ArticleChemistry (Weinheim an der Bergstrasse, Germany)2021
Replacing the Rhamnose-Xylose Moiety of QS-21 with Simpler Terminal Disaccharide Units Attenuates Adjuvant Activity in Truncated Saponin Variants.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 15 papers.
What it found
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The trial behind it
Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.
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Who cites it
15 citing papers in PubMed, 17 citations in OpenAlex.
- Synthesis and In Vivo Immunological Evaluation of Novel Saponin-Antigen Conjugates Incorporating Tumor-Associated Carbohydrate and Peptide Epitopes.Chemistry (Weinheim an der Bergstrasse, Germany) · 2026Article
- Article
- Impact of Side Chain Structure and Aglycon Carbonyl Group on the Immunostimulatory Activities of Semisynthetic Saponin Adjuvants.ACS pharmacology & translational science · 2026Article
- Immunological and Toxicological Assessment of Triterpenoid Saponins Bearing Lewis-X- and QS-21-Based Trisaccharides.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025Article
- Monophosphoryl Lipid A-Rhamnose Conjugates as a New Class of Vaccine Adjuvants.Journal of medicinal chemistry · 2024Article
- Design and Synthesis of Immunoadjuvant QS-21 Analogs and Their Biological Evaluation.Biomedicines · 2024Article
- A newly identified β-amyrin synthase gene hypothetically involved in oleanane-saponin biosynthesis fromHeliyon · 2023Article
- Article
- Development of synthetic, self-adjuvanting, and self-assembling anticancer vaccines based on a minimal saponin adjuvant and the tumor-associated MUC1 antigen.Chemical science · 2023Article
- 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
- Rational Vaccine Design in Times of Emerging Diseases: The Critical Choices of Immunological Correlates of Protection, Vaccine Antigen and Immunomodulation.Pharmaceutics · 2021Review
- 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 Saponins as Vaccine Adjuvants.Vaccines · 2021Review
- Analysis of carbohydrates and glycoconjugates by matrix-assisted laser desorption/ionization mass spectrometry: An update for 2021-2022.Mass spectrometry reviewsReview
Corrections and comments
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Authors and funding
7 authors at 2 institutions in 1 country.
Funding
Abstract
Adjuvants are key immunostimulatory components in vaccine formulations, which improve the immune response to the co-administered antigen. The saponin natural product QS-21 is one of the most promising immunoadjuvants in the development of vaccines against cancer and infectious diseases but suffers from limitations that have hampered its widespread human use. Previous structure-activity relationship studies have identified simplified saponin variants with truncated carbohydrate chains, but have not focused on the influence of the linear oligosaccharide domain of QS-21 in adjuvant activity. Herein, an expeditious 15-step synthesis of new linear trisaccharide variants of simplified QS-21-derived adjuvants is reported, in which the complex terminal xylose-rhamnose moiety has been replaced with commercially available, simpler lactose and cellobiose disaccharides in a β-anomeric configuration. In vivo immunological evaluation of the synthetic saponins showed attenuated antibody responses, highlighting the negative impact of such carbohydrate modifications on adjuvant activity, which could be associated with higher saponin conformational flexibility.
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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.