Spatially controlled photochemical peptide and polymer conjugation on biosurfaces

Tischer, T., Claus, T. K., Bruns, M., Trouillet, V., Linkert, K., Rodriguez-Emmenegger, C., Goldmann, A. S., Perrier, S., Börner, H. G., & Barner-Kowollik, C. (2013) Spatially controlled photochemical peptide and polymer conjugation on biosurfaces. Biomacromolecules, 14(12).

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Abstract

An efficient phototriggered Diels-Alder conjugation is utilized to graft in an effective and straightforward approach poly(trifluoro ethyl methacrylate) (Mn = 3700 Da, Crossed D sign = 1.27) and a model peptide (GIGKFLHS) onto thin hyaluronan films and cellulose surfaces. The surfaces were functionalized with an o-quinodimethane moiety - capable of releasing a caged diene - via carbodiimide mediated coupling. The o-quinodimethane group is employed as a photoactive linker to tether predefined peptide/polymer strands in a spatially controlled manner onto the biosurface by photoenol ligation. An in-depth characterization employing XPS, ToF-SIMS, SPR, ellipsometry, and AFM was conducted to evidence the effectiveness of the presented approach. © 2013 American Chemical Society.

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22 citations in Web of Science®

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ID Code: 99366
Item Type: Journal Article
Refereed: Yes
Additional Information: Cited By :19
Export Date: 5 September 2016
CODEN: BOMAF
Correspondence Address: Barner-Kowollik, C.; Preparative Macromolecular Chemistry, Institut für Technische Chemie und Polymerchemie, Karlsruhe Institute of Technology (KIT), Engesserstr. 18, 76128 Karlsruhe, Germany; email: christopher.barner-kowollik@kit.edu
Chemicals/CAS: cellulose, 61991-22-8, 68073-05-2, 9004-34-6; cyanamide, 151-51-9, 420-04-2; hyaluronic acid, 31799-91-4, 9004-61-9, 9067-32-7; methane, 74-82-8
Tradenames: K-Alpha spectrometer, Thermo, United Kingdom; MFP-3D-BIO AFM, Asylum Research, United States; Spectroscopic Imaging auto-nulling ellipsometer EP3-SE, Nanofilm Technologies, Germany; TOF.SIMS5 instrument, ION-TOF, Germany
Manufacturers: Asylum Research, United States; ION-TOF, Germany; Nanofilm Technologies, Germany; Thermo, United Kingdom
Funding Details: Alexander von Humboldt Foundation
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Keywords: Bio-surfaces, Carbodiimides, Cellulose surfaces, Diels-Alder, Ethyl methacrylates, Functionalized, Hyaluronan, Model peptides, Cellulose films, Secondary ion mass spectrometry, Peptides, 2 quinodimethane derivative, cellulose, cyanamide, glycylisoleucylglycyllysylphenylalanylleucylhistidylserine, hyaluronic acid, methane, peptide, poly(trifluoroethyl methacrylate), polymer, polymethacrylic acid derivative, unclassified drug, article, atomic force microscopy, chemical modification, chemical reaction, chemical structure, conjugation, covalent bond, Diels Alder reaction, ellipsometry, film, isomerization, photochemistry, physical chemistry, priority journal, surface plasmon resonance, surface property, synthesis, time of flight mass spectrometry, time of flight secondary ion mass spectrometry, ultraviolet irradiation, X ray photoelectron spectroscopy, Cellulose Film, Mass Spectrometers, Amino Acid Sequence, Coated Materials, Biocompatible, Cross-Linking Reagents, Humans, Microscopy, Atomic Force, Peptide Fragments, Photochemical Processes, Polymethacrylic Acids, Surface Properties, Tissue Engineering
DOI: 10.1021/bm401274v
ISSN: 15257797
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: 29 Sep 2016 05:20

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