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Polymers
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Polymer Micelles II
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Polymer Micelles II

A special issue of Polymers (ISSN 2073-4360). This special issue belongs to the section "Polymer Chemistry".

Deadline for manuscript submissions: closed (31 December 2020) | Viewed by 36642

Special Issue Editors

Prof. Dr. Shin-Ichi Yusa

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Guest Editor
Department of Materials Science and Chemistry, University of Hyogo, Shosha, Himeji 2167, Hyogo, Japan
Interests: controlled/living radical polymerization; RAFT; TERP; water-soluble polymer; self-organization; polymer micelle; bioconjugate polymer
Special Issues, Collections and Topics in MDPI journals
Prof. Dr. Pratap Bahadur

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Guest Editor
Department of Chemistry, Veer Narmad South Gujarat University, Surat 395007, India
Interests: surface; colloid; nano and polymer science; surfactant; block copolymer
Special Issues, Collections and Topics in MDPI journals
Prof. Dr. Hideki Matsuoka

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Guest Editor
Department of Polymer Chemistry, Kyoto University, Katsura, Nishikyo, Kyoto 615-8510, Japan
Interests: polymer surfactant; amphiphilic polymer; polymer micelle; polymer monolayer; polymer brush; polymer partile; ionic polymer
Special Issues, Collections and Topics in MDPI journals
Prof. Dr. Takahiro Sato

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Guest Editor
Department of Macromolecular Science, Graduate School of Science, Osaka University , 1-1 Machikaneyama-cho, Toyonaka, Osaka 560-0043, Japan
Interests: polymer assemblies; concentrated polymer solutions; helical polymers
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Various applications of aggregates formed from water-soluble polymers—such as drug delivery systems (DDS), diagnosis, separation, concentration, and catalysts—have been reported, but they are not the only ones that form aggregates: Various other polymers do so as well, such as amphiphilic random copolymers, block copolymers, graft copolymers, hyperbranched polymers, star-shaped polymers, and dendrimers. The driving forces of aggregate formation are hydrophobic, electrostatic, hydrogen bonding, and van der Waals interactions, and the structure of the aggregate, unimer micelles, core–shell spherical micelles, worms, and vesicles also play a role. Crosslinking of the core or shell and nanogel structures has also been prepared. In recent years, advances in synthesis techniques, such as controlled living radical polymerization, polymerization-induced self-assembly (PISA), and click chemistries have made it possible to design various polymers with a well-controlled structure. Furthermore, stimuli-responsive polymers are an important class of building blocks of polymers, and a large number of stimuli-responsive polymer micelles have been prepared. The aggregation state can be controlled by external stimuli, such as temperature, pH, light, magnetic and electric fields, salt concentration, specific chemicals, and biomolecules.

Back in 2017, we released “Polymer micelles”; the research environment around polymer micelles has changed rapidly since then, which is why we have decided to plan a continuation of that successful Special Issue, “Polymer Micelles II”. We hope that this new Special Issue will contribute similarly to the research field of polymer micelles. Both original contributions and reviews are welcome.

Prof. Shin-ichi Yusa
Prof. Pratap Bahadur
Prof. Hideki Matsuoka
Prof. Takahiro Sato
Guest Editor

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All submissions that pass pre-check are peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Polymers is an international peer-reviewed open access semimonthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 2700 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.

Keywords

  • Polymer micelles
  • Polymer self-assembly in aqueous solvents
  • Polymer self-assembly in non-aqueous solvents
  • Polymer vesicles
  • Unimolecular micelles
  • Self-assembly by non-surface active polymers
  • Amphiphilic polymers
  • Stimuli-responsive
  • Drug delivery
  • Self-organization
  • Polymerization-induced self-assembly (PISA)

Published Papers (10 papers)

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Research

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12 pages, 1655 KiB  
Article
Characterization of the Micelle Formed by a Hydrophobically Modified Pullulan in Aqueous Solution: Size Exclusion Chromatography
by Jia Yang and Takahiro Sato
Polymers 2021, 13(8), 1237; https://doi.org/10.3390/polym13081237 - 11 Apr 2021
Cited by 2 | Viewed by 1681
Abstract
Size exclusion chromatography equipped with a multi-angle, light-scattering online detector (SEC-MALS) measurements were carried out on a hydrophobically modified pullulan (PUL-OSA) with degrees of substitution (DS) of 0.14, 0.2, and 0.3 in 0.01 M aqueous NaCl to obtain the degree of [...] Read more.
Size exclusion chromatography equipped with a multi-angle, light-scattering online detector (SEC-MALS) measurements were carried out on a hydrophobically modified pullulan (PUL-OSA) with degrees of substitution (DS) of 0.14, 0.2, and 0.3 in 0.01 M aqueous NaCl to obtain the degree of polymerization (N0) dependence of the radius of gyration (⟨S2⟩1/2) for PUL-OSA in the aqueous NaCl. The result was consistent with the loose flower necklace model proposed in a previous study, and the increase in the chain size with introducing OSA groups was explained by the backbone stiffness of the loose flower necklace formed by PUL-OSA. For PUL-OSA samples with DS = 0.2 and 0.3, ⟨S2⟩1/2 obtained by SEC-MALS in a high N0 region deviated downward from ⟨S2⟩1/2 expected by the loose flower necklace model. This deviation came from a tiny amount of the aggregating component of PUL-OSA, taking a branched architecture composed of loose flower necklaces. Although the aggregating component of PUL-OSA was also detected by previous small angle X-ray scattering measurements, its conformation was revealed in this study by SEC-MALS. Full article
(This article belongs to the Special Issue Polymer Micelles II)
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12 pages, 3554 KiB  
Article
Effect of Molecular Architecture on Associating Behavior of Star-Like Amphiphilic Polymers Consisting of Plural Poly(ethylene oxide) and One Alkyl Chain
by Daisuke Kugimoto, Aoi Taniguchi, Masaki Kinoshita and Isamu Akiba
Polymers 2021, 13(3), 460; https://doi.org/10.3390/polym13030460 - 31 Jan 2021
Viewed by 2251
Abstract
Associating behavior of star-like amphiphilic polymers consisting of two or three poly(ethylene oxide) (PEO) chains and one stearyl chain (C18) was investigated. Although the aggregation number (Nagg) of linear analogue of amphiphilic polymers monotonically decreased with increasing number-average molecular weight [...] Read more.
Associating behavior of star-like amphiphilic polymers consisting of two or three poly(ethylene oxide) (PEO) chains and one stearyl chain (C18) was investigated. Although the aggregation number (Nagg) of linear analogue of amphiphilic polymers monotonically decreased with increasing number-average molecular weight of PEO (Mn,PEO), the Nagg of micelles of star-like amphiphilic polymers with Mn,PEO = 550 g/mol was smaller than that with Mn,PEO = 750 g/mol, whereas that with Mn,PEO ≥ 750 g/mol showed general Mn,PEO dependence. Small-angle X-ray scattering analyses revealed that the occupied area of one PEO chain on the interface between hydrophobic core and corona layer in the micelles of star-like polymers was much narrower than that in the linear amphiphilic polymers. This result indica ted the PEO chains of star-like polymers partially took unfavorable conformation near the core–corona interface in polymer micelles. The effect of local conformation of PEO chains near the interface on the associating behavior became significant as Mn,PEO decreased. Therefore, in polymer micelles of star-like amphiphilic polymers containing PEO with Mn,PEO = 550 g/mol, the enlargement of occupied area of PEO on the core–corona interface should be caused to avoid the formation of unfavorable conformations of partial PEO chains, resulting in a decrease in Naggs. Full article
(This article belongs to the Special Issue Polymer Micelles II)
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10 pages, 2526 KiB  
Article
Thermo-Responsive Behavior of Mixed Aqueous Solution of Hydrophilic Polymer with Pendant Phosphorylcholine Group and Poly(Acrylic Acid)
by Hirokazu Fukumoto, Kazuhiko Ishihara and Shin-Ichi Yusa
Polymers 2021, 13(1), 148; https://doi.org/10.3390/polym13010148 - 01 Jan 2021
Cited by 6 | Viewed by 2756
Abstract
A mixed aqueous solution of hydrophilic poly(2-methacryloyloxyethyl phosphorylcholine) (PMPC) and poly(acrylic acid) (PAAc) becomes cloudy under acidic conditions at room temperature. The pendant carboxylic acid groups in PAAc form hydrogen bonds with the ester and phosphate groups in PMPC. While the polymers aggregate [...] Read more.
A mixed aqueous solution of hydrophilic poly(2-methacryloyloxyethyl phosphorylcholine) (PMPC) and poly(acrylic acid) (PAAc) becomes cloudy under acidic conditions at room temperature. The pendant carboxylic acid groups in PAAc form hydrogen bonds with the ester and phosphate groups in PMPC. While the polymers aggregate under acidic conditions, neither one associate under basic conditions because of the deprotonation of the pendant carboxy groups in PAAc. We observed that the interpolymer complex formed from PMPC, and PAAc was dissociated in aqueous solutions with increasing temperature, which is an upper critical solution temperature behavior. With increasing temperature, the molecular motion increased to dissociate the interpolymer complex. The phase transition temperature increased with increasing polymer and salt concentrations, and with decreasing pH. Full article
(This article belongs to the Special Issue Polymer Micelles II)
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18 pages, 4493 KiB  
Article
Tuning Size and Morphology of mPEG-b-p(HPMA-Bz) Copolymer Self-Assemblies Using Microfluidics
by Jaleesa Bresseleers, Mahsa Bagheri, Coralie Lebleu, Sébastien Lecommandoux, Olivier Sandre, Imke A. B. Pijpers, Alexander F. Mason, Silvie Meeuwissen, Cornelus F. van Nostrum, Wim E. Hennink and Jan C.M. van Hest
Polymers 2020, 12(11), 2572; https://doi.org/10.3390/polym12112572 - 02 Nov 2020
Cited by 15 | Viewed by 3645
Abstract
The careful design of nanoparticles, in terms of size and morphology, is of great importance to developing effective drug delivery systems. The ability to precisely tailor nanoparticles in size and morphology during polymer self-assembly was therefore investigated. Four poly(ethylene glycol)-b-poly(N [...] Read more.
The careful design of nanoparticles, in terms of size and morphology, is of great importance to developing effective drug delivery systems. The ability to precisely tailor nanoparticles in size and morphology during polymer self-assembly was therefore investigated. Four poly(ethylene glycol)-b-poly(N-2-benzoyloxypropyl methacrylamide) mPEG-b-p(HPMA-Bz) block copolymers with a fixed hydrophilic block of mPEG 5 kDa and a varying molecular weight of the hydrophobic p(HPMA-Bz) block (A: 17.1, B: 10.0, C: 5.2 and D: 2.7 kDa) were self-assembled into nanoparticles by nanoprecipitation under well-defined flow conditions, using microfluidics, at different concentrations. The nanoparticles from polymer A, increased in size from 55 to 90 nm using lower polymer concentrations and slower flow rates and even polymer vesicles were formed along with micelles. Similarly, nanoparticles from polymer D increased in size from 35 to 70 nm at slower flow rates and also formed vesicles along with micelles, regardless of the used concentration. Differently, polymers B and C mainly self-assembled into micelles at the different applied flow rates with negligible size difference. In conclusion, this study demonstrates that the self-assembly of mPEG-b-p(HPMA-Bz) block copolymers can be easily tailored in size and morphology using microfluidics and is therefore an attractive option for further scaled-up production activities. Full article
(This article belongs to the Special Issue Polymer Micelles II)
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12 pages, 3384 KiB  
Article
Synthesis, Colloidal Characterization and Targetability of Phenylboronic Acid Functionalized α-Tocopheryl Polyethylene Glycol Succinate in Cancer Cells
by Sanjay Tiwari, Jayant Sarolia, Vrushti Kansara, Nishith A. Chudasama, Kamalesh Prasad, Debes Ray, Vinod K Aswal and Pratap Bahadur
Polymers 2020, 12(10), 2258; https://doi.org/10.3390/polym12102258 - 01 Oct 2020
Cited by 8 | Viewed by 2868
Abstract
This study reports targetable micelles developed after covalent functionalization of α-tocopheryl polyethylene glycol succinate (TPGS) with amino phenylboronic acid (APBA). Nuclear magnetic resonance (NMR) and infrared (IR) spectroscopic results showed successful attachment of APBA to the hydrophilic segment of TPGS. Dynamic light scattering [...] Read more.
This study reports targetable micelles developed after covalent functionalization of α-tocopheryl polyethylene glycol succinate (TPGS) with amino phenylboronic acid (APBA). Nuclear magnetic resonance (NMR) and infrared (IR) spectroscopic results showed successful attachment of APBA to the hydrophilic segment of TPGS. Dynamic light scattering and small-angle neutron scattering studies revealed that the conjugate self-assembled in water to produce spherical core-shell micelles (14–20 nm) which remained stable against temperature (ca. 25–45 °C) and pH changes. The micelles could solubilize a high payload of paclitaxel (PLX) without exhibiting changes in the average size. However, at the saturation solubility, drug molecules migrated from the core to the shell region and engaged with APBA groups via π–π stacking interaction. Confocal microscopy and cell sorting analyses verified the effective translocation ability of TPGS-APBA micelles in sialic acid (SA) expressing MDA-MB-453 cells. At equivalent PLX dose, TPGS-APBA micelles showed about a twofold improvement in apoptotic death among the cells exposed for 2 h. Our findings indicate that the attachment of APBA can be a potential strategy for improving the intra-cellular localization of carriers among cancer cells expressing SA residues. Full article
(This article belongs to the Special Issue Polymer Micelles II)
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16 pages, 5850 KiB  
Article
Self-Assembly of Linear Amphiphilic Pentablock Terpolymer PAAx-PS48-PEO46-PS48-PAAxin Dilute Aqueous Solution
by Jia Gao, Kun An, Chao Lv, Jingjing Nie, Junting Xu and Binyang Du
Polymers 2020, 12(10), 2183; https://doi.org/10.3390/polym12102183 - 24 Sep 2020
Cited by 6 | Viewed by 2114
Abstract
A series of linear amphiphilic pentablock terpolymer PAAx-b-PS48-b-PEO46-b-PS48-b-PAAx (AxS48O46S48Ax) with various lengths x of the PAA [...] Read more.
A series of linear amphiphilic pentablock terpolymer PAAx-b-PS48-b-PEO46-b-PS48-b-PAAx (AxS48O46S48Ax) with various lengths x of the PAA block (x = 15, 40, 60, and 90) were synthesized via a two-step atom transfer radical polymerization (ATRP) using Br-poly(ethylene oxide)-Br (Br-PEO46-Br) as the macroinitiator, styrene (St) as the first monomer, and tert-butyl acrylate (tBA) as the second monomer, followed with the hydrolysis of PtBA blocks. The AxS48O46S48Ax pentablock terpolymers formed micelles in dilute aqueous solution, of which the morphologies were dependent on the length x of the PAA block. Cryogenic transmission electron microscopy (cryo-TEM), dynamic light scattering (DLS), and zeta potential measurement were employed to investigate the morphologies, chain structures, size, and size distribution of the obtained micelles. The morphology of AxS48O46S48Ax micelles changed from spherical vesicles with ordered porous membranes to long double nanotubes, then to long nanotubes with inner modulated nanotubes or short nanotubes, and finally, to spherical micelles or large compound vesicles with spherical micelles inside when x increased from 15 to 90. The hydrophobic PS blocks formed the walls of vesicles and nanotubes as well as the core of spherical micelles. The hydrophilic PEO and PAA block chains were located on the surfaces of vesicle membranes, nanotubes, and spherical micelles. The PAA block chains were partially ionized, leading to the negative zeta potential of AxS48O46S48Ax micelles in dilute aqueous solutions. Full article
(This article belongs to the Special Issue Polymer Micelles II)
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23 pages, 2951 KiB  
Article
Association between Nonionic Amphiphilic Polymer and Ionic Surfactant in Aqueous Solutions: Effect of Polymer Hydrophobicity and Micellization
by Samhitha Kancharla, Nathan A. Zoyhofski, Lucas Bufalini, Boris F. Chatelais and Paschalis Alexandridis
Polymers 2020, 12(8), 1831; https://doi.org/10.3390/polym12081831 - 15 Aug 2020
Cited by 43 | Viewed by 6343
Abstract
The interaction in aqueous solutions of surfactants with amphiphilic polymers can be more complex than the surfactant interactions with homopolymers. Interactions between the common ionic surfactant sodium dodecyl sulfate (SDS) and nonionic amphiphilic polymers of the poly(ethylene oxide)–poly(propylene oxide)–poly(ethylene oxide) (PEO-PPO-PEO) type have [...] Read more.
The interaction in aqueous solutions of surfactants with amphiphilic polymers can be more complex than the surfactant interactions with homopolymers. Interactions between the common ionic surfactant sodium dodecyl sulfate (SDS) and nonionic amphiphilic polymers of the poly(ethylene oxide)–poly(propylene oxide)–poly(ethylene oxide) (PEO-PPO-PEO) type have been probed utilizing a variety of experimental techniques. The polymer amphiphiles studied here are Pluronic F127 (EO100PO65EO100) and Pluronic P123 (EO19PO69EO19), having the same length PPO block but different length PEO blocks and, accordingly, very different critical micellization concentrations (CMC). With increasing surfactant concentration in aqueous solutions of fixed polymer content, SDS interacts with unassociated PEO-PPO-PEO molecules to first form SDS-rich SDS/Pluronic assemblies and then free SDS micelles. SDS interacts with micellized PEO-PPO-PEO to form Pluronic-rich SDS/Pluronic assemblies, which upon further increase in surfactant concentration, break down and transition into SDS-rich SDS/Pluronic assemblies, followed by free SDS micelle formation. The SDS-rich SDS/Pluronic assemblies exhibit polyelectrolyte characteristics. The interactions and mode of association between nonionic macromolecular amphiphiles and short-chain ionic amphiphiles are affected by the polymer hydrophobicity and its concentration in the aqueous solution. For example, SDS binds to Pluronic F127 micelles at much lower concentrations (~0.01 mM) when compared to Pluronic P123 micelles (~1 mM). The critical association concentration (CAC) values of SDS in aqueous PEO-PPO-PEO solutions are much lower than CAC in aqueous PEO homopolymer solutions. Full article
(This article belongs to the Special Issue Polymer Micelles II)
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14 pages, 2318 KiB  
Article
Synthesis of Amphiphilic Statistical Copolymers Bearing Methoxyethyl and Phosphorylcholine Groups and Their Self-Association Behavior in Water
by Thi Lien Nguyen, Yuuki Kawata, Kazuhiko Ishihara and Shin-ichi Yusa
Polymers 2020, 12(8), 1808; https://doi.org/10.3390/polym12081808 - 12 Aug 2020
Cited by 8 | Viewed by 3127
Abstract
Biocompatible amphiphilic statistical copolymers P(MEA/MPCm) composed of 2-methoxyethyl acrylate (MEA) and 2-methacryloyloxyethyl phosphorylcholine (MPC) were prepared with three different mol% of the hydrophilic unit MPC (m = 6, 12 and 46 mol%). The monomer reactivity ratios of MEA (r [...] Read more.
Biocompatible amphiphilic statistical copolymers P(MEA/MPCm) composed of 2-methoxyethyl acrylate (MEA) and 2-methacryloyloxyethyl phosphorylcholine (MPC) were prepared with three different mol% of the hydrophilic unit MPC (m = 6, 12 and 46 mol%). The monomer reactivity ratios of MEA (rMEA) and MPC (rMPC) were 0.53 and 2.21, respectively. The rMEA × rMPC value of 1.17 demonstrated that statistical copolymerization was successful. P(MEA/MPC12) and P(MEA/MPC46) copolymers did not undergo aggregation in water, whereas the P(MEA/MPC6) copolymer formed micelles in water with a hydrodynamic radius (Rh) of 96.9 nm and a critical aggregation concentration, which was determined using pyrene fluorescence, at 0.0082 g/L. The restricted motion of the protons in the hydrophobic MEA units in the micelles’ cores provided additional evidence of self-association in P(MEA/MPC6). Full article
(This article belongs to the Special Issue Polymer Micelles II)
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17 pages, 4151 KiB  
Article
Water-Soluble and Cytocompatible Phospholipid Polymers for Molecular Complexation to Enhance Biomolecule Transportation to Cells In Vitro
by Kazuhiko Ishihara, Shohei Hachiya, Yuuki Inoue, Kyoko Fukazawa and Tomohiro Konno
Polymers 2020, 12(8), 1762; https://doi.org/10.3390/polym12081762 - 06 Aug 2020
Cited by 5 | Viewed by 2848
Abstract
Water-soluble and cytocompatible polymers were investigated to enhance a transporting efficiency of biomolecules into cells in vitro. The polymers composed of a 2-methacryloyloxyethyl phosphorylcholine (MPC) unit, a hydrophobic monomer unit, and a cationic monomer unit bearing an amino group were synthesized for complexation [...] Read more.
Water-soluble and cytocompatible polymers were investigated to enhance a transporting efficiency of biomolecules into cells in vitro. The polymers composed of a 2-methacryloyloxyethyl phosphorylcholine (MPC) unit, a hydrophobic monomer unit, and a cationic monomer unit bearing an amino group were synthesized for complexation with model biomolecules, siRNA. The cationic MPC polymer was shown to interact with both siRNA and the cell membrane and was successively transported siRNA into cells. When introducing 20–50 mol% hydrophobic units into the cationic MPC polymer, transport of siRNA into cells. The MPC units (10–20 mol%) in the cationic MPC polymer were able to impart cytocompatibility, while maintaining interaction with siRNA and the cell membrane. The level of gene suppression of the siRNA/MPC polymer complex was evaluated in vitro and it was as the same level as that of a conventional siRNA transfection reagent, whereas its cytotoxicity was significantly lower. We concluded that these cytocompatible MPC polymers may be promising complexation reagent for introducing biomolecules into cells, with the potential to contribute to future fields of biotechnology, such as in vitro evaluation of gene functionality, and the production of engineered cells with biological functions. Full article
(This article belongs to the Special Issue Polymer Micelles II)
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Review

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33 pages, 4836 KiB  
Review
Micellar Drug Delivery Systems Based on Natural Biopolymers
by Leonard Ionut Atanase
Polymers 2021, 13(3), 477; https://doi.org/10.3390/polym13030477 - 02 Feb 2021
Cited by 113 | Viewed by 7639
Abstract
The broad diversity of structures and the presence of numerous functional groups available for chemical modifications represent an enormous advantage for the development of safe, non-toxic, and cost-effective micellar drug delivery systems (DDS) based on natural biopolymers, such as polysaccharides, proteins, and peptides. [...] Read more.
The broad diversity of structures and the presence of numerous functional groups available for chemical modifications represent an enormous advantage for the development of safe, non-toxic, and cost-effective micellar drug delivery systems (DDS) based on natural biopolymers, such as polysaccharides, proteins, and peptides. Different drug-loading methods are used for the preparation of these micellar systems, but it appeared that dialysis is generally recommended, as it avoids the formation of large micellar aggregates. Moreover, the preparation method has an important influence on micellar size, morphology, and drug loading efficiency. The small size allows the passive accumulation of these micellar systems via the permeability and retention effect. Natural biopolymer-based micellar DDS are high-value biomaterials characterized by good compatibility, biodegradability, long blood circulation time, non-toxicity, non-immunogenicity, and high drug loading, and they are biodegraded to non-toxic products that are easily assimilated by the human body. Even if some recent studies reported better antitumoral effects for the micellar DDS based on polysaccharides than for commercial formulations, their clinical use is not yet generalized. This review is focused on the studies from the last decade concerning the preparation as well as the colloidal and biological characterization of micellar DDS based on natural biopolymers. Full article
(This article belongs to the Special Issue Polymer Micelles II)
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