Michael-Type Addition Reactions for the In Situ Formation of Poly(vinyl alcohol)-Based Hydrogels

Tortora, Mariarosaria; Cavalieri, Francesca; Chiessi, Ester; Paradossi, Gaio

doi:10.1021/bm0607269

Cited by 43 publications

(18 citation statements)

References 19 publications

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“…These peaks were not present in the spectrum of the starting material ( Figure 1C) There are two possible reaction routes for chemical modifications of polymers through the use of the glycidyl methacrylate: transesterification and epoxide ringopening mechanisms. 28,29 The reaction mechanism of glycidyl methacrylate and dextran by using DMSO as a solvent has been found that transesterification is the predominant route for the polymer methacrylation. 30 In the case of laminarin, a definitive conclusion cannot be drawn from the NMR and FTIR analysis.…”

Section: Synthesis and Characterization Of Methacrylated Laminarinmentioning

confidence: 99%

Photo-Cross-Linked Laminarin-Based Hydrogels for Biomedical Applications

2016

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Laminarin is a low-molecular-weight (<10 kDa) glucan found in brown algae made up of β(1→3)-glucan with β(1→6)-branches. This is one of the most abundant carbon sources in the marine ecosystem. Laminarin has been found to possess various biological interesting properties, such as antioxidant and antimicrobial activities. An attractive feature of laminarin is its inherently low viscosity and high solubility in organic and aqueous solvents that facilitate processing. This makes laminarin an appealing material for the development of new hydrogels that can be easily injected through minimally invasive procedures or used for microfabrication of hydrogels. An approach for synthesizing photo-cross-linkable laminarin hydrogels is presented in this work for the first time. Photo-cross-linkable laminarin was prepared by chemical modification with acrylate groups. The synthesized photo-cross-linkable laminarin material provides the basis for the development of a new injectable system for biomedical purposes that could be used alone or with encapsulated cells or biological molecules. The cross-linking of the methacrylated laminarin is straightforward via photoinitiated polymerization. The possibility to control the methacrylation degree of laminarin and to prepare solutions up to at least 15% w/v permits us to obtain hydrogels with tuned and wide range of stiffness and swelling. Furthermore, the encapsulation of human-adipose-derived stem cells encapsulated in the photo-cross-linked hydrogels demonstrated in vitro biocompatibility.

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Section: Synthesis and Characterization Of Methacrylated Laminarinmentioning

confidence: 99%

Photo-Cross-Linked Laminarin-Based Hydrogels for Biomedical Applications

2016

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“…[52] Both amines and thiols on proteins participate in the reaction and it is possible to control where the reaction takes place based on the reaction pH relative to the pK a of the amino acid functional group. [2,49] In this study, we go beyond the characterization of secondary structure using Raman spectroscopy to show that quantitative chemical results can be achieved. First, using single amino acids and then full proteins, we compare the extent of reaction and specific reaction site of functionalized amine and thiol groups measured with Raman spectroscopy against standard protocols.…”

Section: Introductionmentioning

confidence: 99%

Quantifying amino acid and protein substitution using Raman spectroscopy

Budhavaram

Barone

2011

J Raman Spectroscopy

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Raman spectroscopy can be a powerful tool for the characterization of modified amino acids and proteins. In addition to the potential for quantitative results, it offers the advantage of not requiring any sample preparation. Modification of amines and thiols on amino acids and proteins are common reactions used for medical, biological, food, and agricultural purposes. We hypothesized that the Raman spectrum could be used to quantify the reactions and would be more informative than typical characterization techniques such as the ninhydrin test. To prove the hypothesis, the amino acids alanine, cysteine, and lysine were modified with ethyl vinyl sulfone (EVS) using a nucleophilic addition reaction known as the Michael addition and the product was characterized using Raman spectroscopy. The Raman spectroscopy results were compared with ultraviolet-visible spectroscopy results based on ninhydrin analysis of the modified amino acids. The Raman spectroscopy analysis was able to discern site-specific reactions on the amino acids and suggested that more amino acid moieties were substituted than predicted using the ninhydrin test alone. Substitution of the full protein ovalbumin with EVS showed similar results. The ninhydrin test showed the substitution of primary amines and thiols but could not detect substitution of secondary amines remaining after loss of the primary amine.

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“…The Michael addition of nucleophiles (amine or thiol group) to α,β-unsaturated carbonyl compounds or α,β-unsaturated sulfones in water forms hydrogels. Various functionalized polymers, such as poly(ethylene glycol) (PEG) [24][25][26], poly(vinyl alcohol) (PVA) [27], N-isopropylacrylamide (NIPAAm) [28], and natural polymers [14,29] have been crosslinked via Michael addition and formed hydrogels. The copper [Cu(I)] catalyzed azide-alkyne cycloaddition is one of the most popular click chemistry reactions.…”

Section: Chemical Hydrogelsmentioning

confidence: 99%

Introduction to In Situ Forming Hydrogels for Biomedical Applications

Choi

Loh

Tan

et al. 2014

In-Situ Gelling Polymers

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In situ gelling polymer aqueous solutions undergo sol-to-gel transition through chemical and/or physical crosslinking. The criterion on sol and gel is an important issue, therefore, rheology of hydrogel have been discussed in detail. The in situ gelling system has been investigated for minimally invasive drug delivery, injectable tissue engineering, gene delivery, and wound healing. In this chapter, in situ gelling systems and their various biomedical applications were briefly summarized.

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Michael-Type Addition Reactions for the In Situ Formation of Poly(vinyl alcohol)-Based Hydrogels

Cited by 43 publications

References 19 publications

Photo-Cross-Linked Laminarin-Based Hydrogels for Biomedical Applications

Photo-Cross-Linked Laminarin-Based Hydrogels for Biomedical Applications

Quantifying amino acid and protein substitution using Raman spectroscopy

Introduction to In Situ Forming Hydrogels for Biomedical Applications

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