PEGylation of 6-amino-6-deoxy-curdlan for efficient in vivo siRNA delivery

Altangerel, Altanzul; Cai, Jinguang; Liu, Lixia; Wu, Yinga; Baigude, Huricha; Han, Jingfen

doi:10.1016/j.carbpol.2015.12.077

Cited by 22 publications

(3 citation statements)

References 30 publications

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“…To create a siRNA carrier based on naturally occurring macromolecules with active targeting capacity to primary macrophages, we chemically modified 6-amino-6-deoxy-curdlan, which exhibited a great potential for siRNA delivery to various cell lines in our previous studies. ,,− To chemically functionalize the curdlan derivative, we first conjugated mannose moieties to 6-amino-6-deoxy-curdlan. This was achieved by reacting 6-amino-6-deoxy-curdlan with 4-isothiocyanatophenyl α- d -mannopyranoside, which is an isothiocyanate-activated mannose that readily reacts with primary amines; then, imidazole groups were also attached to the backbone of the curdlan derivative by reacting with 4-imidazoleacetic acid using 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide as a condensing reagent (Scheme ).…”

Section: Resultsmentioning

confidence: 99%

Design of Mannose-Functionalized Curdlan Nanoparticles for Macrophage-Targeted siRNA Delivery

Ganbold

Baigude

2018

ACS Appl. Mater. Interfaces

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6-Amino-6-deoxy-curdlan is a promising nucleic acid carrier that efficiently delivers plasmid DNA as well as short interfering RNA (siRNA) to various cell lines. The highly reactive C6-NH groups of 6-amino-6-deoxy-curdlan prompt conjugation of various side groups including tissue-targeting ligands to enhance cell-type-specific nucleic acid delivery to specific cell lines. Herein, to test the primary-cell-targeting efficiency of the curdlan derivative, we chemically conjugated a macrophage-targeting ligand, mannose, to 6-amino-6-deoxy-curdlan. The resulting curdlan derivative (denoted CMI) readily complexed with siRNA and formed nanoparticles with a diameter of 50-80 nm. The CMI nanoparticles successfully delivered a dye-labeled siRNA to mouse peritoneal macrophages. The delivery efficiency was blocked by mannan, a natural ligand for a macrophage surface mannose receptor (CD206), but not by zymosan, a ligand for the dectin-1 receptor, which is also present on the surface of macrophages. Moreover, CMI nanoparticles were internalized by macrophages only at 37 °C, suggesting that the cellular uptake of CMI nanoparticles was energy-dependent. Furthermore, CMI nanoparticle efficiently delivered siRNA against tumor necrosis factor α (TNFα) to lipopolysaccharide-stimulated primary mouse peritoneal macrophages. In vivo experiments demonstrated that CMI nanoparticles successfully delivered siTNFα to mouse peritoneal macrophages, liver, and lung and induced significant knockdown of the TNFα expression at both messenger RNA and protein levels. Therefore, our design of CMI may be a promising siRNA carrier for targeting CD206-expressing primary cells such as macrophage and dendritic cells.

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Section: Resultsmentioning

confidence: 99%

Design of Mannose-Functionalized Curdlan Nanoparticles for Macrophage-Targeted siRNA Delivery

Ganbold

Baigude

2018

ACS Appl. Mater. Interfaces

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“…Furthermore, the preparation of DNA/β‐1,3‐D‐glucan complex requires the DNA with a poly (dA)‐tail, which significantly increases the production cost and complexity. Han et al and Altangerel et al prepared a water‐soluble aminated β‐1,3‐D‐glucan and a PEGylated aminated β‐1,3‐D‐glucan for in vitro and in vivo siRNA delivery 17,18 . Although these aminated β‐1,3‐D‐glucan are water‐soluble and possess positive charges after amination, the electrostatic interaction between cationic β‐1,3‐D‐glucan and anionic siRNA is not strong, which requires further enhancement for application as an effective DNA delivery system.…”

Section: Introductionmentioning

confidence: 99%

Preparation of a water soluble aminated β‐1,3‐D‐glucan for gene carrier: The in vitro study of the anti‐inflammatory activity and transfection efficiency

Jin

Rong

Zhang

et al. 2021

J Biomedical Materials Res

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β‐1,3‐D‐glucan has been reported to have a series of bioactivities including antitumor, antimicrobial, anti‐inflammatory and antioxidative effects; however, its insolubility in neutral aqueous solution significantly restricts the potential application in biological and medicine fields. Herein, a water‐soluble aminated β‐1,3‐D‐glucan (AG) was synthesized and the anti‐inflammatory effect, cytotoxicity and plasmid DNA (pDNA) binding capacity of AG, serum stability, the particle sizes and zeta potentials of AG/pDNA nanocomposites, and the transfection efficiency and mechanism of action were studied. AG shows no obvious cytotoxicity within the range of working concentration (1–64 μg/ml) and it exerts potent anti‐inflammatory effect independent on Dectin‐1 and TLR2. AG/pDNA nanocomposites prepared by electrostatic interaction possess an appropriate particle size ranged from 192.8 to 118.4 nm and zeta potentials ranged from 20.880 to 27.16 mV with the N/P ratios from 5 to 100. AG/pDNA nanocomposites at the N/P ratios of 10 and 20 were able to show superior transfection efficiencies in RAW 264.7 cells as a result of their suitable particle size, zeta potential, anti‐inflammatory effect, and the specific interaction with pattern recognition receptors (Dectin‐1 and TLR2). These results indicate that AG is a potential candidate for DNA delivery system due to its potent anti‐inflammatory effect and high transfection efficiency.

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“…Chitosan has been extensively explored for the potential application of efficient siRNA delivery [17,18]. We reported in vitro and in vivo siRNA delivery by 6-amino-6-deoxy-curdlan and its derivatives including galactose functionalized hepatocytes targeting curdlan nanoparticles [19,20,21,22,23]. These studies demonstrated that carbohydrate containing polymers have great potential for effective siRNA delivery.…”

Section: Introductionmentioning

confidence: 99%

Sugar Functionalized Synergistic Dendrimers for Biocompatible Delivery of Nucleic Acid Therapeutics

et al. 2018

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Sugars containing cationic polymers are potential carriers for in vitro and in vivo nucleic acid delivery. Monosaccharides such as glucose and galactose have been chemically conjugated to various materials of synergistic poly-lysine dendrimer systems for efficient and biocompatible delivery of short interfering RNA (siRNA). The synergistic dendrimers, which contain lipid conjugated glucose terminalized lysine dendrimers, have significantly lower adverse impact on cells while maintaining efficient cellular entry. Moreover, the synergistic dendrimers complexed to siRNA induced RNA interference (RNAi) in the cells and profoundly knocked down green fluorescence protein (GFP) as well as the endogenously expressing disease related gene Plk1. The new synergic dendrimers may be promising system for biocompatible and efficient siRNA delivery.

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PEGylation of 6-amino-6-deoxy-curdlan for efficient in vivo siRNA delivery

Cited by 22 publications

References 30 publications

Design of Mannose-Functionalized Curdlan Nanoparticles for Macrophage-Targeted siRNA Delivery

Design of Mannose-Functionalized Curdlan Nanoparticles for Macrophage-Targeted siRNA Delivery

Preparation of a water soluble aminated β‐1,3‐D‐glucan for gene carrier: The in vitro study of the anti‐inflammatory activity and transfection efficiency

Sugar Functionalized Synergistic Dendrimers for Biocompatible Delivery of Nucleic Acid Therapeutics

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