Lectin recognizable biomaterials synthesized via nitroxide-mediated polymerization of a methacryloyl galactose monomer

Ting, SRS; Min, EH; Escalé, P; Save, M; Billon, L; Stenzel, MH

Lectin recognizable biomaterials synthesized via nitroxide-mediated polymerization of a methacryloyl galactose monomer

Ting, SRS

Min, EH Escalé, P Save, M Billon, L Stenzel, MH

Permalink

Publication Type:: Journal Article
Citation:: Macromolecules, 2009, 42 (24), pp. 9422 - 9434
Issue Date:: 2009-12-22

Closed Access

	Filename	Description	Size
	2011001735OK.pdf	Published Version	2.6 MB	Adobe PDF	View/Open

Copyright Clearance Process

Recently Added
In Progress
Closed Access

This item is closed access and not available.

Full metadata record

Field	Value	Language
dc.contributor.author	Ting, SRS https://orcid.org/0000-0002-7787-7906	en_US
dc.contributor.author	Min, EH	en_US
dc.contributor.author	Escalé, P	en_US
dc.contributor.author	Save, M	en_US
dc.contributor.author	Billon, L	en_US
dc.contributor.author	Stenzel, MH	en_US
dc.date.issued	2009-12-22	en_US
dc.identifier.citation	Macromolecules, 2009, 42 (24), pp. 9422 - 9434	en_US
dc.identifier.issn	0024-9297	en_US
dc.identifier.uri	http://hdl.handle.net/10453/31344
dc.description.abstract	The preparation of poly(2-(2',3',4',6'-tetra-O-acetyl-β-D- galactosyloxy)ethyl methacrylateco-styrene) (P(AcGalEMA-co-S)) glycopolymer was performed via nitroxide-mediated polymerization using a methacrylic acid-based alkoxyamine with N-tert-butyl-N-(1-diethylphosphono-2,2-dimethylpropyl) (SGl) nitroxide as mediating agent. In the presence of a low proportion of styrene, the polymerization of the glycomonomer was conducted in a controlled fashion at 85 °C. The synthesis of the diblock copolymers was investigated via two routes by using either P(AcGalEMA-co-S) or polystyrene macroinitiators capped with SG1 nitroxide to yield P(AcGalEMA-co-S)-b-PS and PS-b-P(AcGalEMA-co-S), respectively. The AcGalEMA moieties on the diblock copolymer were deacetylated to afford carbohydrate-based amphiphilic diblock copolymer, polystyrene-block- poly(2-(β-D-galactosyloxy)ethyl methacrylate-co-styrene) (PS-b-P(GalEMAco-S)). The self-assembling properties of PS-è-P(GalEMA-co- S) amphiphilic diblock copolymers were thoroughly exploited to obtain micellar structures and porous films. Lectin binding assays were conducted using the UV-vis spectroscopy and dynamic light scattering to test the biofunctionality of the β-galactose moieties with peanut agglutinin (PNA) on the micelles. The polymer was used to prepare honeycomb structured porous films with bioactivity. Fluorescent PNA was eventually conjugated with the sugar moieties on the porous films. Most protein was conjugated to glycopolymer inside the pore, demonstrating that this procedure can be a simple route to pattern proteins onto surfaces. © 2009 American Chemical Society.	en_US
dc.relation.ispartof	Macromolecules	en_US
dc.relation.isbasedon	10.1021/ma9019015	en_US
dc.subject.classification	Polymers	en_US
dc.title	Lectin recognizable biomaterials synthesized via nitroxide-mediated polymerization of a methacryloyl galactose monomer	en_US
dc.type	Journal Article
utslib.citation.volume	24	en_US
utslib.citation.volume	42	en_US
utslib.for	0903 Biomedical Engineering	en_US
utslib.for	0303 Macromolecular and Materials Chemistry	en_US
utslib.for	03 Chemical Sciences	en_US
utslib.for	09 Engineering	en_US
pubs.embargo.period	Not known	en_US
pubs.organisational-group	/University of Technology Sydney
pubs.organisational-group	/University of Technology Sydney/Faculty of Engineering and Information Technology
pubs.organisational-group	/University of Technology Sydney/Strength - CHT - Health Technologies
utslib.copyright.status	closed_access
pubs.issue	24	en_US
pubs.publication-status	Published	en_US
pubs.volume	42	en_US

Abstract:

The preparation of poly(2-(2',3',4',6'-tetra-O-acetyl-β-D- galactosyloxy)ethyl methacrylateco-styrene) (P(AcGalEMA-co-S)) glycopolymer was performed via nitroxide-mediated polymerization using a methacrylic acid-based alkoxyamine with N-tert-butyl-N-(1-diethylphosphono-2,2-dimethylpropyl) (SGl) nitroxide as mediating agent. In the presence of a low proportion of styrene, the polymerization of the glycomonomer was conducted in a controlled fashion at 85 °C. The synthesis of the diblock copolymers was investigated via two routes by using either P(AcGalEMA-co-S) or polystyrene macroinitiators capped with SG1 nitroxide to yield P(AcGalEMA-co-S)-b-PS and PS-b-P(AcGalEMA-co-S), respectively. The AcGalEMA moieties on the diblock copolymer were deacetylated to afford carbohydrate-based amphiphilic diblock copolymer, polystyrene-block- poly(2-(β-D-galactosyloxy)ethyl methacrylate-co-styrene) (PS-b-P(GalEMAco-S)). The self-assembling properties of PS-è-P(GalEMA-co- S) amphiphilic diblock copolymers were thoroughly exploited to obtain micellar structures and porous films. Lectin binding assays were conducted using the UV-vis spectroscopy and dynamic light scattering to test the biofunctionality of the β-galactose moieties with peanut agglutinin (PNA) on the micelles. The polymer was used to prepare honeycomb structured porous films with bioactivity. Fluorescent PNA was eventually conjugated with the sugar moieties on the porous films. Most protein was conjugated to glycopolymer inside the pore, demonstrating that this procedure can be a simple route to pattern proteins onto surfaces. © 2009 American Chemical Society.

Please use this identifier to cite or link to this item:

http://hdl.handle.net/10453/31344