Synthesis, photophysical properties, and photodynamic activity of positional isomers of TFPP-glucose conjugates

Arif Fadlan; Hiroki Tanimoto; Tatsuya Ito; Yusuke Aritomi; Maho Ueno; Masaya Tokuda; Shiho Hirohara; Makoto Obata; Tsumoru Morimoto; Kiyomi Kakiuchi

doi:10.1016/j.bmc.2018.02.031

Synthesis, photophysical properties, and photodynamic activity of positional isomers of TFPP-glucose conjugates

Arif Fadlan, Hiroki Tanimoto, Tatsuya Ito, Yusuke Aritomi, Maho Ueno, Masaya Tokuda, Shiho Hirohara^*, Makoto Obata, Tsumoru Morimoto, Kiyomi Kakiuchi

^*この論文の責任著者

生体認識化学研究室

研究成果: ジャーナルへの寄稿 › 学術論文 › 査読

13 被引用数 (Scopus)

抄録

The synthesis and characterization of a ‘complete set’ of positional isomers of tetrakis(perfluorophenyl)porphyrins (TFPP)-glucose conjugates (1OH, 2OH, 3OH, 4OH, and 6OH) are reported herein. The cellular uptake and photocytotoxicity of these conjugates were examined in order to investigate the influence of location of the TFPP moiety on the D-glucose molecule on the biological activity of the conjugates. An In vitro biological evaluation revealed that the certain of these isomers have a greater effect on cellular uptake and cytotoxicity than others. The TFPP-glucose conjugates 1OH, 3OH, and 4OH were found to exert exceptional photocytotoxicity in several types of cancer cells compared to 2OH and 6OH substituted isomers.

本文言語	英語
ページ（範囲）	1848-1858
ページ数	11
ジャーナル	Bioorganic and Medicinal Chemistry
巻	26
号	8
DOI	https://doi.org/10.1016/j.bmc.2018.02.031
出版ステータス	出版済み - 2018/05/01

ASJC Scopus 主題領域

生化学
分子医療
分子生物学
薬科学
創薬
臨床生化学
有機化学

UN SDG

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10.1016/j.bmc.2018.02.031

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title = "Synthesis, photophysical properties, and photodynamic activity of positional isomers of TFPP-glucose conjugates",

abstract = "The synthesis and characterization of a {\textquoteleft}complete set{\textquoteright} of positional isomers of tetrakis(perfluorophenyl)porphyrins (TFPP)-glucose conjugates (1OH, 2OH, 3OH, 4OH, and 6OH) are reported herein. The cellular uptake and photocytotoxicity of these conjugates were examined in order to investigate the influence of location of the TFPP moiety on the D-glucose molecule on the biological activity of the conjugates. An In vitro biological evaluation revealed that the certain of these isomers have a greater effect on cellular uptake and cytotoxicity than others. The TFPP-glucose conjugates 1OH, 3OH, and 4OH were found to exert exceptional photocytotoxicity in several types of cancer cells compared to 2OH and 6OH substituted isomers.",

keywords = "Cellular uptake, Glucosylated TFPP, Photocytotoxicity, Photodynamic therapy (PDT), Positional isomers",

author = "Arif Fadlan and Hiroki Tanimoto and Tatsuya Ito and Yusuke Aritomi and Maho Ueno and Masaya Tokuda and Shiho Hirohara and Makoto Obata and Tsumoru Morimoto and Kiyomi Kakiuchi",

note = "Publisher Copyright: {\textcopyright} 2018 Elsevier Ltd",

year = "2018",

month = may,

day = "1",

doi = "10.1016/j.bmc.2018.02.031",

language = "英語",

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TY - JOUR

T1 - Synthesis, photophysical properties, and photodynamic activity of positional isomers of TFPP-glucose conjugates

AU - Fadlan, Arif

AU - Tanimoto, Hiroki

AU - Ito, Tatsuya

AU - Aritomi, Yusuke

AU - Ueno, Maho

AU - Tokuda, Masaya

AU - Hirohara, Shiho

AU - Obata, Makoto

AU - Morimoto, Tsumoru

AU - Kakiuchi, Kiyomi

PY - 2018/5/1

Y1 - 2018/5/1

N2 - The synthesis and characterization of a ‘complete set’ of positional isomers of tetrakis(perfluorophenyl)porphyrins (TFPP)-glucose conjugates (1OH, 2OH, 3OH, 4OH, and 6OH) are reported herein. The cellular uptake and photocytotoxicity of these conjugates were examined in order to investigate the influence of location of the TFPP moiety on the D-glucose molecule on the biological activity of the conjugates. An In vitro biological evaluation revealed that the certain of these isomers have a greater effect on cellular uptake and cytotoxicity than others. The TFPP-glucose conjugates 1OH, 3OH, and 4OH were found to exert exceptional photocytotoxicity in several types of cancer cells compared to 2OH and 6OH substituted isomers.

AB - The synthesis and characterization of a ‘complete set’ of positional isomers of tetrakis(perfluorophenyl)porphyrins (TFPP)-glucose conjugates (1OH, 2OH, 3OH, 4OH, and 6OH) are reported herein. The cellular uptake and photocytotoxicity of these conjugates were examined in order to investigate the influence of location of the TFPP moiety on the D-glucose molecule on the biological activity of the conjugates. An In vitro biological evaluation revealed that the certain of these isomers have a greater effect on cellular uptake and cytotoxicity than others. The TFPP-glucose conjugates 1OH, 3OH, and 4OH were found to exert exceptional photocytotoxicity in several types of cancer cells compared to 2OH and 6OH substituted isomers.

KW - Cellular uptake

KW - Glucosylated TFPP

KW - Photocytotoxicity

KW - Photodynamic therapy (PDT)

KW - Positional isomers

UR - http://www.scopus.com/inward/record.url?scp=85042599771&partnerID=8YFLogxK

U2 - 10.1016/j.bmc.2018.02.031

DO - 10.1016/j.bmc.2018.02.031

M3 - 学術論文

C2 - 29496414

AN - SCOPUS:85042599771

SN - 0968-0896

VL - 26

SP - 1848

EP - 1858

JO - Bioorganic and Medicinal Chemistry

JF - Bioorganic and Medicinal Chemistry

IS - 8

ER -

Synthesis, photophysical properties, and photodynamic activity of positional isomers of TFPP-glucose conjugates

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ASJC Scopus 主題領域

UN SDG

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