Grafting of steroids to hyaluronan towards the design of delivery systems for antioxidants: The role of hydrophobic core
Language English Country Great Britain, England Media print-electronic
Document type Journal Article
PubMed
29773394
DOI
10.1016/j.carbpol.2018.04.021
PII: S0144-8617(18)30394-1
Knihovny.cz E-resources
- Keywords
- Amphiphilic polymers, Antioxidants, Cholesterol (PubChem CID 5997), Cholic Acid (PubChem CID 221493), Coenzyme Q10 (PubChem CID: 5281915), Curcumin (PubChem CID: 101736865), Desoxycholic acid (PubChem CID 222528), Encapsulation, Hyaluronic acid, Sodium hyaluronate (PubChem CID: 53447380), Vitamin E (PubChem CID 14985),
- MeSH
- Antioxidants chemistry pharmacology MeSH
- NIH 3T3 Cells MeSH
- Hydrophobic and Hydrophilic Interactions MeSH
- Hyaluronic Acid chemistry pharmacology MeSH
- Drug Delivery Systems * MeSH
- Molecular Conformation MeSH
- Mice MeSH
- Cell Proliferation drug effects MeSH
- Drug Design * MeSH
- Steroids chemistry pharmacology MeSH
- Cell Survival drug effects MeSH
- Dose-Response Relationship, Drug MeSH
- Structure-Activity Relationship MeSH
- Animals MeSH
- Check Tag
- Mice MeSH
- Animals MeSH
- Publication type
- Journal Article MeSH
- Names of Substances
- Antioxidants MeSH
- Hyaluronic Acid MeSH
- Steroids MeSH
In this work, amphiphilic hyaluronic acid (HA) was synthesized by the chemical bonding of steroids. Particularly, succinyl cholesterol (SCH), cholic acid (CA), deoxycholic acid (DOCA), and 18β-glycyrrhetinic acid (GA) were activated by benzoyl chloride towards the esterification reaction of HA in water. The degree of substitution can be controlled by varying the feed ratio of mixed anhydride to HA and up to 25% (mol/mol) can be obtained. Due to mild reaction conditions, no degradation of the polysaccharide was observed. The prepared amphiphilic polymers were characterized by NMR, infrared spectroscopy (FT-IR) and SEC/MALLS, as well as turbidity and size of the aggregates. The developed system is proposed for the delivery of hydrophobic drugs; for this purpose, curcumin, vitamin E and coenzyme Q10 were used as hydrophobic models; these molecules were loaded into the conjugates with high efficiency. The loading capacity was a function of degree of substitution. Furthermore, the biocompatibility of the derivatives and the cellular uptake of the delivery system enabled us to demonstrate the potential of the prepared delivery systems.
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