Polymer Bulletin

, Volume 74, Issue 10, pp 4069–4085 | Cite as

Catechol-modified hyaluronic acid: in situ-forming hydrogels by auto-oxidation of catechol or photo-oxidation using visible light

  • Takeshi Sato
  • Takao Aoyagi
  • Mitsuhiro Ebara
  • Rachel Auzély-Velty
Original Paper
First Online:
Received:
Revised:
Accepted:

Abstract

Mussel-inspired polymers have emerged as attractive candidates for the synthesis of injectable hydrogels with tissue-adhesive properties. In these systems, polymer crosslinking occurs via the oxidative coupling of catechol groups grafted on the polymer backbone, performed in the presence of an enzyme or a chemical oxidant. Here, we show that catechol-modified hyaluronic acid (HA-CA) can self-crosslink in physiological conditions without any requirement of oxidizing reagents. A careful rheological analysis of gelation of HA-CA solutions indicated that both the degree of substitution and the molar mass of HA-CA are key parameters controlling the gelation kinetics. Interestingly, the gelation time could be dramatically lowered by photo-oxidation of catechol using visible light in the presence of eosin Y as a photosensitizer. This strategy can be advantageously used to manage viscosity and gelation kinetics during injection, which paves the way for various biomedical applications of HA-CA including wound closure and healing as well as drug delivery.

Keywords

Self-crosslinking polymer Tissue-adhesive polymer Hyaluronic acid 
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Notes

Acknowledgements

This work was financially supported by a Grant-in-Aid for JSPS Fellows KAKENHI (Grant No. 265612). We are grateful to Prof. M. R. Block for the cell viability testing of the HA-CA hydrogels. We thank Eric Bayma-Pecit for his technical help in the rheological experiments.

Supplementary material

289_2017_1937_MOESM1_ESM.docx (3.6 mb)
Supplementary material 1 (DOCX 3637 kb)

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Copyright information

© Springer-Verlag Berlin Heidelberg 2017

Authors and Affiliations

  • Takeshi Sato
    • 1
    • 2
    • 3
  • Takao Aoyagi
    • 4
  • Mitsuhiro Ebara
    • 2
    • 3
    • 5
  • Rachel Auzély-Velty
    • 1
  1. 1.Grenoble Alpes University, CERMAV-CNRSGrenobleFrance
  2. 2.Graduate School of Pure and Applied SciencesUniversity of TsukubaTsukubaJapan
  3. 3.International Center for Materials Nanoarchitectonics (MANA)National Institute for Materials Science (NIMS)TsukubaJapan
  4. 4.College of Science and TechnologyNihon UniversityTokyoJapan
  5. 5.Graduate School of Industrial Science and TechnologyTokyo University of ScienceTokyoJapan

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