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  1. Article: Electropolymerization of Polydopamine at Electrode-Supported Insulating Mesoporous Films.

    Varol, H Samet / Herberger, Tilmann / Kirsch, Marius / Mikolei, Joanna / Veith, Lothar / Kannan-Sampathkumar, Venkataprasanna / Brand, Raoul D / Synatschke, Christopher V / Weil, Tanja / Andrieu-Brunsen, Annette

    Chemistry of materials : a publication of the American Chemical Society

    2023  Volume 35, Issue 21, Page(s) 9192–9207

    Abstract: Bioinspired, stimuli-responsive, polymer-functionalized mesoporous films are promising platforms for precisely regulating nanopore transport toward applications in water management, iontronics, catalysis, sensing, drug delivery, or energy conversion. ... ...

    Abstract Bioinspired, stimuli-responsive, polymer-functionalized mesoporous films are promising platforms for precisely regulating nanopore transport toward applications in water management, iontronics, catalysis, sensing, drug delivery, or energy conversion. Nanopore technologies still require new, facile, and effective nanopore functionalization with multi- and stimuli-responsive polymers to reach these complicated application targets. In recent years, zwitterionic and multifunctional polydopamine (PDA) films deposited on planar surfaces by electropolymerization have helped surfaces respond to various external stimuli such as light, temperature, moisture, and pH. However, PDA has not been used to functionalize nanoporous films, where the PDA-coating could locally regulate the ionic nanopore transport. This study investigates the electropolymerization of homogeneous thin PDA films to functionalize nanopores of mesoporous silica films. We investigate the effect of different mesoporous film structures and the number of electropolymerization cycles on the presence of PDA at mesopores and mesoporous film surfaces. Our spectroscopic, microscopic, and electrochemical analysis reveals that the amount and location (pores and surface) of deposited PDA at mesoporous films is related to the combination of the number of electropolymerization cycles and the mesoporous film thickness and pore size. In view of the application of the proposed PDA-functionalized mesoporous films in areas requiring ion transport control, we studied the ion nanopore transport of the films by cyclic voltammetry. We realized that the amount of PDA in the nanopores helps to limit the overall ionic transport, while the pH-dependent transport mechanism of pristine silica films remains unchanged. It was found that (i) the pH-dependent deprotonation of PDA and silica walls and (ii) the insulation of the indium-tin oxide (ITO) surface by increasing the amount of PDA within the mesoporous silica film affect the ionic nanopore transport.
    Language English
    Publishing date 2023-11-02
    Publishing country United States
    Document type Journal Article
    ZDB-ID 1500399-1
    ISSN 1520-5002 ; 0897-4756
    ISSN (online) 1520-5002
    ISSN 0897-4756
    DOI 10.1021/acs.chemmater.3c01890
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  2. Article: Like Dissolves Like? A Comprehensive Evaluation of Partial Solubility Parameters to Predict Polymer–Drug Compatibility in Ultrahigh Drug-Loaded Polymer Micelles

    Lübtow, Michael M / Haider, Malik Salman / Kirsch, Marius / Klisch, Stefanie / Luxenhofer, Robert

    Biomacromolecules. 2019 June 24, v. 20, no. 8

    2019  

    Abstract: Despite decades of research, our understanding of the molecular interactions between drugs and polymers in drug-loaded polymer micelles does not extend much beyond concepts such as “like-dissolves-like” or hydrophilic/hydrophobic. However, polymer–drug ... ...

    Abstract Despite decades of research, our understanding of the molecular interactions between drugs and polymers in drug-loaded polymer micelles does not extend much beyond concepts such as “like-dissolves-like” or hydrophilic/hydrophobic. However, polymer–drug compatibility strongly affects formulation properties and therefore the translation of a formulation into the clinics. Specific interactions such as hydrogen-bonding, π–π stacking, or coordination interactions can be utilized to increase drug loading. This is commonly based on trial and error and eventually leads to an optimized drug carrier. Unfortunately, due to the unique characteristics of each drug, the deduction of advanced general concepts remains challenging. Furthermore, the introduction of complex moieties or specifically modified polymers hampers systematic investigations regarding polymer–drug compatibility as well as clinical translation. In this study, we reduced the complexity to isolate the crucial factors determining drug loading. Therefore, the compatibility of 18 different amphiphilic polymers for five different hydrophobic drugs was determined empirically. Subsequently, the obtained specificities were compared to theoretical compatibilities derived from either the Flory–Huggins interaction parameters or the Hansen solubility parameters. In general, the Flory–Huggins interaction parameters were less suited to correctly estimate the experimental drug solubilization compared to the Hansen solubility parameters. The latter were able to correctly predict some trend regarding good and poor solubilizers, yet the overall predictive strength of Hansen solubility parameters is clearly unsatisfactory.
    Keywords drug carriers ; drugs ; hydrogen bonding ; hydrophilicity ; hydrophobicity ; micelles ; moieties ; polymers ; solubility ; solubilization
    Language English
    Dates of publication 2019-0624
    Size p. 3041-3056.
    Publishing place American Chemical Society
    Document type Article
    ISSN 1526-4602
    DOI 10.1021/acs.biomac.9b00618
    Database NAL-Catalogue (AGRICOLA)

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  3. Article ; Online: Like Dissolves Like? A Comprehensive Evaluation of Partial Solubility Parameters to Predict Polymer-Drug Compatibility in Ultrahigh Drug-Loaded Polymer Micelles.

    Lübtow, Michael M / Haider, Malik Salman / Kirsch, Marius / Klisch, Stefanie / Luxenhofer, Robert

    Biomacromolecules

    2019  Volume 20, Issue 8, Page(s) 3041–3056

    Abstract: Despite decades of research, our understanding of the molecular interactions between drugs and polymers in drug-loaded polymer micelles does not extend much beyond concepts such as "like-dissolves-like" or hydrophilic/hydrophobic. However, polymer-drug ... ...

    Abstract Despite decades of research, our understanding of the molecular interactions between drugs and polymers in drug-loaded polymer micelles does not extend much beyond concepts such as "like-dissolves-like" or hydrophilic/hydrophobic. However, polymer-drug compatibility strongly affects formulation properties and therefore the translation of a formulation into the clinics. Specific interactions such as hydrogen-bonding, π-π stacking, or coordination interactions can be utilized to increase drug loading. This is commonly based on trial and error and eventually leads to an optimized drug carrier. Unfortunately, due to the unique characteristics of each drug, the deduction of advanced general concepts remains challenging. Furthermore, the introduction of complex moieties or specifically modified polymers hampers systematic investigations regarding polymer-drug compatibility as well as clinical translation. In this study, we reduced the complexity to isolate the crucial factors determining drug loading. Therefore, the compatibility of 18 different amphiphilic polymers for five different hydrophobic drugs was determined empirically. Subsequently, the obtained specificities were compared to theoretical compatibilities derived from either the Flory-Huggins interaction parameters or the Hansen solubility parameters. In general, the Flory-Huggins interaction parameters were less suited to correctly estimate the experimental drug solubilization compared to the Hansen solubility parameters. The latter were able to correctly predict some trend regarding good and poor solubilizers, yet the overall predictive strength of Hansen solubility parameters is clearly unsatisfactory.
    MeSH term(s) Hydrophobic and Hydrophilic Interactions ; Micelles ; Pharmaceutical Preparations/chemistry ; Polymers/chemistry ; Solubility
    Chemical Substances Micelles ; Pharmaceutical Preparations ; Polymers
    Language English
    Publishing date 2019-07-18
    Publishing country United States
    Document type Evaluation Study ; Journal Article ; Research Support, Non-U.S. Gov't
    ISSN 1526-4602
    ISSN (online) 1526-4602
    DOI 10.1021/acs.biomac.9b00618
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  4. Article ; Online: Complexation and Release of N-Heterocyclic Carbene-Aminoborylene Ligands from Group VI and VIII Metals.

    Pranckevicius, Conor / Jimenéz-Halla, J Oscar C / Kirsch, Marius / Krummenacher, Ivo / Braunschweig, Holger

    Journal of the American Chemical Society

    2018  Volume 140, Issue 33, Page(s) 10524–10529

    Abstract: The coordination chemistry and stability of aminoborylene ligands bearing different N-heterocyclic carbene (NHC) stabilizing groups has been investigated with Group VI and VIII metals. NHC-aminoborylene complexes have been accessed via reduction of NHC- ... ...

    Abstract The coordination chemistry and stability of aminoborylene ligands bearing different N-heterocyclic carbene (NHC) stabilizing groups has been investigated with Group VI and VIII metals. NHC-aminoborylene complexes have been accessed via reduction of NHC-dihaloaminoborane adducts with Na
    Language English
    Publishing date 2018-08-10
    Publishing country United States
    Document type Journal Article ; Research Support, Non-U.S. Gov't
    ZDB-ID 3155-0
    ISSN 1520-5126 ; 0002-7863
    ISSN (online) 1520-5126
    ISSN 0002-7863
    DOI 10.1021/jacs.8b05398
    Database MEDical Literature Analysis and Retrieval System OnLINE

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    In stock of ZB MED Bonn / Germany

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  5. Article ; Online: More Is Sometimes Less: Curcumin and Paclitaxel Formulations Using Poly(2-oxazoline) and Poly(2-oxazine)-Based Amphiphiles Bearing Linear and Branched C9 Side Chains.

    Lübtow, Michael M / Keßler, Larissa / Appelt-Menzel, Antje / Lorson, Thomas / Gangloff, Niklas / Kirsch, Marius / Dahms, Selma / Luxenhofer, Robert

    Macromolecular bioscience

    2018  Volume 18, Issue 11, Page(s) e1800155

    Abstract: A known limitation of polymer micelles for the formulation of hydrophobic drugs is their low loading capacity (LC), which rarely exceeds 20 wt%. One general strategy to overcome this limitation is to increase the amphiphilic contrast, that is, to make ... ...

    Abstract A known limitation of polymer micelles for the formulation of hydrophobic drugs is their low loading capacity (LC), which rarely exceeds 20 wt%. One general strategy to overcome this limitation is to increase the amphiphilic contrast, that is, to make the hydrophobic core of the micelles more hydrophobic. However, in the case of poly(2-oxazoline) (POx)-based amphiphilic triblock copolymers, a minimal amphiphilic contrast was reported to be beneficial. Here, this subject is revisited in more detail using long hydrophobic side chains that are either linear (nonyl) or branched (3-ethylheptyl). Two different backbones within the hydrophobic block are investigated, in particular POx and poly(2-oxazine) (POzi), for the solubilization and co-solubilization of the two highly water insoluble compounds, curcumin and paclitaxel. Even though high loading capacities can be achieved for curcumin using POzi-based triblock copolymers, the solubilization capacity of all investigated polymers with longer side chains is significantly lower compared to POx and poly(2-oxazine)s with shorter side chains. Although the even lower LC for paclitaxel can be somehow improved by co-formulating curcumin, this study corroborates that in the case of POx and POzi-based polymer micelles, an increased amphiphilic contrast leads to less drug solubilization.
    MeSH term(s) Cells, Cultured ; Curcumin/chemistry ; Curcumin/pharmacokinetics ; Curcumin/pharmacology ; Fibroblasts/cytology ; Fibroblasts/metabolism ; Humans ; Oxazoles/chemistry ; Paclitaxel/chemistry ; Paclitaxel/pharmacokinetics ; Paclitaxel/pharmacology ; Solubility
    Chemical Substances Oxazoles ; poly(2-oxazoline) ; Curcumin (IT942ZTH98) ; Paclitaxel (P88XT4IS4D)
    Language English
    Publishing date 2018-09-05
    Publishing country Germany
    Document type Journal Article ; Research Support, Non-U.S. Gov't
    ZDB-ID 2039130-4
    ISSN 1616-5195 ; 1616-5187
    ISSN (online) 1616-5195
    ISSN 1616-5187
    DOI 10.1002/mabi.201800155
    Database MEDical Literature Analysis and Retrieval System OnLINE

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