Green chemistry for the cross-linking of photo-sensitive furan modified gelatin

García‐Astrain, Clara; Peña-Rodríguez, Cristina; Retegi, Aloña; Eceiza, Arantxa; Corcuera, María Ángeles; Gabilondo, Nagore

doi:10.1016/j.matlet.2015.07.096

Cited by 17 publications

(10 citation statements)

References 18 publications

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“…A proposed photo-reversible crosslinking system takes advantage of functionalities which can undergo a photo-reversible dimerization reaction by irradiation at different wavelengths 3). However, photo-reversibility was not explored in the reported work [58].…”

Section: Photo-reversible Systems: π-π Cycloadditionmentioning

confidence: 99%

“…Reports have shown that introducing (bulky) groups (i.e. acyl groups) to the side chains of gelatin can hamper the triple helix formation and the associated renaturation properties associated to the physical gelation of gelatin (Figure 1 B, D, C, M) [16,58,61,100,135]. Since the transition from helix to coil is accompanied by endothermal heat, the effect of a modification on triple helix formation and associated physical gelation properties can be quantified using differential scanning calorimetry (DSC).…”

Section: Influence Of Modification On Triple Helix Formationmentioning

confidence: 99%

“…These measurements can either be performed in solution or in the gel state during which the associated energies related to the physical gelation around 30°C can be assessed [16,41,136]. Alternatively, also strategies were reported in which the sample is first dehydrated by heating above 100°C followed by rapid cooling to prevent renaturation and by performing a second heating run during which differences in the glass transition (Tg), which is associated to the triple helix formation of gelatin, can be compared [47,58,61].…”

Section: Influence Of Modification On Triple Helix Formationmentioning

confidence: 99%

“…Derivatives for enzymatic crosslinking (white): gelatin-tyramine (U) [4,11], gelatin/tyramine/heparin (V) [4]; Derivatives suitable for photo-oxidation (green): gelatin-FA (W) [54], gelatin-FI (X) [55] gel-FGE (Y) [56,57]; π-π cycloaddition (yellow): gel-MFVF (Z) [58], gel-AC (α) [59], gel-NC (β) [59];…”

Section: Introductionmentioning

confidence: 99%

“…Finally, a non-exhaustive overview of all presented gelatin derivatives and their processability potential towards specific additive manufacturing technologies is provided. Figure 1: Non-exhaustive overview of different crosslinkable gelatins including their method of preparation classified according to their crosslinking chemistry: Chain-growth derivatives (blue): gel-MOD/gel-MA(A) [9], gel-MOD-AEMA (B) [16], gel-MA-DA (C) [36], GMA (D) [37], gel-AA (E) [38], gelatin-acrylamide (F) [39], gel-BTHE (G) [40], gel-Boc-AEMA (H) [41], methacrylated poly(ethylene glycol)-modified gelatin(MPG) (I) [42,43], gelatin-PEG (K) [44]; Thiolated gelatins suitable for disulphide chemistry of thiol-ene chemistry (purple): gel-SH (J) [44,45], gel-SH (L) [45,46], aminated gelatin (M) [5,47], aminated-thiolated-gelatin (N) [47], gelatin-Cys-2-MPD (O) [48], gelatin-Cys (P) [48], gel-PEG-Cys (Q) [49], gelatin-TBA-MNA (R) [50], gel-S (S) [51,52], gelatin-thiobutyrolacton (T) [53]; Derivatives for enzymatic crosslinking (white): gelatin-tyramine (U) [4,11], gelatin/tyramine/heparin (V) [4]; Derivatives suitable for photo-oxidation (green): gelatin-FA (W) [54], gelatin-FI (X) [55] gel-FGE (Y) [56,57]; π-π cycloaddition (yellow): gel-MFVF (Z) [58], gel-AC (α) [59], gel-NC (β) [59]; Derivatives suitable for Diels-Alder click (light green): gel-furan (γ) [60], gel-FGE (δ) …”

Section: Introductionmentioning

confidence: 99%

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(Photo-)crosslinkable gelatin derivatives for biofabrication applications

et al. 2019

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Over the recent decades gelatin has proven to be very suitable as an extracellular matrix mimic for biofabrication and tissue engineering applications. However, gelatin is prone to dissolution at typical cell culture conditions and is therefore often chemically modified to introduce (photo-)crosslinkable functionalities. These modifications allow to tune the material properties of gelatin, making it suitable for a wide range of biofabrication techniques both as a bioink and as a biomaterial ink (component).The present review provides a non-exhaustive overview of the different reported gelatin modification strategies to yield crosslinkable materials that can be used to form hydrogels suitable for 2 biofabrication applications. The different crosslinking chemistries are discussed and classified according to their crosslinking mechanism including chain-growth and step-growth polymerization.The step-growth polymerization mechanisms are further classified based on the specific chemistry including different (photo-)click chemistries and reversible systems. The benefits and drawbacks of each chemistry are also briefly discussed. Furthermore, focus is placed on different biofabrication strategies applying inkjet, deposition and light-based additive manufacturing techniques, and the applications of the obtained 3D constructs.

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Section: Photo-reversible Systems: π-π Cycloadditionmentioning

confidence: 99%

Section: Influence Of Modification On Triple Helix Formationmentioning

confidence: 99%

Section: Influence Of Modification On Triple Helix Formationmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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(Photo-)crosslinkable gelatin derivatives for biofabrication applications

et al. 2019

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Light and Shape‐Memory Polymers: Characterization, Preparation, Stimulation, and Application

Fang,

Yan,

Chen

et al. 2023

Macro Materials & Eng

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Shape‐memory polymers (SMPs) are smart materials that change shape when exposed to stimuli and have various applications in different fields due to their unique properties. Light, as a kind of electromagnetic radiation, plays an important role in understanding the structure‐property relations of SMPs, preparing original shapes, using them as non‐contact stimuli sources, and tuning the optical properties of SMPs. This review provides a comprehensive review of the involvement of light in structure‐preparation‐stimuli‐application of SMPs. The review is divided into four sections. First, applications of optical/spectroscopic approaches that provide information for understanding structure‐property relations in SMPs, especially during programming and recovery. Second, describes how to build SMPs with light, including different photochemical reactions and 3D photocuring technologies. Third, discusses how light is used to trigger the shape change of SMPs through both photochemical and photothermal mechanisms. Last, focuses on how to take advantage of the shape‐memory effect to tune the optical characteristics of polymers, including various structures of SMP color‐changing materials and their synthetic strategies. Future research could focus on developing efficient photothermal fillers, new 3D printing techniques for SMPs, exploring their use in biomedical and wearable devices, and optimizing SMPs for industrial applications.

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