Synthesis of Glycopolymer Micelles for Antibiotic Delivery
In this work, we designed biodegradable glycopolymers consisting of a carbohydrate conjugated to a biodegradable polymer, poly(lactic acid) (PLA), through a poly(ethylene glycol) (PEG) linker. The glycopolymers were synthesized by coupling alkyne end-functionalized PEG-PLA with azide-derivatized man...
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| Format: | Article |
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MDPI AG
2023-05-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/28/10/4031 |
| _version_ | 1827740521852829696 |
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| author | Xuan Chen Bin Wu Harini A. Perera Mingdi Yan |
| author_facet | Xuan Chen Bin Wu Harini A. Perera Mingdi Yan |
| author_sort | Xuan Chen |
| collection | DOAJ |
| description | In this work, we designed biodegradable glycopolymers consisting of a carbohydrate conjugated to a biodegradable polymer, poly(lactic acid) (PLA), through a poly(ethylene glycol) (PEG) linker. The glycopolymers were synthesized by coupling alkyne end-functionalized PEG-PLA with azide-derivatized mannose, trehalose, or maltoheptaose via the click reaction. The coupling yield was in the range of 40–50% and was independent of the size of the carbohydrate. The resulting glycopolymers were able to form micelles with the hydrophobic PLA in the core and the carbohydrates on the surface, as confirmed by binding with the lectin Concanavalin A. The glycomicelles were ~30 nm in diameter with low size dispersity. The glycomicelles were able to encapsulate both non-polar (rifampicin) and polar (ciprofloxacin) antibiotics. Rifampicin-encapsulated micelles were much smaller (27–32 nm) compared to the ciprofloxacin-encapsulated micelles (~417 nm). Moreover, more rifampicin was loaded into the glycomicelles (66–80 μg/mg, 7–8%) than ciprofloxacin (1.2–2.5 μg/mg, 0.1–0.2%). Despite the low loading, the antibiotic-encapsulated glycomicelles were at least as active or 2–4 times more active than the free antibiotics. For glycopolymers without the PEG linker, the antibiotics encapsulated in micelles were 2–6 times worse than the free antibiotics. |
| first_indexed | 2024-03-11T03:27:01Z |
| format | Article |
| id | doaj.art-03e7d312653541e2b9bfb8e151864864 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-11T03:27:01Z |
| publishDate | 2023-05-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-03e7d312653541e2b9bfb8e1518648642023-11-18T02:38:23ZengMDPI AGMolecules1420-30492023-05-012810403110.3390/molecules28104031Synthesis of Glycopolymer Micelles for Antibiotic DeliveryXuan Chen0Bin Wu1Harini A. Perera2Mingdi Yan3Department of Chemistry, University of Massachusetts Lowell, Lowell, MA 01854, USADepartment of Chemistry, University of Massachusetts Lowell, Lowell, MA 01854, USADepartment of Chemistry, University of Massachusetts Lowell, Lowell, MA 01854, USADepartment of Chemistry, University of Massachusetts Lowell, Lowell, MA 01854, USAIn this work, we designed biodegradable glycopolymers consisting of a carbohydrate conjugated to a biodegradable polymer, poly(lactic acid) (PLA), through a poly(ethylene glycol) (PEG) linker. The glycopolymers were synthesized by coupling alkyne end-functionalized PEG-PLA with azide-derivatized mannose, trehalose, or maltoheptaose via the click reaction. The coupling yield was in the range of 40–50% and was independent of the size of the carbohydrate. The resulting glycopolymers were able to form micelles with the hydrophobic PLA in the core and the carbohydrates on the surface, as confirmed by binding with the lectin Concanavalin A. The glycomicelles were ~30 nm in diameter with low size dispersity. The glycomicelles were able to encapsulate both non-polar (rifampicin) and polar (ciprofloxacin) antibiotics. Rifampicin-encapsulated micelles were much smaller (27–32 nm) compared to the ciprofloxacin-encapsulated micelles (~417 nm). Moreover, more rifampicin was loaded into the glycomicelles (66–80 μg/mg, 7–8%) than ciprofloxacin (1.2–2.5 μg/mg, 0.1–0.2%). Despite the low loading, the antibiotic-encapsulated glycomicelles were at least as active or 2–4 times more active than the free antibiotics. For glycopolymers without the PEG linker, the antibiotics encapsulated in micelles were 2–6 times worse than the free antibiotics.https://www.mdpi.com/1420-3049/28/10/4031glycopolymerpoly(lactic acid)carbohydratedrug deliveryantibiotics |
| spellingShingle | Xuan Chen Bin Wu Harini A. Perera Mingdi Yan Synthesis of Glycopolymer Micelles for Antibiotic Delivery Molecules glycopolymer poly(lactic acid) carbohydrate drug delivery antibiotics |
| title | Synthesis of Glycopolymer Micelles for Antibiotic Delivery |
| title_full | Synthesis of Glycopolymer Micelles for Antibiotic Delivery |
| title_fullStr | Synthesis of Glycopolymer Micelles for Antibiotic Delivery |
| title_full_unstemmed | Synthesis of Glycopolymer Micelles for Antibiotic Delivery |
| title_short | Synthesis of Glycopolymer Micelles for Antibiotic Delivery |
| title_sort | synthesis of glycopolymer micelles for antibiotic delivery |
| topic | glycopolymer poly(lactic acid) carbohydrate drug delivery antibiotics |
| url | https://www.mdpi.com/1420-3049/28/10/4031 |
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