Surface-Initiated, Atom Transfer Radical Polymerization of Oligo(ethylene glycol) Methyl Ether Methacrylate and Subsequent Click Chemistry for Bioconjugation

Lee, Bong Soo; Lee, Jungkyu K.; Kim, Wan Joong; Jung, Yang‐Il; Sim, Sang Jun; Lee, Jeewon; Choi, Insung S.

doi:10.1021/bm060782+

Cited by 130 publications

(92 citation statements)

References 55 publications

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“…Various methods have been used to introduce functional groups into pMPC by attachment of an initiator as a potentially functionalizable site onto the polymer chain end [94] or copolymerization with a monomer bearing a functional group such as p-nitrophenylcarbonyloxyethyl methacrylate. [95] Similar to MPC, active groups can be introduced into pOEG with an initiator for further functionalization [96] or a functional monomer such as N-acryloxysuccinimide for copolymerization. [97] The ratio of functional to nonfouling segments needs to be adjusted to reach a compromise between functionalization and nonfouling properties.…”

Section: Functionalizable Zwiterionic Materialsmentioning

confidence: 99%

Ultralow‐Fouling, Functionalizable, and Hydrolyzable Zwitterionic Materials and Their Derivatives for Biological Applications

2010

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In recent years, zwitterionic materials such as poly(carboxybetaine) (pCB) and poly(sulfobetaine) (pSB) have been applied to a broad range of biomedical and engineering materials. Due to electrostatically induced hydration, surfaces coated with zwitterionic groups are highly resistant to nonspecific protein adsorption, bacterial adhesion, and biofilm formation. Among zwitterionic materials, pCB is unique due to its abundant functional groups for the convenient immobilization of biomolecules. pCB can also be prepared in a hydrolyzable form as cationic pCB esters, which can kill bacteria or condense DNA. The hydrolysis of cationic pCB esters into nonfouling zwitterionic groups will lead to the release of killed microbes or the irreversible unpackaging of DNA. Furthermore, mixed-charge materials have been shown to be equivalent to zwitterionic materials in resisting nonspecific protein adsorption when they are uniformly mixed at the molecular scale.

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Section: Functionalizable Zwiterionic Materialsmentioning

confidence: 99%

Ultralow‐Fouling, Functionalizable, and Hydrolyzable Zwitterionic Materials and Their Derivatives for Biological Applications

2010

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“…Similarly, 1,3-dipolar cycloadditions on acetylenyl-terminated SAMs and azide compounds were used as a versatile tool for tailoring surface functionalities under mild conditions. [28][29][30] For example, Huisgen's dipolar cycloaddition was employed to immobilize azide-functionalized sugars (mannose, lactose, and a-galactose) onto alkyne-terminated SAMs on gold (Fig. 2).…”

Section: Role Of Click Chemistry In Surface Engineeringmentioning

confidence: 99%

Click Chemistry: Versatility and Control in the Hands of Materials Scientists

2007

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The increasing need for materials with tightly controlled structures will continue to fuel the induction of synthetic organic concepts into materials science. One powerful example is the embracement of “click chemistry” by the materials science community. Because of their high selectivity, near‐perfect reliability, high yields, and exceptional tolerance towards a wide range of functional groups and reaction conditions click reactions have recently attracted increased attention, specifically for use in polymer synthesis as well as for the modification of surfaces and nanometer‐ and mesoscale structures. As outlined in this Review article, click chemistry, such as the CuI‐catalyzed Huisgen 1,3‐dipolar cycloaddition and the Diels–Alder reaction, presents a synthetic concept that lends itself superbly to the controlled preparation of multifunctional materials.

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“…One of the advantages of the SPR technique is its high sensitivity without any fluorescent or other labeling of the interactants. For example, Lee et al [61] used SPR to investigate the binding of streptavidin (SA) onto a biotin presenting surface. Figure 2 shows the SPR sensorgrams of the association and dissociation phases for SA and other proteins.…”

Section: Surface Plasmon Resonance (Spr)mentioning

confidence: 99%

“…The modification generally requires the construction of surfaces that present chemically active functional groups with non-biofouling property of the supporting materials. Lee et al [162] used click chemistry as a candidate for coupling reactions between polymeric surfaces and incoming molecules of interest. In this case, the azide groups were present at the terminal of the non-biofouling polymeric film of pOEGMA [polyoligo(ethylene glycol)methyl ether methacrylate].…”

Section: Polymeric Surfacesmentioning

confidence: 99%

Orthogonal Transformations on Solid Substrates: Efficient Avenues to Surface Modification

2009

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The performance of solid substrates is not only governed by their molecular constitution, but is also critically influenced by their surface constitution at the solid/gas or solid/liquid interface. In here, we critically review the use of orthogonal chemical transformations (so‐called click chemistry) to achieve efficient surface modifications of materials ranging from gold and silica nanoparticles, polymeric films, and microspheres to fullerenes as well as carbon nanotubes. In addition, the functionalization of surfaces via click chemistry with biomolecules is explored. Although a large host of reactions fulfilling the click‐criteria exist, pericyclic reactions are most frequently employed for efficient surface modifications. The advent of the click chemistry concept has led—as evident from the current literature—to a paradigm shift in current approaches for materials modification: Away from unspecific and nonselective reactions to highly specific true surface engineering.

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Surface-Initiated, Atom Transfer Radical Polymerization of Oligo(ethylene glycol) Methyl Ether Methacrylate and Subsequent Click Chemistry for Bioconjugation

Cited by 130 publications

References 55 publications

Ultralow‐Fouling, Functionalizable, and Hydrolyzable Zwitterionic Materials and Their Derivatives for Biological Applications

Ultralow‐Fouling, Functionalizable, and Hydrolyzable Zwitterionic Materials and Their Derivatives for Biological Applications

Click Chemistry: Versatility and Control in the Hands of Materials Scientists

Orthogonal Transformations on Solid Substrates: Efficient Avenues to Surface Modification

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