ArticleBioorganic & medicinal chemistry2014
Design, synthesis, and immunologic evaluation of vaccine adjuvant conjugates based on QS-21 and tucaresol.
Article in Bioorganic & medicinal chemistry, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 15 papers.
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Who cites it
15 citing papers in PubMed.
- 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
- Chemical and biological characterization of vaccine adjuvant QS-21 produced via plant cell culture.iScience · 2024Article
- 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
- Glycoconjugates: Synthesis, Functional Studies, and Therapeutic Developments.Chemical reviews · 2022Review
- Novel Oxime-Derivatized Synthetic Triterpene Glycosides as Potent Saponin Vaccine Adjuvants.Frontiers in immunology · 2022Article
- ISCOM-like Nanoparticles Formulated withVaccines · 2021Article
- Design, synthesis, and initial immunological evaluation of glycoconjugates based on saponin adjuvants and the Tn antigen.Chemical communications (Cambridge, England) · 2021Article
- Natural and synthetic carbohydrate-based vaccine adjuvants and their mechanisms of action.Nature reviews. Chemistry · 2021Review
- Pre-Erythrocytic Vaccines against Malaria.Vaccines · 2020Review
- Synthesis and Evaluation of QS-7-Based Vaccine Adjuvants.ACS infectious diseases · 2019Article
- Saponins fromMolecules (Basel, Switzerland) · 2019Review
- Semisynthesis of Analogues of the Saponin Immunoadjuvant QS-21.Methods in molecular biology (Clifton, N.J.) · 2017Article
- Development of Improved Vaccine Adjuvants Based on the Saponin Natural Product QS-21 through Chemical Synthesis.Accounts of chemical research · 2016Article
- Synthesis, Formulation, and Adjuvanticity of Monodesmosidic Saponins with Olenanolic Acid, Hederagenin and Gypsogenin Aglycones, and some C-28 Ester Derivatives.ChemistryOpen · 2015Article
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Authors and funding
8 authors.
Funding
Abstract
Immunoadjuvants are used to potentiate the activity of modern subunit vaccines that are based on molecular antigens. An emerging approach involves the combination of multiple adjuvants in a single formulation to achieve optimal vaccine efficacy. Herein, to investigate such potential synergies, we synthesized novel adjuvant conjugates based on the saponin natural product QS-21 and the aldehyde tucaresol via chemoselective acylation of an amine at the terminus of the acyl chain domain in QS saponin variants. In a preclinical mouse vaccination model, these QS saponin-tucaresol conjugates induced antibody responses similar to or slightly higher than those generated with related QS saponin variants lacking the tucaresol motif. The conjugates retained potent adjuvant activity, low toxicity, and improved activity-toxicity profiles relative to QS-21 itself and induced IgG subclass profiles similar to those of QS-21, indicative of both Th1 cellular and Th2 humoral immune responses. This study opens the door to installation of other substituents at the terminus of the acyl chain domain to develop additional QS saponin conjugates with desirable immunologic properties.
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