Acid-Labile Polyvinylamine Micro- and Nanogel Capsules

Shi, Lianjun; Berkland, Cory

doi:10.1021/ma070443o

Cited by 62 publications

(54 citation statements)

References 42 publications

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“…The interaction and self-assembly of these particles results in the observed sol–gel transition [363]. Colloidal gel shear-thinning occurs when the surface interactions are disrupted under applied shear, while self-healing is the reinstatement of those favorable interactions [363,508–512]. A colloidal system based on charged poly( d , l -lactic-co-glycolic acid) (PLGA) nanoparticles was developed by Shi et al One set of PLGA nanoparticles was coated with a positively charged polyvinylamine while the other set is coated with a negatively charged poly(ethylene-co-maleic acid).…”

Section: Shear Stress Responsive Hydrogelsmentioning

confidence: 99%

Stimulus-responsive hydrogels: Theory, modern advances, and applications

Koetting

Peters

Steichen

et al. 2015

Materials Science and Engineering: R: Reports

905

688

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Over the past century, hydrogels have emerged as effective materials for an immense variety of applications. The unique network structure of hydrogels enables very high levels of hydrophilicity and biocompatibility, while at the same time exhibiting the soft physical properties associated with living tissue, making them ideal biomaterials. Stimulus-responsive hydrogels have been especially impactful, allowing for unprecedented levels of control over material properties in response to external cues. This enhanced control has enabled groundbreaking advances in healthcare, allowing for more effective treatment of a vast array of diseases and improved approaches for tissue engineering and wound healing. In this extensive review, we identify and discuss the multitude of response modalities that have been developed, including temperature, pH, chemical, light, electro, and shear-sensitive hydrogels. We discuss the theoretical analysis of hydrogel properties and the mechanisms used to create these responses, highlighting both the pioneering and most recent work in all of these fields. Finally, we review the many current and proposed applications of these hydrogels in medicine and industry.

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Section: Shear Stress Responsive Hydrogelsmentioning

confidence: 99%

Stimulus-responsive hydrogels: Theory, modern advances, and applications

Koetting

Peters

Steichen

et al. 2015

Materials Science and Engineering: R: Reports

905

688

View full text Add to dashboard Cite

show abstract

“…Those spectra all had bands that are due to 52 amide I (1650 cm À1 ) and amide II (1540 cm À1 ) and are consistent with spectra for PNVF reported earlier. 39 Alkali hydrolysis of the PNVF-xNVEE dispersions caused major changes in the spectra (see Fig. 6).…”

Section: Physical Measurementsmentioning

confidence: 98%

Poly(vinylamine) microgels: pH-responsive particles with high primary amine contents

et al. 2013

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pH-responsive microgels are crosslinked polymer colloid particles that swell when the pH approaches the pK a of the polybase or polyacid chains. Poly(vinylamine) (PVAM) has the highest primary amine content of all amine-containing polymers. Despite much effort the preparation of colloidally stable PVAM microgels is still elusive. Here, we introduce a simple and scalable, two-step method for preparation of pH-responsive PVAM microgels. First, non-aqueous dispersion (NAD) polymerization was used to prepare new monodisperse water-swellable poly(N-vinylformamide-co-2-(N-vinylformamido)ethyl ether microgels (PNVF-xNVEE). Here, x is the mol% of the alkali-stable crosslinker (NVEE) used. Alkali-hydrolysis of the PNVF-xNVEE microgels in water gave colloidally stable poly(vinylamine-co-bis(ethyl vinylamine)ether) (PVAM-xBEVAME) microgel dispersions. SEM images showed that both the PNVF-9NVEE and PVAM-9BEVAME microgel particles had cluster-like morphologies. The PVAM-xBEVAME particles were positively charged at pH values less than 12. The hydrodynamic diameters and electrophoretic mobilities increased strongly as the pH decreased. In order to demonstrate that primary amines could be used as chemical handles for conjugation, pyrene carboxylic acid was coupled using N-(3-dimethylaminopropyl)-N 0ethylcarbodiimide (EDC) chemistry and its presence confirmed by fluorescence microscopy. Because this new family of colloidally stable microgels has very high primary amine contents and was prepared by a scalable synthetic method there should be potential applications in a wide range of areas from surface coatings and new hybrid particles to delivery.

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“…177 The concept of acid-labile crosslinkers can even be extended to more complex structures such as e.g. hollow microgel capsules prepared from polyvinylamine (PVAm) with ketal moieties containing crosslinks described by Shi et al 178 In addition to pH changes throughout the body, another biological relevant trigger is the presence of certain reducing agents in specific compartments. As an example, the accumulation of glutathione in the cytosol is worth mentioning.…”

Section: Microgels Containing Hydrolytically Cleavable Crosslinkersmentioning

confidence: 99%

Light-Sensitive Polymeric Nanoparticles Based on Photo-Cleavable Chromophores

Klinger

2013

Springer Theses

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This thesis focuses on the design, synthesis and characterization of novel photo-sensitive microgels and nanoparticles as potential materials for the loading and light-triggered release/accessibility of functional compounds. In order to realize this concept, different approaches to irradiation-dependent response mechanisms have been investigated.Novel light-cleavable divinyl functionalized monomeric crosslinkers based on o-nitrobenzyl derivatives were synthesized and used for the preparation of either PMMA or hydroxyl functionalized PHEMA microgels swellable and degradable in organic solvents. By the introduction of anionic MAA moieties into the PHEMA microgels, this concept was successfully transferred to double stimuli-responsive p(HEMA-co-MAA) hydrogel nanoparticles exhibiting a pH-dependent swelling and light-induced degradation behavior in aqueous media. This sensitivity to two orthogonal triggers is proposed to combine a pHinduced post-formation loading mechanism with a pH-and light-triggered release. In addition, a new class of enzyme-and light-sensitive PAAm microgels based on (meth-)acrylate functionalized dextrans as photo-and enzymatically degradable macromolecular crosslinkers was developed by introducing a photo-labile linker between the enzymatically degradable dextran chain and the polymerizable vinyl moieties. Here, the water solubility of the crosslinkers is assumed to enable an in situ loading approach of hydrophilic compounds.A different approach to the loading of microgels is based on photo-labile covalent microgel-drug conjugates. The first step to the realization of this concept was achieved by the development of a novel functional monomer consisting of a doxorubicin molecule covalently attached to a radically polymerizable methacrylate group via a photo-cleavable linker.Moreover, in order to enable the release of hydrophobic substances in aqueous media, hydrophobic nanoparticles consisting of a photo-resist polymer were designed to be degradable upon irradiation in water. Light-triggered conversion of the initial hydrophobic polymer into hydrophilic PMAA induced in situ particle dissolution and release of nile red.Since the introduction of a stimuli-responsive shell around a microgel is assumed to prevent leakage of embedded compounds, studies on non-stimuli-responsive shell formation around preformed microgel seed particles and the formation of microgel cores in polymeric shells were conducted to investigate potential synthetic pathways to this approach.In a last attempt, the surface of PHEMA and p(HEMA-co-MAA) microgels was functionalized with cinnamoyl groups in order to trigger the (reversible) particles interaction with each other by light-induced [2+2] cycloaddition reactions.

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Acid-Labile Polyvinylamine Micro- and Nanogel Capsules

Cited by 62 publications

References 42 publications

Stimulus-responsive hydrogels: Theory, modern advances, and applications

Stimulus-responsive hydrogels: Theory, modern advances, and applications

Poly(vinylamine) microgels: pH-responsive particles with high primary amine contents

Light-Sensitive Polymeric Nanoparticles Based on Photo-Cleavable Chromophores

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