Thiol‐Reactive Parylenes as a Robust Coating for Biomedical Materials

Sun, Ho-Yi; Fang, Cheng-Yuan; Lin, Tyrone T.; Chen, Yung-Chih; Lin, Chih-Yeh; Ho, Hsin-Ying; Chen, M. H.-C.; Yu, Jihong; Lee, Dai-Jen; Chang, Chien Hsin; Chen, Hsien‐Yeh

doi:10.1002/admi.201400093

Cited by 21 publications

(15 citation statements)

References 39 publications

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“…A multi-blade cross-cut tester was used to create two sets of crosswise scratches on the modied substrate, and a piece of Scotch tape was applied and then removed steadily from the scratched samples. 47 Fig.…”

Section: Surface Modications and Characterizationmentioning

confidence: 99%

Compatibility balanced antibacterial modification based on vapor-deposited parylene coatings for biomaterials

et al. 2014

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Advanced antibacterial surfaces are designed based on covalently attached antibacterial agents, avoiding potential side effects associated with overdosed or eluted agents. The technique is widely applicable regardless of the underlying substrate material. In addition, antibacterial surfaces are effective against the early stages of bacterial adhesion and can significantly reduce the formation of biofilm, without compromising biocompatibility. Here, this concept was realized by employing a benzoyl-functionalized parylene coating. The antibacterial agent chlorhexidine was used as a proof of concept. Chlorhexidine was immobilized by reaction with photoactivated benzoyl-functionalized surfaces, including titanium alloy, stainless steel, polyether ether ketone, polymethyl methacrylate, and polystyrene. A low concentration of chlorhexidine (1.4 AE 0.08 nmol cm À2 ) covalently bound to surfaces rendered them sufficiently resistant to an Enterobacter cloacae inoculum and its adherent biofilm. Compared to unmodified surfaces, up to a 30-fold reduction in bacterial attachment was achieved with this coating technology. The immobilization of chlorhexidine was verified with infrared reflection absorption spectroscopy (IRRAS) and X-ray photoelectron spectroscopy (XPS), and a leaching test was performed to confirm that the chlorhexidine molecules were not dislodged. Cell compatibility was examined by culturing fibroblasts and osteoblasts on the modified surfaces, revealing greater than 93% cell viability.This coating technology may be broadly applicable for a wide range of other antibacterial agents and allow the design of new biomaterials.

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Section: Surface Modications and Characterizationmentioning

confidence: 99%

Compatibility balanced antibacterial modification based on vapor-deposited parylene coatings for biomaterials

et al. 2014

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“…Surface modification through TEC chemistry has also been applied to the design of antifouling protein surfaces. Chen and co‐workers reported the preparation of thiol‐reactive poly‐ p ‐xylylene polymers as coatings for the attachment of biomolecules on various commonly used substrates for biomedical applications, including titanium alloy, stainless steel, organic polymers, silicon, glass, and ceramic substrates . In this work, the alkene‐functionalized polymers were synthesized via a chemical vapor deposition (CVD) polymerization onto the substrate, which allowed the immobilization of thiol‐terminated molecules through a photochemically activated TEC reaction (365 nm, with DMPA as radical initiator).…”

Section: Thiol‐ene Click Reactionsmentioning

confidence: 99%

Metal‐Free Click Chemistry Reactions on Surfaces

Escorihuela

Marcelis

Zuilhof

2015

Adv Materials Inter

110

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In the last decade, interest in the functionalization of surfaces and materials has increased dramatically. In this regard, click chemistry deserves a central focus because of its mild reaction conditions, high efficiency, and easy post‐treatment. Among such novel click reactions, those that do not require any metal catalyst are of special interest, as metals may have undesirable effects in many fields. In this Review, the backgrounds and application of such metal‐free click reactions for the modification of surfaces are highlighted.

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“…[8,5,9] The presence of substituents such as aldehyde, ketone, alcohol, ester,a mine, as well as fluorinated groups, thiol reactive groups,A TRP initiator groups, photosensitiveo ra lkynyl groups in the precursor and consequently in the polymer coatingh as enabled variousp ost-modification strategies. [2,[10][11][12][13][14][15][16][17][18][19][20][21][22][23] Attachmento fp roteins, short peptides, nucleotides, and other smallb iologically activem olecules onto this functional coating can dramatically influence the response of adherent cells. [10,11,13,19] Therefore, precise design of surface chemistry provided by CVD enables the control of cell behavior by tailoringi nteractions between CVD coatings and living organisms.…”

Section: Introductionmentioning

confidence: 99%

“…[2,[10][11][12][13][14][15][16][17][18][19][20][21][22][23] Attachmento fp roteins, short peptides, nucleotides, and other smallb iologically activem olecules onto this functional coating can dramatically influence the response of adherent cells. [10,11,13,19] Therefore, precise design of surface chemistry provided by CVD enables the control of cell behavior by tailoringi nteractions between CVD coatings and living organisms. [24] However, strategies taking advantage of the Gorhamp rocess to deposit vapor-based reactive coatings have so far almosta lwaysb een limitedt op oly-p-xylylenes, that is, entirelyc arbon-based polymer backbones with prominent hydrophobicity.…”

Section: Introductionmentioning

confidence: 99%

Polylutidines: Multifunctional Surfaces through Vapor‐Based Polymerization of Substituted Pyridinophanes

Gall

Hussal

Kramer

et al. 2017

Chemistry A European J

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We report a new class of functionalized polylutidine polymers that are prepared by chemical vapor deposition polymerization of substituted [2](1,4)benzeno[2](2,5)pyridinophanes. To prepare sufficient amounts of monomer for CVD polymerization, a new synthesis route for ethynylpyridinophane has been developed in three steps with an overall yield of 59 %. Subsequent CVD polymerization yielded well-defined films of poly(2,5-lutidinylene-co-p-xylylene) and poly(4-ethynyl-2,5-lutidinylene-co-p-xylylene). All polymers were characterized by infrared reflection-absorption spectroscopy, ellipsometry, contact angle studies, and X-ray photoelectron spectroscopy. Moreover, ζ-potential measurements revealed that polylutidine films have higher isoelectric points than the corresponding poly-xylylene surfaces owing to the nitrogen atoms in the polymer backbone. The availability of reactive alkyne groups on the surface of poly(4-ethynyl-2,5-lutidinylene-co-p-xylylene) coatings was confirmed by spatially controlled surface modification by means of Huisgen 1,3-dipolar cycloaddition. Compared to the more hydrophobic poly-p-xylylyenes, the presence of the heteroatom in the polymer backbone of polylutidine polymers resulted in surfaces that supported an increased adhesion of primary human umbilical vein endothelial cells (HUVECs). Vapor-based polylutidine coatings are a new class of polymers that feature increased hydrophilicity and increased cell adhesion without limiting the flexibility in selecting appropriate functional side groups.

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Thiol‐Reactive Parylenes as a Robust Coating for Biomedical Materials

Cited by 21 publications

References 39 publications

Compatibility balanced antibacterial modification based on vapor-deposited parylene coatings for biomaterials

Compatibility balanced antibacterial modification based on vapor-deposited parylene coatings for biomaterials

Metal‐Free Click Chemistry Reactions on Surfaces

Polylutidines: Multifunctional Surfaces through Vapor‐Based Polymerization of Substituted Pyridinophanes

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