Reactive Nanoparticles Derived from Polysaccharide Phenyl Carbonates.

Martin Gericke,Joachim H Clement,Cornelia Jörke,Katja Geitel,Thomas Heinze

doi:10.3390/molecules26134026

Martin Gericke, Joachim H Clement + Show 3 more

Open Access

https://doi.org/10.3390/molecules26134026

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Abstract

Polysaccharide (PS) based nanoparticles (NP) are of great interest for biomedical applications. A key challenge in this regard is the functionalization of these nanomaterials. The aim of the present work was the development of reactive PS-NP that can be coupled with an amino group containing compounds under mild aqueous conditions. A series of cellulose phenyl carbonates (CPC) and xylan phenyl carbonates (XPC) with variable degrees of substitution (DS) was obtained by homogeneous synthesis. The preparation of PS-NP by self-assembling of these hydrophobic derivatives was studied comprehensively. While CPC mostly formed macroscopic aggregates, XPC formed well-defined spherical NP with diameters around 100 to 200 nm that showed a pronounced long-term stability in water against both particle aggregation as well as cleavage of phenyl carbonate moieties. Using an amino group functionalized dye it was demonstrated that the novel XPC-NP are reactive towards amines. A simple coupling procedure was established that enables direct functionalization of the reactive NP in an aqueous dispersion. Finally, it was demonstrated that dye functionalized XPC-NP are non-cytotoxic and can be employed in advanced biomedical applications.

Highlights

Nanomaterials possess unique properties that are different compared to the individual molecule or the bulk compound due to their nm-scaled size [1,2]
The goal of this work was to comprehensively study the nano self-assembling of hydrophobic PS phenyl carbonate derivatives and to verify or disprove three hypothesis: (i) cellulose phenyl carbonates (CPC) and xylan phenyl carbonates (XPC) are suitable for the preparation of PS-NP, (ii) the PS-NP obtained possess reactive phenyl carbonate groups on the surface that can be converted with amines under aqueous conditions, and (iii) the reactive PS-NP are suitable for biomedical applications
Homogeneous synthesis procedures were employed in order to tune the degrees of substitution (DS) over a broad range [18,19,20]

Summary

Introduction

Nanomaterials possess unique properties that are different compared to the individual molecule or the bulk compound due to their nm-scaled size [1,2]. Nanoparticles (NP) derived from organic polymers are highly versatile because their surface chemistry as well as their overall physical and biological properties can be tuned to a vast degree by taking advantage of the possibilities provided by modern organic chemistry. They are studied intensively for therapeutic drug delivery purposes [5,6]. In the context of these biomedical applications, nanomaterials derived from biopolymers such as polysaccharides (PS) possess inherent advantages because of their native biocompatibility and biodegradability [9,10]

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