Preparation of glycoside polymer micelles with antioxidant polyphenolic cores using alkylated poly(arbutin)s

This paper describes the synthesis of long-chain-alkylated poly(arbutin)s (poly(Arb)- , where = alkyl-chain length and = degree of substitution (DS)) and their aqueous micelle formation. DS was controlled by tailoring the alkyl reagent/main-chain phenol substituent feed ratio. The critical micelle c...

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Bibliographic Details
Published in:RSC advances 2019-01, Vol.9 (14), p.7777-7785
Main Authors: Seto, Ayaka, Kajiwara, Rika, Song, Jaeeun, Shin, Eeseul, Kim, Byeong-Su, Kofujita, Hisayoshi, Oishi, Yoshiyuki, Shibasaki, Yuji
Format: Article
Language:English
Subjects:
Alkylation
Antioxidants
Bleaching
Carotene
Chemistry
Micelles
Reagents
Surface tension
Toxicity
Transmission electron microscopy
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Summary:This paper describes the synthesis of long-chain-alkylated poly(arbutin)s (poly(Arb)- , where = alkyl-chain length and = degree of substitution (DS)) and their aqueous micelle formation. DS was controlled by tailoring the alkyl reagent/main-chain phenol substituent feed ratio. The critical micelle concentrations (CMCs) of poly(Arb)- were determined as 1.3-5.2 mg mL by the surface tension method. Introduction of longer alkyl substituents decreased CMC and also decreased aqueous solubility. In DLS measurement, the average micelle diameters were 225-616 nm, and micelle size decreased with increasing DS because of increased stabilization by hydrophobic alkyl substituents. Transmission electron microscopy indicated that mainly wormlike cylindrical micelles were formed, even with highly hydrophilic polymers. The alkylated polymer exhibited no cytotoxicity, and their antioxidant abilities were evaluated by the β-carotene bleaching method. Only 0.049 mol equivalents of poly(Arb)-C8 to linoleic acid was sufficient to preserve the β-carotene.
ISSN:2046-2069
2046-2069
DOI:10.1039/c8ra09090d