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

Ayaka Seto, Rika Kajiwara, Jaeeun Song, Eeseul Shin, Byeong Su Kim, Hisayoshi Kofujita, Yoshiyuki Oishi, Yuji Shibasaki

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Abstract

This paper describes the synthesis of long-chain-alkylated poly(arbutin)s (poly(Arb)-Rx, where R = alkyl-chain length and x = 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)-Rx were determined as 1.3-5.2 mg mL−1 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)-C830 to linoleic acid was sufficient to preserve the β-carotene.

Original languageEnglish
Pages (from-to)7777-7785
Number of pages9
JournalRSC Advances
Volume9
Issue number14
DOIs
Publication statusPublished - 2019 Jan 1

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All Science Journal Classification (ASJC) codes

  • Chemistry(all)
  • Chemical Engineering(all)

Cite this

Seto, A., Kajiwara, R., Song, J., Shin, E., Kim, B. S., Kofujita, H., Oishi, Y., & Shibasaki, Y. (2019). Preparation of glycoside polymer micelles with antioxidant polyphenolic cores using alkylated poly(arbutin)s. RSC Advances, 9(14), 7777-7785. https://doi.org/10.1039/C8RA09090D