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Effect of Glycoconjugation on Cytotoxicity and Selectivity of 8-Aminoquinoline Derivatives Compared to 8-Hydroxyquinoline.
Molecules
January 2025
Department of Organic Chemistry, Bioorganic Chemistry and Biotechnology, Silesian University of Technology, B. Krzywoustego 4, 44-100 Gliwice, Poland.
Numerous emerging chemotherapeutic agents incorporate -heterocyclic fragments in their structures, with the quinoline skeleton being particularly significant. Our recent works have focused on glycoconjugates of 8-hydroxyquinoline (8-HQ), which demonstrated enhanced bioavailability and solubility compared to their parent compounds, although they fell short in selectivity. In this study, our objective was to improve the selectivity of glycoconjugates by replacing the oxygen atom with nitrogen by substituting the 8-HQ moiety with 8-aminoquinoline (8-AQ).
View Article and Find Full Text PDFSynthetic β-d-Glucuronides: Substrates for Exploring Glucuronide Degradation by Human Gut Bacteria.
ACS Omega
January 2025
Department of Biochemistry, Cell and Systems Biology, ISMIB, University of Liverpool, Crown Street, Liverpool L69 7ZB, U.K.
The human gut microbiota (HGM) is a complex ecosystem subtly dependent on the interplay between hundreds of bacterial species and numerous metabolites. Dietary phenols, whether ingested (e.g.
View Article and Find Full Text PDFStereoselective 1,1'-glycosylation reactivity tuning with protecting groups.
Org Biomol Chem
January 2025
Department of Chemistry, University of Natural Resources and Life Sciences, Muthgasse 18, Vienna, A-1190 Austria.
Chemical 1,1'-glycosylation for the synthesis of non-reducing disaccharides is complicated by the need to simultaneously control the stereochemistry at two anomeric centers. While considerable progress has been made in the synthesis of α,α-disaccharides, the assembly of 1,1'-β,β- and 1,1'-β,α-linked non-reducing sugars has received comparatively less attention. Many naturally occurring non-reducing disaccharides and their biologically active mimetics feature asymmetrically located functional groups at different positions on the two pyranose rings, highlighting the demand for reliable stereoselective methods to synthesize fully orthogonally protected 1,1'-conjugated sugars suitable for targeted functionalisation to create important biomolecules.
View Article and Find Full Text PDFStructure and function of a β-1,2-galactosidase from Bacteroides xylanisolvens, an intestinal bacterium.
Commun Biol
January 2025
Department of Applied Biological Science, Faculty of Science and Technology, Tokyo University of Science, 2641 Yamazaki, Noda, Chiba, 278-8510, Japan.
Galactosides are major carbohydrates that are found in plant cell walls and various prebiotic oligosaccharides. Studying the detailed biochemical functions of β-galactosidases in degrading these carbohydrates is important. In particular, identifying β-galactosidases with new substrate specificities could help in the production of potentially beneficial oligosaccharides.
View Article and Find Full Text PDFTransition State Analogs of Human DNPH1 Reveal Two Electrophile Migration Mechanisms.
J Med Chem
January 2025
Department of Biochemistry, Albert Einstein College of Medicine, Bronx, New York 10461, United States.
DNPH1 is responsible for eliminating the epigenetically modified nucleotide, 5-hydroxymethyl-2'-deoxyuridine 5'-monophosphate (hmdUMP), preventing formation of hmdUTP, a mutation-inducing nucleotide. Loss of DNPH1 activity sensitizes PARP inhibition-resistant BRCA-deficient cancers by causing incorporation of hmdUTP into DNA. Hydrolysis of hmdUMP by DNPH1 proceeds through a covalent intermediate between Glu104 and 2-deoxyribose 5-phosphate, followed by hydrolysis, a reaction cycle with two transition states.
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