Lipophilic glucose monoesters and glycosides are potent human Mincle agonists

Braganza, Chriselle D.; Kodar, Kristel; Teunissen, Thomas; Andreassend, Sarah K.; Khan, Ayesha; Timmer, Mattie S. M.; Stocker, Bridget L.

doi:10.1039/d1ob02111g

Org. Biomol. Chem.

2022

DOI: 10.1039/d1ob02111g

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Lipophilic glucose monoesters and glycosides are potent human Mincle agonists

Chriselle D. Braganza

Kristel Kodar

Thomas Teunissen

et al.

Abstract: Docosyl α-glucopyranoside is a Mincle ligand that leads to high levels of IL-1β and IL-8 production by human monocytes.

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2024

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Cited by 2 publications

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Migration of para‐Nitrophenyl Groups in Methyl Pyranosides: Configuration and Conformation Determine the Kinetics

Friedrich,

Lütjohann,

Hartke

et al. 2024

Chemistry A European J

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para‐Nitrophenyl (PNP) ethers of glycosides are important building blocks en route to functional carbohydrates. They are stable in neutral media, however, under basic conditions such as during the Zemplén deacylation of sugars, aryl migration is frequently observed. We have employed a library of O‐PNP‐substituted methyl glycosides of the manno‐, galacto‐, gluco‐ and altro‐series to study the kinetics of aryl migration in MeOH/sodium methoxide using NMR spectroscopy revealing that migration between cis‐oriented OH groups is faster than between trans‐oriented ones. The rate constants of migration decrease in the order of Alt > Man > Gal > Glc and are related to the energy barriers of chair conformation inversion. The energy profile of the 3 to 4‐PNP migration in methyl mannoside was calculated using DFT methods suggesting the Meisenheimer complex is an intermediate of PNP migration and that coordination of the sodium cation has a major impact on the energy profile.

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Migration of para‐Nitrophenyl Groups in Methyl Pyranosides: Configuration and Conformation Determine the Kinetics

Friedrich,

Lütjohann,

Hartke

et al. 2024

Chemistry A European J

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Recent Advances in the Development of Mincle-Targeting Vaccine Adjuvants

Weth,

Dangerfield,

Timmer

et al. 2024

Vaccines

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The Macrophage-inducible C-type lectin (Mincle) is a pattern-recognition receptor (PRR), which has shown much promise as a molecular target for the development of TH1/TH17-skewing vaccine adjuvants. In 2009, the first non-proteinaceous Mincle ligands, trehalose dimycolate (TDM) and trehalose dibehenate (TDB), were identified. This prompted a search for other Mincle agonists and the exploration of Mincle agonists as vaccine adjuvants for both preventative and therapeutic (anti-cancer) vaccines. In this review, we discuss those classes of Mincle agonists that have been explored for their adjuvant potential. These Mincle agonists have been used as stand-alone adjuvants or in combination with other pathogen-associated molecular patterns (PAMPs) or immunomodulatory agents. We will also highlight recently identified Mincle ligands with hitherto unknown adjuvanticity. Conjugate vaccines that contain covalently linked adjuvants and/or adjuvant–antigen combinations are also presented, as well as the different formulations (e.g., oil-in-water emulsions, liposomes, and particulate delivery systems) that have been used for the codelivery of antigens and adjuvants. Insofar the reader is presented with a thorough review of the potential of Mincle-mediated vaccine adjuvants, including historical context, present-day research and clinical trials, and outstanding research questions, such as the role of ligand presentation and Mincle clustering, which, if better understood, will aid in the development of the much-needed TH1/TH17-skewing vaccine adjuvants.

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Lipophilic glucose monoesters and glycosides are potent human Mincle agonists

Abstract: Docosyl α-glucopyranoside is a Mincle ligand that leads to high levels of IL-1β and IL-8 production by human monocytes.

Cited by 2 publications

References 46 publications

Migration of para‐Nitrophenyl Groups in Methyl Pyranosides: Configuration and Conformation Determine the Kinetics

Migration of para‐Nitrophenyl Groups in Methyl Pyranosides: Configuration and Conformation Determine the Kinetics

Recent Advances in the Development of Mincle-Targeting Vaccine Adjuvants

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