Photo-sensitive PMMA microgels: light-triggered swelling and degradation

Klinger, Daniel; Landfester, Katharina

doi:10.1039/c0sm00638f

Cited by 81 publications

(98 citation statements)

References 52 publications

(69 reference statements)

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“…Both crosslinkers were found to degrade completely upon irradiation with UV light of wavelengths with= 315-390 nm. As shown before, 295 the elugram of crosslinker CL-4B exhibits the direct formation of one main photo-product accompanied by the generation of the dimeric azoxybenzene side product. In comparison, the elugram of CL-5B displays the formation of an intermediary compound (peak at 6.6 min) during irradiation in addition to the main photo-product (peak at 5.0 min).…”

Section: Photolysis Of the Cleavable Crosslinkers In Solutionmentioning

confidence: 99%

“…As shown for photo-degradable PMMA microgels, the covalent attachment of those side products to the polymer backbone hinders complete particle degradation due to the formation of new crosslinking points in the respective gels. 295 Even though a dramatic increase in the degree of swelling for those particles could be detected for the mentioned irradiation conditions, complete microgel disintegration enhances the potential for delivery applications. Therefore, the symmetric molecular structure of CL-5B was designed to generate only carboxylic acid groups on the polymer backbone by photolytic cleavage of the o-nitrobenzyl ester bonds.…”

Section: Photolysis Of the Cleavable Crosslinkers In Solutionmentioning

confidence: 99%

“…In comparison to the studies performed on CL-4B, 295 the photo-degradation behavior of the crosslinker CL-5B in equimolar THF solution was first investigated by irradiation timedependent UV-vis measurements. The respective plot of CL-5B is shown in Figure 50.…”

Section: Photolysis Of the Cleavable Crosslinkers In Solutionmentioning

confidence: 99%

“…Investigations on photosensitive PMMA polymeric gel microgels revealed the synthesized crosslinker CL-4B as the compound exhibiting the best photolytic properties under mild irradiation conditions. 295 Based on these considerations concerning the utilized chromophore, a new crosslinker CL-5B was synthesized in order to investigate the influence of the molecular structure on the degradation behavior of the hydrogel particles. The synthetic pathway to CL-5B in comparison to CL-4B is shown in Figure 49 together with the reaction conditions.…”

Section: Dual Stimuli-responsive P(hema-co-maa) Microgels: Phdependenmentioning

confidence: 99%

“…Both structures are based on 4-(4-(1-hydroxyethyl)-2-methoxy-5-nitrophenoxy)butanoic acid (HEMNPBA) which was synthesized accordingly to a previous publication. 295 Briefly, acetovanillone was reacted with methyl 4-bromobutyrate to the corresponding keto ester (5) under basic conditions. A subsequent nitration of the crude product was achieved by the reaction with acetic anhydride and nitric acid.…”

Section: Dual Stimuli-responsive P(hema-co-maa) Microgels: Phdependenmentioning

confidence: 99%

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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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Section: Photolysis Of the Cleavable Crosslinkers In Solutionmentioning

confidence: 99%

Section: Photolysis Of the Cleavable Crosslinkers In Solutionmentioning

confidence: 99%

Section: Photolysis Of the Cleavable Crosslinkers In Solutionmentioning

confidence: 99%

Section: Dual Stimuli-responsive P(hema-co-maa) Microgels: Phdependenmentioning

confidence: 99%

Section: Dual Stimuli-responsive P(hema-co-maa) Microgels: Phdependenmentioning

confidence: 99%

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Light-Sensitive Polymeric Nanoparticles Based on Photo-Cleavable Chromophores

Klinger

2013

Springer Theses

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Light‐Controlled Encapsulation and Release Enabled by Photoresponsive Polymer Self‐Assemblies

Barrio

Piñol

Oriol

2018

Photoactive Functional Soft Materials

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Activated‐Ester‐Type Photocleavable Crosslinker for Preparation of Photodegradable Hydrogels Using a Two‐Component Mixing Reaction

Yanagawa

Sugiura

Takagi

et al. 2014

Adv Healthcare Materials

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Photodegradable hydrogels have emerged as powerful platforms for studying and directing cellular behavior in a spatiotemporally controlled manner. Photodegradable hydrogels have previously been formed by free radical polymerizations, Michael-type addition reactions, and orthogonal click reactions. Here, an ester-activated photocleavable crosslinker is presented for preparing photodegradable hydrogels by means of a one-step mixing reaction between the crosslinker and a biocompatible polymer containing amino moieties (amino-terminated tetra-arm poly(ethylene glycol) or gelatin). It is demonstrated that photodegradable hydrogels micropatterned by photolithography can be used to culture cells with high viability and proliferation rates. The resulting micropatterned cell-laden structures can potentially be used to create 3D biomaterials for various tissue-engineering applications.

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Photo-sensitive PMMA microgels: light-triggered swelling and degradation

Cited by 81 publications

References 52 publications

Light-Sensitive Polymeric Nanoparticles Based on Photo-Cleavable Chromophores

Light-Sensitive Polymeric Nanoparticles Based on Photo-Cleavable Chromophores

Light‐Controlled Encapsulation and Release Enabled by Photoresponsive Polymer Self‐Assemblies

Activated‐Ester‐Type Photocleavable Crosslinker for Preparation of Photodegradable Hydrogels Using a Two‐Component Mixing Reaction

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