ArticleJournal of the American Chemical Society2012
Synthesis and preclinical evaluation of QS-21 variants leading to simplified vaccine adjuvants and mechanistic probes.
Article in Journal of the American Chemical Society, 2012. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 29 papers.
What it found
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Who cites it
29 citing papers in PubMed, 63 citations in OpenAlex.
- Advances in the heterologous biosynthesis of QS saponins: a review.Microbial cell factories · 2026Review
- Article
- Enzymology and Structural Basis of Glycosyltransferases Involved in Saponin C28 Carboxylic AcidJACS Au · 2025Article
- Novel adjuvant delivery system constructed by alum-emulsion hybrid nanoparticles with TLR9 agonists boosts vaccine immunity.Journal of nanobiotechnology · 2025Article
- Immunological and Toxicological Assessment of Triterpenoid Saponins Bearing Lewis-X- and QS-21-Based Trisaccharides.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Article
- A streamlined synthetic approach to the truncated linear trisaccharide fragment of QS-21.Frontiers in chemistry · 2025Article
- Terpenes and Terpenoids Conjugated with BODIPYs: An Overview of Biological and Chemical Properties.Journal of natural products · 2024Review
- Chemical and biological characterization of vaccine adjuvant QS-21 produced via plant cell culture.iScience · 2024Article
- A review: structure-activity relationship between saponins and cellular immunity.Molecular biology reports · 2023Review
- Article
- Structure-Activity Relationship Study ofJournal of medicinal chemistry · 2022Article
- Novel Oxime-Derivatized Synthetic Triterpene Glycosides as Potent Saponin Vaccine Adjuvants.Frontiers in immunology · 2022Article
- Design, synthesis, and initial immunological evaluation of glycoconjugates based on saponin adjuvants and the Tn antigen.Chemical communications (Cambridge, England) · 2021Article
- Replacing the Rhamnose-Xylose Moiety of QS-21 with Simpler Terminal Disaccharide Units Attenuates Adjuvant Activity in Truncated Saponin Variants.Chemistry (Weinheim an der Bergstrasse, Germany) · 2021Article
- Natural and synthetic carbohydrate-based vaccine adjuvants and their mechanisms of action.Nature reviews. Chemistry · 2021Review
- Synthesis and Evaluation of QS-7-Based Vaccine Adjuvants.ACS infectious diseases · 2019Article
- Synthesis of the hexacyclic triterpene core of the jujuboside saponins via tandem Wolff rearrangement-intramolecular ketene hetero-Diels-Alder reaction.Tetrahedron · 2018Article
- Rapid assembly of the doubly-branched pentasaccharide domain of the immunoadjuvant jujuboside A via convergent B(CChemical communications (Cambridge, England) · 2017Article
- Semisynthesis of Analogues of the Saponin Immunoadjuvant QS-21.Methods in molecular biology (Clifton, N.J.) · 2017Article
- Synthesis and Evaluation of QS-21-Based Immunoadjuvants with a Terminal-Functionalized Side Chain Incorporated in the West Wing Trisaccharide.The Journal of organic chemistry · 2016Article
Corrections and comments
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Authors and funding
8 authors at 2 institutions in 1 country.
Funding
Abstract
QS-21 is a potent immunostimulatory saponin that is currently under clinical investigation as an adjuvant in various vaccines to treat infectious diseases, cancers, and cognitive disorders. Herein, we report the design, synthesis, and preclinical evaluation of simplified QS-21 congeners to define key structural features that are critical for adjuvant activity. Truncation of the linear tetrasaccharide domain revealed that a trisaccharide variant is equipotent to QS-21, while the corresponding disaccharide and monosaccharide congeners are more toxic and less potent, respectively. Modification of the acyl chain domain in the trisaccharide series revealed that a terminal carboxylic acid is well-tolerated while a terminal amine results in reduced adjuvant activity. Acylation of the terminal amine can, in some cases, restore adjuvant activity and enables the synthesis of fluorescently labeled QS-21 variants. Cellular studies with these probes revealed that, contrary to conventional wisdom, the most highly adjuvant active of these fluorescently labeled saponins does not simply associate with the plasma membrane, but rather is internalized by dendritic cells.
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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.