Tyramine modified alginates via periodate oxidation for peroxidase induced hydrogel formation and immobilization

Prodanović, Olivera; Spasojević, Dragica; Prokopijević, Miloš; Radotić, Ksenija; Markovic, Nevena; Blažić, Marija; Prodanović, Radivoje

doi:10.1016/j.reactfunctpolym.2015.06.004

Cited by 29 publications

(20 citation statements)

References 31 publications

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“…The absorptions at 1516 and 830 cm −1 are attributed to tyramine moieties because of the aromatic C=C stretching and aromatic C-H bending vibrations. 30, 31 Furthermore, the unreacted secondary hydroxyl groups in PGS-SA show absorption at 3467 cm −1 that turns into a broader band at 3367 cm −1 in both PGS-TA spectra. It is likely that the absorptions of phenolic hydroxyl and amide groups from the immobilized tyramine moieties are merged with the unreacted secondary hydroxyl groups in the resultant PGS-TA.…”

Section: Resultsmentioning

confidence: 99%

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Tyramine functionalization of poly(glycerol sebacate) increases the elasticity of the polymer

Ding

Gao

et al. 2017

J. Mater. Chem. B

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Poly(glycerol sebacate) (PGS) is an elastomer used widely in tissue engineering studies due to good biocompatibility. Hereby we report a tyramine functionalized PGS called PGS-TA. Tyramine adds a stronger physical bonding capability to PGS-TA. Tensile tests showed that the softness and toughness of the material were similar to PGS. However, PGS-TA demonstrated 16-folds increase of elastic deformations compared to PGS processed under identical conditions. The in vitro studies demonstrated that the viability, and metabolic activity of baboon smooth muscle cells were the same as those on tissue culture polystyrene. Porous subcutaneous implants of PGS-TA substantially degraded in vivo over two weeks, showing good biodegradability and biocompatibility. We expect PGS-TA to be useful for applications in tissues and organs that are subjected to large reversible mechanical deformations.

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Section: Resultsmentioning

confidence: 99%

“…To our knowledge, tyramine is typically used to functionalize a biopolymer for horseradish peroxidase triggered oxidation to form a covalent crosslink. 25, 31, 32 This work will demonstrate the utilization of tyramine to form physical interactions for biomaterial design.…”

Section: Introductionmentioning

confidence: 99%

Tyramine functionalization of poly(glycerol sebacate) increases the elasticity of the polymer

Ding

Gao

et al. 2017

J. Mater. Chem. B

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“…The increased content of free carboxylic groups should, however, promote pectin's gelling properties, as well. The presence of tyramine originated aromatic rings within the modified polymer is proven by the presence of peaks at 1518 and 1417 cm −1 (C-C in-ring stretching vibrations) (Prodanovic et al 2015;Siddiqui et al 2009) in FTIR spectra of tyramine-pectin. Modification of pectin and introduction of aromatic rings was also confirmed by 1 H NMR spectra (Figs.…”

Section: Modification Of Pectin and Its Characterizationmentioning

confidence: 99%

Tyramine-modified pectins via periodate oxidation for soybean hull peroxidase induced hydrogel formation and immobilization

Prokopijević

Prodanović

Spasojević

et al. 2016

Appl Microbiol Biotechnol

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Pectin was modified by oxidation with sodium periodate at molar ratios of 2.5, 5, 10, 15 and 20 mol% and reductive amination with tyramine and sodium cyanoborohydride afterwards. Concentration of tyramine groups within modified pectin ranged from 54.5 to 538 μmol/g of dry pectin while concentration of ionizable groups ranged from 3.0 to 4.0 mmol/g of dry polymer compared to 1.5 mmol/g before modification due to the introduction of amino group. All tyramine-pectins showed exceptional gelling properties and could form hydrogel both by cross-linking of carboxyl groups with calcium or by cross-linking phenol groups with peroxidase in the presence of hydrogen peroxide. These hydrogels were tested as carriers for soybean hull peroxidase (SHP) immobilization within microbeads formed in an emulsion based enzymatic polymerization reaction. SHP immobilized within tyramine-pectin microbeads had an increased thermal and organic solvent stability compared to the soluble enzyme. Immobilized SHP was more active in acidic pH region and had slightly decreased K value of 2.61 mM compared to the soluble enzyme. After 7 cycles of repeated use in batch reactor for pyrogallol oxidation microbeads, immobilized SHP retained half of the initial activity.

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“…Tyramine, a biogenic amine occurring in plants and animals, owns a phenolic component and a terminal amino group which represents a suitable binding site for the amidation with alginate using the carbodiimide chemistry. In previous studies, tyramine was coupled to a wide range of natural polymers such as hyaluronic acid, dextran, and alginate to induce an enzyme‐mediated gelation using horseradish peroxidase (HRP) and hydrogen peroxide . These bioresponsive systems were mainly applied for encapsulations and 3D printing as in situ ‐forming, injectable hydrogels.…”

Section: Introductionmentioning

confidence: 99%

Tyramine‐conjugated alginate hydrogels as a platform for bioactive scaffolds

Schulz

Gepp

Stracke

et al. 2018

J Biomedical Materials Res

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Alginate‐based hydrogels represent promising microenvironments for cell culture and tissue engineering, as their mechanical and porous characteristics are adjustable toward in vivo conditions. However, alginate scaffolds are bioinert and thus inhibit cellular interactions. To overcome this disadvantage, bioactive alginate surfaces were produced by conjugating tyramine molecules to high‐molecular‐weight alginates using the carbodiimide chemistry. Structural elucidation using nuclear magnetic resonance spectroscopy and contact angle measurements revealed a surface chemistry and wettability of tyramine‐alginate hydrogels similar to standard cell culture treated polystyrene. In contrast to stiff cell culture plastic, tyramine‐alginate scaffolds were found to be soft (60–80 kPa), meeting the elastic moduli of human tissues such as liver and heart. We further demonstrated an enhanced protein adsorption with increasing tyramine conjugation, stable for several weeks. Cell culture studies with human mesenchymal stem cells and human pluripotent stem cell‐derived cardiomyocytes qualified tyramine‐alginate hydrogels as bioactive platforms enabling cell adhesion and contraction on (structured) 2‐D layer and spherical matrices. Due to the alginate functionalization with tyramines, stable cell–matrix interactions were observed beneficial for an implementation in biology, biotechnology, and medicine toward efficient cell culture and tissue substitutes. © 2018 The Authors. Journal of Biomedical Materials Research Part A published by Wiley Periodicals, Inc. J Biomed Mater Res Part A: 107A: 114–121, 2019.

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Tyramine modified alginates via periodate oxidation for peroxidase induced hydrogel formation and immobilization

Cited by 29 publications

References 31 publications

Tyramine functionalization of poly(glycerol sebacate) increases the elasticity of the polymer

Tyramine functionalization of poly(glycerol sebacate) increases the elasticity of the polymer

Tyramine-modified pectins via periodate oxidation for soybean hull peroxidase induced hydrogel formation and immobilization

Tyramine‐conjugated alginate hydrogels as a platform for bioactive scaffolds

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