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Highly reactive thiol-norbornene photo-click hydrogels : toward improved processability

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Abstract
In the present work, gelatin type B is modified with highly reactive norbornene functionalities (Gel-NB) following a one-pot synthesis approach to enable subsequent thiol-ene photo-click crosslinking. The modification strategy displays close control over the amount of introduced functionalities. Additionally, Gel-NB exhibits considerably improved processing capabilities in terms of two-photon polymerization when benchmarked to earlier-reported crosslinkable gelatin derivatives (e.g., gelatin-methacrylamide (Gel-MOD) and gelatin-methacrylamide-aminoethylmethacrylate (Gel-MOD-AEMA)). The improvement is especially apparent in terms of minimally required laser power (20 mW vs >= 60 mW (Gel-MOD) vs >= 40 mW (Gel-MOD-AEMA) at 100 mm s(-1) scan speed) and processable concentration range (>= 5 w/v% vs >= 10 w/v% (Gel-MOD/Gel-MOD-AEMA)). Furthermore, the proposed functionalization scheme maintains the excellent biocompatibility and cell interactivity of gelatin. Additionally, the norbornene functionalities have potential for straightforward postprocessing thiol-ene surface grafting of active molecules. As a consequence, a very promising material toward tissue engineering applications and more specifically, biofabrication, is presented.
Keywords
gelatin, two-photon polymerization, tissue engineering, additive manufacturing, thiol-ene, hydrogel, GELATIN, CHEMISTRY

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MLA
Van Hoorick, Jasper, et al. “Highly Reactive Thiol-Norbornene Photo-Click Hydrogels : Toward Improved Processability.” MACROMOLECULAR RAPID COMMUNICATIONS, vol. 39, no. 14, 2018, doi:10.1002/marc.201800181.
APA
Van Hoorick, J., Gruber, P., Markovic, M., Rollot, M., Graulus, G.-J., Vagenende, M., … Van Vlierberghe, S. (2018). Highly reactive thiol-norbornene photo-click hydrogels : toward improved processability. MACROMOLECULAR RAPID COMMUNICATIONS, 39(14). https://doi.org/10.1002/marc.201800181
Chicago author-date
Van Hoorick, Jasper, Peter Gruber, Marica Markovic, Mélanie Rollot, Geert-Jan Graulus, Maxime Vagenende, Maximilian Tromayer, et al. 2018. “Highly Reactive Thiol-Norbornene Photo-Click Hydrogels : Toward Improved Processability.” MACROMOLECULAR RAPID COMMUNICATIONS 39 (14). https://doi.org/10.1002/marc.201800181.
Chicago author-date (all authors)
Van Hoorick, Jasper, Peter Gruber, Marica Markovic, Mélanie Rollot, Geert-Jan Graulus, Maxime Vagenende, Maximilian Tromayer, Jürgen Van Erps, Hugo Thienpont, José Martins, Stefan Baudis, Aleksandr Ovsianikov, Peter Dubruel, and Sandra Van Vlierberghe. 2018. “Highly Reactive Thiol-Norbornene Photo-Click Hydrogels : Toward Improved Processability.” MACROMOLECULAR RAPID COMMUNICATIONS 39 (14). doi:10.1002/marc.201800181.
Vancouver
1.
Van Hoorick J, Gruber P, Markovic M, Rollot M, Graulus G-J, Vagenende M, et al. Highly reactive thiol-norbornene photo-click hydrogels : toward improved processability. MACROMOLECULAR RAPID COMMUNICATIONS. 2018;39(14).
IEEE
[1]
J. Van Hoorick et al., “Highly reactive thiol-norbornene photo-click hydrogels : toward improved processability,” MACROMOLECULAR RAPID COMMUNICATIONS, vol. 39, no. 14, 2018.
@article{8569053,
  abstract     = {{In the present work, gelatin type B is modified with highly reactive norbornene functionalities (Gel-NB) following a one-pot synthesis approach to enable subsequent thiol-ene photo-click crosslinking. The modification strategy displays close control over the amount of introduced functionalities. Additionally, Gel-NB exhibits considerably improved processing capabilities in terms of two-photon polymerization when benchmarked to earlier-reported crosslinkable gelatin derivatives (e.g., gelatin-methacrylamide (Gel-MOD) and gelatin-methacrylamide-aminoethylmethacrylate (Gel-MOD-AEMA)). The improvement is especially apparent in terms of minimally required laser power (20 mW vs >= 60 mW (Gel-MOD) vs >= 40 mW (Gel-MOD-AEMA) at 100 mm s(-1) scan speed) and processable concentration range (>= 5 w/v% vs >= 10 w/v% (Gel-MOD/Gel-MOD-AEMA)). Furthermore, the proposed functionalization scheme maintains the excellent biocompatibility and cell interactivity of gelatin. Additionally, the norbornene functionalities have potential for straightforward postprocessing thiol-ene surface grafting of active molecules. As a consequence, a very promising material toward tissue engineering applications and more specifically, biofabrication, is presented.}},
  articleno    = {{1800181}},
  author       = {{Van Hoorick, Jasper and Gruber, Peter and Markovic, Marica and Rollot, Mélanie and Graulus, Geert-Jan and Vagenende, Maxime and Tromayer, Maximilian and Van Erps, Jürgen and Thienpont, Hugo and Martins, José and Baudis, Stefan and Ovsianikov, Aleksandr and Dubruel, Peter and Van Vlierberghe, Sandra}},
  issn         = {{1022-1336}},
  journal      = {{MACROMOLECULAR RAPID COMMUNICATIONS}},
  keywords     = {{gelatin,two-photon polymerization,tissue engineering,additive manufacturing,thiol-ene,hydrogel,GELATIN,CHEMISTRY}},
  language     = {{eng}},
  number       = {{14}},
  pages        = {{7}},
  title        = {{Highly reactive thiol-norbornene photo-click hydrogels : toward improved processability}},
  url          = {{http://doi.org/10.1002/marc.201800181}},
  volume       = {{39}},
  year         = {{2018}},
}

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