Reactive Nanoparticles Derived from Polysaccharide Phenyl Carbonates
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 compoun...
| Main Authors: | , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2021-07-01
|
| Series: | Molecules |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1420-3049/26/13/4026 |
| _version_ | 1797527960811470848 |
|---|---|
| author | Martin Gericke Katja Geitel Cornelia Jörke Joachim H. Clement Thomas Heinze |
| author_facet | Martin Gericke Katja Geitel Cornelia Jörke Joachim H. Clement Thomas Heinze |
| author_sort | Martin Gericke |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-03-10T09:51:17Z |
| format | Article |
| id | doaj.art-e3c4be8e6e894d889cea616e3a67d91a |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T09:51:17Z |
| publishDate | 2021-07-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-e3c4be8e6e894d889cea616e3a67d91a2023-11-22T02:46:48ZengMDPI AGMolecules1420-30492021-07-012613402610.3390/molecules26134026Reactive Nanoparticles Derived from Polysaccharide Phenyl CarbonatesMartin Gericke0Katja Geitel1Cornelia Jörke2Joachim H. Clement3Thomas Heinze4Institute of Organic Chemistry and Macromolecular Chemistry, Friedrich-Schiller-University of Jena, Humboldtstr 10, 07743 Jena, GermanyDepartment of Hematology and Medical Oncology, Jena University Hospital, Am Klinikum 1, 07747 Jena, GermanyDepartment of Hematology and Medical Oncology, Jena University Hospital, Am Klinikum 1, 07747 Jena, GermanyDepartment of Hematology and Medical Oncology, Jena University Hospital, Am Klinikum 1, 07747 Jena, GermanyInstitute of Organic Chemistry and Macromolecular Chemistry, Friedrich-Schiller-University of Jena, Humboldtstr 10, 07743 Jena, GermanyPolysaccharide (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.https://www.mdpi.com/1420-3049/26/13/4026polysaccharide derivativeshomogeneous synthesisnanoparticlesxylan derivativesbiocompatibilitydye functionalization |
| spellingShingle | Martin Gericke Katja Geitel Cornelia Jörke Joachim H. Clement Thomas Heinze Reactive Nanoparticles Derived from Polysaccharide Phenyl Carbonates Molecules polysaccharide derivatives homogeneous synthesis nanoparticles xylan derivatives biocompatibility dye functionalization |
| title | Reactive Nanoparticles Derived from Polysaccharide Phenyl Carbonates |
| title_full | Reactive Nanoparticles Derived from Polysaccharide Phenyl Carbonates |
| title_fullStr | Reactive Nanoparticles Derived from Polysaccharide Phenyl Carbonates |
| title_full_unstemmed | Reactive Nanoparticles Derived from Polysaccharide Phenyl Carbonates |
| title_short | Reactive Nanoparticles Derived from Polysaccharide Phenyl Carbonates |
| title_sort | reactive nanoparticles derived from polysaccharide phenyl carbonates |
| topic | polysaccharide derivatives homogeneous synthesis nanoparticles xylan derivatives biocompatibility dye functionalization |
| url | https://www.mdpi.com/1420-3049/26/13/4026 |
| work_keys_str_mv | AT martingericke reactivenanoparticlesderivedfrompolysaccharidephenylcarbonates AT katjageitel reactivenanoparticlesderivedfrompolysaccharidephenylcarbonates AT corneliajorke reactivenanoparticlesderivedfrompolysaccharidephenylcarbonates AT joachimhclement reactivenanoparticlesderivedfrompolysaccharidephenylcarbonates AT thomasheinze reactivenanoparticlesderivedfrompolysaccharidephenylcarbonates |