A new unsaturated derivative of hyaluronic acid – Synthesis, analysis and applications

• Published in: Carbohydrate polymers Vol. 163; pp. 247 - 253
• Main Authors: Buffa, Radovan, Šedová, Petra, Basarabová, Ivana, Bobula, Tomáš, Procházková, Pavlína, Vágnerová, Hana, Dolečková, Iva, Moravčíková, Soňa, Hejlová, Lenka, Velebný, Vladimír
• Format: Journal Article
• Language: English
• Published: England Elsevier Ltd 01-05-2017
• Subjects: Addition; Anticancer; Antioxidation; Hyaluronan; Oxidation; APS; Mw; MTT; COSY; DS; DOSY; Hyaluronan; 3T3; DMAP; NHDF; GlcNAc; Oxidation; Antioxidation; NBS; w/v; PBS; GlcA; Addition; DPPH; h; TMEDA; SEC-MALLS; UV/vis; TEA; NMR; δ; Trolox; HA; IPA; HSQC; Anticancer
• ISSN: 0144-8617; 1879-1344
• DOI: 10.1016/j.carbpol.2017.01.071

•A new derivative of hyaluronic acid – ΔHA – (4,5-anhydro(GlcN)-HA) was prepared.•Optimized reaction parameters suitable for large scale pharma production.•Structural analysis of ΔHA by advanced NMR methodologies, UV–vis and SEC-MALLS.•Selective cytostatic activity of ΔHA on Human cancer lines MDA-MB-231, A-549 and HEP-G2 in comparison with standard human fibroblasts.•Enhanced reactivity of ΔHA with a wide range of oxidants including radicals.
Hyaluronic acid (HA) containing CC double bond in positions 4 and 5 of N-acetyl-glucosamine ring (ΔHA) is an unique material, which could be used for biomedical applications and cosmetics. The main advantage of the CC double bond is its ability to react with a wide range of oxidation agents. Location of the CC double bond directly on the glucopyranose ring allows to change the chemical capabilities and simultaneously to mimic the intrinsic physical properties of HA without introduction of linkers or other substances. The synthesis, structural analysis and basic chemical and biological characteristics of this novel biopolymer are described in details. In vitro cytotoxicity assays showed selective activity of ΔHA against cancer cell lines in comparison with standard human fibroblasts so this material has great potential in the field of anticancer drugs.