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  1. Article ; Online: Aldehyde-Functional Diblock Copolymer Nano-objects

    Brotherton, Emma E / Smallridge, Mark J / Armes, Steven P

    Biomacromolecules

    2021  Volume 22, Issue 12, Page(s) 5382–5389

    Abstract: We report the rational design of aldehyde-functional sterically stabilized diblock copolymer nano-objects in aqueous ... ...

    Abstract We report the rational design of aldehyde-functional sterically stabilized diblock copolymer nano-objects in aqueous solution
    MeSH term(s) Alcohols ; Aldehydes ; Polymerization ; Polymers/chemistry ; Water/chemistry
    Chemical Substances Alcohols ; Aldehydes ; Polymers ; Water (059QF0KO0R)
    Language English
    Publishing date 2021-11-23
    Publishing country United States
    Document type Journal Article ; Research Support, Non-U.S. Gov't
    ISSN 1526-4602
    ISSN (online) 1526-4602
    DOI 10.1021/acs.biomac.1c01327
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  2. Article: Hydrophilic Aldehyde-Functional Polymer Brushes: Synthesis, Characterization, and Potential Bioapplications.

    Brotherton, Emma E / Johnson, Edwin C / Smallridge, Mark J / Hammond, Deborah B / Leggett, Graham J / Armes, Steven P

    Macromolecules

    2023  Volume 56, Issue 5, Page(s) 2070–2080

    Abstract: Surface-initiated activators regenerated by electron transfer atom transfer radical polymerization (ARGET ATRP) is used to polymerize ... ...

    Abstract Surface-initiated activators regenerated by electron transfer atom transfer radical polymerization (ARGET ATRP) is used to polymerize a
    Language English
    Publishing date 2023-02-22
    Publishing country United States
    Document type Journal Article
    ZDB-ID 3436-8
    ISSN 0024-9297
    ISSN 0024-9297
    DOI 10.1021/acs.macromol.2c02471
    Database MEDical Literature Analysis and Retrieval System OnLINE

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  3. Article ; Online: Histidine-Functionalized Diblock Copolymer Nanoparticles Exhibit Enhanced Adsorption onto Planar Stainless Steel.

    Brotherton, Emma E / Josland, Daniel / György, Csilla / Johnson, Edwin C / Chan, Derek H H / Smallridge, Mark J / Armes, Steven P

    Macromolecular rapid communications

    2023  Volume 44, Issue 16, Page(s) e2200903

    Abstract: RAFT aqueous emulsion polymerization of isopropylideneglycerol monomethacrylate (IPGMA) is used to prepare a series of ... ...

    Abstract RAFT aqueous emulsion polymerization of isopropylideneglycerol monomethacrylate (IPGMA) is used to prepare a series of PGEO5MA
    MeSH term(s) Histidine/chemistry ; Stainless Steel ; Adsorption ; Polymers/chemistry ; Nanoparticles/chemistry
    Chemical Substances Histidine (4QD397987E) ; Stainless Steel (12597-68-1) ; Polymers
    Language English
    Publishing date 2023-01-09
    Publishing country Germany
    Document type Journal Article
    ZDB-ID 1475027-2
    ISSN 1521-3927 ; 1022-1336
    ISSN (online) 1521-3927
    ISSN 1022-1336
    DOI 10.1002/marc.202200903
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  4. Article: Aldehyde-Functional Diblock Copolymer Nano-objects via RAFT Aqueous Dispersion Polymerization

    Brotherton, Emma E. / Smallridge, Mark J. / Armes, Steven P.

    Biomacromolecules. 2021 Nov. 24, v. 22, no. 12

    2021  

    Abstract: We report the rational design of aldehyde-functional sterically stabilized diblock copolymer nano-objects in aqueous solution via polymerization-induced self-assembly. More specifically, reversible addition–fragmentation chain transfer aqueous dispersion ...

    Abstract We report the rational design of aldehyde-functional sterically stabilized diblock copolymer nano-objects in aqueous solution via polymerization-induced self-assembly. More specifically, reversible addition–fragmentation chain transfer aqueous dispersion polymerization of 2-hydroxypropyl methacrylate is conducted using a water-soluble precursor block in which every methacrylic repeat unit contains a pendent oligo(ethylene glycol) side chain capped with a cis-diol unit. Systematic variation of the reaction conditions enables the construction of a pseudo-phase diagram, which ensures the reproducible targeting of pure spheres, worms, or vesicles. Selective oxidation of the pendent cis-diol groups using aqueous sodium periodate under mild conditions introduces geminal diols (i.e., the hydrated form of an aldehyde obtained in the presence of water) into the steric stabilizer chains without loss of colloidal stability. In the case of diblock copolymer vesicles, such derivatization leads to the formation of a worm population, indicating partial loss of the original morphology. However, this problem can be circumvented by cross-linking the membrane-forming block prior to periodate oxidation. Moreover, such covalently stabilized aldehyde-functionalized vesicles can be subsequently reacted with either glycine or histidine in aqueous solution, followed by reductive amination to prevent hydrolysis of the labile imine bond. ζ potential measurements confirm that this derivatization significantly affects the electrophoretic behavior of these vesicles. Similarly, the membrane-crosslinked aldehyde-functionalized vesicles can be reacted with a model globular protein, bovine serum albumin, to produce “stealthy” protein-decorated vesicles.
    Keywords aldehydes ; amination ; aqueous solutions ; bovine serum albumin ; chemical bonding ; composite polymers ; crosslinking ; derivatization ; electrophoresis ; glycols ; histidine ; hydrolysis ; imines ; oxidation ; polymerization ; sodium ; stabilizers ; water solubility
    Language English
    Dates of publication 2021-1124
    Size p. 5382-5389.
    Publishing place American Chemical Society
    Document type Article
    ISSN 1526-4602
    DOI 10.1021/acs.biomac.1c01327
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  5. Article ; Online: Mucoadhesive pickering nanoemulsions via dynamic covalent chemistry

    Hunter, Saul J. / Abu Elella, Mahmoud H. / Johnson, Edwin C. / Taramova, Laura / Brotherton, Emma E. / Armes, Steven P. / Khutoryanskiy, Vitaliy V. / Smallridge, Mark J.

    Journal of Colloid And Interface Science. 2023 Dec., v. 651 p.334-345

    2023  

    Abstract: Hypothesis. Submicron oil droplets stabilized using aldehyde-functionalized nanoparticles should adhere to the primary amine groups present at the surface of sheep nasal mucosal tissue via Schiff base chemistry. Experiments. Well-defined sterically- ... ...

    Abstract Hypothesis. Submicron oil droplets stabilized using aldehyde-functionalized nanoparticles should adhere to the primary amine groups present at the surface of sheep nasal mucosal tissue via Schiff base chemistry. Experiments. Well-defined sterically-stabilized diblock copolymer nanoparticles of 20 nm diameter were prepared in the form of concentrated aqueous dispersions via reversible addition-fragmentation chain transfer (RAFT) aqueous emulsion polymerization of 2,2,2-trifluoroethyl methacrylate (TFEMA) using a water-soluble methacrylic precursor bearing cis-diol groups. Some of these hydroxyl-functional nanoparticles were then selectively oxidized using an aqueous solution of sodium periodate to form a second batch of nanoparticles bearing pendent aldehyde groups within the steric stabilizer chains. Subjecting either hydroxyl- or aldehyde-functional nanoparticles to high-shear homogenization with a model oil (squalane) produced oil-in-water Pickering macroemulsions of 20–30 µm diameter. High-pressure microfluidization of such macroemulsions led to formation of the corresponding Pickering nanoemulsions with a mean droplet diameter of around 200 nm. Quartz crystal microbalance (QCM) experiments were used to examine adsorption of both nanoparticles and oil droplets onto a model planar substrate bearing primary amine groups, while a fluorescence microscopy-based mucoadhesion assay was developed to assess adsorption of the oil droplets onto sheep nasal mucosal tissue. Findings. Squalane droplets coated with aldehyde-functional nanoparticles adhered significantly more strongly to sheep nasal mucosal tissue than those coated with the corresponding hydroxyl-functional nanoparticles. This difference was attributed to the formation of surface imine bonds via Schiff base chemistry and was also observed for the two types of nanoparticles alone in QCM studies. Preliminary biocompatibility studies using planaria indicated only mild toxicity for these new mucoadhesive Pickering nanoemulsions, suggesting potential applications for the localized delivery of hydrophobic drugs.
    Keywords adsorption ; aldehydes ; aqueous solutions ; bioadhesives ; biocompatibility ; composite polymers ; droplets ; emulsions ; fluorescence microscopy ; homogenization ; hydrophobicity ; imines ; mucoadhesion ; nanoparticles ; nose ; oils ; polymerization ; quartz crystal microbalance ; schiff bases ; sheep ; sodium ; stabilizers ; toxicity ; water solubility ; Nanoemulsions ; Pickering emulsions ; Block copolymers ; Sterically-stabilized nanoparticles ; Schiff base chemistry ; Aldehyde-functional
    Language English
    Dates of publication 2023-12
    Size p. 334-345.
    Publishing place Elsevier Inc.
    Document type Article ; Online
    ZDB-ID 241597-5
    ISSN 1095-7103 ; 0021-9797
    ISSN (online) 1095-7103
    ISSN 0021-9797
    DOI 10.1016/j.jcis.2023.07.162
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  6. Article ; Online: New Aldehyde-Functional Methacrylic Water-Soluble Polymers.

    Brotherton, Emma E / Jesson, Craig P / Warren, Nicholas J / Smallridge, Mark J / Armes, Steven P

    Angewandte Chemie (International ed. in English)

    2021  Volume 60, Issue 21, Page(s) 12032–12037

    Abstract: Aldehyde groups enable facile conjugation to proteins, enzymes, oligonucleotides or fluorescent dyes, yet there are no literature examples of water-soluble aldehyde-functional vinyl monomers. We report the synthesis of a new hydrophilic cis-diol-based ... ...

    Abstract Aldehyde groups enable facile conjugation to proteins, enzymes, oligonucleotides or fluorescent dyes, yet there are no literature examples of water-soluble aldehyde-functional vinyl monomers. We report the synthesis of a new hydrophilic cis-diol-based methacrylic monomer (GEO5MA) by transesterification of isopropylideneglycerol penta(ethylene glycol) using methyl methacrylate followed by acetone deprotection via acid hydrolysis. The corresponding water-soluble aldehyde monomer, AGEO5MA, is prepared by aqueous periodate oxidation of GEO5MA at 22 °C. RAFT polymerization of GEO5MA yields the water-soluble homopolymer, PGEO5MA. Aqueous periodate oxidation of the terminal cis-diol units on PGEO5MA at 22 °C affords a water-soluble aldehyde-functional homopolymer (PAGEO5MA). Moreover, a library of hydrophilic statistical copolymers bearing cis-diol and aldehyde groups was prepared using sub-stoichiometric periodate/cis-diol molar ratios. The aldehyde groups on PAGEO5MA homopolymer were reacted in turn with three amino acids to demonstrate synthetic utility.
    Language English
    Publishing date 2021-05-03
    Publishing country Germany
    Document type Journal Article ; Research Support, Non-U.S. Gov't
    ZDB-ID 2011836-3
    ISSN 1521-3773 ; 1433-7851
    ISSN (online) 1521-3773
    ISSN 1433-7851
    DOI 10.1002/anie.202015298
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  7. Article: Aldehyde-functional thermoresponsive diblock copolymer worm gels exhibit strong mucoadhesion.

    Brotherton, Emma E / Neal, Thomas J / Kaldybekov, Daulet B / Smallridge, Mark J / Khutoryanskiy, Vitaliy V / Armes, Steven P

    Chemical science

    2022  Volume 13, Issue 23, Page(s) 6888–6898

    Abstract: A series of thermoresponsive diblock copolymer worm gels is ... ...

    Abstract A series of thermoresponsive diblock copolymer worm gels is prepared
    Language English
    Publishing date 2022-05-26
    Publishing country England
    Document type Journal Article
    ZDB-ID 2559110-1
    ISSN 2041-6539 ; 2041-6520
    ISSN (online) 2041-6539
    ISSN 2041-6520
    DOI 10.1039/d2sc02074b
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  8. Article ; Online: Mucoadhesive pickering nanoemulsions via dynamic covalent chemistry.

    Hunter, Saul J / Abu Elella, Mahmoud H / Johnson, Edwin C / Taramova, Laura / Brotherton, Emma E / Armes, Steven P / Khutoryanskiy, Vitaliy V / Smallridge, Mark J

    Journal of colloid and interface science

    2023  Volume 651, Page(s) 334–345

    Abstract: Hypothesis: Submicron oil droplets stabilized using aldehyde-functionalized nanoparticles should adhere to the primary amine groups present at the surface of sheep nasal mucosal tissue via Schiff base chemistry.: Experiments: Well-defined sterically- ... ...

    Abstract Hypothesis: Submicron oil droplets stabilized using aldehyde-functionalized nanoparticles should adhere to the primary amine groups present at the surface of sheep nasal mucosal tissue via Schiff base chemistry.
    Experiments: Well-defined sterically-stabilized diblock copolymer nanoparticles of 20 nm diameter were prepared in the form of concentrated aqueous dispersions via reversible addition-fragmentation chain transfer (RAFT) aqueous emulsion polymerization of 2,2,2-trifluoroethyl methacrylate (TFEMA) using a water-soluble methacrylic precursor bearing cis-diol groups. Some of these hydroxyl-functional nanoparticles were then selectively oxidized using an aqueous solution of sodium periodate to form a second batch of nanoparticles bearing pendent aldehyde groups within the steric stabilizer chains. Subjecting either hydroxyl- or aldehyde-functional nanoparticles to high-shear homogenization with a model oil (squalane) produced oil-in-water Pickering macroemulsions of 20-30 µm diameter. High-pressure microfluidization of such macroemulsions led to formation of the corresponding Pickering nanoemulsions with a mean droplet diameter of around 200 nm. Quartz crystal microbalance (QCM) experiments were used to examine adsorption of both nanoparticles and oil droplets onto a model planar substrate bearing primary amine groups, while a fluorescence microscopy-based mucoadhesion assay was developed to assess adsorption of the oil droplets onto sheep nasal mucosal tissue.
    Findings: Squalane droplets coated with aldehyde-functional nanoparticles adhered significantly more strongly to sheep nasal mucosal tissue than those coated with the corresponding hydroxyl-functional nanoparticles. This difference was attributed to the formation of surface imine bonds via Schiff base chemistry and was also observed for the two types of nanoparticles alone in QCM studies. Preliminary biocompatibility studies using planaria indicated only mild toxicity for these new mucoadhesive Pickering nanoemulsions, suggesting potential applications for the localized delivery of hydrophobic drugs.
    Language English
    Publishing date 2023-07-27
    Publishing country United States
    Document type Journal Article
    ZDB-ID 241597-5
    ISSN 1095-7103 ; 0021-9797
    ISSN (online) 1095-7103
    ISSN 0021-9797
    DOI 10.1016/j.jcis.2023.07.162
    Database MEDical Literature Analysis and Retrieval System OnLINE

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    In stock of ZB MED Bonn / Germany

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  9. Article: Synthesis of High Molecular Weight Poly(glycerol monomethacrylate) via RAFT Emulsion Polymerization of Isopropylideneglycerol Methacrylate.

    Jesson, Craig P / Cunningham, Victoria J / Smallridge, Mark J / Armes, Steven P

    Macromolecules

    2018  Volume 51, Issue 9, Page(s) 3221–3232

    Abstract: High molecular weight water-soluble polymers are widely used as flocculants or thickeners. However, synthesis of such polymers via solution polymerization invariably results in highly viscous fluids, which makes subsequent processing somewhat problematic. ...

    Abstract High molecular weight water-soluble polymers are widely used as flocculants or thickeners. However, synthesis of such polymers via solution polymerization invariably results in highly viscous fluids, which makes subsequent processing somewhat problematic. Alternatively, such polymers can be prepared as colloidal dispersions; in principle, this is advantageous because the particulate nature of the polymer chains ensures a much lower fluid viscosity. Herein we exemplify the latter approach by reporting the convenient one-pot synthesis of high molecular weight poly(glycerol monomethacrylate) (PGMA) via the reversible addition-fragmentation chain transfer (RAFT) aqueous emulsion polymerization of a water-immiscible protected monomer precursor, isopropylideneglycerol methacrylate (IPGMA) at 70 °C, using a water-soluble poly(glycerol monomethacrylate) (PGMA) chain transfer agent as a steric stabilizer. This formulation produces a low-viscosity aqueous dispersion of PGMA-PIPGMA diblock copolymer nanoparticles at 20% solids. Subsequent acid deprotection of the hydrophobic core-forming PIPGMA block leads to particle dissolution and affords a viscous aqueous solution comprising high molecular weight PGMA homopolymer chains with a relatively narrow molecular weight distribution. Moreover, it is shown that this latex precursor route offers an important advantage compared to the RAFT aqueous solution polymerization of glycerol monomethacrylate since it provides a significantly faster rate of polymerization (and hence higher monomer conversion) under comparable conditions.
    Language English
    Publishing date 2018-04-16
    Publishing country United States
    Document type Journal Article
    ZDB-ID 3436-8
    ISSN 0024-9297
    ISSN 0024-9297
    DOI 10.1021/acs.macromol.8b00294
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  10. Article: Order-Order Morphological Transitions for Dual Stimulus Responsive Diblock Copolymer Vesicles.

    Lovett, Joseph R / Warren, Nicholas J / Armes, Steven P / Smallridge, Mark J / Cracknell, Robert B

    Macromolecules

    2016  Volume 49, Issue 3, Page(s) 1016–1025

    Abstract: A series of non-ionic poly(glycerol monomethacrylate)-poly(2-hydroxypropyl methacrylate) (PGMA-PHPMA) diblock copolymer vesicles has been prepared by reversible addition-fragmentation chain transfer (RAFT) aqueous dispersion polymerization of HPMA at 70 ° ...

    Abstract A series of non-ionic poly(glycerol monomethacrylate)-poly(2-hydroxypropyl methacrylate) (PGMA-PHPMA) diblock copolymer vesicles has been prepared by reversible addition-fragmentation chain transfer (RAFT) aqueous dispersion polymerization of HPMA at 70 °C at low pH using a carboxylic acid-based chain transfer agent. The degree of polymerization (DP) of the PGMA block was fixed at 43, and the DP of the PHPMA block was systematically varied from 175 to 250 in order to target vesicle phase space. Based on our recent work describing the analogous PGMA-PHPMA diblock copolymer
    Language English
    Publishing date 2016-01-28
    Publishing country United States
    Document type Journal Article
    ZDB-ID 3436-8
    ISSN 0024-9297
    ISSN 0024-9297
    DOI 10.1021/acs.macromol.5b02470
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