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. |
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| 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] |
| Copyright of Journal of Molecular Structure is the property of Elsevier B.V. and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract. (Copyright applies to all Abstracts.) | |
| Database: | Engineering Source |
| FullText | Text: Availability: 0 |
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| Header | DbId: egs DbLabel: Engineering Source An: 191760572 AccessLevel: 6 PubType: Academic Journal PubTypeId: academicJournal PreciseRelevancyScore: 0 |
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| Items | – Name: Title Label: Title Group: Ti Data: 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. – Name: Author Label: Authors Group: Au Data: <searchLink fieldCode="AR" term="%22Hoelm%2C+Marta%22">Hoelm, Marta</searchLink><relatesTo>1</relatesTo> (AUTHOR)<i> marta.hoelm@chemia.uni.lodz.pl</i><br /><searchLink fieldCode="AR" term="%22Porwański%2C+Stanisław%22">Porwański, Stanisław</searchLink><relatesTo>2</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Kinart%2C+Zdzisław%22">Kinart, Zdzisław</searchLink><relatesTo>1</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Pawlowska%2C+Roza%22">Pawlowska, Roza</searchLink><relatesTo>3</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Kowalska%2C+Karolina%22">Kowalska, Karolina</searchLink><relatesTo>3</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Kost%2C+Bartłomiej%22">Kost, Bartłomiej</searchLink><relatesTo>3</relatesTo> (AUTHOR)<br /><searchLink fieldCode="AR" term="%22Staniec%2C+Paulina%22">Staniec, Paulina</searchLink><relatesTo>1</relatesTo> (AUTHOR) – Name: TitleSource Label: Source Group: Src Data: <searchLink fieldCode="JN" term="%22Journal+of+Molecular+Structure%22">Journal of Molecular Structure</searchLink>. May2026, Vol. 1359, pN.PAG-N.PAG. 1p. – Name: Subject Label: Subjects Group: Su Data: <searchLink fieldCode="DE" term="%22Cryptands%22">Cryptands</searchLink><br /><searchLink fieldCode="DE" term="%22Density+functional+theory%22">Density functional theory</searchLink><br /><searchLink fieldCode="DE" term="%22Nuclear+magnetic+resonance+spectroscopy%22">Nuclear magnetic resonance spectroscopy</searchLink><br /><searchLink fieldCode="DE" term="%22Cytotoxins%22">Cytotoxins</searchLink><br /><searchLink fieldCode="DE" term="%22Fluorine+compounds%22">Fluorine compounds</searchLink><br /><searchLink fieldCode="DE" term="%22Hydrogen+bonding%22">Hydrogen bonding</searchLink><br /><searchLink fieldCode="DE" term="%22Conformational+analysis%22">Conformational analysis</searchLink> – Name: Abstract Label: Abstract Group: Ab Data: • 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] – Name: AbstractSuppliedCopyright Label: Group: Ab Data: <i>Copyright of Journal of Molecular Structure is the property of Elsevier B.V. and its content may not be copied or emailed to multiple sites without the copyright holder's express written permission. Additionally, content may not be used with any artificial intelligence tools or machine learning technologies. However, users may print, download, or email articles for individual use. This abstract may be abridged. No warranty is given about the accuracy of the copy. Users should refer to the original published version of the material for the full abstract.</i> (Copyright applies to all Abstracts.) |
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| RecordInfo | BibRecord: BibEntity: Identifiers: – Type: doi Value: 10.1016/j.molstruc.2026.145431 Languages: – Code: eng Text: English PhysicalDescription: Pagination: PageCount: 1 StartPage: N.PAG Subjects: – SubjectFull: Cryptands Type: general – SubjectFull: Density functional theory Type: general – SubjectFull: Nuclear magnetic resonance spectroscopy Type: general – SubjectFull: Cytotoxins Type: general – SubjectFull: Fluorine compounds Type: general – SubjectFull: Hydrogen bonding Type: general – SubjectFull: Conformational analysis Type: general Titles: – TitleFull: 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. Type: main BibRelationships: HasContributorRelationships: – PersonEntity: Name: NameFull: Hoelm, Marta – PersonEntity: Name: NameFull: Porwański, Stanisław – PersonEntity: Name: NameFull: Kinart, Zdzisław – PersonEntity: Name: NameFull: Pawlowska, Roza – PersonEntity: Name: NameFull: Kowalska, Karolina – PersonEntity: Name: NameFull: Kost, Bartłomiej – PersonEntity: Name: NameFull: Staniec, Paulina IsPartOfRelationships: – BibEntity: Dates: – D: 05 M: 05 Text: May2026 Type: published Y: 2026 Identifiers: – Type: issn-print Value: 00222860 Numbering: – Type: volume Value: 1359 Titles: – TitleFull: Journal of Molecular Structure Type: main |
| ResultId | 1 |
