Hemolytic and Antimicrobial Activities of a Series of Cationic Amphiphilic Copolymers Comprised of Same Centered Comonomers with Thiazole Moieties and Polyethylene Glycol Derivatives

R. Cuervo-Rodríguez; A. Muñoz-Bonilla; F. López-Fabal; M. Fernández-García

doi:10.3390/polym12040972

Hemolytic and Antimicrobial Activities of a Series of Cationic Amphiphilic Copolymers Comprised of Same Centered Comonomers with Thiazole Moieties and Polyethylene Glycol Derivatives

Polymers ◽

10.3390/polym12040972 ◽

2020 ◽

Vol 12 (4) ◽

pp. 972 ◽

Cited By ~ 3

Author(s):

R. Cuervo-Rodríguez ◽

A. Muñoz-Bonilla ◽

F. López-Fabal ◽

M. Fernández-García

Keyword(s):

Ethylene Glycol ◽

Raft Polymerization ◽

Antimicrobial Activities ◽

Thiazole Ring ◽

Amphiphilic Copolymers ◽

Cationic Polymers ◽

Poly Ethylene Glycol ◽

Human Red Blood Cells ◽

Hydrophobic Chain ◽

Poly Ethylene

A series of well-defined antimicrobial polymers composed of comonomers bearing thiazole ring (2-(((2-(4-methylthiazol-5-yl)ethoxy)carbonyl)oxy)ethyl methacrylate monomer (MTZ)) and non-hemotoxic poly(ethylene glycol) side chains (poly(ethylene glycol) methyl ether methacrylate (PEGMA)) were synthesized by reversible addition-fragmentation chain transfer (RAFT) polymerization. By post-polymerization functionalization strategy, polymers were quaternized with either butyl or octyl iodides to result in cationic amphiphilic copolymers incorporating thiazolium groups, thus with variable hydrophobic/hydrophilic balance associated to the length of the alkylating agent. Likewise, the molar percentage of PEGMA was modulated in the copolymers, also affecting the amphiphilicity. The antimicrobial activities of these cationic polymers were determined against Gram-positive and Gram-negative bacteria and fungi. Minimum inhibitory concentration (MIC) was found to be dependent on both length of the alkyl hydrophobic chain and the content of PEGMA in the copolymers. More hydrophobic octylated copolymers were found to be more effective against all tested microorganisms. The incorporation of non-ionic hydrophilic units, PEGMA, reduces the hydrophobicity of the system and the activity is markedly reduced. This effect is dramatic in the case of butylated copolymers, in which the hydrophobic/hydrophilic balance is highly affected. The hemolytic properties of polymers analyzed against human red blood cells were greatly affected by the hydrophobic/hydrophilic balance of the copolymers and the content of PEGMA, which drastically reduces the hemotoxicity. The copolymers containing longer hydrophobic chain, octyl, are much more hemotoxic than their corresponding butylated copolymers.

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Poly(ethylene glycol)-b-poly(1,3-trimethylene carbonate) Amphiphilic Copolymers for Long-Acting Injectables: Synthesis, Non-Acylating Performance and In Vivo Degradation

Molecules ◽

10.3390/molecules26051438 ◽

2021 ◽

Vol 26 (5) ◽

pp. 1438

Author(s):

Silvio Curia ◽

Feifei Ng ◽

Marie-Emérentienne Cagnon ◽

Victor Nicoulin ◽

Adolfo Lopez-Noriega

Keyword(s):

Ethylene Glycol ◽

Ring Opening ◽

Gel Chromatography ◽

Amphiphilic Copolymers ◽

Trimethylene Carbonate ◽

Poly Ethylene Glycol ◽

Poly Ethylene ◽

Long Acting ◽

In Vivo Degradation

This article presents the evaluation of diblock and triblock poly(ethylene glycol)-b-poly(1,3-trimethylene carbonate) amphiphilic copolymers (PEG-PTMCs) as excipients for the formulation of long-acting injectables (LAIs). Copolymers were successfully synthesised through bulk ring-opening polymerisation. The concomitant formation of PTMC homopolymer could not be avoided irrespective of the catalyst amount, but the by-product could easily be removed by gel chromatography. Pure PEG-PTMCs undergo faster erosion in vivo than their corresponding homopolymer. Furthermore, these copolymers show outstanding stability compared to their polyester analogues when formulated with amine-containing reactive drugs, which makes them particularly suitable as LAIs for the sustained release of drugs susceptible to acylation.

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Comparing Zwitterionic and PEG Exteriors of Polyelectrolyte Complex Micelles

Molecules ◽

10.3390/molecules25112553 ◽

2020 ◽

Vol 25 (11) ◽

pp. 2553

Author(s):

Jeffrey M. Ting ◽

Alexander E. Marras ◽

Joseph D. Mitchell ◽

Trinity R. Campagna ◽

Matthew V. Tirrell

Keyword(s):

Ethylene Glycol ◽

Polyelectrolyte Complex ◽

Serum Proteins ◽

Raft Polymerization ◽

Sodium Acrylate ◽

Structure Property ◽

Poly Ethylene Glycol ◽

Poly Ethylene ◽

Complex Micelles

A series of model polyelectrolyte complex micelles (PCMs) was prepared to investigate the consequences of neutral and zwitterionic chemistries and distinct charged cores on the size and stability of nanocarriers. Using aqueous reversible addition-fragmentation chain transfer (RAFT) polymerization, we synthesized a well-defined diblock polyelectrolyte system, poly(2-methacryloyloxyethyl phosphorylcholine methacrylate)-block-poly((vinylbenzyl) trimethylammonium) (PMPC-PVBTMA), at various neutral and charged block lengths to compare directly against PCM structure–property relationships centered on poly(ethylene glycol)-block-poly((vinylbenzyl) trimethylammonium) (PEG-PVBTMA) and poly(ethylene glycol)-block-poly(l-lysine) (PEG-PLK). After complexation with a common polyanion, poly(sodium acrylate), the resulting PCMs were characterized by dynamic light scattering (DLS) and small angle X-ray scattering (SAXS). We observed uniform assemblies of spherical micelles with a diameter ~1.5–2× larger when PMPC-PVBTMA was used compared to PEG-PLK and PEG-PVBTMA via SAXS and DLS. In addition, PEG-PLK PCMs proved most resistant to dissolution by both monovalent and divalent salt, followed by PEG-PVBTMA then PMPC-PVBTMA. All micelle systems were serum stable in 100% fetal bovine serum over the course of 8 h by time-resolved DLS, demonstrating minimal interactions with serum proteins and potential as in vivo drug delivery vehicles. This thorough study of the synthesis, assembly, and characterization of zwitterionic polymers in PCMs advances the design space for charge-driven micelle assemblies.

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Poly(ethylene glycol) as a ‘green solvent’ for the RAFT polymerization of methyl methacrylate

Polymer ◽

10.1016/j.polymer.2010.06.022 ◽

2010 ◽

Vol 51 (17) ◽

pp. 3836-3842 ◽

Cited By ~ 22

Author(s):

Andrew G. West ◽

Christopher Barner-Kowollik ◽

Sébastien Perrier

Keyword(s):

Ethylene Glycol ◽

Methyl Methacrylate ◽

Raft Polymerization ◽

Green Solvent ◽

Poly Ethylene Glycol ◽

Poly Ethylene

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Fluorinated amphiphilic block copolymers via RAFT polymerization and their application as surf-RAFT agent in miniemulsion polymerization

RSC Advances ◽

10.1039/c4ra14151b ◽

2015 ◽

Vol 5 (20) ◽

pp. 15461-15468 ◽

Cited By ~ 15

Author(s):

Bishnu P. Koiry ◽

Arindam Chakrabarty ◽

Nikhil K. Singha

Keyword(s):

Block Copolymer ◽

Block Copolymers ◽

Ethylene Glycol ◽

Raft Polymerization ◽

Miniemulsion Polymerization ◽

Amphiphilic Block Copolymers ◽

Poly Ethylene Glycol ◽

Raft Agent ◽

Poly Ethylene ◽

Glycol Methyl Ether

Preparation of an amphiphilic block copolymer (Am-BCP) based on poly(ethylene glycol) methyl ether methacrylate (PEGMA) and heptafluorobutyl acrylate (HFBA) via RAFT polymerization and application of this Am-BCP as surf-RAFT agent for polymerization of styrene.

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Single component thermo-gelling electroactive hydrogels from poly(caprolactone)–poly(ethylene glycol)–poly(caprolactone)-graft-aniline tetramer amphiphilic copolymers

Journal of Materials Chemistry B ◽

10.1039/c5tb01658d ◽

2015 ◽

Vol 3 (43) ◽

pp. 8459-8468 ◽

Cited By ~ 23

Author(s):

Xin Zhao ◽

Baolin Guo ◽

Peter X. Ma

Keyword(s):

Ethylene Glycol ◽

Single Component ◽

Amphiphilic Copolymers ◽

Poly Ethylene Glycol ◽

Poly Ethylene ◽

Conductive Hydrogels ◽

Poly Caprolactone

Single component injectable degradable conductive hydrogels with excellent biocompatibility based on poly(caprolactone)–poly(ethylene glycol)–poly(caprolactone) and aniline tetramer were prepared via a thermo-gelling approach.

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Poly(ethylene glycol)-based amphiphilic model conetworks: Synthesis by RAFT polymerization and characterization

Journal of Polymer Science Part A Polymer Chemistry ◽

10.1002/pola.23061 ◽

2008 ◽

Vol 46 (22) ◽

pp. 7556-7565 ◽

Cited By ~ 43

Author(s):

Mariliz Achilleos ◽

Thomas M. Legge ◽

Sébastien Perrier ◽

Costas S. Patrickios

Keyword(s):

Ethylene Glycol ◽

Raft Polymerization ◽

Poly Ethylene Glycol ◽

Poly Ethylene

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Iron-mediated (dual) concurrent ATRP–RAFT polymerization of water-soluble poly(ethylene glycol) monomethyl ether methacrylate

Polymer Chemistry ◽

10.1039/c3py00671a ◽

2013 ◽

Vol 4 (23) ◽

pp. 5664 ◽

Cited By ~ 11

Author(s):

Jinlong Pan ◽

Jie Miao ◽

Lifen Zhang ◽

Zhangyong Si ◽

Changwen Zhang ◽

...

Keyword(s):

Ethylene Glycol ◽

Raft Polymerization ◽

Monomethyl Ether ◽

Water Soluble ◽

Poly Ethylene Glycol ◽

Ethylene Glycol Monomethyl Ether ◽

Glycol Monomethyl Ether ◽

Poly Ethylene ◽

Soluble Poly

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Poly(ethylene glycol) (PEG)-crosslinked poly(vinyl pyridine)–PEG–poly(vinyl pyridine)-based triblock copolymers prepared by RAFT polymerization as novel gel polymer electrolytes

Polymer Chemistry ◽

10.1039/c8py01097h ◽

2018 ◽

Vol 9 (42) ◽

pp. 5190-5199 ◽

Cited By ~ 10

Author(s):

Inseop Shin ◽

Jaebin Nam ◽

Kukjoo Lee ◽

Eunsoo Kim ◽

Tae-Hyun Kim

Keyword(s):

Ethylene Glycol ◽

Polymer Electrolytes ◽

Triblock Copolymers ◽

Raft Polymerization ◽

Gel Polymer Electrolytes ◽

Poly Ethylene Glycol ◽

Vinyl Pyridine ◽

Poly Ethylene

A series of triblock copolymers based on poly(vinyl pyridine)–PEG–poly(vinyl pyridine) (PVP–PEG–PVP) with different PEG-to-PVP ratios (1 : 200, 1 : 250, and 1 : 500) were prepared using the RAFT polymerization.

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Chemical Synthesis and Characterization of Poly(poly(ethylene glycol) methacrylate)-Grafted CdTe Nanocrystals via RAFT Polymerization for Covalent Immobilization of Adenosine

Polymers ◽

10.3390/polym11010077 ◽

2019 ◽

Vol 11 (1) ◽

pp. 77 ◽

Cited By ~ 1

Author(s):

Trinh Duy Nguyen ◽

Hieu Vu-Quang ◽

Thanh Sang Vo ◽

Duy Chinh Nguyen ◽

Dai-Viet N. Vo ◽

...

Keyword(s):

Ethylene Glycol ◽

Photoelectron Spectroscopy ◽

Raft Polymerization ◽

Condensation Reaction ◽

Covalent Bond ◽

Poly Ethylene Glycol ◽

X Ray ◽

Glycol Methacrylate ◽

Cdte Qds ◽

Poly Ethylene

This paper describes the functionalization of poly(poly(ethylene glycol) methacrylate) (PPEGMA)-grafted CdTe (PPEGMA-g-CdTe) quantum dots (QDs) via surface-initiated reversible addition–fragmentation chain transfer (SI-RAFT) polymerization for immobilization of adenosine. Initially, the hydroxyl-coated CdTe QDs, synthesized using 2-mercaptoethanol (ME) as a capping agent, were coupled with a RAFT agent, S-benzyl S′-trimethoxysilylpropyltrithiocarbonate (BTPT), through a condensation reaction. Then, 2,2′-azobisisobutyronitrile (AIBN) was used to successfully initiate in situ RAFT polymerization to generate PPEGMA-g-CdTe nanocomposites. Adenosine-above-PPEGMA-grafted CdTe (Ado-i-PPEGMA-g-CdTe) hybrids were formed by the polymer shell, which had successfully undergone bioconjugation and postfunctionalization by adenosine (as a nucleoside). Fourier transform infrared (FT-IR) spectrophotometry, energy-dispersive X-ray (EDX) spectroscopy, thermogravimetric analysis (TGA), X-ray photoelectron spectroscopy (XPS), and transmission electron microscopy results indicated that a robust covalent bond was created between the organic PPEGMA part, cadmium telluride (CdTe) QDs, and the adenosine conjugate. The optical properties of the PPEGMA-g-CdTe and Ado-i-PPEGMA-g-CdTe hybrids were investigated by photoluminescence (PL) spectroscopy, and the results suggest that they have a great potential for application as optimal materials in biomedicine.

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