Biological surface modification by ‘thiol-ene’ addition of polymers synthesised by catalytic chain transfer polymerisation (CCTP)

Slavin, Stacy; Khoshdel, Ezat; Haddleton, David M.

doi:10.1039/c2py20040f

Cited by 25 publications

(26 citation statements)

References 30 publications

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“…In these applications, precise control over the polymerization properties is imperative since delicate changes can result in repulsion layers or affinity layers [16]. The application of ATRP in aqueous systems tremendously increased the importance of it for functionalization of biocompatible systems [17][18][19] or bio-surfaces [20] but also for biomedical applications [21,22]. It allowed for the modification of proteins in order to tailor new hybrid materials [23][24][25].…”

Section: Introductionmentioning

confidence: 99%

Surface Initiated Polymerizations via e-ATRP in Pure Water

Hosseiny

Rijn

2013

Polymers

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Abstract:Here we describe the combined process of surface modification with electrochemical atom transfer radical polymerization (e-ATRP) initiated from the surface of a modified gold-electrode in a pure aqueous solution without any additional supporting electrolyte. This approach allows for a very controlled growth of the polymer chains leading towards a steady increase in film thickness. Electrochemical quartz crystal microbalance displayed a highly regular increase in surface confined mass only after the addition of the pre-copper catalyst which is reduced in situ and transformed into the catalyst. Even after isolation and washing of the modified electrode surface, reinitiation was achieved with retention of the controlled electrochemical ATRP reaction. This reinitiation after isolation proves the livingness of the polymerization. This approach has interesting potential for smart thin film materials and offers also the possibility of post-modification via additional electrochemical induced reactions.

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Section: Introductionmentioning

confidence: 99%

Surface Initiated Polymerizations via e-ATRP in Pure Water

Hosseiny

Rijn

2013

Polymers

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“…That M-␤-CD is a good choice for biological functionalization is because a number of biomaterials contain proteins with cysteine residues (thiol source), thus fitting well with our platform. We also demonstrated that thiol moieties could be generated by reducing cystine disulfide bridges in biomaterial (mucin protein) with either the well-known tris (2-carboxyethyl) phosphine (TCEP) or the non-toxic vitamin C. The use of acrylate containing polymer to attach to keratin via thiol-ene click reaction has also been demonstrated previously (Slavin, Khoshdel, & Haddleton, 2012). Here, as proof of concept examples, three biomaterials (hair strands, soluble keratin and mucin surface) were grafted with the synthesized M-␤-CD, and their drug retention ability was demonstrated using curcumin and 1-anilinonapthalene-8-sulfonic acid (1,8-ANS) as model payload compounds.…”

Section: Introductionmentioning

confidence: 67%

Sustaining guest molecules on bio-surfaces by grafting the surfaces with cyclodextrins

Kongprathet

Wanichwecharungruang

2015

Carbohydrate Polymers

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“…The thiolated FITC was incubated with alkene decorated fibers and UV irradiated to undergo the thiol-ene reaction (Figure S3). 29 This reaction resulted in approximately one half of the surface coverage relative to the alkyne and ketone modified fibers, however, with the same trend of increasing surface coverage with increased irradiation time. This discrepancy is likely a result of steric hindrance, as the PEGylated fluorescein is ~1.5 kDa, occluding accessibility to modification in accordance with the small molecule dyes.…”

Section: Resultsmentioning

confidence: 94%

Multifunctional and spatially controlled bioconjugation to melt coextruded nanofibers

et al. 2015

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Polymeric fibers have drawn recent interest for uses in biomedical technologies that span drug delivery, regenerative medicine, and wound-healing patches, amongst others. We have recently reported a new class of fibrous biomaterials fabricated using coextrusion and a photochemical modification procedure to introduce functional groups onto the fibers. In this report, we extend our methodology to control surface modification density, describe methods to synthesize multifunctional fibers, and provide methods to spatially control functional group modification. Several different functional fibers are reported for bioconjugation, including propargyl, alkene, alkoxyamine, and ketone modified fibers. The modification scheme allows for control over surface density and provides a handle for downstream functionalization with appropriate bioconjugation chemistries. Through the use of multiple orthogonal chemistries, fiber chemistry could be differentially controlled to append multiple modifications. Spatial control on the fiber surface was also realized, leading to reverse gradients of small molecule dyes. One application is demonstrated for pH-responsive drug delivery of an anti-cancer therapeutics. Finally, the introduction of orthogonal chemical modifications onto these fibers allowed for modification with multiple cell-responsive peptides providing a substrate for osteoblast differentiation.

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Biological surface modification by ‘thiol-ene’ addition of polymers synthesised by catalytic chain transfer polymerisation (CCTP)

Cited by 25 publications

References 30 publications

Surface Initiated Polymerizations via e-ATRP in Pure Water

Surface Initiated Polymerizations via e-ATRP in Pure Water

Sustaining guest molecules on bio-surfaces by grafting the surfaces with cyclodextrins

Multifunctional and spatially controlled bioconjugation to melt coextruded nanofibers

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