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Application of theoretical methods to the structural characterization of a new glucose cryptand and its complex with a fluorine-based cytotoxic molecule: Comparison with experimental data.

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Title: Application of theoretical methods to the structural characterization of a new glucose cryptand and its complex with a fluorine-based cytotoxic molecule: Comparison with experimental data.
Authors: Hoelm, Marta1 (AUTHOR) marta.hoelm@chemia.uni.lodz.pl, Porwański, Stanisław2 (AUTHOR), Kinart, Zdzisław1 (AUTHOR), Pawlowska, Roza3 (AUTHOR), Kowalska, Karolina3 (AUTHOR), Kost, Bartłomiej3 (AUTHOR), Staniec, Paulina1 (AUTHOR)
Source: Journal of Molecular Structure. May2026, Vol. 1359, pN.PAG-N.PAG. 1p.
Subjects: Cryptands, Density functional theory, Nuclear magnetic resonance spectroscopy, Cytotoxins, Fluorine compounds, Hydrogen bonding, Conformational analysis
Abstract: • SMT, a sugar-based cryptand, adopts compact geometry stabilized by H-bonds. • SMT forms a stable non-inclusion complex with BFS via intermolecular H-bonds. • M06-2X predicts NMR shifts and Gibbs energies closest to experimental values. • ωB97X and TPSSh best predict NMR shifts of the SMT:BFS complex in solution. • SMT reduces BFS cytotoxicity in HL-60 cells, acting as a potential carrier. The sugar-based cryptand 1,10- N,N′ -bis-(β- d -ureidoglucosyl)-4,7,13,16-tetraoxa-1,10-diazacyclopentadecane (SMT) and its complex with the fluorine-containing cytotoxic compound butane-1,4-diyl bis(2,2,2-trifluoroethane-1-sulfonate) (BFS) were synthesized and structurally characterized. The formation and structure of SMT and the SMT:BFS complex were confirmed using a combination of 1D and 2D spectroscopic techniques, including 1H and 13C NMR, 1H–1H and 1H–13C correlation experiments, supported by FT-IR spectroscopy and conductometric studies. Spectroscopic and thermodynamic analyses indicate that SMT forms a stable non-inclusion complex with BFS stabilized by intermolecular hydrogen bonding. Density functional theory (DFT) calculations were applied to support the experimental findings and to analyze the structural and energetic features of SMT and its complex. The calculations reveal a compact geometry of SMT, in which the glucose units are located in close proximity above the diazacrown ether moiety as a result of intramolecular hydrogen bonding. Among the tested DFT approaches, M06-2X and M08-HX showed the best agreement with experimental spectroscopic data. Biological evaluation demonstrates that BFS is cytotoxic toward leukemia cell lines (K562 and HL-60), whereas SMT is non-toxic and the SMT:BFS complex exhibits reduced cytotoxicity, suggesting that SMT may act as a protective carrier. [Display omitted] [ABSTRACT FROM AUTHOR]
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Database: Engineering Source
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Abstract:• SMT, a sugar-based cryptand, adopts compact geometry stabilized by H-bonds. • SMT forms a stable non-inclusion complex with BFS via intermolecular H-bonds. • M06-2X predicts NMR shifts and Gibbs energies closest to experimental values. • ωB97X and TPSSh best predict NMR shifts of the SMT:BFS complex in solution. • SMT reduces BFS cytotoxicity in HL-60 cells, acting as a potential carrier. The sugar-based cryptand 1,10- N,N′ -bis-(β- d -ureidoglucosyl)-4,7,13,16-tetraoxa-1,10-diazacyclopentadecane (SMT) and its complex with the fluorine-containing cytotoxic compound butane-1,4-diyl bis(2,2,2-trifluoroethane-1-sulfonate) (BFS) were synthesized and structurally characterized. The formation and structure of SMT and the SMT:BFS complex were confirmed using a combination of 1D and 2D spectroscopic techniques, including 1H and 13C NMR, 1H–1H and 1H–13C correlation experiments, supported by FT-IR spectroscopy and conductometric studies. Spectroscopic and thermodynamic analyses indicate that SMT forms a stable non-inclusion complex with BFS stabilized by intermolecular hydrogen bonding. Density functional theory (DFT) calculations were applied to support the experimental findings and to analyze the structural and energetic features of SMT and its complex. The calculations reveal a compact geometry of SMT, in which the glucose units are located in close proximity above the diazacrown ether moiety as a result of intramolecular hydrogen bonding. Among the tested DFT approaches, M06-2X and M08-HX showed the best agreement with experimental spectroscopic data. Biological evaluation demonstrates that BFS is cytotoxic toward leukemia cell lines (K562 and HL-60), whereas SMT is non-toxic and the SMT:BFS complex exhibits reduced cytotoxicity, suggesting that SMT may act as a protective carrier. [Display omitted] [ABSTRACT FROM AUTHOR]
ISSN:00222860
DOI:10.1016/j.molstruc.2026.145431