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Experimental and Computational Studies on Structure and Energetic Properties of Halogen Derivatives of 2-Deoxy-D-Glucose

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cris.lastimport.scopus2024-02-12T19:29:21Z
dc.abstract.enThe results of structural studies on a series of halogen-substituted derivatives of 2-deoxy-D-glucose (2-DG) are reported. 2-DG is an inhibitor of glycolysis, a metabolic pathway crucial for cancer cell proliferation and viral replication in host cells, and interferes with D-glucose and D-mannose metabolism. Thus, 2-DG and its derivatives are considered as potential anticancer and antiviral drugs. X-ray crystallography shows that a halogen atom present at the C2 position in the pyranose ring does not significantly affect its conformation. However, it has a noticeable effect on the crystal structure. Fluorine derivatives exist as a dense 3D framework isostructural with the parent compound, while Cl- and I-derivatives form layered structures. Analysis of the Hirshfeld surface shows formation of hydrogen bonds involving the halogen, yet no indication for the existence of halogen bonds. Density functional theory (DFT) periodic calculations of cohesive and interaction energies (at the B3LYP level of theory) have supported these findings. NMR studies in the solution show that most of the compounds do not display significant differences in their anomeric equilibria, and that pyranose ring puckering is similar to the crystalline state. For 2-deoxy-2-fluoro-D-glucose (2-FG), electrostatic interaction energies between the ligand and protein for several existing structures of pyranose 2-oxidase were also computed. These interactions mostly involve acidic residues of the protein; single amino-acid substitutions have only a minor impact on binding. These studies provide a better understanding of the structural chemistry of halogen-substituted carbohydrates as well as their intermolecular interactions with proteins determining their distinct biological activity.
dc.affiliationUniwersytet Warszawski
dc.contributor.authorZiemniak, Marcin
dc.contributor.authorZawadzka-Kazimierczuk, Anna
dc.contributor.authorSołtyka, Maja
dc.contributor.authorSkora, Stanisław
dc.contributor.authorKoźmiński, Wiktor
dc.contributor.authorPająk, Beata
dc.contributor.authorFokt, Izabela
dc.contributor.authorZieliński, Rafał
dc.contributor.authorMalińska, Maura
dc.contributor.authorPriebe, Waldemar
dc.contributor.authorWoźniak, Krzysztof
dc.contributor.authorPawlędzio, Sylwia
dc.contributor.authorTrzybiński, Damian
dc.date.accessioned2024-01-25T00:07:46Z
dc.date.available2024-01-25T00:07:46Z
dc.date.copyright2021-04-02
dc.date.issued2021
dc.description.accesstimeAT_PUBLICATION
dc.description.financePublikacja bezkosztowa
dc.description.number7
dc.description.versionFINAL_PUBLISHED
dc.description.volume22
dc.identifier.doi10.3390/IJMS22073720
dc.identifier.issn1422-0067
dc.identifier.urihttps://repozytorium.uw.edu.pl//handle/item/106745
dc.identifier.weblinkhttps://www.mdpi.com/1422-0067/22/7/3720
dc.languageeng
dc.pbn.affiliationchemical sciences
dc.relation.ispartofInternational Journal of Molecular Sciences
dc.relation.pagesart.no. 3720
dc.rightsCC-BY
dc.sciencecloudnosend
dc.subject.en2-deoxy-D-glucose
dc.subject.en2-DG analogues
dc.subject.enhydrogen bonds
dc.subject.enenergy frameworks
dc.subject.enHirshfeld surface
dc.subject.enNMR spectroscopy
dc.subject.enThe University at Buffalo Pseudoatom Databank (UBDB)
dc.subject.englycolysis inhibitors
dc.subject.enelectrostatic interactions
dc.subject.enligand binding
dc.titleExperimental and Computational Studies on Structure and Energetic Properties of Halogen Derivatives of 2-Deoxy-D-Glucose
dc.typeJournalArticle
dspace.entity.typePublication