Click chemistry for 3D bioprinting

Sun, Yangyang; Okoro, Oseweuba Valentine; Deng, Yuewen; Jiang, Guohua; Shavandi, Amin

doi:10.1039/d3mh00516j

Cited by 11 publications

(9 citation statements)

References 303 publications

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“…Printing ink with fast photo-cross-linking ability is strongly desired to build scaffolds with excellent fidelity . Due to the high reactivity of thiol–ene chemistry, the speed of thiol–ene step-growth gelation is much faster than free-radical chain-growth polymerization . In this work, the GelSH was chosen to serve as a (i) temperature-sensitive component to induce temporary solidification and (ii) photo-cross-linker that provides thiol groups for thiol–ene click reaction.…”

Section: Resultsmentioning

confidence: 99%

“…12 Due to the high reactivity of thiol−ene chemistry, the speed of thiol−ene step-growth gelation is much faster than free-radical chain-growth polymerization. 13 In this work, the GelSH was chosen to serve as a (i) temperature-sensitive component to induce temporary solidification and (ii) photo-cross-linker that provides thiol groups for thiol−ene click reaction. Since the curing behavior might be affected by the available thiol groups, we prepared three different NorHA/GelSH bioinks with the GelSH DS varying from 10.1 to 55.7%, and named them as NorHA/GelSH Low (Thiol DS 10.1% thiol/ene ∼0.11), NorHA/GelSH Medium (Thiol DS 35.2%, thiol/ene ∼0.38), and NorHA/GelSH High (Thiol DS 55.7%, thiol/ene ∼0.6).…”

Section: Curing Behavior Evaluationmentioning

confidence: 99%

“…12 In general, based on American Society of Testing and Materials (ASTM) standards, 3D bioprinting can be categorized into three approaches: vat polymerization (VP)based, jetting-based, and extrusion-based bioprinting. 13 VPbased bioprinting has superior resolution and speed, while the inks are mainly limited to photopolymerizable materials. 14 Jetting-based bioprinting allows high flux, noncontact, and ondemand drop fabrication but often faces problems like nozzle clogging, low strength, and limited cell density.…”

Section: Introductionmentioning

confidence: 99%

“…In general, based on American Society of Testing and Materials (ASTM) standards, 3D bioprinting can be categorized into three approaches: vat polymerization (VP)-based, jetting-based, and extrusion-based bioprinting . VP-based bioprinting has superior resolution and speed, while the inks are mainly limited to photopolymerizable materials .…”

Section: Introductionmentioning

confidence: 99%

“…Hence, the development of an alternative photo-cross-linking approach that could avoid these problems is highly desired in 3D bioprinting. In recent years, the thiol–ene click chemistry has attracted more attention for its ability to realize rapid gelation in a cell-friendly and oxygen-tolerating way. , Many bioinks based on norbornene-modified hyaluronic acid (NorHA), methylcellulose (NorMC), collagen (NorCol), gelatin (GelNB), and cross-linker DTT have been used in 3D bioprinting recently. ,− Although these systems preserved the merits of thiol–ene click chemistry, the curing behavior and physical performances are highly sensitive to the initial thiol/ene ratio, which makes the regulation of these properties quite complex . Moreover, the bifunctional thiol DTT also lacks extra thiol groups for potential biological additives conjugation.…”

Section: Introductionmentioning

confidence: 99%

See 4 more Smart Citations

Customization of an Ultrafast Thiol–Norbornene Photo-Cross-Linkable Hyaluronic Acid–Gelatin Bioink for Extrusion-Based 3D Bioprinting

Xiao,

Yang,

Lai

et al. 2023

Biomacromolecules

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Light-based three-dimensional (3D) bioprinting has been widely studied in tissue engineering. Despite the fact that freeradical chain polymerization-based bioinks like hyaluronic acid methacrylate (HAMA) and gelatin methacryloyl (GelMA) have been extensively explored in 3D bioprinting, the thiol−ene hydrogel system has attracted increasing attention for its ability in building hydrogel scaffolds in an oxygen-tolerant and cell-friendly way. Herein, we report a superfast curing thiol−ene bioink composed of norbornene-modified hyaluronic acid (NorHA) and thiolated gelatin (GelSH) for 3D bioprinting. A new facile approach was first introduced in the synthesis of NorHA, which circumvented the cumbersome steps involved in previous works. Additionally, after mixing NorHA with macro-cross-linker GelSH, the customized NorHA/GelSH bioinks exhibited fascinating superiorities over the gold standard GelMA bioinks, such as an ultrafast curing rate (1−5 s), much lowered photoinitiator concentration (0.03% w/v), and flexible physical performances. Moreover, the NorHA/ GelSH hydrogel greatly avoided excess ROS generation, which is important for the survival of the encapsulated cells. Last, compared with the GelMA scaffold, the 3D-printed NorHA/GelSH scaffold not only exhibited excellent cell viability but also guaranteed cell proliferation, revealing its superior bioactivity. In conclusion, the NorHA/GelSH system is a promising candidate for 3D bioprinting and tissue engineering applications.

show abstract

Section: Resultsmentioning

confidence: 99%

Section: Curing Behavior Evaluationmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 3 more Smart Citations

Customization of an Ultrafast Thiol–Norbornene Photo-Cross-Linkable Hyaluronic Acid–Gelatin Bioink for Extrusion-Based 3D Bioprinting

Xiao,

Yang,

Lai

et al. 2023

Biomacromolecules

View full text Add to dashboard Cite

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Metal‐Phenolic Network Directed Coating of Single Probiotic Cell Followed by Photoinitiated Thiol‐Ene Click Fortification to Enhance Oral Therapy

Fang,

Liu

2023

Small

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Probiotics‐based oral therapy has become a promising way to prevent and treat various diseases, while the application of probiotics is primarily restricted by loss of viability due to adverse conditions in the gastrointestinal (GI) tract during oral delivery. Layer‐by‐layer (LbL) single‐cell encapsulation approaches are widely employed to improve the bioavailability of probiotics. However, they are generally time‐ and labor‐intensive owing to multistep operation. Herein, a simple yet efficient LbL technique is developed to coat a model probiotic named Escherichia coli Nissle 1917 (EcN) through polyphenol‐Ca2+ network directed allyl‐modified gelatin (GelAGE) adsorption followed by cross‐linking of GelAGE via photoinitiated thiol‐ene click reaction to protect EcN from harsh microenvironments of GI tract. LbL single‐cell encapsulation can be performed within 1 h through simple operation. It is revealed that coated EcN exhibits significantly improved viability against acidic gastric fluid and bile salts, and enhanced colonization in the intestinal tract without loss of proliferation capabilities. Furthermore, oral therapy of coated EcN remarkably relieves the pathological symptoms associated with colitis in mice including down‐regulating inflammation, repairing epithelial barriers, scavenging reactive oxygen species (ROS), and restoring the homeostasis of gut microbiota. This simplified LbL coating strategy has great potential for various probiotics‐mediated biomedical and nutraceutical applications.

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Tailored endothelialization enabled by engineered endothelial cell vesicles accelerates remodeling of small-diameter vascular grafts

Wang,

Zhou,

et al. 2024

Bioactive Materials

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Click chemistry for 3D bioprinting

Abstract: Bioinks are employed in the fabrication of 3D scaffolds containing cells and macromolecules that can be applied in regenerative medicine. The use of such bioinks facilitates the controlled introduction and...

Cited by 11 publications

References 303 publications

Customization of an Ultrafast Thiol–Norbornene Photo-Cross-Linkable Hyaluronic Acid–Gelatin Bioink for Extrusion-Based 3D Bioprinting

Customization of an Ultrafast Thiol–Norbornene Photo-Cross-Linkable Hyaluronic Acid–Gelatin Bioink for Extrusion-Based 3D Bioprinting

Metal‐Phenolic Network Directed Coating of Single Probiotic Cell Followed by Photoinitiated Thiol‐Ene Click Fortification to Enhance Oral Therapy

Tailored endothelialization enabled by engineered endothelial cell vesicles accelerates remodeling of small-diameter vascular grafts

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