Chondroitin sulfate (CS) was regio-specifically modified to an unsaturated derivative (ΔCS) with a double bond in positions 4 and 5 of N-acetyl-d-galactosamine. The structure of ΔCS was elucidated in detail by two dimensional nuclear magnetic resonance, ultraviolet spectroscopy and mass spectrometry. The introduction of a nucleophilic CC double bond into a polymer backbone had no influence on biocompatibility of CS, which was demonstrated by MTT live-dead assay and enzymatic degradation in vitro. On the other hand the chemical modification significantly enhanced the reactivity of ΔCS towards numerous oxidizing agents, which might be promising for a variety of biomedical and cosmetic applications.
- Klíčová slova
- Antioxidant activity, Chondroitin sulfate, Cosmetics, Oxidation, Reduction,
- MeSH
- bifenylové sloučeniny chemie MeSH
- buňky 3T3 MeSH
- chondroitinsulfáty chemická syntéza chemie toxicita MeSH
- myši MeSH
- oxidace-redukce MeSH
- pikráty chemie MeSH
- scavengery volných radikálů chemická syntéza chemie toxicita MeSH
- techniky syntetické chemie MeSH
- testování materiálů MeSH
- zvířata MeSH
- Check Tag
- myši MeSH
- zvířata MeSH
- Publikační typ
- časopisecké články MeSH
- Názvy látek
- 1,1-diphenyl-2-picrylhydrazyl MeSH Prohlížeč
- bifenylové sloučeniny MeSH
- chondroitinsulfáty MeSH
- pikráty MeSH
- scavengery volných radikálů MeSH
A new photopolymerizable derivative of hyaluronan (methacrylhydrazide-HA, MAHA) was prepared by carbodiimide chemistry. The reaction conditions were optimized for molecular weight (Mw), reaction time and amount of reagents with a degree of methacrylation (DM) ranging from 2% to 58%. Methacrylhydrazide-HA was hydrolytically stable (PBS, 7days, 37°C) in contrast to commonly used methacrylester analoque (23% hydrolyzed). MAHA readily photopolymerized into densely crosslinked hydrogels under physiological conditions. The varied DM, Mw, irradiation time (texp) and macromer concentration in photocrosslinking afforded hydrogels with different physical (swelling ratio, degradation rate) and mechanical properties (stiffness, toughness). Three-dimensional fabrication and surface patterning of MAHA hydrogels were demonstrated by photolithography and light mediated micromolding. A live-dead assay with skin fibroblasts showed convenient biocompatibility of MAHA (16%, 116kDa) for potential scaffolding applications in tissue engineering and regenerative medicine.
- Klíčová slova
- Crosslinking, Hyaluronan, Hydrogel, Photolithography, Polymerization,
- MeSH
- fibroblasty cytologie MeSH
- hydrogely chemická syntéza chemie MeSH
- kultivované buňky MeSH
- kyselina hyaluronová chemie MeSH
- lidé MeSH
- polymerizace MeSH
- reagencia zkříženě vázaná MeSH
- tkáňové inženýrství metody MeSH
- Check Tag
- lidé MeSH
- Publikační typ
- časopisecké články MeSH
- Názvy látek
- hydrogely MeSH
- kyselina hyaluronová MeSH
- reagencia zkříženě vázaná MeSH
Chondroitin sulfate (CS) was chemoselectively oxidized by Tempo/NaClO to C-6 aldehyde of a D-galactosamine subunit (GalNAc). The subsequent, spontaneous desulfatation of oxidized CS gave rise to α,β-unsaturated aldehyde. A new derivative of CS was fully characterized and a degree of oxidation was determined by spectroscopic analysis. The optimization of reaction conditions showed a proportional degree of oxidation to an amount of sodium hypochlorite. The utility of α,β-unsaturated aldehyde for crosslinking and conjugation was demonstrated by a seamless condensation with various N-nucleophiles. We also demonstrated pH-dependent release of biologically active agents from oxidized CS. A live-dead assay in the presence of α,β-unsaturated aldehyde revealed unaffected viability of NIH 3T3 fibroblasts, which made this precursor promising for several biomedical applications including drug delivery and tissue engineering.
- Klíčová slova
- Chondroitin sulfate, Crosslinking, Hydrogel, Oxidation, Tissue engineering,
- MeSH
- aldehydy chemie MeSH
- biokompatibilní materiály škodlivé účinky chemická syntéza chemie MeSH
- buňky 3T3 MeSH
- chondroitinsulfáty chemie MeSH
- fibroblasty účinky léků MeSH
- myši MeSH
- reagencia zkříženě vázaná chemie MeSH
- viabilita buněk MeSH
- zvířata MeSH
- Check Tag
- myši MeSH
- zvířata MeSH
- Publikační typ
- časopisecké články MeSH
- Názvy látek
- aldehydy MeSH
- biokompatibilní materiály MeSH
- chondroitinsulfáty MeSH
- reagencia zkříženě vázaná MeSH
Hyaluronan (HA) was chemically modified to a photocurable derivative by the acylation with a mixed anhydride of trans-cinnamic acid and characterized by UV, IR and 2D NMR spectroscopy. Photocurable HA was processed to a microfibrous structure by wet-spinning technology. Water solubility of otherwise water-soluble HA microfibres was reduced significantly by the solid-state photocrosslinking. We also investigated that the nature of polymer structure had a great impact to a final crosslink ratio. The analysis of the mechanical properties showed higher ultimate tensile strength and increased rigidity of the photocrosslinked fibres in comparison to the untreated ones. Moreover all tested materials are regarded as biocompatible according to the tests of cell viability, phototoxicity and enzymatic degradability, which make them suitable candidates for numerous biomedical applications.
- Klíčová slova
- Cinnamic acid, Fibres, Hyaluronan, Hyaluronan (CID 3084049), Photocrosslinking, Trans-cinnamic acid (CID 444539), Wet-spinning,
- MeSH
- buňky 3T3 MeSH
- fibroblasty účinky léků MeSH
- krystalizace MeSH
- kyselina hyaluronová analogy a deriváty chemie farmakologie MeSH
- myši MeSH
- pevnost v tahu * MeSH
- reagencia zkříženě vázaná chemie MeSH
- rozpustnost MeSH
- ultrafialové záření MeSH
- viskozita MeSH
- zvířata MeSH
- Check Tag
- myši MeSH
- zvířata MeSH
- Publikační typ
- časopisecké články MeSH
- Názvy látek
- kyselina hyaluronová MeSH
- reagencia zkříženě vázaná MeSH
