Homogeneous sulfation of silk fibroin in an ionic liquid

Liu, Xiuying; Xu, Weilin; Zhang, Chaocan; Liu, Hongtao; Jin, Fangming

doi:10.1016/j.matlet.2014.12.140

Cited by 15 publications

(14 citation statements)

References 13 publications

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“…One of the future application areas for proteins will not only be the reprocessing of existing biopolymers, but the ability to derivatise these materials to create new materials properties. For Zein, proof of principle has been achieved in benzoylation (Biswas et al, 2006), and for silks sulfation has been effective (Liu et al, 2015). Such reactions could therefore readily be extended to other proteins.…”

Section: Future Of Proteins and Enzymes In Ionic Liquidsmentioning

confidence: 99%

Proteins in Ionic Liquids: Reactions, Applications, and Futures

et al. 2019

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Biopolymer processing and handling is greatly facilitated by the use of ionic liquids, given the increased solubility, and in some cases, structural stability imparted to these molecules. Focussing on proteins, we highlight here not just the key drivers behind protein-ionic liquid interactions that facilitate these functionalities, but address relevant current and potential applications of protein-ionic liquid interactions, including areas of future interest.

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Section: Future Of Proteins and Enzymes In Ionic Liquidsmentioning

confidence: 99%

Proteins in Ionic Liquids: Reactions, Applications, and Futures

et al. 2019

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“…A second approach to carboxylate the silk fibroin was inspired by published work on modifying the hydroxyl groups of cellulose. 83 Ionic liquid (IL) has been used to modify fibroin with sulfate groups, 84 but not with carboxyl groups. This approach is also described in greater detail in the Supporting Information.…”

Section: Methodsmentioning

confidence: 99%

Dual-Mode Cross-Linking Enhances Adhesion of Silk Fibroin Hydrogels to Intestinal Tissue

Heichel

Burke

2019

ACS Biomater. Sci. Eng.

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Compared to conventional wound closure methods like sutures and staples, polymer-based tissue adhesives afford some distinct advantages, such as greater ease of deployment in spatially constrained surgical sites. One way to achieve aqueous adhesion is by introducing catechol functional groups that form coordinate and covalent bonds with a variety of substrates. This approach, inspired by marine organisms, has been applied to biopolymers and synthetic polymers, but one key challenge is that compositions that are soluble in water are often susceptible to high swelling ratios that can result in undesired compression of neighboring tissues. This work sought to synthesize aqueous adhesive gels that are capable of two modes of association: (1) adhesion and covalent cross-linking reactions arising from catechol oxidation and (2) noncovalent cross-linking arising from self-assembly of polymer backbones within the gelled adhesive. The network’s self-assembly after gelation was envisioned to afford control over swelling and reinforce its strength. Bombyx mori silk fibroin was selected as the backbone of the adhesive network because it can be processed into an aqueous solution yet later be rendered insoluble in water through the assembly of its hydrophobic protein core. Distinct from a previous approach to functionalize silk directly with catechol groups, this work investigated in situ generation of catechol on silk fibroin by enzymatically modifying phenolic side chains, where it was found that this enzymatic approach led to conjugates with higher degrees of catechol functionalization and aqueous solubility. Silk fibroin was functionalized with tyramine to enrich the protein’s phenolic side chains, which were subsequently oxidized into catechol groups using mushroom tyrosinase (MT). The gelation of the silk conjugates with MT was monitored by rheology, and the gels exhibited low water uptake. Phenolic enrichment increased the rate of chemical cross-linking leading to gelation but did not interrupt assembly of silk’s secondary structures. Adhesion of the tyramine–silk conjugates to porcine intestine was found to be superior to fibrin sealant, and induction of β sheet secondary structures was found to further enhance adhesive strength through a second mode of cross-linking. Neither the chemical functionalization nor phenol oxidation affected the ability of intestinal epithelial cells (Caco-2) to attach and proliferate. Phenolic functionalization and oxidative cross-linking of silk fibroin was found to afford a new route to water-soluble, catechol-functionalized polymers, which were found to display excellent adhesion to mucosal tissue and whose secondary structure provides an additional mode to control strength and swelling of adhesive gels.

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“…Electrospun sulfated SF nanofibrous materials and PLGA scaffolds with covalently immobilized sulfated silk for vascular tissue engineering purposes have been fabricated . Recent work explored the feasibility of direct silk sulfonation, dissolved in the 1‐butyl‐3‐methylimidazolium chloride ([BMIM]Cl, an ionic liquid) . Milder reaction conditions and hence lower silk degradation were found to be the main benefits of the presented protocol.…”

Section: Manipulating Silk Fibroin: Chemical and Biochemical Approachmentioning

confidence: 99%

On the Routines of Wild-Type Silk Fibroin Processing Toward Silk-Inspired Materials: A Review

Volkov

Ferreira

Cavaco-Paulo

2015

Macromol. Mater. Eng.

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For years, silk fibroin of a domestic silkworm, Bombyx mori, has been recognized as a valuable material and extensively used. In the last decades, new application fields are emerging for this versatile material. Those final, specific applications of silk dictate the way it has been processed in industry and research. This review focuses on the description of various approaches for silk downstream processing in a laboratory scale, that fall within several categories. The detailed description of workflow possibilities from the naturally found material to a finally formulated product is presented. Considerable attention is given to (bio‐) chemical approaches of silk fibroin transformation, particularly, to its enzyme‐driven modifications. The focus of the current literature survey is exclusively on the methods applied in research and not industry.

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Homogeneous sulfation of silk fibroin in an ionic liquid

Cited by 15 publications

References 13 publications

Proteins in Ionic Liquids: Reactions, Applications, and Futures

Proteins in Ionic Liquids: Reactions, Applications, and Futures

Dual-Mode Cross-Linking Enhances Adhesion of Silk Fibroin Hydrogels to Intestinal Tissue

On the Routines of Wild-Type Silk Fibroin Processing Toward Silk-Inspired Materials: A Review

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