The effect of thiolation on the mechanical and protein adsorption properties of polyurethanes

Alibeik, Sara; Rizkalla, Amin S.; Mequanint, Kibret

doi:10.1016/j.eurpolymj.2006.12.037

Cited by 25 publications

(15 citation statements)

References 28 publications

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“…This approach removes problems associated with ionic groups in the hard segment 159. Other polyurethanes with ene groups incorporated into the 1,4‐polybutadiene main‐chain soft segments were modified by a thermal thiol–ene radical reaction to give soft segments with carboxylic acid and sulfonate ionic groups (Scheme ) 148. These biocompatible segmented polyurethanes have been suggested for use in targeted cell adhesion and potential tissue repair.…”

Section: Thiol–ene Click Reactions: Applicationsmentioning

confidence: 99%

Thiol–Ene Click Chemistry

2010

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Following Sharpless' visionary characterization of several idealized reactions as click reactions, the materials science and synthetic chemistry communities have pursued numerous routes toward the identification and implementation of these click reactions. Herein, we review the radical-mediated thiol-ene reaction as one such click reaction. This reaction has all the desirable features of a click reaction, being highly efficient, simple to execute with no side products and proceeding rapidly to high yield. Further, the thiol-ene reaction is most frequently photoinitiated, particularly for photopolymerizations resulting in highly uniform polymer networks, promoting unique capabilities related to spatial and temporal control of the click reaction. The reaction mechanism and its implementation in various synthetic methodologies, biofunctionalization, surface and polymer modification, and polymerization are all reviewed.

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Section: Thiol–ene Click Reactions: Applicationsmentioning

confidence: 99%

Thiol–Ene Click Chemistry

2010

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“…The probability is the introduction of hydrolytically‐modified h‐ HTBN with pendent ionized groups, as illustrated in surface water uptake and water contact angle measurements. Numerous studies have shown that surface structure and properties such as surface roughness and surface hydrophilicity have a decisive role in increasing the blood compatibility 35, 40. Another possible explanation is that the incorporation of h ‐HTBN decreases the crystallization of PEG chain, thereby improving anti‐clotting function 41.…”

Section: Resultsmentioning

confidence: 99%

“…Furthermore, PUs have great design flexibility because their composition and structure can easily be tailored according to specific needs. These make them suitable for use in a diverse range of implantable medical devices such as artificial heart valves, artificial lungs, artificial skin, artificial blood vessels or vascular grafts, bone tissue engineering, catheters, general‐purpose tubing 5–8…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of novel h‐HTBN/PEG PU copolymers: effect of surface properties on hemocompatibility

Nan

Luo

et al. 2011

Polymers for Advanced Techs

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This work reported the hydrophilicity, hemocompatibility, and cytotoxicity of novel polyurethane (PU) scaffolds for tissue engineering, especially the hydrolysis effect of a soft‐segmented component, a hydrolytically‐modified hydroxyl‐terminated poly(butadiene‐co‐acrylonitrile) (h‐HTBN), on these properties. The PU copolymers were prepared by coupling poly(ethylene glycol) (PEG) with the h‐HTBN together with the help of 1,1‐methylene bis‐(4‐isocyanatocyclohexane) as a bridging reagent. The structure of PU copolymers was characterized by Fourier transformation infrared spectrometry (FTIR). The experimental results indicated that the hydrolytically‐modified HTBN increases water absorption and decreases water contact angles, improving surface hydrophilicity. The synthesized h‐HTBN/PEG PU copolymers display low hemolysis activity, and a little amount of platelet adhesion and activation, implying good compatibility. The methyl tretrazolium (MTT) assays elicited that the cytotoxicity is related to the component ratios of h‐HTBN to PEG and the hydrolysis modification of HTBN. The PU scaffolds can be employed as potential candidates for blood contacting applications. Copyright © 2009 John Wiley & Sons, Ltd.

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“…Dieser Ansatz vermeidet Probleme im Zusammenhang mit ionischen Gruppen im Hartsegment 159. Andere Polyurethane mit En‐Gruppen in den 1,4‐Polybutadien‐Weichsegmenten wurden durch thermische radikalische Thiol‐En‐Reaktion in Produkte mit Carbonsäure‐ und ionischen Sulfonsäuregruppen im Weichsegment überführt (Schema ) 148. Über die Anwendung dieser biokompatiblen Polyurethane in der gerichteten Zelladhäsion und zur Gewebereparatur wurde spekuliert.…”

Section: Thiol‐en‐klickreaktionen: Anwendungenunclassified

Thiol‐En‐Klickchemie

2010

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Nach Sharpless’ visionärer Charakterisierung verschiedener idealisierter Reaktionen als Klick‐Reaktionen hat man innerhalb der Materialwissenschaften und Synthesechemie große Anstrengungen unternommen, um solche Reaktionen zu finden und zu implementieren. In diesem Aufsatz diskutieren wir die radikalvermittelte Thiol‐En‐Reaktion, die über all die Merkmale einer Klick‐Reaktion verfügt: hohe Effizienz, einfache Durchführung, keine Nebenprodukte, hohe Reaktionsgeschwindigkeiten, hohe Ausbeuten. Darüber hinaus besteht die Möglichkeit, die Thiol‐En‐Reaktion photoinitiiert auszuführen, was insbesondere für Photopolymerisationen zur Synthese extrem einheitlicher Polymernetzwerke genutzt wird. Der Reaktionsmechanismus wird nach dem aktuellen Kenntnisstand erläutert, und zentrale Anwendungen der Thiol‐En‐Reaktion in der Material‐ und Molekülsynthese, der Biofunktionalisierung, der Polymersynthese und der Oberflächen‐ und Polymermodifizierung werden zusammengefasst.

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The effect of thiolation on the mechanical and protein adsorption properties of polyurethanes

Cited by 25 publications

References 28 publications

Thiol–Ene Click Chemistry

Thiol–Ene Click Chemistry

Synthesis and characterization of novel h‐HTBN/PEG PU copolymers: effect of surface properties on hemocompatibility

Thiol‐En‐Klickchemie

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