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

^*Corresponding author for this work

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

12 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	1848-1858
Number of pages	11
Journal	Bioorganic and Medicinal Chemistry
Volume	26
Issue number	8
DOIs	https://doi.org/10.1016/j.bmc.2018.02.031
Publication status	Published - 1 May 2018
Externally published	Yes

Keywords

Cellular uptake
Glucosylated TFPP
Photocytotoxicity
Photodynamic therapy (PDT)
Positional isomers

UN SDGs

This output contributes to the following UN Sustainable Development Goals (SDGs)

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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 = "English",

volume = "26",

pages = "1848--1858",

journal = "Bioorganic and Medicinal Chemistry",

issn = "0968-0896",

publisher = "Elsevier Ltd.",

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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 - Article

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

Abstract

Keywords

UN SDGs

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