Change search
CiteExportLink to record
Permanent link

Direct link
Cite
Citation style
  • apa
  • ieee
  • modern-language-association-8th-edition
  • vancouver
  • Other style
More styles
Language
  • de-DE
  • en-GB
  • en-US
  • fi-FI
  • nn-NO
  • nn-NB
  • sv-SE
  • Other locale
More languages
Output format
  • html
  • text
  • asciidoc
  • rtf
Influence of ions to modulate hydrazone and oxime reaction kinetics to obtain dynamically cross-linked hyaluronic acid hydrogels
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Polymer Chemistry. Univ Montreal, Maisonneuve Rosemont Hosp Res Ctr, Montreal, PQ, Canada;Univ Montreal, Dept Ophthalmol, Montreal, PQ, Canada.
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Polymer Chemistry.ORCID iD: 0000-0002-7256-0758
Tampere Univ, Fac Med & Hlth Technol, Bioengn & Nanomed Lab, Korkeakoulunkatu 3, Tampere 33720, Finland;Tampere Univ, BioMediTech Inst, Korkeakoulunkatu 3, Tampere 33720, Finland.
Uppsala University, Disciplinary Domain of Science and Technology, Chemistry, Department of Chemistry - Ångström, Polymer Chemistry.ORCID iD: 0000-0001-6947-9601
Show others and affiliations
2019 (English)In: Polymer Chemistry, ISSN 1759-9954, E-ISSN 1759-9962, Vol. 10, no 31, p. 4322-4327Article in journal (Refereed) Published
Abstract [en]

Dynamic covalent chemistry forming hydrazone and oxime linkages is attractive due to its simplicity, selectivity and compatibility under aqueous conditions. However, the low reaction rate at physiological pH hampers its use in biomedical applications. Herein, we present different monovalent and bivalent aqueous salt solutions as bio-friendly, non-toxic catalysts which can drive the hydrazone and oxime reactions with excellent efficacy at physiological pH. Direct comparison of hydrazone and oxime reactions using a small molecule model, without any salt catalysis, indicated that oxime formation is 6-times faster than hydrazone formation. Addition of different salts (NaCl, NaBr, KCl, LiCl, LiClO4, Na2SO4, MgCl2 and CaCl2) accelerated the pseudo-first-order reaction kinetics by similar to 1.2-4.9-fold for acylhydrazone formation and by similar to 1.5-6.9-fold for oxime formation, in a concentration-dependent manner. We further explored the potential of such catalysts to develop acylhydrazone and oxime cross-linked hyaluronic acid (HA) hydrogels with different physicochemical properties without changing the degree of chemical modification. Analogous to the small molecule model system, the addition of monovalent and divalent salts as catalysts significantly reduced the gelling time. The gelling time for the acylhydrazone cross-linked HA-hydrogel (1.6 wt%) could be reduced from 300 min to 1.2 min by adding 100 mM CaCl2, while that for the oxime cross-linked HA-hydrogel (1.2 wt%) could be reduced from 68 min to 1.1 min by adding 50 mM CaCl2. This difference in the gelling time also resulted in hydrogels with differential swelling properties as measured after 24 h. Our results are the first to demonstrate the use of salts, for catalyzing hydrogel formation under physiologically relevant conditions.

Place, publisher, year, edition, pages
ROYAL SOC CHEMISTRY , 2019. Vol. 10, no 31, p. 4322-4327
National Category
Polymer Chemistry
Identifiers
URN: urn:nbn:se:uu:diva-393329DOI: 10.1039/c9py00862dISI: 000478913500010OAI: oai:DiVA.org:uu-393329DiVA, id: diva2:1355370
Funder
Swedish Foundation for Strategic Research , SBE13-0028
Note

De två första författarna delar förstaförfattarskapet.

Available from: 2019-09-27 Created: 2019-09-27 Last updated: 2019-09-27Bibliographically approved

Open Access in DiVA

fulltext(1568 kB)35 downloads
File information
File name FULLTEXT01.pdfFile size 1568 kBChecksum SHA-512
ab5a3d314568aceb13637e30b1f8c67b4531a8b1d200e10044b4e7423ee2bb9f1ef9fe8159e0587c3dc4d85ac5d3e8a1210e44fa98ad3f9d096427bb3f07ab68
Type fulltextMimetype application/pdf

Other links

Publisher's full text

Search in DiVA

By author/editor
Wang, ShujiangNawale, Ganesh N.Hilborn, JönsVarghese, Oommen P.
By organisation
Polymer Chemistry
In the same journal
Polymer Chemistry
Polymer Chemistry

Search outside of DiVA

GoogleGoogle Scholar
Total: 35 downloads
The number of downloads is the sum of all downloads of full texts. It may include eg previous versions that are now no longer available

doi
urn-nbn

Altmetric score

doi
urn-nbn
Total: 42 hits
CiteExportLink to record
Permanent link

Direct link
Cite
Citation style
  • apa
  • ieee
  • modern-language-association-8th-edition
  • vancouver
  • Other style
More styles
Language
  • de-DE
  • en-GB
  • en-US
  • fi-FI
  • nn-NO
  • nn-NB
  • sv-SE
  • Other locale
More languages
Output format
  • html
  • text
  • asciidoc
  • rtf