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2-Hydroxyethyl Methacrylate

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Daniel Horák – One of the best experts on this subject based on the ideXlab platform.

  • Reductively Degradable Poly(2-Hydroxyethyl Methacrylate) Hydrogels with Oriented Porosity for Tissue Engineering Applications.
    ACS applied materials & interfaces, 2017
    Co-Authors: Hana Macková, Daniel Horák, Zdeněk Plichta, Helena Hlídková, Ondřej Sedláček, Rafał Konefał, Zhansaya Sadakbayeva, Miroslava Dušková-smrčková, Sarka Kubinova

    Abstract:

    Degradable poly(2-Hydroxyethyl Methacrylate) hydrogels were prepared from a linear copolymer (Mw = 49 kDa) of 2-Hydroxyethyl Methacrylate (HEMA), 2-(acethylthio)ethyl Methacrylate (ATEMA), and zwitterionic 2-methacryloyloxyethyl phosphorylcholine (MPC). The deprotection of ATEMA thiol groups by triethylamine followed by their gentle oxidation with 2,2′-dithiodipyridine resulted in the formation of reductively degradable polymers with disulfide bridges. Finally, a hydrogel 3D structure with an oriented porosity was obtained by gelation of the polymer in the presence of needle-like sodium acetate crystals. The pore diameter and porosity of resulting poly(2-Hydroxyethyl Methacrylate-co-2-(acethylthio)ethyl Methacrylate-co-2-methacryloyloxyethyl phosphorylcholine) [P(HEMA-ATEMA-MPC)] hydrogels varied between 59 and 65 μm and between 70 and 79.6 vol % according to Hg porosimetry, and complete degradation of these materials was reached in 86 days in 0.33 mmol solution of l-cysteine/L in phosphate buffer. The cross-linked P(HEMA-ATEMA-MPC) hydrogels were evaluated as a possible support for human mesenchymal stem cells (MSCs). No cytotoxicity was found for the un-cross-linked thiol-containing and protected P(HEMA-ATEMA-MPC) chains up to a concentration of 5 and 1 wt % in α-minimum essential medium, respectively.

  • Reductively Degradable Poly(2-Hydroxyethyl Methacrylate) Hydrogels with Oriented Porosity for Tissue Engineering Applications
    ACS Applied Materials & Interfaces, 2017
    Co-Authors: Hana Macková, Daniel Horák, Zdeněk Plichta, Helena Hlídková, Ondřej Sedláček, Rafał Konefał, Zhansaya Sadakbayeva, Miroslava Dušková-smrčková, Sarka Kubinova

    Abstract:

    Degradable poly(2-Hydroxyethyl Methacrylate) hydrogels were prepared from a linear copolymer (Mw = 49 kDa) of 2-Hydroxyethyl Methacrylate (HEMA), 2-(acethylthio)ethyl Methacrylate (ATEMA), and zwitterionic 2-methacryloyloxyethyl phosphorylcholine (MPC). The deprotection of ATEMA thiol groups by triethylamine followed by their gentle oxidation with 2,2′-dithiodipyridine resulted in the formation of reductively degradable polymers with disulfide bridges. Finally, a hydrogel 3D structure with an oriented porosity was obtained by gelation of the polymer in the presence of needle-like sodium acetate crystals. The pore diameter and porosity of resulting poly(2-Hydroxyethyl Methacrylate-co-2-(acethylthio)ethyl Methacrylate-co-2-methacryloyloxyethyl phosphorylcholine) [P(HEMA-ATEMA-MPC)] hydrogels varied between 59 and 65 μm and between 70 and 79.6 vol % according to Hg porosimetry, and complete degradation of these materials was reached in 86 days in 0.33 mmol solution of l-cysteine/L in phosphate buffer. The cr…

  • cholesterol modified superporous poly 2 hydroxyethyl Methacrylate scaffolds for tissue engineering
    Biomaterials, 2009
    Co-Authors: Sarka Kubinova, Eva Syková, Daniel Horák

    Abstract:

    Modifications of poly(2-Hydroxyethyl Methacrylate) (PHEMA) with cholesterol and laminin have been developed to design scaffolds that promote cell–surface interaction. Cholesterol-modified superporous PHEMA scaffolds have been prepared by the bulk radical copolymerization of 2-Hydroxyethyl Methacrylate (HEMA), cholesterol Methacrylate (CHLMA) and the cross-linking agent ethylene diMethacrylate (EDMA) in the presence of ammonium oxalate crystals to introduce interconnected superpores in the matrix. With the aim of immobilizing laminin (LN), carboxyl groups were also introduced to the scaffold by the copolymerization of the above monomers with 2-[(methoxycarbonyl)methoxy]ethyl Methacrylate (MCMEMA). Subsequently, the MCMEMA moiety in the resulting hydrogel was hydrolyzed to [2(methacryloyloxy)ethoxy]acetic acid (MOEAA), and laminin was immobilized via carbodiimide and N-hydroxysulfosuccinimide chemistry. The attachment, viability and morphology of mesenchymal stem cells (MSCs) were evaluated on both nonporous and superporous laminin-modified as well as lamininunmodified PHEMA and poly(2-Hydroxyethyl Methacrylate-co-cholesterol Methacrylate) P(HEMA– CHLMA) hydrogels. Neat PHEMA and laminin-modified PHEMA (LN–PHEMA) scaffolds facilitated MSC attachment, but did not support cell spreading and proliferation; the viability of the attached cells decreased with time of cultivation. In contrast, MSCs spread and proliferated on P(HEMA–CHLMA) and LN-P(HEMA–CHLMA) hydrogels.

Sarka Kubinova – One of the best experts on this subject based on the ideXlab platform.

  • Reductively Degradable Poly(2-Hydroxyethyl Methacrylate) Hydrogels with Oriented Porosity for Tissue Engineering Applications.
    ACS applied materials & interfaces, 2017
    Co-Authors: Hana Macková, Daniel Horák, Zdeněk Plichta, Helena Hlídková, Ondřej Sedláček, Rafał Konefał, Zhansaya Sadakbayeva, Miroslava Dušková-smrčková, Sarka Kubinova

    Abstract:

    Degradable poly(2-Hydroxyethyl Methacrylate) hydrogels were prepared from a linear copolymer (Mw = 49 kDa) of 2-Hydroxyethyl Methacrylate (HEMA), 2-(acethylthio)ethyl Methacrylate (ATEMA), and zwitterionic 2-methacryloyloxyethyl phosphorylcholine (MPC). The deprotection of ATEMA thiol groups by triethylamine followed by their gentle oxidation with 2,2′-dithiodipyridine resulted in the formation of reductively degradable polymers with disulfide bridges. Finally, a hydrogel 3D structure with an oriented porosity was obtained by gelation of the polymer in the presence of needle-like sodium acetate crystals. The pore diameter and porosity of resulting poly(2-Hydroxyethyl Methacrylate-co-2-(acethylthio)ethyl Methacrylate-co-2-methacryloyloxyethyl phosphorylcholine) [P(HEMA-ATEMA-MPC)] hydrogels varied between 59 and 65 μm and between 70 and 79.6 vol % according to Hg porosimetry, and complete degradation of these materials was reached in 86 days in 0.33 mmol solution of l-cysteine/L in phosphate buffer. The cross-linked P(HEMA-ATEMA-MPC) hydrogels were evaluated as a possible support for human mesenchymal stem cells (MSCs). No cytotoxicity was found for the un-cross-linked thiol-containing and protected P(HEMA-ATEMA-MPC) chains up to a concentration of 5 and 1 wt % in α-minimum essential medium, respectively.

  • Reductively Degradable Poly(2-Hydroxyethyl Methacrylate) Hydrogels with Oriented Porosity for Tissue Engineering Applications
    ACS Applied Materials & Interfaces, 2017
    Co-Authors: Hana Macková, Daniel Horák, Zdeněk Plichta, Helena Hlídková, Ondřej Sedláček, Rafał Konefał, Zhansaya Sadakbayeva, Miroslava Dušková-smrčková, Sarka Kubinova

    Abstract:

    Degradable poly(2-Hydroxyethyl Methacrylate) hydrogels were prepared from a linear copolymer (Mw = 49 kDa) of 2-Hydroxyethyl Methacrylate (HEMA), 2-(acethylthio)ethyl Methacrylate (ATEMA), and zwitterionic 2-methacryloyloxyethyl phosphorylcholine (MPC). The deprotection of ATEMA thiol groups by triethylamine followed by their gentle oxidation with 2,2′-dithiodipyridine resulted in the formation of reductively degradable polymers with disulfide bridges. Finally, a hydrogel 3D structure with an oriented porosity was obtained by gelation of the polymer in the presence of needle-like sodium acetate crystals. The pore diameter and porosity of resulting poly(2-Hydroxyethyl Methacrylate-co-2-(acethylthio)ethyl Methacrylate-co-2-methacryloyloxyethyl phosphorylcholine) [P(HEMA-ATEMA-MPC)] hydrogels varied between 59 and 65 μm and between 70 and 79.6 vol % according to Hg porosimetry, and complete degradation of these materials was reached in 86 days in 0.33 mmol solution of l-cysteine/L in phosphate buffer. The cr…

  • cholesterol modified superporous poly 2 hydroxyethyl Methacrylate scaffolds for tissue engineering
    Biomaterials, 2009
    Co-Authors: Sarka Kubinova, Eva Syková, Daniel Horák

    Abstract:

    Modifications of poly(2-Hydroxyethyl Methacrylate) (PHEMA) with cholesterol and laminin have been developed to design scaffolds that promote cell–surface interaction. Cholesterol-modified superporous PHEMA scaffolds have been prepared by the bulk radical copolymerization of 2-Hydroxyethyl Methacrylate (HEMA), cholesterol Methacrylate (CHLMA) and the cross-linking agent ethylene diMethacrylate (EDMA) in the presence of ammonium oxalate crystals to introduce interconnected superpores in the matrix. With the aim of immobilizing laminin (LN), carboxyl groups were also introduced to the scaffold by the copolymerization of the above monomers with 2-[(methoxycarbonyl)methoxy]ethyl Methacrylate (MCMEMA). Subsequently, the MCMEMA moiety in the resulting hydrogel was hydrolyzed to [2(methacryloyloxy)ethoxy]acetic acid (MOEAA), and laminin was immobilized via carbodiimide and N-hydroxysulfosuccinimide chemistry. The attachment, viability and morphology of mesenchymal stem cells (MSCs) were evaluated on both nonporous and superporous laminin-modified as well as lamininunmodified PHEMA and poly(2-Hydroxyethyl Methacrylate-co-cholesterol Methacrylate) P(HEMA– CHLMA) hydrogels. Neat PHEMA and laminin-modified PHEMA (LN–PHEMA) scaffolds facilitated MSC attachment, but did not support cell spreading and proliferation; the viability of the attached cells decreased with time of cultivation. In contrast, MSCs spread and proliferated on P(HEMA–CHLMA) and LN-P(HEMA–CHLMA) hydrogels.

B. Chithambara Thanoo – One of the best experts on this subject based on the ideXlab platform.

  • Polymerization of 2-Hydroxyethyl Methacrylate as large size spherical beads
    Polymer, 1990
    Co-Authors: Athipettah Jayakrishnan, M. C. Sunny, B. Chithambara Thanoo

    Abstract:

    Poly(2-Hydroxyethyl Methacrylate) (PHEMA) beads of fairly large size (more than 2.0mm in diameter) crosslinked with ethyleneglycol diMethacrylate (EGDM) were prepared by the suspension polymerization of 2-Hydroxyethyl Methacrylate (HEMA) in the presence of benzyl alcohol (BA) in 35% sodium chloride solutions using 2,2′-azobis isobutyronitrile (AIBN) as the polymerization initiator. Magnesium hydroxide formed in situ served as the suspension stabilizer during polymerization. The presence of BA afforded the preparation of clear, large size spherical beads whereas many other inert solvents such as toluene, hexane, isopropanol or cyclohexanol either yielded beads of very small size or particles of irregular shape. The effect of concentration of EGDM, Mg(OH)2 and the stirring speed on the stability of the suspension and particle size was investigated.

  • Polymerization of 2-Hydroxyethyl Methacrylate as large size spherical beads
    Polymer, 1990
    Co-Authors: Athipettah Jayakrishnan, M. C. Sunny, B. Chithambara Thanoo

    Abstract:

    Poly(2-Hydroxyethyl Methacrylate) (PHEMA) beads of fairly large size (more than 2.0mm in diameter) crosslinked with ethyleneglycol diMethacrylate (EGDM) were prepared by the suspension polymerization of 2-Hydroxyethyl Methacrylate (HEMA) in the presence of benzyl alcohol (BA) in 35% sodium chloride solutions using 2,2′-azobis isobutyronitrile (AIBN) as the polymerization initiator. Magnesium hydroxide formed in situ served as the suspension stabilizer during polymerization. The presence of BA afforded the preparation of clear, large size spherical beads whereas many other inert solvents such as toluene, hexane, isopropanol or cyclohexanol either yielded beads of very small size or particles of irregular shape. The effect of concentration of EGDM, Mg(OH)2 and the stirring speed on the stability of the suspension and particle size was investigated.