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

Research output: Contribution to journalArticle

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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Arbutin
Glycosides
Micelles
Antioxidants
Polymers
Substitution reactions
Critical micelle concentration
Carotenoids
Linoleic acid
Linoleic Acid
Cytotoxicity
Bleaching
Phenol
Chain length
Phenols
Surface tension
Stabilization
Solubility
Transmission electron microscopy

All Science Journal Classification (ASJC) codes

  • Chemistry(all)
  • Chemical Engineering(all)

Cite this

Seto, Ayaka ; Kajiwara, Rika ; Song, Jaeeun ; Shin, Eeseul ; Kim, Byeong Su ; Kofujita, Hisayoshi ; Oishi, Yoshiyuki ; Shibasaki, Yuji. / Preparation of glycoside polymer micelles with antioxidant polyphenolic cores using alkylated poly(arbutin)s. In: RSC Advances. 2019 ; Vol. 9, No. 14. pp. 7777-7785.
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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.",
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Seto, A, Kajiwara, R, Song, J, Shin, E, Kim, BS, Kofujita, H, Oishi, Y & Shibasaki, Y 2019, 'Preparation of glycoside polymer micelles with antioxidant polyphenolic cores using alkylated poly(arbutin)s', RSC Advances, vol. 9, no. 14, pp. 7777-7785. https://doi.org/10.1039/C8RA09090D

Preparation of glycoside polymer micelles with antioxidant polyphenolic cores using alkylated poly(arbutin)s. / Seto, Ayaka; Kajiwara, Rika; Song, Jaeeun; Shin, Eeseul; Kim, Byeong Su; Kofujita, Hisayoshi; Oishi, Yoshiyuki; Shibasaki, Yuji.

In: RSC Advances, Vol. 9, No. 14, 01.01.2019, p. 7777-7785.

Research output: Contribution to journalArticle

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AU - Seto, Ayaka

AU - Kajiwara, Rika

AU - Song, Jaeeun

AU - Shin, Eeseul

AU - Kim, Byeong Su

AU - Kofujita, Hisayoshi

AU - Oishi, Yoshiyuki

AU - Shibasaki, Yuji

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