Direct and Indirect Biomimetic Peptide Modification of Alginate: Efficiency, Side Reactions, and Cell Response

Abstract

In the fast-developing field of tissue engineering there is a constant demand for new materials as scaffolds for cell seeding, which can better mimic a natural extracellular matrix as well as control cell behavior. Among other materials, polysaccharides are widely used for this purpose. One of the main candidates for scaffold fabrication is alginate. However, it lacks sites for cell adhesion. That is why one of the steps toward the development of suitable scaffolds for cells is the introduction of the biofunctionality to the alginate structure. In this work we focused on bone-sialoprotein derived peptide (TYRAY) conjugation to the molecule of alginate. Here the comparison study on four different approaches of peptide conjugation was performed including traditional and novel modification methods, based on 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide/N-hydroxy succinimide (EDC/NHS), 4-(4,6-dimethoxy-1,3,5-triazine-2-yl)-4-methylmorpholinium chloride (DMTMM), thiol-Michael addition and Cu-catalyzed azide–alkyne cycloaddition reactions. It was shown that the combination of the alginate amidation with the use of and subsequent Cu-catalyzed azide–alkyne cycloaddition led to efficient peptide conjugation, which was proven with both NMR and XPS methods. Moreover, the cell culture experiment proved the positive effect of peptide presence on the adhesion of human embryonic stem cells.

Colorimetric pH-Responsive Biomaterials Based on Pyranoflavylium-Biopolymer Hybrid Conjugates

“…In general, for the conjugate and free pigment, the proton chemical shifts assigned to the structure of Pyflav-CHT 6 did not alter significantly except for the two singlets assigned to H-3 and H-9 which slightly undergo downfield shifts. The peaks with higher chemical shift (δ 4.83 ppm) in the sodium ALG region were assigned to the guluronic acid anomeric proton (H-4G) in agreement with data previously reported in the literature. , The acquired NMR spectra also allowed the determination of substitution of pigment 5 in ALG to be 1.2%, from the ratio between of the peak integrals corresponding to H-3″ and H-5″ protons of pigment (6.80 ppm) and the one at 4.83 ppm that corresponds to proton H-4G in ALG, as shown in eq …”

Optimization of the Rheological Properties of Self-Assembled Tripeptide/Alginate/Cellulose Hydrogels for 3D Printing

“…Many efforts have been made to induce an appropriate cellular adhesion in alginate gels. Besides the introduction of gelatin or collagen in the ink [ 16 ], one strategy is to graft different cell adhesive peptides to alginate [ 34 , 35 ]. Recently, Criado-Gonzalez and coworkers [ 36 ] showed that the incorporation of a self-assembled phosphorylated tri-peptide, Fmoc-FFY (Fmoc: 9-fluorenylmethoxycarbonyl; F: phenylalanine; Y: tyrosine), within the polyethylene glycol [ 37 ] or hyaluronic acid hydrogels allowed for the promotion of fibroblast cell adhesion [ 36 , 38 ].…”

A guide to functionalisation and bioconjugation strategies to surface-initiated polymer brushes

“…72,73 DMTMM and corresponding reactive ester intermediates are soluble and more stable against hydrolysis, compared to those based on EDC, therefore enabling more effective amide bond formation in a variety of protic solvents. 47,74 Though DMTMM has been used for amidation in a wide range of systems (e.g. to enable ''grafting to'' of free polymer chains onto surfaces, molecular polymer brushes and free polymer chains), [75][76][77][78] only a few recent reports have explored this approach for the functionalization of surfacetethered polymer brushes.…”