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. 2007 Aug 2;70(1):32-37.
doi: 10.1016/j.carbpol.2007.02.027.

Glycosylated polyacrylate nanoparticles by emulsion polymerization

Sampath C Abeylath  1 , Edward Turos
Affiliations

Glycosylated polyacrylate nanoparticles by emulsion polymerization

Sampath C Abeylath et al. Carbohydr Polym. .

Abstract

A selection of glycosylated polyacrylate nanoparticles has been prepared by radical-initiated emulsion polymerization in aqueous media. Using ethyl acrylate as a co-monomer, carbohydrate acrylates were incorporated into the poly(ethyl acrylate) framework to give stable emulsions of glyconanoparticles with an average particle size of around 40 nm. Using this technique a variety of glyconanoparticles were prepared from 3-O-acryloyl-1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose, 1-O-acryloyl-2,3:5,6-di-O-isopropylidene-alpha-D-mannofuranose, 6-O-acryloyl-1,2:3,4-di-O-isopropylidene-alpha-D-galactopyranose, 2-N-acryloyl-1,3,4,6-tetra-O-acetyl-beta-D-glucosamine, 5-O-acryloyl-2,3-isopropylidene-1-methoxy-beta-D-ribofuranose and 4-N-acetyl-5'-O-acryloyl-2',3'-O-isopropylidene cytidine. Scanning electron microscopy, dynamic light scattering and proton NMR analysis of the emulsions indicated essentially 100% incorporation of the carbohydrate acrylate monomer into the polymer with the exception of O-benzyl- and O-benzoyl-protected carbohydrate acrylates, which gave incomplete incorporation. Formation of larger glyconanoparticles of ~80nm with (unprotected) 3-O-acryloyl-D-glucose and 5-O-acryloyl-1-methoxy-beta-D-ribofuranose revealed the influence of free hydroxyl groups in the monomer on the particle size during polymerization, a feature which is also apparently dependent on the amount of carbohydrate in the matrix. This methodology allows for a new, simple route to the synthesis of polymeric glyconanoparticles with potential applications in targeted drug delivery and materials development.

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Figures

Figure 1
Figure 1
Carbohydrate monomers used for the formation of glyconanoparticles: 3-O-acryloyl-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (1), 1-O-acryloyl-2,3:5,6-di-O-isopropylidene-α-D-mannofuranose (2), 6-O-acryloyl-1,2:3,4-di-O-isopropylidene-α-D-galactopyranose (3), N-acryloyl-1,3,4,6-tetra-O-acetyl-β-D-glucosamine (4), and 5-O-acryloyl-1-methoxy-2,3-isopropylidene-β-D-ribofuranose (5).
Figure 2
Figure 2
(a) SEM image and (b) particle size distribution of glyconanoparticles prepared from 3-O-acryloyl-1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (1) and ethyl acrylate by emulsion polymerization.
Figure 3
Figure 3
Typical 1H NMR spectra of (a) 3-O-acryloyl-1,2:5,6-di-O-isopropylidine-α-D-glucofuranose (1) and (b) the glycopolymer obtained from the emulsion after the film formation.
Figure 4
Figure 4
1-O-Acryloyl-2,3,5-tri-O-benzyl-β-D-ribofuranose (6) and 2-N-acryloyl-1,3,4,6-tetra-O-benzoyl-β-D-glucosamine (7).
Figure 5
Figure 5
3-O-Acryloyl-D-glucose (8) and 5-O-acryloyl-1-methoxy-β-D-ribofuranose (9)
Figure 6
Figure 6
Comparison of the effects of using an O-protected versus O-unprotected monosaccharide acrylate on nanoparticle size. (a) Photographs of four different emulsion samples prepared with 20% (by weight) polymer content from 5-O-acryloyl-2,3-O-isopropylidene-1-methoxy-β-D-ribofuranose (5) and 5-O-acryloyl-1-methoxy-β-D-ribofuranose (9) as co-monomers with ethyl acrylate. E1: monomer 5 and ethyl acrylate (1:9 by weight). E2: monomer 9 and ethyl acrylate (1:19 by weight). E3: monomer 9 and ethyl acrylate (1:14 by weight). E4: monomer 9 and ethyl acrylate (1:9 by weight); (b) Average particle sizes of these formulations from DLS analysis.
Figure 7
Figure 7
4-N-Acetyl-5’-O-acryloyl-2’,3’-O-isopropyl-idenecytidine (10)
Scheme 1
Scheme 1
Synthesis of glyconanoparticles by emulsion polymerization
See this image and copyright information in PMC

References

    1. Barker R, Fletcher HG. 2,3,5-Tri-O-benzyl-D-ribosyl and -L-arabinosyl bromides. J Org Chem. 1961;26:4605–4609.
    1. Cho CS, Jeong YI, Ishihara T, Takei R, Park JU, Park KH, Maruyama A, Akaike T. Simple preparation of nanoparticles coated with carbohydrate-carrying polymers. Biomaterials. 1997;18:323–326. - PubMed
    1. Cho CS, Kobayashi A, Takei R, Ishihara T, Maruyama A, Akaike T. Receptor-mediated cell modulator delivery to hepatocyte using nanoparticles coated with carbohydrate-carrying polymers. Biomaterials. 2001;22:45–51. - PubMed
    1. Cooper MJ, Goody RS, Jones AS, Tittensor JR, Walker RT. Synthetic analogues of polynucleotides. Part VII. Further syntheses of 5’-O-acryloylnucleosides and copolymers of these with other acryloyl compounds. J Chem Soc C. 1971;19:3183–3187.
    1. Garcia-Martin MG, Jimenez-Hidalgo C, Al-Kass SSJ, Caraballo I, de Paz MV, Galbis JA. Synthesis and characterization of some new homo- and co-poly(vinylsaccharides). Some preliminary studies as drug delivery. Polymer. 2000;41:821–826.

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