Aqueous RAFT polymerization of 2‐aminoethyl methacrylate to produce well‐defined, primary amine functional homo‐ and copolymers

Alidedeoglu, Alp H.; York, Adam W.; McCormick, Charles L.; Morgan, Sarah E.

doi:10.1002/pola.23590

Cited by 71 publications

(57 citation statements)

References 75 publications

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“…A series of amino‐functionalized PMMA based copolymers was synthesized via RAFT polymerization due to its versatility and suitability for the synthesis of well‐defined amino methacrylate copolymers . Three different commercially available amino methacrylates that have tertiary (DMAEMA), secondary ( t BAEMA) and protonated primary amine functionalities (AEMA · HCI) were used as comonomers.…”

Section: Resultsmentioning

confidence: 99%

RAFT made methacrylate copolymers for reversible pH‐responsive nanoparticles

Yildirim

Rinkenauer

Weber

et al. 2015

J. Polym. Sci., Part A: Polym. Chem.

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In this study, we designed and investigated pHresponsive nanoparticles based on different ratios of monomers with primary, secondary or tertiary amino groups. For this purpose, copolymers of methyl methacrylate (MMA) with different compositions of amino methacrylates (2-(dimethylamino)ethyl methacrylate (DMAEMA), 2-(tert-butylamino)ethyl methacrylate (tBAEMA) and 2-aminoethyl methacrylate hydrochloride (AEMAÁHCI)) were synthesized using the reversible addition-fragmentation chain transfer (RAFT) polymerization process. The controlled nature of the radical polymerization was demonstrated by kinetic studies. All copolymers show low dispersities ( -D M < 1.2) with amino contents between 9 and 21 mol %. For the nanoparticle formation, nanoprecipitation with subsequent solvent evaporation was used. All suspensions were characterized by dynamic light scattering (DLS) and scanning electron microscopy (SEM). Different initial conditions of the formulations resulted in differently sized nanoparticles that have monomodal size distributions, relatively narrow polydispersity index (PDI) values and positive zeta potential values. The pH-stability test results demonstrated that, depending on the structure and amount of the amino content, the obtained nanoparticles reveal a reversible pHresponse, such as dissolution at acidic pH values. The ability of the nanoparticles to encapsulate guest molecules was confirmed by pyrene fluorescence studies. The cytotoxicity assay results showed that the nanoparticles did not have any significant cytotoxic effect.

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Section: Resultsmentioning

confidence: 99%

RAFT made methacrylate copolymers for reversible pH‐responsive nanoparticles

Yildirim

Rinkenauer

Weber

et al. 2015

J. Polym. Sci., Part A: Polym. Chem.

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“…38 The monomer to CTA ratio was 400 : 1 while CTA to initiator ratio was 5 : 1. 38 The monomer to CTA ratio was 400 : 1 while CTA to initiator ratio was 5 : 1.…”

Section: Synthesis Of Poly(amino Ethyl Methacrylate) Paemamentioning

confidence: 99%

Quantitative study on the antifreeze protein mimetic ice growth inhibition properties of poly(ampholytes) derived from vinyl-based polymers

et al. 2014

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PAPER Matthew I. Gibson et al.Quantitative study on the antifreeze protein mimetic ice growth inhibition properties of poly(ampholytes) derived from vinyl-based polymers Volume Antifreeze (glyco) proteins (AF(G)Ps) from the blood of polar fish species are extremely potent ice recrystallization inhibitors (IRI), but are difficult to synthesise or extract from natural sources. Despite this challenge, materials which display IRI are appealing due to their ability to enhance cellular cryopreservation, for applications including regenerative and transplantation medicine. Here, poly(ampholytes), which contain a mixture of cationic and anionic side chains are quantitatively evaluated for their IRI activity. Poly-(aminoethyl methacrylate), obtained by RAFT polymerization, is functionalised with succinic anhydride to generate the poly(ampholytes). The charge balance of the side chains is shown to be crucial, with only 50 : 50 mixtures having strong IRI activity, which also scales with molecular weight. This is the first example of a non-hydroxylated synthetic polymer with quantifiable IRI activity and raises questions about the mechanism of IRI, as the polymers have no obvious ice-binding motif. The ampholytic structure is shown to be transferable to carbohydrate-centred polymers with activity retained, but poly(betaines) are shown to be inactive. † Electronic supplementary information (ESI) available: This includes full characterisation and synthetic details. See

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“…8,18,19 The reversible addition-fragmentation chain transfer (RAFT) polymerization technique has been used for preparation of a number of well-dened polymers having only primary and/or tertiary amine groups. [20][21][22][23][24][25][26][27][28][29][30][31] Some of these polymers could be used efficiently to complex nucleic acid therapeutics and displayed to a certain degree endosome escaping ability possibly through the proton-sponge effect. 27,[29][30][31] A few polymers with proton-sponge capacity were also derived from functional polymer precursors such as oxazoline and pentauorophenyl ester polymers synthesized via RAFT polymerization.…”

Section: -16mentioning

confidence: 99%

A new proton sponge polymer synthesized by RAFT polymerization for intracellular delivery of biotherapeutics

et al. 2014

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A spermine-like polymer was synthesized via reversible addition-fragmentation chain transfer polymerization as a potential endosomal escaping agent. A new methacrylate monomer, 2-((tertbutoxycarbonyl)(2-((tert-butoxycarbonyl)amino)ethyl)amino)ethylmethacrylate (BocAEAEMA), was prepared and then polymerized via RAFT polymerization at constant monomer or initiator concentration increase in M n with monomer conversion was also observed. P(BocAEAEMA)s with controlled molecular weights and narrow molecular weight distributions were obtained. The in vitro cytotoxicity and proton sponge capacity of deprotected polymers P(AEAEMA) were investigated in comparison with a widely used endosomal-disruptive polymer, PEI. P(AEAEMA)s were found to possess proton sponge capacity comparable with PEI. More importantly, P(AEAEMA)s were not toxic on NIH 3T3 cells at concentrations where PEI (25 kDa) was highly toxic (0.4 mM and above). P(AEAEMA) was able to fully condense a DNA fragment at nitrogen/phosphate (N/P) ratios of 10 and above, as evidenced by gel electrophoresis. P(BocAEAEMA) was then chain-extended with a model sugar monomer, mannose-acrylate (ManAc), to yield P(AEAEMA)-b-P(ManAc) block copolymers, to potentially provide cell-recognition ability to the polyplex particles. Although the presence of the P(ManAc) block partially inhibited the interaction of P(AEAEMA) with DNA, P(AEAEMA) 13 -b-P(ManAc) 7 was able to form polyplexes with DNA at N/P ratios ranging between 20/1 and 2/1. Dynamic light scattering measurements showed that while P(AEAEMA) (M n ¼ 5.5 kDa) and DNA formed polyplex particles having a hydrodynamic diameter (D h ) of 125 AE 51 nm, P(AEAEMA) 13 -b-P(ManAc) 7 and DNA formed particles with a smaller D h of 38 AE 10 nm.

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Aqueous RAFT polymerization of 2‐aminoethyl methacrylate to produce well‐defined, primary amine functional homo‐ and copolymers

Cited by 71 publications

References 75 publications

RAFT made methacrylate copolymers for reversible pH‐responsive nanoparticles

RAFT made methacrylate copolymers for reversible pH‐responsive nanoparticles

Quantitative study on the antifreeze protein mimetic ice growth inhibition properties of poly(ampholytes) derived from vinyl-based polymers

A new proton sponge polymer synthesized by RAFT polymerization for intracellular delivery of biotherapeutics

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