Retinoic acid grafted to hyaluronan for skin delivery: Synthesis, stability studies, and biological evaluation
Jazyk angličtina Země Velká Británie, Anglie Médium print-electronic
Typ dokumentu časopisecké články
PubMed
31888823
DOI
10.1016/j.carbpol.2019.115733
PII: S0144-8617(19)31401-8
Knihovny.cz E-zdroje
- Klíčová slova
- (±)-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
- anhydridy chemie MeSH
- antioxidancia chemie farmakologie MeSH
- aplikace kožní MeSH
- buňky NIH 3T3 MeSH
- esterifikace MeSH
- flavonoidy chemie MeSH
- fotolýza účinky léků MeSH
- kůže účinky léků účinky záření MeSH
- kyselina hyaluronová chemická syntéza chemie farmakologie MeSH
- myši MeSH
- norisoprenoidy chemie farmakologie MeSH
- tretinoin chemická syntéza chemie farmakologie MeSH
- ultrafialové záření MeSH
- zvířata MeSH
- Check Tag
- myši MeSH
- zvířata MeSH
- Publikační typ
- časopisecké články MeSH
- Názvy látek
- anhydridy MeSH
- antioxidancia MeSH
- flavonoidy MeSH
- kyselina hyaluronová MeSH
- morin MeSH Prohlížeč
- norisoprenoidy 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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