the MP2(full)/6–311 +  + G** level.

Graphical Abstract

The synergetic effects of hydrogen-bonding interactions and thermodynamic property in the 1: 2 (azacyclopentane-2-one: N-methylolacetamide) ternary systems were investigated using the B3LYP and MP2(full) methods

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Data availability

The datasets generated during and/or analyzed during the current study are available from the corresponding author on reasonable request.

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Funding

The authors received financial support from the Hunan Province Health Commission of China (No. D202313057596).

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Authors and Affiliations

  1. Xiangtan Medicine & Health Vocational College, Xiangtan, 411104, China

    Hai-fei Tang

  2. School of Pharmaceutical Science, Shanxi Medical University, Taiyuan, 030001, China

    Hua Zhong, Ling-ling Zhang, Ming-xing Gong, Shu-qin Song & Qing-ping Tian

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  1. Hai-fei Tang
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  2. Hua Zhong
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  3. Ling-ling Zhang
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  4. Ming-xing Gong
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Contributions

Hai-fei Tang: conceptualization, calculation, data curation, investigation, and writing—original draft. Hua Zhong, Ling-ling Zhang, Ming-xing Gong, and Shu-qin Song: calculation and data curation. Qing-ping Tian: project administration, writing—review and editing.

Corresponding author

Correspondence to Qing-ping Tian.

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Tang, Hf., Zhong, H., Zhang, Ll. et al. A theoretical investigation on the synergetic effect of hydrogen-bonding interactions and thermodynamic property in the 1: 2 (azacyclopentane-2-one: N-methylolacetamide) ternary complex. J Mol Model 29, 68 (2023). https://doi.org/10.1007/s00894-023-05469-9

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