pH-triggered self-assembly of biocompatible histamine-functionalized triblock copolymers

Lundberg, Pontus; Lynd, Nathaniel A.; Zhang, Yuning; Zeng, Xianghui; Krogstad, Daniel V.; Paffen, Tim F. E.; Malkoch, Michael; Nyström, Andreas M.; Hawker, Craig J.

doi:10.1039/c2sm26996a

Cited by 59 publications

(67 citation statements)

References 30 publications

(50 reference statements)

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“…The successful synthesis of the random copolymer is confirmed by 1 H NMR spectroscopy (see Figure 1) due to the presence of the characteristic peak at 2.23 and 8.01 ppm. The actual structure unit ratio is estimated from the integral area.…”

Section: Synthesis Of P(spma-co-dmaema) At Different Rate Of Comonomermentioning

confidence: 76%

“…In recent years, a great deal of stimuli-responsive amphipathic polymer micelles that respond to internal or external stimuli including pH, [1,2] temperature, [3] redox, [4] light, [5], and magnetic field [6] have been abundantly investigated due to their broad range of potential applications as nanocarriers, [7] biosensors, [8,9], and biochemical gates. [10] Among the various stimuli, light is one of the most attractive external stimuli because of the superiority in spatial and temporal control.…”

Section: Introductionmentioning

confidence: 99%

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Self-assembly and morphology transition of amphipathic spiropyran-based random copolymers to control drug release

Chen

Liu

et al. 2016

Designed Monomers and Polymers

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An amphipathic spiropyran-based random copolymer P(SPMA-co-DMAEMA) was synthesized by atom transfer radical polymerization, and the resulting copolymer was characterized by means of 1 H nuclear magnetic resonance spectroscopy, Fourier transform infrared spectroscopy, and gel permeation chromatography. The self-assembly behaviors and morphology transition were systematically investigated under single and combined external environmental stimuli by transmission electron microscopy. With coumarin 102 as the model drug molecule, the selfassembly micelles were used to control drug loading, release, and re-encapsulation to some extent. The characterization results indicated the successful preparation of the spiropyran-based random copolymer P(SPMA-co-DMAEMA). The external stimuli had some influences on the morphology of the self-assembly aggregate, and the 'schizophrenic' behavior was interestingly found in this work. The drug release experiments showed the reversible loading and release process up to a point, which might expand the potential application domain of the amphiphilic spiropyran-based random copolymer in drug delivery.

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Section: Synthesis Of P(spma-co-dmaema) At Different Rate Of Comonomermentioning

confidence: 76%

Section: Introductionmentioning

confidence: 99%

Self-assembly and morphology transition of amphipathic spiropyran-based random copolymers to control drug release

Chen

Liu

et al. 2016

Designed Monomers and Polymers

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“…9 Therefore, pH-responsive polyethers are highly attractive and have been realized by few tertiary amine-containing copolymers with ethylene oxide. 11–13 The incorporation of pH-sensitive groups enables tuning the cloud-point temperature, and triggering micellization or hydrogelation by changes in pH. 5,12–19 Specifically for some applications in biomedical materials, transitions with pH must occur within the window of physiologically-relevant pH variation of ca .…”

Section: Introductionmentioning

confidence: 99%

Physiologically relevant, pH-responsive PEG-based block and statistical copolymers with N,N-diisopropylamine units

et al. 2013

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In order to impart pH-responsiveness within a physiologically-relevant context to PEG-based biomaterials, a new tertiary amine containing repeat unit, N,N-diisopropyl ethanolamine glycidyl ether (DEGE), was developed and incorporated into statistical and block copolymers with ethylene oxide (EO), and allyl glycidyl ether (AGE) via anionic ring-opening polymerization. The reactivity of this novel monomeric building block in copolymerizations with EO was investigated by spectroscopy with observed reactivity ratios of rDEGE = 1.28 ± 0.14 and rEO = 0.82 ± 0.10. It was further demonstrated that DEGE containing copolymers could serve as building blocks for the formation of new pH-responsive materials with a pKa of ca. 9, which allowed macroscopic hydrogels to be prepared from symmetric triblock copolymers PDEGE5.3k-b-PEO20k-b-PDEGE5.3k. The triblock copolymers exhibited clear sol-to-gel transitions in a physiologically-relevant critical gelation range of pH 5.8–6.6 and pH-dependent viscoelastic properties. On the nanometer scale, the preparation of pH-responsive micro- or nanogels was demonstrated by crosslinking P(DEGE-co-AGE) copolymers in miniemulsion droplets stabilized by PEO-b-P(DEGE-co-AGE) diblock terpolymers. These nanoparticles exhibited a reversible pH-dependent swelling profile with a volume phase transition at physiological pH 6.5–7.5.

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“…The synthesis of Im-SH was adapted from Lundberg et al 46 In a 250 mL round-bottom flask equipped with a Teflon TM -coated stir bar and a condenser, 1-(3-aminopropyl)imidazole (10.0 g, 79.9 mmol), γ-thiobutyrolactone (8.2 g, 80.2 mmol), and acetonitrile (135 mL) were added.…”

Section: Synthesis Of N-(2-(1h-imidazol-1-yl)propyl)-4-mercaptobutanamentioning

confidence: 99%

Ion Transport in Dynamic Polymer Networks Based on Metal–Ligand Coordination: Effect of Cross-Linker Concentration

Sanoja

Schauser²,

Bartels³

et al. 2018

Macromolecules

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The development of high-performance ion conducting polymers requires a comprehensive multi-scale understanding of the connection between ion-polymer associations, ionic conductivity, and polymer mechanics. We present polymer networks based on dynamic metal-ligand coordination as model systems to illustrate this relationship. The molecular design of these materials allows for precise and independent control over the nature and concentration of ligand and metal, which are molecular properties critical for bulk ion conduction and polymer mechanics.The model system investigated, inspired by polymerized ionic liquids, is composed of poly(ethylene oxide) with tethered imidazole moieties that facilitate dissociation upon incorporation of nickel (II) bis(trifluoromethylsulfonyl)imide. Nickel-imidazole interactions physically crosslink the polymer, increase the number of elastically active strands, and dramatically enhance the modulus. In addition, a maximum in ionic conductivity is observed due to the competing effects of increasing ion concentration and decreasing ion mobility upon network formation. The simultaneous enhancement of conducting and mechanical properties within a specific concentration regime demonstrates a promising pathway for the development of mechanically robust ion conducting polymers.3

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pH-triggered self-assembly of biocompatible histamine-functionalized triblock copolymers

Cited by 59 publications

References 30 publications

Self-assembly and morphology transition of amphipathic spiropyran-based random copolymers to control drug release

Self-assembly and morphology transition of amphipathic spiropyran-based random copolymers to control drug release

Physiologically relevant, pH-responsive PEG-based block and statistical copolymers with N,N-diisopropylamine units

Ion Transport in Dynamic Polymer Networks Based on Metal–Ligand Coordination: Effect of Cross-Linker Concentration

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