Retinoic acid grafted to hyaluronan for skin delivery: Synthesis, stability studies, and biological evaluation
Language English Country Great Britain, England Media print-electronic
Document type Journal Article
PubMed
31888823
DOI
10.1016/j.carbpol.2019.115733
PII: S0144-8617(19)31401-8
Knihovny.cz E-resources
- Keywords
- (±)-6-Hydroxy-2,5,7,8-tetramethylchromane-2-carboxylic acid (trolox, PubChem CID: 40634), 2-Ethylhexyl 2-cyano-3,3-diphenylacrylate (PubChem CID: 22571), 2-Ethylhexyl 4-methoxycinnamate (PubChem CID: 21630), Antioxidants, Avobenzone (1-(4-Methoxyphenyl)-3-(4-tert-butylphenyl)-1,3-propanedione, CID: 51040), Butylated hydroxyanisole (BHA, PubChem CID: 517036), Butylated hydroxytoluene (BHT, PubChem CID: 31404), Hyaluronic acid (PubChem CID: 24728612), Morin hydrate (2′,3,4′,5,7-Pentahydroxyflavone, PubChem CID: 16219651), Retinoic acid (PubChem CID: 444795), Retinoids, Retinyl palmitate (PubChem CID: 5280531), Skin, hyaluronan,
- MeSH
- Anhydrides chemistry MeSH
- Antioxidants chemistry pharmacology MeSH
- Administration, Cutaneous MeSH
- NIH 3T3 Cells MeSH
- Esterification MeSH
- Flavonoids chemistry MeSH
- Photolysis drug effects MeSH
- Skin drug effects radiation effects MeSH
- Hyaluronic Acid chemical synthesis chemistry pharmacology MeSH
- Mice MeSH
- Norisoprenoids chemistry pharmacology MeSH
- Tretinoin chemical synthesis chemistry pharmacology MeSH
- Ultraviolet Rays MeSH
- Animals MeSH
- Check Tag
- Mice MeSH
- Animals MeSH
- Publication type
- Journal Article MeSH
- Names of Substances
- Anhydrides MeSH
- Antioxidants MeSH
- Flavonoids MeSH
- Hyaluronic Acid MeSH
- morin MeSH Browser
- Norisoprenoids MeSH
- Tretinoin MeSH
All-trans retinoic acid (ATRA) was grafted to hyaluronan (HA) via esterification. The reaction was mediated by mixed anhydrides. A perfect control of the degree of substitution (0.5-7.5%) was obtained by varying the molar ratio of retinoic acid in the feed. The degree of substitution plays a significant role in the long-term stability. The photodegradation of HA-ATRA upon UVA irradiation resulted in β-ionone, β-cyclocitral and 5,6-epoxy-(E)-retinoic acid. The photostability of the conjugate had increased with the combination with morin. The chemical structure of HA-ATRA and its degradation products was elucidated using NMR spectroscopy, SEC-MALLS, and gas chromatography-mass spectrometry (GC-MS). ATRA did not loss its biological activity after conjugation, as demonstrated by gene expression. The derivative was able to penetrate across the stratum corneum. Besides, HA-ATRA downregulated the expression of anti-inflammatory interleukins 6 and 8. HA-ATRA would be expected to be used for transdermal drug delivery or cosmetics.
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