ArticleThe Journal of biological chemistry2009
Deoxygenated disaccharide analogs as specific inhibitors of beta1-4-galactosyltransferase 1 and selectin-mediated tumor metastasis.
Article in The Journal of biological chemistry, 2009. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 23 papers.
What it found
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Who cites it
23 citing papers in PubMed, 40 citations in OpenAlex.
- AssessingACS infectious diseases · 2026Article
- Article
- Molecular Mechanisms Underlying the Loop-Closing Dynamics of β-1,4 Galactosyltransferase 1.Journal of chemical information and modeling · 2025Article
- Thioglycosides Act as Metabolic Inhibitors of Bacterial Glycan Biosynthesis.ACS infectious diseases · 2023Article
- Chemical tools to study bacterial glycans: a tale from discovery of glycoproteins to disruption of their function.Israel journal of chemistry · 2023Article
- Glycoengineering of Therapeutic Antibodies with Small Molecule Inhibitors.Antibodies (Basel, Switzerland) · 2021Review
- Opportunities and Challenges of Bacterial Glycosylation for the Development of Novel Antibacterial Strategies.Frontiers in microbiology · 2021Review
- Selectins-The Two Dr. Jekyll and Mr. Hyde Faces of Adhesion Molecules-A Review.Molecules (Basel, Switzerland) · 2020Review
- Metabolic inhibitors of bacterial glycan biosynthesis.Chemical science · 2020Article
- Article
- An acceptor analogue of β-1,4-galactosyltransferase: Substrate, inhibitor, or both?Carbohydrate research · 2017Article
- Galactose Supplementation in Patients With TMEM165-CDG Rescues the Glycosylation Defects.The Journal of clinical endocrinology and metabolism · 2017Article
- Base-modified UDP-sugars reduce cell surface levels of P-selectin glycoprotein 1 (PSGL-1) on IL-1β-stimulated human monocytes.Glycobiology · 2016Article
- Challenge to the suppression of tumor growth by the β4-galactosyltransferase genes.Proceedings of the Japan Academy. Series B, Physical and biological sciences · 2015Review
- Investigations on β1,4-galactosyltransferase I using 6-sulfo-GlcNAc as an acceptor sugar substrate.Glycoconjugate journal · 2013Article
- B4GALT family mediates the multidrug resistance of human leukemia cells by regulating the hedgehog pathway and the expression of p-glycoprotein and multidrug resistance-associated protein 1.Cell death & disease · 2013Article
- Binding of N-acetylglucosamine (GlcNAc) β1-6-branched oligosaccharide acceptors to β4-galactosyltransferase I reveals a new ligand binding mode.The Journal of biological chemistry · 2012Article
- Developing inhibitors of glycan processing enzymes as tools for enabling glycobiology.Nature chemical biology · 2012Review
- Adhesion receptors as therapeutic targets for circulating tumor cells.Frontiers in oncology · 2012Article
- Peracetylated 4-fluoro-glucosamine reduces the content and repertoire of N- and O-glycans without direct incorporation.The Journal of biological chemistry · 2011Article
Corrections and comments
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Authors and funding
7 authors at 2 institutions in 2 countries.
Funding
Abstract
The disaccharide peracetylated GlcNAcbeta1-3Galbeta-O-naphthalenemethanol (disaccharide 1) diminishes the formation of the glycan sialyl Lewis X (Neu5Acalpha2-3Galbeta1-4(Fucalpha1-3) GlcNAc; sLe(X)) in tumor cells. Previous studies showed that the mechanism of action of disaccharide 1 involves three steps: (i) deacetylation by carboxyesterases, (ii) action as a biosynthetic intermediate for downstream enzymes involved in sLe(X) assembly, and (iii) generation of several glycans related to sLe(X). In this report, we show that GlcNAcbeta1-3Galbeta-O-naphthalenemethanol binds to the acceptor site of human beta1-4-galactosyltransferase much like the acceptor trisaccharide, GlcNAcbeta1-2Manbeta1-6Man, which is present on N-linked glycans. The 4'-deoxy analog, in which the acceptor hydroxyl group was replaced by -H, did not act as a substrate but instead acted as a competitive inhibitor of the enzyme. The acetylated form of this compound inhibited sLe(X) formation in U937 monocytic leukemia cells, suggesting that it had inhibitory activity in vivo as well. A series of synthetic acetylated analogs of 1 containing -H, -F, -N(3), -NH(2), or -OCH(3) instead of the hydroxyl groups at C-3'- and C-4'-positions of the terminal N-acetylglucosamine residue also blocked sLe(X) formation in cells. The reduction of sLe(X) by the 4'-deoxy analog also diminished experimental tumor metastasis by Lewis lung carcinoma in vivo. These data suggest that nonsubstrate disaccharides have therapeutic potential through their ability to bind to glycosyltransferases in vivo and to alter glycan-dependent pathologic processes.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.