Redox and thiol–ene cross-linking of mercapto poly(ε-caprolactone) for the preparation of reversible degradable elastomeric materials

Nottelet, Benjamin; Tambutet, Guillaume; Bakkour, Youssef; Coudane, Jean

doi:10.1039/c2py20436c

Cited by 25 publications

(22 citation statements)

References 34 publications

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“…The molecular weight decrease is classically observed with the anionic activation of polyester, as a consequence of hydrolysis and backbiting side reactions. 39,40 In the present case, and although remarkable in terms of influence on the final molecular weight, this corresponded to less than 0.3% hydrolysis of the ester groups initially present in the polymer chain. tyrosine.…”

Section: Synthesis Of Pcl-yne and Peg-shmentioning

confidence: 73%

From nanospheres to micelles: simple control of PCL-g-PEG copolymers’ amphiphilicity through thiol–yne photografting

et al. 2015

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A simple method for the synthesis of a family of poly(ɛ-caprolactone)-g-polyethylene glycol (PCL-g-PEG) copolymers of controlled amphiphilicity and their use to generate nanospheres or micelles are reported. PCL-g-PEG with various compositions are prepared from a single strategy relying on a combination of post-polymerization modification and subsequent thiol-yne photografting. Alkyne-functional PCL (PCL-yne) are first obtained by anionic activation and reaction with propargyl bromide to yield PCL-yne with 8% alkyne groups. PEG-thiol is then reacted on PCL-yne under UV activation to yield the targeted graft copolymer by thiol-yne photoaddition. The advantage of the approach is that control over the composition is easily achieved yielding to amphiphilic graft copolymers with ethylene glycol/ caprolactone (EG/CL) ratios ranging from 0.1 to 1.3. Starting from this single strategy, it was therefore possible to obtain nanospheres (D H~5 5 nm) or micelles (D H~3 0 nm) by copolymers self-assembly depending on the ratio EG/CL. The potential of the PCL-g-PEG micelles as drug carrier was finally evaluated with curcumin that was efficiently encapsulated, protected and released over 80 days. Interestingly it was found that drug encapsulation efficiency and drug loading were higher for PCL-g-PEG copolymers compared to block PCL-b-PEG.

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Section: Synthesis Of Pcl-yne and Peg-shmentioning

confidence: 73%

From nanospheres to micelles: simple control of PCL-g-PEG copolymers’ amphiphilicity through thiol–yne photografting

et al. 2015

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“…Alternatively, CL has been ring‐opening copolymerized with other functionalized monomers . A different post‐polymerization route was the grafting of functional groups or macromolecular chains onto PCLs through the α‐position of the carbonyl, although chain degradations were hardly avoidable …”

Section: Introductionmentioning

confidence: 99%

“…[33][34][35][36] A different post-polymerization route was the grafting of functional groups or macromolecular chains onto PCLs through the a-position of the carbonyl, although chain degradations were hardly avoidable. [37][38][39][40] A strategy of choice to obtain PCLs functionalized at one end is the polymerization of CL initiated by functional alcohols, such as 2-hydroxyethyl methacrylate, 41 propargyl alcohol, 42,43 2-mercaptoethanol, 44 or a-(2,4-dinitrophenylthio)ethanol. 45 Hedfors et al 44 has also employed functional terminators in an enzyme-catalyzed polymerization process of CL to end-cap PCLs with the thiol functionality.…”

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confidence: 99%

Synthesis of allyl end‐block functionalized poly(ε‐caprolactone)s and their facile post‐functionalization via thiol–ene reaction

Truong

Thai

Nguyên

et al. 2017

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

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A simple and facile strategy for the functionalization of commercial poly(ε‐caprolactone) diols (PCLs) with pendant functionalities at the polymer chain termini is described. Well‐defined allyl‐functionalized PCLs with varying numbers of allyl end‐block side‐groups were synthesized by cationic ring‐opening polymerization of allyl glycidyl ether using PCL diols as macroinitiators. Further functionalization of the allyl‐functionalized PCLs was realized via the UV‐initiated radical addition of a furan‐functionalized thiol to the pendant allyl functional groups, showing the suitability for post‐modification of the PCL materials. Changes in polymer structure as a result of varying the number of pendant functional units at the PCL chain termini were demonstrated. © 2017 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2017, 55, 928–939

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“…One can cite polydisulfide networks proposed as photo-healable or self-healable materials, [38,39] or reducible PNIPAAm [40] or PEG hydrogels. [41][42][43] However, to the best of our knowledge, apart from the PCL-SS-PCL network reported by our group, [44] none of these structures combine elastomeric properties, degradability (even if excretable) and biocompatibility. PCL-SS-PCL network was generated under oxidative conditions starting from thiol-functional PCL.…”

Section: Introductionmentioning

confidence: 99%

Redox Reducible and Hydrolytically Degradable PEG–PLA Elastomers as Biomaterial for Temporary Drug‐Eluting Medical Devices

Rupnik

Buwalda

Dejean

et al. 2016

Macromolecular Bioscience

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With the aim to develop biomaterials for temporary medical devices, a series of novel reducible and/or degradable elastomers has been prepared from PLA-b-PEG-b-PLA copolymers photo-crosslinked with diallyl sulfide or pentaerythritol tetrakis(3-mercaptopropionate). Thermal and mechanical properties, including elastic limit and Young modulus, are assessed. Degradation is then evaluated under standard hydrolytic conditions. Reducibility of a selected elastomer is then illustrated using 2-mercaptoethanol or glutathione as reducing agents. The redox-sensitivity of the selected elastomer and the possibility to modulate the degradability are shown. Considering drug-eluting elastomeric devices applications, anti-inflammatory drug ibuprofen loading is illustrated with the two simplest elastomer formulations. A rapid or slow linear release is observed as a function of the low or high molecular weight of the triblock pre-polymers. Finally, the cytocompatibility of the degradable elastomers is assessed with regard to their potential to favor or inhibit L929 murine fibroblasts proliferation as a function of the hydrophilicity/hydrophobicity of the triblock copolymers.

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Redox and thiol–ene cross-linking of mercapto poly(ε-caprolactone) for the preparation of reversible degradable elastomeric materials

Cited by 25 publications

References 34 publications

From nanospheres to micelles: simple control of PCL-g-PEG copolymers’ amphiphilicity through thiol–yne photografting

From nanospheres to micelles: simple control of PCL-g-PEG copolymers’ amphiphilicity through thiol–yne photografting

Synthesis of allyl end‐block functionalized poly(ε‐caprolactone)s and their facile post‐functionalization via thiol–ene reaction

Redox Reducible and Hydrolytically Degradable PEG–PLA Elastomers as Biomaterial for Temporary Drug‐Eluting Medical Devices

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