Choline supported poly(ionic liquid) graft copolymers as novel delivery systems of anionic pharmaceuticals for anti-inflammatory and anti-coagulant therapy

Abstract New type of carriers based on grafted poly(ionic liquid)s was designed for delivery of ionically attached salicylates (Sal). Choline derived ionic liquid monomeric units were successfully introduced with various content in the side chains by the controlled radical polymerization. Properly high amounts of ionic pharmaceutics in the polymer systems were achieved by the well-fitted length and grafting degree of the side chains. In aqueous solution the graft copolymers were self-assembled into the spherical superstructures with sizes up to 73 nm. Delivery studies showed “burst” release within 4 h, after that it was slower yielding ~70% of released drug within 80 h. Proposed nanocarriers supported low toxicity against human cells (NHDF and BEAS-2B), anti-inflammation activity evaluated with the use of pro-inflammatory interleukins (IL-6 and IL-8) and antibacterial activities towards E. coli. Adjustment of ionic drug content by structural parameters of graft copolymers, including grafting degree and graft length, are advantageous to tailor nanocarriers with self-assembly properties in aqueous media. Effective release process by ionic exchange and biological activity with low toxicity are promising for further development of this type of drug delivery (DDS).

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Poly(ionic liquid)s Based on Copolymers of Poly(ethylene oxide) and Cationic Glycidyl Triazolyl Polymers with Tribranched Side Chains

ACS Macro Letters ◽

10.1021/acsmacrolett.1c00253 ◽

2021 ◽

pp. 831-836

Author(s):

Taichi Ikeda

Keyword(s):

Ionic Liquid ◽

Ethylene Oxide ◽

Side Chains ◽

Poly Ethylene Oxide ◽

Poly Ethylene ◽

Poly Ionic Liquid

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Cationic and dicationic 1,2,3-triazolium-based poly(ethylene glycol ionic liquid)s

Polymer Chemistry ◽

10.1039/c6py02030e ◽

2017 ◽

Vol 8 (5) ◽

pp. 910-917 ◽

Cited By ~ 13

Author(s):

Mona M. Obadia ◽

Antoine Jourdain ◽

Anatoli Serghei ◽

Taichi Ikeda ◽

Eric Drockenmuller

Keyword(s):

Ionic Liquid ◽

Ethylene Glycol ◽

Triethylene Glycol ◽

Side Chains ◽

Poly Ethylene Glycol ◽

Counter Anion ◽

Poly Ethylene ◽

Poly Ionic Liquid

We report the synthesis and in-depth characterization of two novel poly(ionic liquid)s having poly(ethylene glycol) main chains and side chains having either one or two 1,2,3-triazolium cations with triethylene glycol spacers and bis(trifluoromethylsulfonyl)imide counter anion(s).

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Synthesis of Pyrrolidinium-Based Poly(ionic liquid) Electrolytes with Poly(ethylene glycol) Side Chains

Chemistry of Materials ◽

10.1021/cm203790z ◽

2012 ◽

Vol 24 (9) ◽

pp. 1583-1590 ◽

Cited By ~ 96

Author(s):

Markus Döbbelin ◽

Itxaso Azcune ◽

Mélanie Bedu ◽

Alaitz Ruiz de Luzuriaga ◽

Aratz Genua ◽

...

Keyword(s):

Ionic Liquid ◽

Ethylene Glycol ◽

Side Chains ◽

Poly Ethylene Glycol ◽

Liquid Electrolytes ◽

Poly Ethylene ◽

Poly Ionic Liquid

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Poly(ionic liquid)s with branched side chains: polymer design for breaking the conventional record of ionic conductivity

Polymer Chemistry ◽

10.1039/d0py01333a ◽

2021 ◽

Vol 12 (5) ◽

pp. 711-718

Author(s):

Taichi Ikeda

Keyword(s):

Ionic Liquid ◽

Ionic Conductivity ◽

Side Chains ◽

Single Ion Conductors ◽

Poly Ionic Liquid ◽

Ion Conductors

Poly(ionic liquid)s with branched side chains can break the conventional record of ionic conductivity of single-ion conductors.

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Ionic Polymethacrylate Based Delivery Systems: Effect of Carrier Topology and Drug Loading

Pharmaceutics ◽

10.3390/pharmaceutics11070337 ◽

2019 ◽

Vol 11 (7) ◽

pp. 337 ◽

Cited By ~ 5

Author(s):

Dorota Neugebauer ◽

Anna Mielańczyk ◽

Rafał Bielas ◽

Justyna Odrobińska ◽

Maria Kupczak ◽

...

Keyword(s):

Structural Parameters ◽

Drug Loading ◽

Entrapment Efficiency ◽

Water Soluble ◽

Ionic Exchange ◽

Linear Polymers ◽

Self Assembling ◽

Drug Conjugation ◽

Carboxylic Groups ◽

Poly Ionic Liquid

The presented drug delivery polymeric systems (DDS), i.e., conjugates and self-assemblies, based on grafted and star-shaped polymethacrylates have been studied for the last few years in our group. This minireview is focused on the relationship of polymer structure to drug conjugation/entrapment efficiency and release capability. Both graft and linear polymers containing trimethylammonium groups showed the ability to release the pharmaceutical anions by ionic exchange, but in aqueous solution they were also self-assembled into nanoparticles with encapsulated nonionic drugs. Star-shaped polymers functionalized with ionizable amine/carboxylic groups were investigated for drug conjugation via ketimine/amide linkers. However, only the conjugates of polybases were water-soluble, giving opportunity for release studies, whereas the self-assembling polyacidic stars were encapsulated with the model drugs. Depending on the type of drug loading in the polymer matrix, their release rates were ordered as follows: Physical ≥ ionic > covalent. The studies indicated that the well-defined ionic polymethacrylates, including poly(ionic liquid)s, are advantageous for designing macromolecular carriers due to the variety of structural parameters, which are efficient for tuning of drug loading and release behavior in respect to the specific drug interactions.

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The Power of Shielding: Low Toxicity and High Transfection Performance of Cationic Graft Copolymers Containing Poly(2-oxazoline) Side Chains

Biomacromolecules ◽

10.1021/acs.biomac.8b00362 ◽

2018 ◽

Vol 19 (7) ◽

pp. 2759-2771 ◽

Cited By ~ 4

Author(s):

Anne-Kristin Trützschler ◽

Tanja Bus ◽

Martin Sahn ◽

Anja Traeger ◽

Christine Weber ◽

...

Keyword(s):

Graft Copolymers ◽

Side Chains ◽

Low Toxicity

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A Novel Poly(Ionic Liquid) as the Thermal Insulating Material

Recent Innovations in Chemical Engineering (Formerly Recent Patents on Chemical Engineering) ◽

10.2174/2405520413666200207114107 ◽

2020 ◽

Vol 13 (3) ◽

pp. 241-247

Author(s):

Wenxin Wei ◽

Guifeng Ma ◽

Hongtao Wang ◽

Jun Li

Keyword(s):

Thermal Conductivity ◽

Ionic Liquid ◽

Glass Transition ◽

Transition Temperature ◽

Glass Transition Temperature ◽

Flame Resistance ◽

Insulating Material ◽

Low Thermal Conductivity ◽

Thermal Insulating ◽

Poly Ionic Liquid

Objective: A new poly(ionic liquid)(PIL), poly(p-vinylbenzyltriphenylphosphine hexafluorophosphate) (P[VBTPP][PF6]), was synthesized by quaternization, anion exchange reaction, and free radical polymerization. Then a series of the PIL were synthesized at different conditions. Methods: The specific heat capacity, glass-transition temperature and melting temperature of the synthesized PILs were measured by differential scanning calorimeter. The thermal conductivities of the PILs were measured by the laser flash analysis method. Results: Results showed that, under optimized synthesis conditions, P[VBTPP][PF6] as the thermal insulator had a high glass-transition temperature of 210.1°C, high melting point of 421.6°C, and a low thermal conductivity of 0.0920 W m-1 K-1 at 40.0°C (it was 0.105 W m-1 K-1 even at 180.0°C). The foamed sample exhibited much low thermal conductivity λ=0.0340 W m-1 K-1 at room temperature, which was comparable to a commercial polyurethane thermal insulating material although the latter had a much lower density. Conclusion: In addition, mixing the P[VBTPP][PF6] sample into polypropylene could obviously increase the Oxygen Index, revealing its efficient flame resistance. Therefore, P[VBTPP][PF6] is a potential thermal insulating material.

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Ion conformation and orientational order in a dicationic ionic liquid crystal studied by solid-state nuclear magnetic resonance spectroscopy

Scientific Reports ◽

10.1038/s41598-021-85021-y ◽

2021 ◽

Vol 11 (1) ◽

Author(s):

Debashis Majhi ◽

Sergey V. Dvinskikh

Keyword(s):

Ionic Liquid ◽

Ionic Liquids ◽

Liquid Crystals ◽

Bond Order ◽

Van Der Waals ◽

Orientational Order ◽

Smectic Phase ◽

Side Chains ◽

Dicationic Ionic Liquid ◽

Ionic Liquid Crystals

AbstractIonic liquids crystals belong to a special class of ionic liquids that exhibit thermotropic liquid-crystalline behavior. Recently, dicationic ionic liquid crystals have been reported with a cation containing two single-charged ions covalently linked by a spacer. In ionic liquid crystals, electrostatic and hydrogen bonding interactions in ionic sublayer and van der Waals interaction in hydrophobic domains are the main forces contributing to the mesophase stabilization and determining the molecular orientational order and conformation. How these properties in dicationic materials are compared to those in conventional monocationic analogs? We address this question using a combination of advanced NMR methods and DFT analysis. Dicationic salt 3,3′-(1,6-hexanediyl)bis(1-dodecylimidazolium)dibromide was studied. Local bond order parameters of flexible alkyl side chains, linker chain, and alignment of rigid polar groups were analyzed. The dynamic spacer effectively “decouples” the motion of two ionic moieties. Hence, local order and alignment in dicationic mesophase were similar to those in analogous single-chain monocationic salts. Bond order parameters in the side chains in the dicationic smectic phase were found consistently lower compared to double-chain monocationic analogs, suggesting decreasing contribution of van der Waals forces. Overall dication reorientation in the smectic phase was characterized by low values of orientational order parameter S. With increased interaction energy in the polar domain the layered structure is stabilized despite less ordered dications. The results emphasized the trends in the orientational order in ionic liquid crystals and contributed to a better understanding of interparticle interactions driving smectic assembly in this and analogous ionic mesogens.

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