ArticleChemMedChem2019
4"-O-Alkylated α-Galactosylceramide Analogues as iNKT-Cell Antigens: Synthetic, Biological, and Structural Studies.
Article in ChemMedChem, 2019. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
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Who cites it
8 citing papers in PubMed, 17 citations in OpenAlex.
- Highly Potent Th1-Type NKT Cell Agonists as Immunotherapeutic Agents via Conformational Restriction Design.JACS Au · 2026Article
- A Humanized Mouse Model Coupled with Computational Analysis Identifies Potent Glycolipid Agonist of Invariant NKT Cells.ACS chemical biology · 2024Article
- Conformationally Restricted Analogues of α-Galactosylceramide as Adjuvant in COVID-19 Subunit Vaccine.ACS medicinal chemistry letters · 2023Article
- Halogenation Reactions of Alkyl Alcohols Employing Methyl Grignard Reagents.The Journal of organic chemistry · 2022Article
- Natural and synthetic carbohydrate-based vaccine adjuvants and their mechanisms of action.Nature reviews. Chemistry · 2021Review
- Amide-Linked C4″-Saccharide Modification of KRN7000 Provides Potent Stimulation of Human Invariant NKT Cells and Anti-Tumor Immunity in a Humanized Mouse Model.ACS chemical biology · 2020Article
- A DesignedAdvanced science (Weinheim, Baden-Wurttemberg, Germany) · 2020Article
- A sustainable innovation for the tandem synthesis of sugar-containing coumarin derivatives catalyzed by lipozyme TL IM fromRSC advances · 2020Article
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Authors and funding
9 authors at 3 institutions in 2 countries.
Funding
Abstract
Invariant natural killer T-cells (iNKT) are a glycolipid-responsive subset of T-lymphocytes that fulfill a pivotal role in the immune system. The archetypical synthetic glycolipid, α-galactosylceramide (α-GalCer), whose molecular framework is inspired by a group of amphiphilic natural products, remains the most studied antigen for iNKT-cells. Nonetheless, the potential of α-GalCer as an immunostimulating agent is compromised by the fact that this glycolipid elicits simultaneous secretion of Th1- and Th2-cytokines. This has incited medicinal chemistry efforts to identify analogues that are able to perturb the Th1/Th2 balance. In this work, we present the synthesis of an extensive set of 4"-O-alkylated α-GalCer analogues, which were evaluated in vivo for their cytokine induction. We have found that conversion of the 4"-OH group to ether moieties decreases the immunogenic potential in mice relative to α-GalCer. Yet, the benzyl-modified glycolipids are able to produce a distinct pro-inflammatory immune response. The crystal structures suggest an extra hydrophobic interaction between the benzyl moiety and the α2-helix of CD1d.
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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.