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A DFT study on the structure activity relationship of the natural xanthotoxin-based pharmaceutical cocrystals

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Abstract   

In this work, the pharmaceutical cocrystals xanthotoxin-para-aminobenzoic acid (XT-PABA) and xanthotoxin-oxalic acid (XT-OA) were systematically investigated in the gas and water phases by using the quantum chemical approach. The weak intermolecular interactions have been estimated and the O1…H4 (O1…H5) intermolecular hydrogen bond (IHB) with moderate intensity and partial covalent natures was confirmed based on the computed structural parameters, topology analysis, and reduced density gradient (RDG) isosurfaces. The electrophilic and nucleophilic reactivities of different positions associated with intermolecular interactions in XT, PABA, and OA were predicted by plotting the molecular electrostatic potential (MESP) diagrams. The calculated natural bond orbital (NBO) population analysis has quantitatively unveiled the intrinsic reason for the variations in weak intermolecular interactions within XT-PABA and XT-OA cocrystals, from the gas phase to the water phase. Besides, the frontier molecular orbitals (FMOs), Fukui function, and various global reactivity descriptors were computed to measure the chemical reactivity of all the investigated molecular systems. The XT-PABA and XT-OA cocrystals explored in this work could be regarded as valuable exemplar systems to design and synthesize the high-efficiency pharmaceutical cocrystals in the experiment.

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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

This work was financially supported by the Fundamental Research Funds for the Central Universities of China (2572019CG03), Heilongjiang Touyan Innovation Team Program (Tree Genetics and Breeding Innovation Team), the 111 Project (B20088), and the National Training Program of Innovation and Entrepreneurship for Undergraduates (202010225140).

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Authors and Affiliations

  1. College of Chemistry, Chemical Engineering and Resource Utilization, Northeast Forestry University, Harbin, 150040, China

    Shaohang Yuan, Zhiguang Yang, Danyang Yang, Yuxuan Wang, Haifei Qi, Lingling Wang & Xiuhua Zhao

  2. College of Science, Northeast Forestry University, Harbin, 150040, China

    Changjiao Shang & Chaofan Sun

  3. Heilongjiang Provincial Key Laboratory of Ecological Utilization of Forestry-Based Active Substances, Northeast Forestry University, Harbin, 150040, China

    Lingling Wang & Xiuhua Zhao

  4. Key Laboratory of Forest Plant Ecology, Ministry of Education, Northeast Forestry University, Harbin, 150040, China

    Lingling Wang & Xiuhua Zhao

Authors
  1. Shaohang Yuan
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  2. Zhiguang Yang
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  3. Changjiao Shang
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  4. Danyang Yang
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  5. Yuxuan Wang
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  6. Haifei Qi
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  7. Chaofan Sun
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  8. Lingling Wang
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  9. Xiuhua Zhao
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Contributions

Shaohang Yuan: conceptualization, data curation, writing–original draft. Zhiguang Yang: investigation, writing–review and editing. Changjiao Shang, Danyang Yang, Yuxuan Wang, and Haifei Qi: writing–review and editing. Chaofan Sun: conceptualization, methodology, software, writing–review and editing. Lingling Wang: conceptualization, methodology, investigation, writing–review and editing. Xiuhua Zhao: conceptualization, investigation, methodology, resources, writing–review and editing.

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Correspondence to Lingling Wang or Xiuhua Zhao.

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Yuan, S., Yang, Z., Shang, C. et al. A DFT study on the structure activity relationship of the natural xanthotoxin-based pharmaceutical cocrystals. J Mol Model 28, 155 (2022). https://doi.org/10.1007/s00894-022-05152-5

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  • DOI: https://doi.org/10.1007/s00894-022-05152-5

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