Synthesis and self-assembly of amphiphilic precision glycomacromolecules

Banger, Alexander; Sindram, Julian; Otten, Marius; Kania, Jessica; Wilms, Dimitri; Strzelczyk, Alexander K.; Miletic, Sean; Marlovits, Thomas C.; Karg, Matthias; Hartmann, Laura

doi:10.1039/d1py00422k

Cited by 4 publications

(5 citation statements)

References 57 publications

(56 reference statements)

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“…As building blocks, previously established TDS (triple‐bond diethylenetriamine coupled with succinic acid), [ 9 ] ADS (azide diethylenetriamine coupled succinic acid), HDM (hexamethylenediamine coupled with maleic acid) along with azido‐functionalized acetylated α ‐D‐Man, β ‐Gal, CATE (carboxylated aromatic thioether luminophore) and the commercially available functional TPE luminophores were used. [ 37–43 ]…”

Section: Resultsmentioning

confidence: 99%

“…As building blocks, previously established TDS (triple-bond diethylenetriamine coupled with succinic acid), [9] ADS (azide diethylenetriamine coupled succinic acid), HDM (hexamethylenediamine coupled with maleic acid) along with azido-functionalized acetylated 𝛼-D-Man, 𝛽-Gal, CATE (carboxylated aromatic thioether luminophore) and the commercially available functional TPE luminophores were used. [37][38][39][40][41][42][43] In short, the synthesis started from an amine-functionalized preloaded glycine resin and employed the stepwise addition of building blocks, which carry a free carboxylic acid group for attachment onto the resin and a protected amine group. Coupling was promoted by using the activation reagent benzotriazol-1-yloxytripyrrolidinophosphonium hexafluorophosphate to form the active ester derivative.…”

Section: Synthesis Of Aie-apgsmentioning

confidence: 99%

“…Therefore, a concentration series in water was prepared and the fluorescence intensity was measured based on the dye's emissive characteristics (for detailed information see Supporting a) According to literature, CMC was determined via Nile red. [37] Information). The fluorescence intensity values were then plotted against the logarithmic concentration of the respective APG.…”

Section: Self-assembly and Aie Behavior Of Apgsmentioning

confidence: 99%

“…By employing stepwise assembly of tailor‐made building blocks on solid support, a series of amphiphilic glyco‐functionalized oligo(amidoamines) was accessible and demonstrated to spontaneously form micellar assemblies in water. [ 37 ] Within these assemblies, the carbohydrate‐containing head groups are able to mediate interaction with lectins, as shown for model lectin ConA as well as E. Coli bacteria. Here we now introduce AIE luminophores into the hydrophobic part of the APGs during solid phase assembly.…”

Section: Introductionmentioning

confidence: 99%

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Detection of Lectin Clustering in Self‐Assembled, Glycan‐Functionalized Amphiphiles by Aggregation‐Induced Emission Luminophores

Banger

Pasch

Blawitzki

et al. 2022

Macro Chemistry & Physics

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Amphiphilic glycan-functionalized oligomers are derived by solid-phase polymer synthesis and applied in both, self-assembled micelles as well as giant unilamellar vesicles, as simplified models of the cell's glycocalyx. Additionally, an aggregation-induced luminophore is introduced into the amphiphilic glycomacromolecules showing no fluorescence when the molecule is free in solution. Combining glycomacromolecules carrying a binding glycan motif and the luminophore with glycomacromolecules or other amphiphiles with no binding motifs and no luminophore in self-assembled structures, micelles and vesicles exhibiting no or only very little fluorescence are obtained. Only upon clustering of the binding glycan motifs through interaction with a multivalent lectin receptor, an increase in fluorescence is observed. Thus, clustering events within these self-assembled structures can be detected and localized.

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Section: Resultsmentioning

confidence: 99%

Section: Synthesis Of Aie-apgsmentioning

confidence: 99%

Section: Self-assembly and Aie Behavior Of Apgsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Detection of Lectin Clustering in Self‐Assembled, Glycan‐Functionalized Amphiphiles by Aggregation‐Induced Emission Luminophores

Banger

Pasch

Blawitzki

et al. 2022

Macro Chemistry & Physics

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“…In a study from our own lab, Banger et al 134 demonstrated that fixing spherical architectures of glycomacromolecules by cross-linking can benefit the binding of bacteria. Using solid-phase polymer synthesis with tailor-made building blocks, a small library of monodisperse amphiphilic glycomacromolecules (APGs) was generated.…”

Section: Introductionmentioning

confidence: 99%

Glycopolymers against pathogen infection

et al. 2023

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Synthesis of Dual‐Responsive Amphiphilic Glycomacromolecules: Controlled Release of Glycan Ligands via pH and UV Stimuli

Jäck,

Hemming,

Hartmann

2024

Macromol. Rapid Commun.

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This work presents a versatile strategy for the synthesis of dual stimuli‐responsive amphiphilic glycomacromolecules with tailored release properties. Amphiphilic precision glycomacromolecules (APGs) derived from tailor‐made building blocks using solid phase polymer synthesis form glycofunctionalized micelles, a versatile class of materials with applications in drug delivery, as antiinfection agents as well as simple cell mimetics. In this work, this concept is extended by integrating cleavable building blocks into APGs now allowing stimuli‐responsive release of glycan ligands or destruction of the micelles. This study incorporates a newly designed acid‐labile building block, 4‐(4‐(((((9H‐fluoren‐9‐yl)methoxy)carbonyl)amino)methyl)‐1,3‐dioxolan‐2‐yl)benzoic acid (DBA), suitable also for other types of solid phase or amide chemistry, and an established UV‐cleavable 2‐nitrobenzyl linker (PL). The results demonstrate that both linkers can be cleaved independently and thus allow dual stimuli‐responsive release from the APG micelles. By choosing the APG design e.g., placing the cleavable linkers between glycomacromolecular blocks presenting different types of carbohydrates, they can tune APG and micellar stability as well as the interaction and cluster formation with a carbohydrate‐recognizing lectin. Such dual‐responsive glycofunctionalized micelles have wide potential for use in drug delivery applications or for the development as anti‐adhesion agents in antiviral and antibacterial treatments.

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Synthesis and self-assembly of amphiphilic precision glycomacromolecules

Abstract: We present the synthesis of so called amphiphilic glycomacromolecules (APGs) by using solid-phase polymer synthesis. Based on tailor made building blocks, monosdisperse APGs with varying compositions are synthesized, introducing carbohydrate...

Cited by 4 publications

References 57 publications

Detection of Lectin Clustering in Self‐Assembled, Glycan‐Functionalized Amphiphiles by Aggregation‐Induced Emission Luminophores

Detection of Lectin Clustering in Self‐Assembled, Glycan‐Functionalized Amphiphiles by Aggregation‐Induced Emission Luminophores

Glycopolymers against pathogen infection

Synthesis of Dual‐Responsive Amphiphilic Glycomacromolecules: Controlled Release of Glycan Ligands via pH and UV Stimuli

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