Expedient synthesis of functional single-component glycoliposomes using thiol–yne chemistry

Goyard, David; Shiao, Tze Chieh; Fraleigh, Nya L.; Vu, Hai-Yen; Lee, H.; Díaz‐Mitoma, Francisco; Le, Hoang-Thanh; Roy, René

doi:10.1039/c6tb00344c

Cited by 17 publications

(28 citation statements)

References 40 publications

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“…We prepared n -alkyl 1-thio-β--glycosides from unprotected sugar anomeric thiols, commercial n -alkenes and one synthetic lipophilic scaffold presenting two reactive alkenyl ends. Although thiyl-radical-mediated reactions have been extensively investigated for the preparation of carbohydrate derivatives [20] and some dithioether phospholipid and glycolipid analogues [21–22], no examples were reported for the synthesis of n -alkyl thioglycosides by using thiol–ene coupling [18–19]. In addition to its high efficiency and selectivity, the TEC reaction does not require any metal, a key feature for the preparation of potential vaccines.…”

Section: Introductionmentioning

confidence: 99%

Towards the preparation of synthetic outer membrane vesicle models with micromolar affinity to wheat germ agglutinin using a dialkyl thioglycoside

Fayolle¹,

Berthet²,

Doumèche³

et al. 2019

Beilstein J. Org. Chem.

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A series of alkyl thioglycosides and alkyl thiodiglycosides bearing glucose and N-acetylglucosamine residues were prepared by thiol–ene coupling in moderate to good yields (40–85%). Their binding ability towards wheat germ agglutinin was measured by competitive enzyme-linked lectin assays. One of the synthetic compounds presenting two GlcNAc units showed the highest inhibitory effect of this study with an IC50 of 11 µM corresponding to a 3182-fold improvement compared to GlcNAc. These synthetic molecules were used to produce giant vesicles, alone or in mixture with phospholipids, mimicking bacterial outer membrane vesicles (OMV) with potential antiadhesive properties.

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Section: Introductionmentioning

confidence: 99%

Towards the preparation of synthetic outer membrane vesicle models with micromolar affinity to wheat germ agglutinin using a dialkyl thioglycoside

Fayolle¹,

Berthet²,

Doumèche³

et al. 2019

Beilstein J. Org. Chem.

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“…The preparation of ML-C 14 followed the previously published methods [ 42 ], and the compound was kept stored at -20 °C as a lyophilized powder. Purity was determined to be ≥ 95% as indicated by thin-layer chromatography and nuclear magnetic resonance spectroscopic analyses.…”

Section: Methodsmentioning

confidence: 99%

“…As part of our efforts towards the development of particle-based delivery systems, we have previously investigated a library of novel ambiphilic neoglycolipids that form monodisperse liposomes through self-assembly when added to water [ 42 ]. From this library, a C 14 -alkyl-mannopyranoside (ML-C 14 , Fig 1 ) emerged as a promising candidate in the development of sugar-based nanoparticles.…”

Section: Introductionmentioning

confidence: 99%

Strengthening peptide-based drug activity with novel glyconanoparticle

et al. 2018

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The therapeutic application of peptide-based drugs is significantly limited by the rapid proteolytic degradation that occurs when in blood. Encapsulation of these peptide structures within a delivery system, such as liposomes, can greatly improve both stability and target delivery. As part of our work focused on novel ambiphilic mannosylated neoglycolipids as targeted drug delivery systems, we have developed a C14-alkyl-mannopyranoside that forms self-assembled monodisperse liposomes. Herein, these glycoliposomes are investigated as a potential method to improve the plasma stability of peptide-based drugs. Reversed phase high-performance liquid chromatography (RP-HPLC) and mass spectrometry (MS) methods were developed to assess the in vitro plasma stability of two structurally diverse peptides, including the kappa opioid receptor selective antagonist dynantin, and the NOD2 innate immune receptor ligand muramyl dipeptide (MDP). The RP-HPLC methods developed were able to resolve the peptides from background plasma contaminants and provided suitable response levels and linearity over an appropriate concentration range. Both compounds were found to be significantly degraded in rat plasma. Increasing degrees of both entrapment and stabilization were noted when dynantin was combined with the C14-alkyl-mannopyranoside in increasing peptide:glycoside ratios. The combination of MDP with the glycolipid also led to peptide entrapment, which greatly improved the plasma stability of the peptide. Overall, the results clearly indicate that the stability of peptide-based structures, which are subject to degradation in plasma, can be greatly improved via entrapment within C14-alkyl-mannopyranoside-bearing glycoliposomes.

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“…To efficiently link a sugar derivative to a lipidic tail, thiol-yne/ene click-chemistry already quoted in Section 3.3 ) can be considered as a complementary tool to the Hüisgen (CuAAC) reaction [ 72 ]. In a recent publication, Goyard et al [ 24 ] reacted 1-propargyl-2,3,4,6-tetra- O -acetyl-β- d -glucopyranoside 49 with dodecane-, tetradecane- and hexadecanethiols in the presence of AIBN to give the expected GL derivatives (as 1:1 diastereoisomer mixtures) in very high yields ( Scheme 9 ).…”

Section: Vesicles Liposomesmentioning

confidence: 99%

Recent Advances in the Chemistry of Glycoconjugate Amphiphiles

2018

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Glyconanoparticles essentially result from the (covalent or noncovalent) association of nanometer-scale objects with carbohydrates. Such glyconanoparticles can take many different forms and this mini review will focus only on soft materials (colloids, liposomes, gels etc.) with a special emphasis on glycolipid-derived nanomaterials and the chemistry involved for their synthesis. Also this contribution presents Low Molecular Weight Gels (LMWGs) stabilized by glycoconjugate amphiphiles. Such soft materials are likely to be of interest for different biomedical applications.

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Expedient synthesis of functional single-component glycoliposomes using thiol–yne chemistry

Abstract: The preparation of a set of eight unprecedented amphiphilic neoglycolipids forming liposome nanoparticles is reported.

Cited by 17 publications

References 40 publications

Towards the preparation of synthetic outer membrane vesicle models with micromolar affinity to wheat germ agglutinin using a dialkyl thioglycoside

Towards the preparation of synthetic outer membrane vesicle models with micromolar affinity to wheat germ agglutinin using a dialkyl thioglycoside

Strengthening peptide-based drug activity with novel glyconanoparticle

Recent Advances in the Chemistry of Glycoconjugate Amphiphiles

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