Polyvinyl butyral nanobeads: preparation, characterization, biocompatibility and cancer cell uptake

Posavec, Damir; Dorsch, Andre; Bogner, U.; Bernhardt, Güenther; Nagl, Stefan

doi:10.1007/s00604-011-0573-8

Cited by 19 publications

(16 citation statements)

References 19 publications

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“…Based on our previously described results on the successful exploitation of functionalized DMN-derivatives for several biomedical applications (Posavec et al 2012, Posavec et al 2011, endoperoxide loaded films or nanoparticles of the polymer PVB-SA-DMN could potentially be used as novel materials with interesting anticancer and antibiotic effects. In this context it is important to note that the concentration of endoperoxide forming groups in PVB-SA-DMN is expected to be sufficient for inducing a significant cytostatic effect (estimated concentration necessary is >15 µM) (Posavec et al 2012).…”

Section: Discussionmentioning

confidence: 99%

“…As an extension of our previous work (Posavec et al 2012), we wish to report here our results on the covalent attachment of such functional 1,4-dimethyl-naphthalen-2-yl subunits to a polyvinylbutyrate (PVB) polymer backbone. PVB has been selected as a carrier medium for drug delivery because of its excellent biocompatibility, non-toxicity and the possibility of preparing spherical PVB nanoparticles that have been shown to be efficiently taken up without further surface modifications by human cancer cells (Posavec et al 2011). This novel approach enables to reach a very high local concentration of endoperoxide-forming groups in the target region.…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Polyvinyl butyral DMN-conjugates for the controlled release of singlet oxygen in medical and antimicrobial applications

Posavec¹,

Müller²,

Bogner³

et al. 2014

Biomaterials and Biomedical Engineering

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Covalent attachment of 1, 4-dimethylnaphthalene (DMN) based endoperoxide forming subunits to a polyvinyl butyral (PVB) backbone has been achieved. The functionalized polymer materials prepared and characterized here can serve as biocompatible carrier systems for studying cellular uptake, intermediate storage and delayed release of singlet oxygen, which opens up new doors for optimizing a variety of medical applications of photogenerated DMN-endoperoxides such as antiviral, antibacterial, antiplasmodial and antitumor activity.

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Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Polyvinyl butyral DMN-conjugates for the controlled release of singlet oxygen in medical and antimicrobial applications

Posavec¹,

Müller²,

Bogner³

et al. 2014

Biomaterials and Biomedical Engineering

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“…Confocal laser scanning microscopy (CLSM) and mammalian cell culture experiments with MDA-MB-231 human breast cancer cells were carried out as recently described in more detail. 10 …”

Section: Methods and Instrumentationmentioning

confidence: 99%

“…To the best of our knowledge, the only existing systematic study concentrates on electronic and steric effects of different methylation patterns on the reversible endoperoxide formation in a series of hydrophobic naphthalene derivatives. 2 Here we report our first results on the synthesis, spectroscopic and structural characterization of two novel photoreactive DMNderivatives, which were functionalized in order to adjust their solubility in media of different polarity, to enable incorporation into various biocompatible carrier and drug delivery materials such as liposomes or polymer nanoparticles, 10 and to introduce the possibility of synergistic interactions between multiple dioxygen activation sites for the improvement of their reactivity in terms of potential chemotherapeutic applications.…”

Section: Introductionmentioning

confidence: 99%

Functionalized derivatives of 1,4-dimethylnaphthalene as precursors for biomedical applications: synthesis, structures, spectroscopy and photochemical activation in the presence of dioxygen

et al. 2012

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Decomposition of endoperoxide containing molecules is an attractive approach for the delayed release of singlet oxygen under mild reaction conditions. Here we describe a new method for the adaptation of the corresponding decay times by controlling the supramolecular functional structure of the surrounding matrix in the immediate vicinity of embedded singlet oxygen precursors. Thus, a significant prolongation of the lifetime of the endoperoxide species is possible by raising the energy barrier of the thermal 1 O 2 -releasing step via a restriction of the free volume of the applied carrier material. Enabling such a prolonged decomposition period is crucial for potential biomedical applications of endoperoxide containing molecules, since sufficient time for appropriate cell uptake and transport to the desired target region must be available under physiological conditions before the tissue damaging-power of the reactive oxygen species formed is completely exhausted. Two novel polyaromatic systems for the intermediate storage and transport of endoperoxides and the controlled release of singlet oxygen in the context of anticancer and antibiotic activity have been prepared and characterized. These compounds are based on functionalized derivatives of the 1,4-dimethylnaphthalene family which are readily forming metastable endoperoxide species in the presence of dioxygen, a photosensitizer molecule such as methylene blue and visible light. In contrast to previously known systems of similar photoreactivity, the endoperoxide carrying molecules have been designed with optimized molecular properties in terms of potential chemotherapeutic applications. These include modifications of polarity to improve their incorporation into various biocompatible carrier materials, the introduction of hydrogen bonding motifs to additionally influence the endoperoxide decay kinetics, and the synthesis of bifunctional derivatives to enable synergistic effects of multiple singlet oxygen binding sites with an enhanced local concentration of reactive species. With these compounds, a promising degree of endoperoxide stability adjustment within the carrier matrix has been achieved ( polymer films or nanoparticles), which now opens the stage for appropriate targeting of the corresponding pro-drugs into live cells. First results on cytocidal and cytostatic properties of these compounds embedded in ethylcellulose nanoparticles are presented. Furthermore, an efficient low-cost method for the photochemical production of reactive endoperoxides based on high-power 660 nm LED excitation at room temperature and ambient conditions in ethanol solution is reported.

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“…Among the polymers spun with our device, PVB caught our attention because of its ability to dissolve in ethanol but not in water (Yener and Jirsak 2012 ). Moreover, PVB has been shown to possess biocompatibility and non-toxicity (Posavec et al 2011 ). We previously used an ethanol–methanol mixture to dissolve the polymer (Mouthuy et al 2014 ).…”

Section: Introductionmentioning

confidence: 99%

Direct electrospinning of poly(vinyl butyral) onto human dermal fibroblasts using a portable device

Chui

Mouthuy

2018

Biotechnol Lett

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ObjectiveTo demonstrate that uniform poly(vinyl butyral) (PVB) fibres can be safely electrospun onto a monolayer of human dermal fibroblasts using a portable device.ResultsPVB in solvent mixtures containing various amounts of ethanol and water was electrospun. Six percent (weight-to-volume ratio) PVB in a 9:1 ethanol:water ratio was the solution with the highest content in water that could be electrospun into consistent fibres with an average diameter of 0.9 μm (± 0.1 μm). Four and five percent PVB solutions created beaded fibres. A 8:2 ethanol:water solution lead to microbead formation while a 7:3 ethanol:water mix failed to fully dissolve. The selected solution was successfully electrospun onto a monolayer of human dermal fibroblasts and the process had no significant effect (p < 0.05) on cell viability compared to the control without fibres.ConclusionsPVB–ethanol–water solutions could be electrospun without damaging the exposed cell layer. However, further work is required to demonstrate the long-term effect of PVB as a wound healing material.

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Polyvinyl butyral nanobeads: preparation, characterization, biocompatibility and cancer cell uptake

Cited by 19 publications

References 19 publications

Polyvinyl butyral DMN-conjugates for the controlled release of singlet oxygen in medical and antimicrobial applications

Polyvinyl butyral DMN-conjugates for the controlled release of singlet oxygen in medical and antimicrobial applications

Functionalized derivatives of 1,4-dimethylnaphthalene as precursors for biomedical applications: synthesis, structures, spectroscopy and photochemical activation in the presence of dioxygen

Direct electrospinning of poly(vinyl butyral) onto human dermal fibroblasts using a portable device

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