Tunable coverage of immobilized biomolecules for biofunctional interface design

Wu, Jyun‐Ting; Sun, Ting-Pi; Huang, Chao‐Wei; Su, Chiao-Tzu; Wu, Chih‐Yu; Yeh, Shu-Yun; Yang, Deng-Kai; Chen, Lin-Chi; Ding, Shih‐Torng; Chen, Hsien‐Yeh

doi:10.1039/c5bm00127g

Cited by 15 publications

(15 citation statements)

References 16 publications

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“…Of the two functionalities, ester alkyne has been demonstrated to be specific and rapid toward a Huisgen 1,3-dipolar cycloaddition to click azides and terminal alkynes, 54,55 and the maleimide moiety provides an efficient pathway toward the conjugation of a thiol group via Michael-type addition with the formation of a stable thioester bond. 56 The resultant porous bulk material of poly-p-xylylene was represented mechanically by an engineered building block with a porous structure and chemically defined and addressable properties on the material interface. In the experiments, an ice template with dimensions of 400 × 400 × 400 μm 3 was used for vapor deposition copolymerization from two vaporized monomer sources, ester alkyne-p-xylylene and maleimide-p-xylylene, performed by a dual-sourced installation of the monomer inlets, which has independent monomer feeding control and pyrolysis settings.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Fabrication of Asymmetrical and Gradient Hierarchy Structures of Poly-p-xylylenes on Multiscale Regimes Based on a Vapor-Phase Sublimation and Deposition Process

Chiu

Hsu

et al. 2020

Chem. Mater.

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An elegant and precise method to fabricate asymmetrical structures and/or gradient structures was developed based on a vapor-phase sublimation and deposition process. The fabricated materials exhibited versatility and had advantages such as well-controlled pore structures and functional properties ranging from an asymmetrical distribution to a gradient hierarchy; precisely addressed interface chemistries and properties for the constructed materials; and flexibility to produce the materials at multiple scales. By using a time-dependent customization parameter to control the bulk size and/or the dispersion of molecules, fabrication of the materials was demonstrated, producing particles with hierarchical pore structures and with bulk sizes ranging from >500 μm to submicrons, as well as gradients with both continuously varied porosity and chemical functionality that were demonstrated to be in a controlled direction and varied across multiple scales (centimeter, millimeter, and micrometer). By exploiting chemical vapor deposition to enable multicomponent copolymerization during the fabrication process, multifunctional poly-p-xylylenes formed building blocks for these hierarchical materials and provided the defined surface chemistries. The proposed functional hierarchical materials were constructed and assembled in the vapor phase and in one step, and prospective materials produced by this method are expected to have novel properties and unlimited applications.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Fabrication of Asymmetrical and Gradient Hierarchy Structures of Poly-p-xylylenes on Multiscale Regimes Based on a Vapor-Phase Sublimation and Deposition Process

Chiu

Hsu

et al. 2020

Chem. Mater.

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“…To further examine the corresponding chemical reactivities of PPX‐d‐NB, i.e., the NHS ester‐amine coupling reaction of the NHS ester motif and the photochemical reaction of the benzoyl motif, a two‐step conjugation process was devised, selecting a fluorescein‐labeled Arg‐Arg‐Cys‐Cys (FITC‐RRCC) peptide and an unmodified biotin molecule for the conjugation reactions. The conjugation concentration/efficiency can be extrapolated based on the findings from previous reports for similar polymer systems, and a suggested conjugation concentration of ≈10 −9 mol cm −2 for small molecules and 10 −11 mol cm −2 for macromolecules is estimated . Specifically, the NHS ester‐amine coupling reaction occurred spontaneously under ambient conditions (pH = 7.4) at room temperature without a catalyst.…”

Section: Resultsmentioning

confidence: 94%

Multifunctional Surface Modification: Facile and Flexible Reactivity toward a Precisely Controlled Biointerface

Yuan

Tung

et al. 2016

Macromolecular Bioscience

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A multicomponent functional polymer is synthesized to support specific reactivity for successful conjugation with the vast array of functionality present in biological systems and the flexibility to conjugate biomolecules without requiring additional modification to install a terminal functional group. The multifunctional surface is realized using a novel coating composed of distinct N-hydroxysuccinimide (NHS) ester and benzoyl functionalities, which can provide accessibility to both the NHS ester-amine coupling reaction and the photochemically induced benzophenone crosslinking reaction, respectively. In addition, the multifunctional polymer is fabricated and transformed to form nanoscale colloids through the solvent displacement of a water/DMF system due to solubility characteristics of the resulting polymer with high polarity. A facile and efficient fabrication approach using the multifunctional nanocolloid is thus demonstrated to create a drug carrier by installing paclitaxel and folic acid for targeted cancer therapy.

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“…The second gradient of propiolates was accessible for the immobilization of azide-terminated biomolecules via a copper-free alkyne and azide click reaction. Two chemical composition gradients with orthogonal and continuously distributed properties were finally produced, and the concentration/density of the immobilized molecules can be estimated 31 and complied with the reaction kinetics. A selected peptide molecule of cyanine5-conjugated Arg-Gly-Asp-Ala-Cys-Cys (Cy5-RGDACC) was used for the immobilization to create the first gradient via the thermo-activated thiol−yne reaction with a temperature gradient from 10 to 90 °C.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Multifunctional and Continuous Gradients of Biointerfaces Based on Dual Reverse Click Reactions

Guan

et al. 2016

ACS Appl. Mater. Interfaces

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Chemical or biological gradients that are composed of multifunctional and/or multidirectional guidance cues are of fundamental importance for prospective biomaterials and biointerfaces. As a proof of concept, a general modification approach for generating multifunctional and continuous gradients was realized via two controlled and reversed click reactions, namely, thermo-activated thiol-yne and copper-free alkyne and azide click reactions. The cell adhesion property of fibroblasts was guided in a gradient with an enhancement, showing that the PEG molecule and RGD peptide were countercurrently immobilized to form such reversed gradients (with negating of the cell adhesion property). Using the gradient modification protocol to also create countercurrent distributions of FGF-2 and BMP-2 gradients, the demonstration of not only multifunctional but also gradient biointerfacial properties was resolved in time latencies on one surface by showing the manipulation in gradients toward proliferation and osteogenic differentiation for adipose-derived stem cells.

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Tunable coverage of immobilized biomolecules for biofunctional interface design

Cited by 15 publications

References 16 publications

Fabrication of Asymmetrical and Gradient Hierarchy Structures of Poly-p-xylylenes on Multiscale Regimes Based on a Vapor-Phase Sublimation and Deposition Process

Fabrication of Asymmetrical and Gradient Hierarchy Structures of Poly-p-xylylenes on Multiscale Regimes Based on a Vapor-Phase Sublimation and Deposition Process

Multifunctional Surface Modification: Facile and Flexible Reactivity toward a Precisely Controlled Biointerface

Multifunctional and Continuous Gradients of Biointerfaces Based on Dual Reverse Click Reactions

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