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

doi:10.1039/C8RA09090D

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

Department of Chemistry

Research output: Contribution to journal › Article › peer-review

5 Citations (Scopus)

Abstract

This paper describes the synthesis of long-chain-alkylated poly(arbutin)s (poly(Arb)-R_x, 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)-R_x 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 language	English
Pages (from-to)	7777-7785
Number of pages	9
Journal	RSC Advances
Volume	9
Issue number	14
DOIs	https://doi.org/10.1039/C8RA09090D
Publication status	Published - 2019

Bibliographical note

Funding Information:
This work was supported by a JSPS KAKENHI Grant-in-Aid for Scientic Research (C) (Grant Number JP18K05211). The authors also thank to Mr Kuniaki Sasaki (technical staff in Iwate University) for TEM measurement. The authors would like to thank Enago (http://www.enago.jp) for the English language review.

Publisher Copyright:
© The Royal Society of Chemistry.

All Science Journal Classification (ASJC) codes

Chemistry(all)
Chemical Engineering(all)

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10.1039/C8RA09090D

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

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.",

author = "Ayaka Seto and Rika Kajiwara and Jaeeun Song and Eeseul Shin and Kim, {Byeong Su} and Hisayoshi Kofujita and Yoshiyuki Oishi and Yuji Shibasaki",

note = "Funding Information: This work was supported by a JSPS KAKENHI Grant-in-Aid for Scientic Research (C) (Grant Number JP18K05211). The authors also thank to Mr Kuniaki Sasaki (technical staff in Iwate University) for TEM measurement. The authors would like to thank Enago (http://www.enago.jp) for the English language review. Publisher Copyright: {\textcopyright} The Royal Society of Chemistry.",

year = "2019",

doi = "10.1039/C8RA09090D",

language = "English",

volume = "9",

pages = "7777--7785",

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publisher = "Royal Society of Chemistry",

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T1 - Preparation of glycoside polymer micelles with antioxidant polyphenolic cores using alkylated poly(arbutin)s

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

N1 - Funding Information: This work was supported by a JSPS KAKENHI Grant-in-Aid for Scientic Research (C) (Grant Number JP18K05211). The authors also thank to Mr Kuniaki Sasaki (technical staff in Iwate University) for TEM measurement. The authors would like to thank Enago (http://www.enago.jp) for the English language review. Publisher Copyright: © The Royal Society of Chemistry.

PY - 2019

Y1 - 2019

N2 - 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.

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

Abstract

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