Phototriggered functionalization of hierarchically structured polymer brushes

De Los Santos Pereira, A., Kostina, N. Y., Bruns, M., Rodriguez-Emmenegger, C., & Barner-Kowollik, C. (2015) Phototriggered functionalization of hierarchically structured polymer brushes. Langmuir, 31(21).

View at publisher

Abstract

The precise design of bioactive surfaces, essential for the advancement of many biomedical applications, depends on achieving control of the surface architecture as well as on the ability to attach bioreceptors to antifouling surfaces. Herein, we report a facile avenue toward hierarchically structured antifouling polymer brushes of oligo(ethylene glycol) methacrylates via surface-initiated atom transfer radical polymerization (SI-ATRP) presenting photoactive tetrazole moieties, which permitted their functionalization via nitrile imine-mediated tetrazole-ene cyclocloaddition (NITEC). A maleimide-functional ATRP initiator was photoclicked to the side chains of a brush enabling a subsequent polymerization of carboxybetaine acrylamide to generate a micropatterned graft-on-graft polymer architecture as evidenced by X-ray photoelectron spectroscopy (XPS) and time-of-flight secondary ion mass spectrometry (ToF-SIMS). Furthermore, the spatially resolved biofunctionalization of the tetrazole-presenting brushes was accessed by the photoligation of biotin-maleimide and subsequent binding of streptavidin. The functionalized brushes bearing streptavidin were able to resist the fouling from blood plasma (90% reduction with respect to bare gold). Moreover, they were employed to demonstrate a model biosensor by immobilization of a biotinylated antibody and subsequent capture of an antigen as monitored in real time by surface plasmon resonance. © 2015 American Chemical Society.

Impact and interest:

15 citations in Scopus
Search Google Scholar™
6 citations in Web of Science®

Citation counts are sourced monthly from Scopus and Web of Science® citation databases.

These databases contain citations from different subsets of available publications and different time periods and thus the citation count from each is usually different. Some works are not in either database and no count is displayed. Scopus includes citations from articles published in 1996 onwards, and Web of Science® generally from 1980 onwards.

Citations counts from the Google Scholar™ indexing service can be viewed at the linked Google Scholar™ search.

ID Code: 99424
Item Type: Journal Article
Refereed: Yes
Additional Information: Cited By :9
Export Date: 5 September 2016
CODEN: LANGD
Correspondence Address: Rodriguez-Emmenegger, C.; Institute of Macromolecular Chemistry, Academy of Sciences of the Czech Republic, V.v.i., Heyrovsky sq. 2, Czech Republic
References: Blaszykowski, C., Sheikh, S., Thompson, M., Surface chemistry to minimize fouling from blood-based fluids (2012) Chem. Soc. Rev., 41 (17), pp. 5599-5612; Blaszykowski, C., Sheikh, S., Thompson, M., Biocompatibility and antifouling: Is there really a link? (2014) Trends Biotechnol., 32 (2), pp. 61-62; Yu, Q., Zhang, Y., Wang, H., Brash, J., Chen, H., Anti-fouling bioactive surfaces (2011) Acta Biomater., 7 (4), pp. 1550-1557; Xu, F.J., Neoh, K.G., Kang, E.T., Bioactive surfaces and biomaterials via atom transfer radical polymerization (2009) Prog. Polym. Sci., 34 (8), pp. 719-761; Rodriguez-Emmenegger, C., Preuss, C.M., Yameen, B., Pop-Georgievski, O., Bachmann, M., Mueller, J.O., Bruns, M., Barner-Kowollik, C., Controlled cell adhesion on poly(dopamine) interfaces photopatterned with non-fouling brushes (2013) Adv. Mater., 25 (42), pp. 6123-6127; Ma, H., Hyun, J., Stiller, P., Chilkoti, A., "non-fouling" oligo(ethylene glycol)-Functionalized polymer brushes synthesized by surface-initiated atom transfer radical polymerization (2004) Adv. Mater., 16 (4), pp. 338-341; Hucknall, A., Kim, D.H., Rangarajan, S., Hill, R.T., Reichert, W.M., Chilkoti, A., Simple Fabrication of Antibody Microarrays on Nonfouling Polymer Brushes with Femtomolar Sensitivity for Protein Analytes in Serum and Blood (2009) Adv. Mater., 21 (19), pp. 1968-1971; Gautrot, J.E., Huck, W.T., Welch, M., Ramstedt, M., Protein-resistant NTA-functionalized polymer brushes for selective and stable immobilization of histidine-tagged proteins (2010) ACS Appl. Mater. Interfaces, 2 (1), pp. 193-202; Barbey, R., Lavanant, L., Paripovic, D., Schuwer, N., Sugnaux, C., Tugulu, S., Klok, H.A., Polymer brushes via surface-initiated controlled radical polymerization: Synthesis, characterization, properties, and applications (2009) Chem. Rev., 109 (11), pp. 5437-5527; Krishnamoorthy, M., Hakobyan, S., Ramstedt, M., Gautrot, J.E., Surface-initiated polymer brushes in the biomedical field: Applications in membrane science, biosensing, cell culture, regenerative medicine and antibacterial coatings (2014) Chem. Rev., 114 (21), pp. 10976-11026; Gunkel, G., Weinhart, M., Becherer, T., Haag, R., Huck, W.T., Effect of polymer brush architecture on antibiofouling properties (2011) Biomacromolecules, 12 (11), pp. 4169-4172; Huang, C.J., Li, Y., Jiang, S., Zwitterionic polymer-based platform with two-layer architecture for ultra low fouling and high protein loading (2012) Anal. Chem., 84 (7), pp. 3440-3445; Peng, S.J., Bhushan, B., Smart polymer brushes and their emerging applications (2012) RSC Adv., 2 (23), pp. 8557-8578; Chen, Y.X., Triola, G., Waldmann, H., Bioorthogonal chemistry for site-specific labeling and surface immobilization of proteins (2011) Acc. Chem. Res., 44 (9), pp. 762-773; Tugulu, S., Arnold, A., Sielaff, I., Johnsson, K., Klok, H.A., Protein-functionalized polymer brushes (2005) Biomacromolecules, 6 (3), pp. 1602-1607; De Los Santos Pereira, A., Riedel, T., Brynda, E., Rodriguez-Emmenegger, C., Hierarchical antifouling brushes for biosensing applications (2014) Sens. Actuators, B, 202, pp. 1313-1321; Trmcic-Cvitas, J., Hasan, E., Ramstedt, M., Li, X., Cooper, M.A., Abell, C., Huck, W.T., Gautrot, J.E., Biofunctionalized protein resistant oligo(ethylene glycol)-derived polymer brushes as selective immobilization and sensing platforms (2009) Biomacromolecules, 10 (10), pp. 2885-2894; Orski, S., Sheppard, G., Arnold, R., Grubbs, J., Locklin, J., Post-polymerization modification of polymer brushes (2012) Functional Polymers by Post-Polymerization Modification: Concepts, Guidelines, and Applications, , Theato, P. Klok, H. A. Wiley-VCH Verlag GmbH & Co. KGaA: Weinheim, Germany; Sheikh, S., Sheng, J.C.C., Blaszykowski, C., Thompson, M., New oligoethylene glycol linkers for the surface modification of an ultra-high frequency acoustic wave biosensor (2010) Chem. Sci., 1 (2), pp. 271-275; Ayres, N., Polymer brushes: Applications in biomaterials and nanotechnology (2010) Polym. Chem., 1 (6), pp. 769-777; Ebara, M., Yamato, M., Aoyagi, T., Kikuchi, A., Sakai, K., Okano, T., A novel approach to observing synergy effects of PHSRN on integrin-RGD binding using intelligent surfaces (2008) Adv. Mater., 20 (16), pp. 3034-3038; Kuzmyn, A.R., De Los Santos Pereira, A., Pop-Georgievski, O., Bruns, M., Brynda, E., Rodriguez-Emmenegger, C., Exploiting end group functionalization for the design of antifouling bioactive brushes (2014) Polym. Chem., 5 (13), pp. 4124-4131; Tischer, T., Claus, T.K., Bruns, M., Trouillet, V., Linkert, K., Rodriguez-Emmenegger, C., Goldmann, A.S., Barner-Kowollik, C., Spatially controlled photochemical peptide and polymer conjugation on biosurfaces (2013) Biomacromolecules, 14 (12), pp. 4340-4350; Jonkheijm, P., Weinrich, D., Kohn, M., Engelkamp, H., Christianen, P.C., Kuhlmann, J., Maan, J.C., Waldmann, H., Photochemical surface patterning by the thiol-ene reaction (2008) Angew. Chem., Int. Ed. Engl., 47 (23), pp. 4421-4424; Lin, P.C., Weinrich, D., Waldmann, H., Protein Biochips: Oriented Surface Immobilization of Proteins (2010) Macromol. Chem. Phys., 211 (2), pp. 136-144; Orski, S.V., Poloukhtine, A.A., Arumugam, S., Mao, L., Popik, V.V., Locklin, J., High density orthogonal surface immobilization via photoactivated copper-free click chemistry (2010) J. Am. Chem. Soc., 132 (32), pp. 11024-11026; Preuss, C.M., Tischer, T., Rodriguez-Emmenegger, C., Zieger, M.M., Bruns, M., Goldmann, A.S., Barner-Kowollik, C., A bioinspired light induced avenue for the design of patterned functional interfaces (2014) J. Mater. Chem. B, 2 (1), pp. 36-40; Tischer, T., Rodriguez-Emmenegger, C., Trouillet, V., Welle, A., Schueler, V., Mueller, J.O., Goldmann, A.S., Barner-Kowollik, C., Photo-patterning of non-fouling polymers and biomolecules on paper (2014) Adv. Mater., 26 (24), pp. 4087-4092; Glassner, M., Oehlenschlaeger, K.K., Welle, A., Bruns, M., Barner-Kowollik, C., Polymer surface patterning via Diels-Alder trapping of photo-generated thioaldehydes (2013) Chem. Commun. (Cambridge, U. K.), 49 (6), pp. 633-635; Wang, Y., Hu, W.J., Song, W., Lim, R.K., Lin, Q., Discovery of long-wavelength photoactivatable diaryltetrazoles for bioorthogonal 1,3-dipolar cycloaddition reactions (2008) Org. Lett., 10 (17), pp. 3725-3728; Yu, Z., Ho, L.Y., Wang, Z., Lin, Q., Discovery of new photoactivatable diaryltetrazoles for photoclick chemistry via 'scaffold hopping' (2011) Bioorg. Med. Chem. Lett., 21 (17), pp. 5033-5036; Jones, D.M., Brown, A.A., Huck, W.T.S., Surface-initiated polymerizations in aqueous media: Effect of initiator density (2002) Langmuir, 18 (4), pp. 1265-1269; Rodriguez-Emmenegger, C., Hasan, E., Pop-Georgievski, O., Houska, M., Brynda, E., Alles, A.B., Controlled/living surface-initiated ATRP of antifouling polymer brushes from gold in PBS and blood sera as a model study for polymer modifications in complex biological media (2012) Macromol. Biosci., 12 (4), pp. 525-532; Rodriguez-Emmenegger, C., Kylian, O., Houska, M., Brynda, E., Artemenko, A., Kousal, J., Alles, A.B., Biederman, H., Substrate-independent approach for the generation of functional protein resistant surfaces (2011) Biomacromolecules, 12 (4), pp. 1058-1066; Parry, K.L., Shard, A.G., Short, R.D., White, R.G., Whittle, J.D., Wright, A., ARXPS characterisation of plasma polymerised surface chemical gradients (2006) Surf. Interface Anal., 38 (11), pp. 1497-1504; Scofield, J.H., Hartree-Slater subshell photoionization cross-sections at 1254 and 1487 eV (1976) J. Electron Spectrosc. Relat. Phenom., 8 (2), pp. 129-137; Tanuma, S., Powell, C.J., Penn, D.R., Calculations of electron inelastic mean free paths. V. Data for 14 organic compounds over the 50-2000 eV range (1994) Surf. Interface Anal., 21 (3), pp. 165-176; Homola, J., Surface plasmon resonance sensors for detection of chemical and biological species (2008) Chem. Rev., 108 (2), pp. 462-493; Ma, H., Li, D., Sheng, X., Zhao, B., Chilkoti, A., Protein-resistant polymer coatings on silicon oxide by surface-initiated atom transfer radical polymerization (2006) Langmuir, 22 (8), pp. 3751-3756; Pop-Georgievski, O., Rodriguez-Emmenegger, C., De Los Santos Pereira, A., Proks, V., Brynda, E., Rypáček, F., Biomimetic non-fouling surfaces: Extending the concepts (2013) J. Mater. Chem. B, 1, pp. 2859-2867; Fan, X., Lin, L., Dalsin, J.L., Messersmith, P.B., Biomimetic anchor for surface-initiated polymerization from metal substrates (2005) J. Am. Chem. Soc., 127 (45), pp. 15843-15847; Riedel, T., Rodriguez-Emmenegger, C., De Los Santos Pereira, A., Bedajankova, A., Jinoch, P., Boltovets, P.M., Brynda, E., Diagnosis of Epstein-Barr virus infection in clinical serum samples by an SPR biosensor assay (2014) Biosens. Bioelectron., 55, pp. 278-284; Love, J.C., Estroff, L.A., Kriebel, J.K., Nuzzo, R.G., Whitesides, G.M., Self-assembled monolayers of thiolates on metals as a form of nanotechnology (2005) Chem. Rev., 105 (4), pp. 1103-1169; Vaisocherova, H., Zhang, Z., Yang, W., Cao, Z., Cheng, G., Taylor, A.D., Piliarik, M., Jiang, S., Functionalizable surface platform with reduced nonspecific protein adsorption from full blood plasma-Material selection and protein immobilization optimization (2009) Biosens. Bioelectron., 24 (7), pp. 1924-1930; Vaisocherova, H., Sevcu, V., Adam, P., Spackova, B., Hegnerova, K., De Los Santos Pereira, A., Rodriguez-Emmenegger, C., Homola, J., Functionalized ultra-low fouling carboxy- and hydroxy-functional surface platforms: Functionalization capacity, biorecognition capability and resistance to fouling from undiluted biological media (2014) Biosens. Bioelectron., 51, pp. 150-157; Scarano, S., Mascini, M., Turner, A.P., Minunni, M., Surface plasmon resonance imaging for affinity-based biosensors (2010) Biosens. Bioelectron., 25 (5), pp. 957-966; Shumaker-Parry, J.S., Zareie, M.H., Aebersold, R., Campbell, C.T., Microspotting streptavidin and double-stranded DNA arrays on gold for high-throughput studies of protein-DNA interactions by surface plasmon resonance microscopy (2004) Anal. Chem., 76 (4), pp. 918-929; Rusmini, F., Zhong, Z., Feijen, J., Protein immobilization strategies for protein biochips (2007) Biomacromolecules, 8 (6), pp. 1775-1789; Brault, N.D., Sundaram, H.S., Huang, C.J., Li, Y., Yu, Q., Jiang, S., Two-layer architecture using atom transfer radical polymerization for enhanced sensing and detection in complex media (2012) Biomacromolecules, 13 (12), pp. 4049-4056
Keywords: Acrylic monomers, Copolymers, Dendrimers, Ethylene, Ethylene glycol, Free radical reactions, Grafting (chemical), Mass spectrometry, Medical applications, Organic polymers, Polymerization, Polymers, Proteins, Secondary ion mass spectrometry, Surface plasmon resonance, X ray photoelectron spectroscopy, Biofunctionalization, Biomedical applications, Biotinylated antibodies, Oligo(ethylene glycol) methacrylate, Polymer architecture, Surface architectures, Surface initiated atom transfer radical polymerization (SI ATRP), Time of flight secondary ion mass spectrometry, Atom transfer radical polymerization
DOI: 10.1021/acs.langmuir.5b01114
ISSN: 07437463
Divisions: Current > Schools > School of Chemistry, Physics & Mechanical Engineering
Current > Institutes > Institute for Future Environments
Current > QUT Faculties and Divisions > Science & Engineering Faculty
Deposited On: 22 Sep 2016 04:50
Last Modified: 26 Sep 2016 02:24

Export: EndNote | Dublin Core | BibTeX

Repository Staff Only: item control page