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A multifunctional lactose-containing molecule: Structural characterization, biocompatibility and host-guest
Marta Hoelm1, Stanisław Porwański2, Zdzisław Kinart1
1University of Lodz, Faculty of Chemistry, Department of Physical Chemistry, Pomorska 163/165, Lodz, 90-236, Poland.
Carbohydrate Research
|August 14, 2026
Summary
A novel carbohydrate molecule, 1,10-N,N'-bis-(β-d-ureidolactosyl)-4,7,13,16-tetraoxa-1,10-diazacyclooctadecane (TL), exhibits favorable physicochemical properties. TL forms a stable, non-toxic complex with butane-1,4-diyl bis(2,2,2-trifluoroethane-1-sulfonate) (BFS), reducing BFS cytotoxicity.
Area of Science:
- Carbohydrate chemistry
- Supramolecular chemistry
- Medicinal chemistry
Background:
- Novel carbohydrate-based molecules offer unique physicochemical properties.
- Diazacrown ethers and urea linkages can modulate molecular behavior.
- Understanding host-guest complexation is crucial for developing new therapeutic agents.
Purpose of the Study:
- To synthesize and characterize a novel carbohydrate-based molecule, 1,10-N,N'-bis-(β-d-ureidolactosyl)-4,7,13,16-tetraoxa-1,10-diazacyclooctadecane (TL).
- To investigate the host-guest complexation properties of TL with butane-1,4-diyl bis(2,2,2-trifluoroethane-1-sulfonate) (BFS).
- To evaluate the biological activity and physicochemical properties of TL and its complex with BFS.
Main Methods:
- Multistep synthesis and Zemplén deacetylation for TL preparation.
- Host-guest complexation studies using BFS.
- Characterization via multidimensional NMR, FT-IR spectroscopy, and conductometric analysis.
- Biological assays on HaCaT cells and theoretical calculations.
Main Results:
- TL was successfully synthesized and characterized, showing good water solubility (25.74 g/100 mL).
- TL demonstrated non-toxicity towards HaCaT cells.
- Complexation with BFS resulted in a stable complex (complexation energy: -79.94 kJ/mol) and reduced BFS cytotoxicity.
- Theoretical calculations revealed a conformation stabilized by extensive intramolecular hydrogen bonding.
Conclusions:
- The novel carbohydrate-based molecule TL possesses favorable physicochemical properties and low toxicity.
- TL effectively forms stable complexes with BFS, modulating its cytotoxic activity.
- This study highlights the potential of TL as a scaffold for developing new host-guest systems with therapeutic applications.
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