Poly(2-oxazoline)s based biomaterials: A comprehensive and critical update

Lorson, Thomas; Lübtow, Michael M; Wegener, Erik; Haider, Malik Salman; Borova, Solomiia; Nahm, Daniel; Jordan, Rainer; Sokolski-Papkov, Marina; Kabanov, Alexander V.; Luxenhofer, Robert

doi:10.1016/j.biomaterials.2018.05.022

Cited by 302 publications

(242 citation statements)

References 354 publications

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“…[7] Thel iving CROP of 2-oxazolines allows the preparation of aw ide range of defined polymers having different physicochemical properties,r anging,e .g.,f rom very hydrophilic to hydrophobic and fluorophilic as well as from amorphous (both high and low glass transition temperatures) up to semi-crystalline with melting transition temperatures up to 300 8 8C. [9] Theh igh tunability of the PAOx polymer structure in combination with its high biocompatibility and non-fouling behaviour have raised significant interest in the use of PAOx for biomedical applications.For acomprehensive overview of recent developments,t he reader is referred to an excellent review by Luxenhofer et al [10] Theu se of PAOx for biomedical applications has been established beyond proof-of-concept research as the first in human studies (Phase 1a clinical trials) were successfully finished by Serina Therapeutics for aP AOx-drug conjugate. [9] Theh igh tunability of the PAOx polymer structure in combination with its high biocompatibility and non-fouling behaviour have raised significant interest in the use of PAOx for biomedical applications.For acomprehensive overview of recent developments,t he reader is referred to an excellent review by Luxenhofer et al [10] Theu se of PAOx for biomedical applications has been established beyond proof-of-concept research as the first in human studies (Phase 1a clinical trials) were successfully finished by Serina Therapeutics for aP AOx-drug conjugate.…”

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confidence: 99%

Defined High Molar Mass Poly(2‐Oxazoline)s

et al. 2018

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Poly(2-alkyl-2-oxazoline)s (PAOx) are regaining interest for biomedical applications.H owever,t heir full potential is hampered by the inability to synthesise uniform high-molar mass PAOx. In this work, we proposed alternative intrinsic chain transfer mechanisms based on 2-oxazoline and oxazolinium chain-end tautomerisation and derived improved polymerization conditions to suppress chain transfer,allowing the synthesis of highly defined poly(2-ethyl-2-oxazoline)s up to ca. 50 kDa (dispersity () < 1.05) and defined polymers up to at least 300 kDa ( < 1.2). The determination of the chain transfer constants for the polymerisations hinted towards the tautomerisation of the oxazolinium chain end as most plausible cause for chain transfer.Finally,the method was applied for the preparation of up to 60 kDa molar mass copolymers of 2-ethyl-2-oxazoline and 2-methoxycarbonylethyl-2-oxazoline.

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confidence: 99%

Defined High Molar Mass Poly(2‐Oxazoline)s

et al. 2018

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“…Poly(2‐alkyl/aryl‐2‐oxazoline)s (PAOx's) are a polymer class possessing a large structural versatility, allowing straightforward tuning of the polymer properties and functionality . This appealing feature and their excellent physicochemical stability in combination with biocompatibility have led to their rising popularity as a biomedical material, for example, polymer–drug conjugates, tissue engineering, matrix excipient, and controlled drug release . Within most of these applications, postpolymerization modification reactions play a central role in the synthesis of functional polymers, enabling to overcome the limitations of the cationic ring‐opening polymerization (CROP).…”

Section: Introductionmentioning

confidence: 99%

Acyl guanidine functional poly(2‐oxazoline)s as reactive intermediates and stimuli‐responsive materials

Guyse

Hoogenboom

2019

J. Polym. Sci. Part A: Polym. Chem.

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The many postpolymerization modification opportunities of biocompatible poly(2‐alkyl/aryl‐2‐oxazoline)s (PAOx), such as thiol–ene/thiol–yne, azide–alkyne cycloadditions, amidation, and transesterification, are one of the most appealing features of this polymer class for its popularity in biomedicine. Inspired by recent reports on guanidine‐catalyzed transesterification and amidation reactions of methyl ester substrates, we explored the use of guanidines as a reactant for the modification of methyl ester functional PAOx, to obtain the respective acyl guanidines. The obtained acyl guanidines functional polymers display reactivity toward α‐haloketones, yielding imidazole functional PAOx. The obtained polymer structures are protonated in a broad pH range, and the acyl guanidine moiety is demonstrated to be a cleavable linker under basic conditions. © 2019 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2019, 57, 2616–2624

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“…88). They find applications in various areas such as hydrogels, surface modifications, the health field, and surfactants . Their use as a surfactant was reported for the first time by Kobayashi et al .…”

Section: Introductionmentioning

confidence: 99%

“…They find applications in various areas such as hydrogels, surface modifications, the health field, and surfactants. [31][32][33][34][35][36][37][38] Their use as a surfactant was reported for the first time by Kobayashi et al who designed copolymers containing both hydrophilic and lipophilic POx blocks. 39 More recently, POx blocks have been linked to bio-based blocks such as glycopolymers and fatty derivatives or to petro-based blocks including polysiloxanes, aliphatic polyesters and fluorinated chains, giving various amphiphilic copolymers with surfactant or self-assembling properties.…”

Section: Introductionmentioning

confidence: 99%

Polyoxazoline associated with cardanol for bio‐based linear alkyl benzene surfactants

Delage

Briou

Brossier

et al. 2019

Polymer International

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Well‐defined linear alkyl benzene surfactants (COxn) were successfully synthesized using cardanol as a green phenolic alternative and initiator for polyoxazoline (POx), the hydrophilic block of nonionic surfactants. Various hydrophilic lipophilic balance values were investigated by varying the POx length according to the [monomer]/[initiator] ratio. The chemical structure of the surfactants, in particular the terminal groups, was well identified by matrix assisted laser desorption ionization time of flight mass spectrometry demonstrating the good progress of the cationic ring‐opening polymerization. The COxn surfactants spontaneously self‐assembled in water at a critical aggregation concentration of 1–2 µmol L−1 into nano‐objects characterized by a hydrodynamic diameter of 11–24 nm and a number of aggregations ranging from 30 to 60 according to the worm‐like micelle model. © 2019 Society of Chemical Industry

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Poly(2-oxazoline)s based biomaterials: A comprehensive and critical update

Cited by 302 publications

References 354 publications

Defined High Molar Mass Poly(2‐Oxazoline)s

Defined High Molar Mass Poly(2‐Oxazoline)s

Acyl guanidine functional poly(2‐oxazoline)s as reactive intermediates and stimuli‐responsive materials

Polyoxazoline associated with cardanol for bio‐based linear alkyl benzene surfactants

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