Influence of trehalose 6,6′-diester (TDX) chain length on the physicochemical and immunopotentiating properties of DDA/TDX liposomes

Kallerup, Rie Selchau; Madsen, Cecilie Maria; Schiøth, Mikkel Lohmann; Franzyk, Henrik; Rose, Fabrice; Christensen, Dennis; Korsholm, Karen Smith; Foged, Camilla

doi:10.1016/j.ejpb.2014.10.015

Cited by 15 publications

(52 citation statements)

References 40 publications

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“…This selection was corroborated by recent results showing optimal physicochemical properties and adjuvant activity of DDA/TDS liposomes (similar to that of DDA/TDB liposomes) as compared with TDB analogues with symmetrically shortened acyl moieties. 8 Thus, the ability of the formulations to induce Th1 and Th17 responses was evaluated by measuring the induction of the cytokines IFN-γ and IL-17a, which was compared with that of DDA/TDB-2 liposomes known to induce a mixed Th1/Th17 response profile. 2,3,8,19 …”

Section: Resultsmentioning

confidence: 99%

“…8 Thus, the ability of the formulations to induce Th1 and Th17 responses was evaluated by measuring the induction of the cytokines IFN-γ and IL-17a, which was compared with that of DDA/TDB-2 liposomes known to induce a mixed Th1/Th17 response profile. 2,3,8,19 …”

Section: Resultsmentioning

confidence: 99%

“…The analogues were synthesized and purified as previously reported, and the final identity and purity of the compounds were validated by NMR spectroscopy. 8 …”

Section: Methodsmentioning

confidence: 99%

“…8,14 Briefly, weighed amounts of DDA and glycolipid were dissolved in CHCl 3 -MeOH (9:1, v/v) in a round-bottomed flask. The organic solvents were evaporated under vacuum resulting in the formation of a thin lipid film.…”

Section: Methodsmentioning

confidence: 99%

“…The quality of each liposome batch was confirmed by measuring the particle size distribution, the polydispersity index and the zeta-potential, as previously described (results not shown). 8 …”

Section: Methodsmentioning

confidence: 99%

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Trehalose diester glycolipids are superior to the monoesters in binding to Mincle, activation of macrophages in vitro and adjuvant activity in vivo

et al. 2016

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The T-cell adjuvanticity of mycobacterial cord factor trehalose 6,6'-dimycolate (TDM) is well established. The identification of the C-type lectin Mincle on innate immune cells as the receptor for TDM and its synthetic analogue trehalose 6,6'-dibehenate (TDB) has raised interest in development of synthetic Mincle ligands as novel adjuvants. Trehalose mono- (TMXs) and diesters (TDXs) with symmetrically shortened acyl chains [denoted by X: arachidate (A), stearate (S), palmitate (P), and myristate (M)] were tested. Upon stimulation of murine macrophages, G-CSF secretion and NO production were strongly augmented by all TDXs tested, in a wide concentration range. In contrast, the TMXs triggered macrophage activation only at high concentrations. Macrophage activation by all TDXs required Mincle, but was independent of MyD88. The superior capacity of TDXs for activating macrophages was paralleled by direct binding of TDXs, but not of TMXs, to a Mincle-Fc fusion protein. Insertion of a short polyethylene glycol between the sugar and acyl chain in TDS reduced Mincle-binding and macrophage activation. Immunization of mice with cationic liposomes containing the analogues demonstrated the superior adjuvant activity of trehalose diesters. Overall, immune activation in vitro and in vivo by trehalose esters of simple fatty acids requires two acyl chains of length and involves Mincle.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

“…The analogues were synthesized and purified as previously reported, and the final identity and purity of the compounds were validated by NMR spectroscopy. 8 …”

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

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Trehalose diester glycolipids are superior to the monoesters in binding to Mincle, activation of macrophages in vitro and adjuvant activity in vivo

et al. 2016

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Solid‐in‐oil nanodispersions for transdermal drug delivery systems

Kitaoka

Wakabayashi

Kamiya

et al. 2016

Biotechnology Journal

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Transdermal administration of drugs has advantages over conventional oral administration or administration using injection equipment. The route of administration reduces the opportunity for drug evacuation before systemic circulation, and enables long‐lasting drug administration at a modest body concentration. In addition, the skin is an attractive route for vaccination, because there are many immune cells in the skin. Recently, solid‐in‐oil nanodisperison (S/O) technique has demonstrated to deliver cosmetic and pharmaceutical bioactives efficiently through the skin. S/O nanodispersions are nanosized drug carriers designed to overcome the skin barrier. This review discusses the rationale for preparation of efficient and stable S/O nanodispersions, as well as application examples in cosmetic and pharmaceutical materials including vaccines. Drug administration using a patch is user‐friendly, and may improve patient compliance. The technique is a potent transcutaneous immunization method without needles.

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Immune Recognition of Pathogen-Derived Glycolipids Through Mincle

Miyake

Yamasaki

2020

Advances in Experimental Medicine and Biology

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Influence of trehalose 6,6′-diester (TDX) chain length on the physicochemical and immunopotentiating properties of DDA/TDX liposomes

Cited by 15 publications

References 40 publications

Trehalose diester glycolipids are superior to the monoesters in binding to Mincle, activation of macrophages in vitro and adjuvant activity in vivo

Trehalose diester glycolipids are superior to the monoesters in binding to Mincle, activation of macrophages in vitro and adjuvant activity in vivo

Solid‐in‐oil nanodispersions for transdermal drug delivery systems

Immune Recognition of Pathogen-Derived Glycolipids Through Mincle

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