Efficient functionalization of alginate biomaterials

Abstract Peptide coupled alginates obtained by chemical functionalization of alginates are commonly used as scaffold materials for cells in regenerative medicine and tissue engineering. We here present an alternative to the commonly used carbodiimide chemistry, using partial periodate oxidation foll...

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Bibliographic Details
Published in:Biomaterials 2016-02, Vol.80, p.146-156
Main Authors: Dalheim, Marianne Ø, Vanacker, Julie, Najmi, Maryam A, Aachmann, Finn L, Strand, Berit L, Christensen, Bjørn E
Format: Article
Language:English
Subjects:
Advanced Basic Science
Alginate
Alginates
Alginates - chemistry
Amination
Animals
Biocompatible Materials - chemistry
Biomaterials
Biomedical materials
Byproducts
Cell Adhesion
Cell Line
Dental materials
Dentistry
Glucuronic Acid - chemistry
Hexuronic Acids - chemistry
Humans
Joining
Mice
Myoblasts - cytology
Oligopeptides - chemistry
Oxidation-Reduction
Peptides
Periodate oxidation
Periodic Acid - chemistry
Reductive amination
RGD peptide
Stem Cells - cytology
Tissue engineering
Tyrosine - analogs & derivatives
Tyrosine - chemistry
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Summary:Abstract Peptide coupled alginates obtained by chemical functionalization of alginates are commonly used as scaffold materials for cells in regenerative medicine and tissue engineering. We here present an alternative to the commonly used carbodiimide chemistry, using partial periodate oxidation followed by reductive amination. High and precise degrees of substitution were obtained with high reproducibility, and without formation of by-products. A protocol was established using l -Tyrosine methyl ester as a model compound and the non-toxic pic-BH3 as the reducing agent. DOSY was used to indirectly verify covalent binding and the structure of the product was further elucidated using NMR spectroscopy. The coupling efficiency was to some extent dependent on alginate composition, being most efficient on mannuronan. Three different bioactive peptide sequences (GRGDYP, GRGDSP and KHIFSDDSSE) were coupled to 8% periodate oxidized alginate resulting in degrees of substitution between 3.9 and 6.9%. Cell adhesion studies of mouse myoblasts (C2C12) and human dental stem cells (RP89) to gels containing various amounts of GRGDSP coupled alginate demonstrated the bioactivity of the material where RP89 cells needed higher peptide concentrations to adhere.
ISSN:0142-9612
1878-5905
DOI:10.1016/j.biomaterials.2015.11.043