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Light-activatable prodrugs based on hyaluronic acid biomaterials
Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - Ångström, Polymerkemi. Uppsala universitet, Science for Life Laboratory, SciLifeLab.
Uppsala universitet, Teknisk-naturvetenskapliga vetenskapsområdet, Kemiska sektionen, Institutionen för kemi - Ångström, Polymerkemi.
Karolinska Inst, Dept Med, Rheumatol Unit, SE-17176 Stockholm, Sweden.ORCID-id: 0000-0002-2090-7705
2018 (engelsk)Inngår i: Carbohydrate Polymers, ISSN 0144-8617, E-ISSN 1879-1344, Vol. 180, s. 145-155Artikkel i tidsskrift (Fagfellevurdert) Published
Abstract [en]

Photosensitive in situ cross-linked hyaluronan (HA) hydrogels are prepared by modular chemoselective assembly from the biopolymer precursors and novel heterobifunctional linkers with middle photo-labile ortho-nitrobenzyl group and orthogonally reactive terminals. Starting from the thiol-modified HA and a linker with activated disulfide and hydrazide terminals, a photo-degradable HA hydrogel was prepared by the hydrazone cross-linking reaction. Moreover, a light-triggered drug-releasing hydrogel prodrug was constructed by an orthogonal conjugation of dopamine (DA) via a photo-labile linker to HA dually modified with thiol and hydrazide groups (hy-HA-SH) and a subsequent cross-linking with aldehyde-derivatized HA (HA-al). On-demand release of DA from the hydrogel was achieved upon exposure of the hydrogel to UV light whereas 11-fold less release of the drug was observed in the absence of light. The mechanical properties of the hydrogels, photodegradation kinetics, photorelease of the model drugs were studied by rheology, spectrophotometry, chromatography, and mass spectrometry. For the first time, integration of photolabile components into an actual polysaccharide of extracellular matrix was implemented for the light-controlled release of drug molecules.

sted, utgiver, år, opplag, sider
2018. Vol. 180, s. 145-155
Emneord [en]
Prodrug, Light responsive, Self-immolative, Hydrogel, Hyaluronic acid, Dopamine
HSV kategori
Identifikatorer
URN: urn:nbn:se:uu:diva-386332DOI: 10.1016/j.carbpol.2017.10.028ISI: 000416369800017PubMedID: 29103490OAI: oai:DiVA.org:uu-386332DiVA, id: diva2:1327485
Forskningsfinansiär
EU, FP7, Seventh Framework ProgrammeTilgjengelig fra: 2019-06-19 Laget: 2019-06-19 Sist oppdatert: 2019-06-19bibliografisk kontrollert

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