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DFT studies on the physicochemical properties of a new potential drug carrier containing cellobiose units and its complex with paracetamol

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Abstract

The formation of a carrier-drug complex may enhance the biodistribution of the drug and, consequently, improve its therapeutic effect. Since the biodistribution of the tied drug strongly depends on the properties of the carrier molecule, it is advisable to determine its structural features and other physicochemical parameters. Therefore, in this work, the properties of the new potential drug carrier 1,10-N,N’-bis-(β-\(\small{\text{D}}\)-ureidocellobiosyl)-4,7,13-trioxa-1,10-diazacyclopentadecane (L2) were investigated using different quantum chemical methods. The most stable structures obtained from the B3LYP-GD2/6-31G(d,p) calculations have a very compact geometry due to the formation of intramolecular hydrogen bonds between the cellobiose fragments. The Mulliken charge distribution shows that L2 is strongly polar, so it is expected to bind efficiently polar molecules. The complexation ability of the host towards the polar drug paracetamol (PAR) in a stoichiometry 1:1 was investigated for various host-drug structures using the same density functional. The formation of L2:PAR is very profitable: for the most stable configuration, the complexation energy is −18.5 kcal/mol. In all structures, paracetamol is externally attached to the host, interacting mainly with the cellobiose units. The NMR chemical shifts obtained from the quantum calculations for L2 and its complex L2:PAR, are analyzed and compared with the available experimental data.

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Acknowledgements

DFT calculations have been carried out using resources provided by Wroclaw Centre for Networking and Supercomputing (http://wcss.pl), grant No. 443.

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  1. Theoretical and Structural Group, Department of Physical Chemistry, Faculty of Chemistry, University of Lodz, Pomorska 163/165, 90-236, Lodz, Poland

    Marta Adamiak & Anna Ignaczak

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Conceptualization: Anna Ignaczak. Methodology: Anna Ignaczak and Marta Adamiak. Formal analysis and investigation: Marta Adamiak. Writing, original draft preparation: Marta Adamiak. Writing, review and editing: Anna Ignaczak. Supervision: Anna Ignaczak. All authors read and approved the final manuscript.

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Correspondence to Marta Adamiak.

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Adamiak, M., Ignaczak, A. DFT studies on the physicochemical properties of a new potential drug carrier containing cellobiose units and its complex with paracetamol. Struct Chem 33, 1365–1378 (2022). https://doi.org/10.1007/s11224-022-01950-y

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