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Preparation of multifunctional hydrogels with accessible isothiouronium groups via radical cross-linking copolymerization

2023 , Grübel, Jana , L Albernaz, Vanessa , Tsianaka, Anastasia , Jauch, Corinna O. , Quirin, Silia , Kerger, Christian , Kohl, Christina , Burger-Kentischer, Anke , Tovar, Günter , Southan, Alexander

Hydrogels can be equipped with functional groups for specific purposes. Isothiouronium groups can enhance adsorptivity, or allow coupling of other functional groups through mild reactions after transformation to thiol groups. Here we present a method to prepare multifunctional hydrogels by introducing isothiouronium groups into poly(ethylene glycol) diacrylate (PEGDA) hydrogels, and convert them into thiol-functionalized hydrogels by the reduction of the isothiouronium groups. For this purpose, the amphiphilic monomer 2-(11-(acryloyloxy)-undecyl)isothiouronium bromide (AUITB), containing an isothiouronium group, was synthesized and copolymerized with PEGDA. In this convenient way, it was possible to incorporate up to 3 wt% AUITB into the hydrogels without changing their equilibrium swelling degree. The successful functionalization was demonstrated by surface analysis of the hydrogels with water contact angle measurements and increased isoelectric points of the hydrogel surfaces from 4.5 to 9.0 due to the presence of the isothiouronium groups. The hydrogels showed a suitability as an adsorbent, as exemplified by the pronounced adsorption of the anionic drug diclofenac. The potential of the functionalization for (bio)conjugation reactions was demonstrated by the reduction of isothiouronium groups to thiols and subsequent immobilization of the functional enzyme horseradish peroxidase on the hydrogels. The results show that fully accessible isothiouronium groups can be introduced into radically cross-linked hydrogels.

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Teilvorhaben: Automatisierte Biosensoren, selbstlernende Monitoring-Tools und Konzepte für sichere Sensornetzwerke zur Erhöhung der Resilienz von Trinkwasserinfrastrukturen

2018 , Bernard, Thomas , Burger-Kentischer, Anke , Frick, Konstantin , Jacubasch, Andreas , Kerger, Christian , Kohl, Christina , Kühnert, Christian , Meier, David , Trick, Iris

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Enzyme-functionalized biomimetic apatites: Concept and perspectives in view of innovative medical approaches

2014 , Weber, Christina G. , Müller, Michaela , Vandecandelaere, Nicolas , Trick, Iris , Burger-Kentischer, Anke , Maucher, Tanja , Drouet, Christophe

Biomimetic nanocrystalline calcium-deficient apatite compounds are particularly attractive for the setup of bioactive bone-repair scaffolds due to their high similarity to bone mineral in terms of chemical composition, structural and substructural features. As such, along with the increasingly appealing development of moderate temperature engineered routes for sample processing, they have widened the armamentarium of orthopedic and maxillofacial surgeons in the field of bone tissue engineering. This was made possible by exploiting the exceptional surface reactivity of biomimetic apatite nanocrystals, capable of easily exchanging ions or adsorbing (bio)molecules, thus leading to highly-versatile drug delivery systems. In this contribution we focus on the preparation of hybrid materials combining biomimetic nanocrystalline apatites and enzymes (lysozyme and subtilisin). This paper reports physico-chemical data as well as cytotoxicity evaluations towards Cal-72 osteoblast-like cells and finally antimicrobial assessments towards selected strains of interest in bone surgery. Biomimetic apatite/enzyme hybrids could be prepared in varying buffers. They were found to be non-cytotoxic toward osteoblastic cells and the enzymes retained their biological activity (e.g. bond cleavage or antibacterial properties) despite the immobilization and drying processes. Release properties were also examined. Beyond these illustrative examples, the concept of biomimetic apatites functionalized with enzymes is thus shown to be useable in practice, e.g. for antimicrobial purposes, thus widening possible therapeutic perspectives.

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Reduction of the aortic inflammatory response in spontaneous atherosclerosis by blockade of macrophage migration inhibitory factor (MIF)

2006 , Burger-Kentischer, A. , Göbel, H. , Kleemann, R. , Zernecke, A. , Bucala, R. , Leng, L. , Finkelmeier, D. , Geiger, G. , Schaefer, H.E. , Schober, A. , Weber, C. , Brunner, H. , Rütten, H. , Ihling, C. , Bernhagen, J.

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Nanocrystalline apatites: Post-immersion acidification and how to avoid it - application to antibacterial bone substitutes

2023 , Drouet, Christophe , Vandecandelaère, Nicolas , Burger-Kentischer, Anke , Trick, Iris , Kohl, Christina , Maucher, Tanja , Müller, Michaela , Weber, Franz

Biomimetic nanocrystalline apatites analogous to bone mineral can be prepared using soft chemistry. Due to their high similarity to bone apatite, as opposed to stoichiometric hydroxyapatite for example, they now represent an appealing class of compounds to produce bioactive ceramics for which drug delivery and ion exchange abilities have been described extensively. However, immersion in aqueous media of dried non-carbonated biomimetic apatite crystals may generate an acidification event, which is often disregarded and not been clarified to-date. Yet, this acidification process could limit their further development if it is not understood and overcome if necessary. This may, for example, alter biological test outcomes, during their evaluation as bone repair materials, due to potentially deleterious effects of the acidic environment on cells, especially in in vitro static conditions. In this study, we explore the origins of this acidification phenomenon based on complementary experimental data and we point out the central role of the hydrated ionic layer present on apatite nanocrystals. We then propose a practical strategy to circumvent this acidification effect using an adequate post-precipitation equilibration step that was optimized. Using this enutralization protocol, we then showed the possibility of performing (micro)biological assessments on such compounds and provide an illustration with the examples of post-equilibrated Cu2+- and Ag+-doped nanocrystalline apatites. We demonstrate their non-cytotoxicity to osteoblast cells and their antibacterial features as tested versus five major pathogens involved in bone infections, therefore pointing to their relevance in the field of antibacterial bone substitutes. The preliminary in vivo implantation of a relevant sample in a rat’s calvarial defect confirmed its biocompatibility and the absence of adverse reaction. Understanding and eliminating this technical barrier should help promoting biomimetic apatites as a genuine new class of biomaterial-producing compounds for bone regeneration applications, e.g., with antibacterial features, far from being solely considered as “laboratory curiosities”.

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On-line monitoring of drinking water based on a biological broad-spectrum sensor

2016 , Bernard, Thomas , Jacubasch, Andreas , Trick, Iris , Burger-Kentischer, Anke , Kohl, Christina

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Vermeidung von Biofilm und Unterdrückung von Virulenzfaktoren pathogener Mikroorganismen an Grenzflächen

2012 , Müller, Michaela , Kohl, Christina , Kerger, Christian , Burger-Kentischer, Anke , Trick, Iris , Hirth, Thomas

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Human-Based Immune Responsive In Vitro Infection Models for Validation of Novel TLR4 Antagonists Identified by Computational Discovery

2022 , Merk, H. , Amran-Gealia, T. , Finkelmeier, Doris , Kohl, Christina , Pichota, Isabelle , Stern, N. , Rupp, S. , Goldblum, A. , Burger-Kentischer, Anke

Infectious diseases are still a major problem worldwide. This includes microbial infections, with a constant increase in resistance to the current anti-infectives employed. Toll-like receptors (TLRs) perform a fundamental role in pathogen recognition and activation of the innate immune response. Promising new approaches to combat infections and inflammatory diseases involve modulation of the host immune system via TLR4. TLR4 and its co-receptors MD2 and CD14 are required for immune response to fungal and bacterial infection by recognition of microbial cell wall components, making it a prime target for drug development. To evaluate the efficacy of anti-infective compounds early on, we have developed a series of human-based immune responsive infection models, including immune responsive 3D-skin infection models for modeling fungal infections. By using computational methods: pharmacophore modeling and molecular docking, we identified a set of 46 potential modulators of TLR4, which were screened in several tests systems of increasing complexity, including immune responsive 3D-skin infection models. We could show a strong suppression of cytokine and chemokine response induced by lipopolysacharide (LPS) and Candida albicans for individual compounds. The development of human-based immune responsive assays provides a more accurate and reliable basis for development of new anti-inflammatory or immune-modulating drugs.

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Control of drinking water by linking biosensors with physicochemical methods

2015 , Cimalla, Volker , Hugger, Stefan , Fuchs, Frank , Anzt, Johannes , Bitterling, Moritz , Yang, Nianjun , Kohl, Christina , Maucher, Tanja , Mühlemeier, Ilka , Burger-Kentischer, Anke , Trick, Iris

An alarm system is developed for the direct detection of toxic substances in drinking water. The vitality of living organisms or cells is monitored continuously by electrochemical and infrared spectroscopic methods. Mammalian cells or bacteria are acting as highly sensitive biosensors and are monitored simultaneously by infrared and electro-chemical techniques. It enables the nonspecific detection of toxins with short response times for implementation in water supplies.

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Biofilmvermeidung durch natürliche Wirkstoffe - gezielte und langfristige Freisetzung durch ein PEG-basiertes Depotsystem

2011 , Weber, Christina , Burger-Kentischer, Anke , Müller, Michaela , Trick, Iris , Hirth, Thomas