Selective accumulation of [62Zn]-labeled glycoconjugated porphyrins as multi-functional positron emission tomography tracers in cancer cells

Masato Tamura; Hirofumi Matsui; Shiho Hirohara; Kiyomi Kakiuchi; Masao Tanihara; Naruto Takahashi; Kozi Nakai; Yasukazu Kanai; Hiroshi Watabe; Jun Hatazawa

doi:10.1016/j.bmc.2014.02.021

Selective accumulation of [⁶²Zn]-labeled glycoconjugated porphyrins as multi-functional positron emission tomography tracers in cancer cells

Masato Tamura, Hirofumi Matsui, Shiho Hirohara, Kiyomi Kakiuchi, Masao Tanihara, Naruto Takahashi, Kozi Nakai, Yasukazu Kanai, Hiroshi Watabe, Jun Hatazawa

Cyclotron and Radioisotope Center (CYRIC)

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

16 Citations (Scopus)

Abstract

Positron-emission tomography (PET) can be used to visualize active stage cancer. Fluorine-18 ([¹⁸F])-labeled 2-([¹⁸F])2-deoxy-2- fluoroglucose (([¹⁸F])-FDG), which accumulates in glucose-dependent tissues, is a good cancer-targeting tracer. However, ([¹⁸F])-FDG is obscured in glucose-dependent normal tissues. In this study, we assessed the cancer-selective accumulation of zinc-labeled glycoconjugated 5,10,15,20-tetrakis(pentafluorophenyl)porphyrin (ZnGlc1-4), both in vitro and in vivo. Experiments using both normal and cancer cells confirmed the relationship between cancer cell-selective accumulation and the substitution numbers and orientations of glycoconjugated porphyrins. ZnGlctrans-2 accumulated at greater levels in cancer cells compared with other glycoconjugated porphyrins. PET imaging showed that ZnGlctrans-2 accumulated in tumor.

Original language	English
Pages (from-to)	2563-2570
Number of pages	8
Journal	Bioorganic and Medicinal Chemistry
Volume	22
Issue number	8
DOIs	https://doi.org/10.1016/j.bmc.2014.02.021
Publication status	Published - 2014 Apr 15

Keywords

Cancer selective accumulation
Positron emission tomography

UN SDGs

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

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10.1016/j.bmc.2014.02.021

Cite this

Tamura, M., Matsui, H., Hirohara, S., Kakiuchi, K., Tanihara, M., Takahashi, N., Nakai, K., Kanai, Y., Watabe, H., & Hatazawa, J. (2014). Selective accumulation of [⁶²Zn]-labeled glycoconjugated porphyrins as multi-functional positron emission tomography tracers in cancer cells. Bioorganic and Medicinal Chemistry, 22(8), 2563-2570. https://doi.org/10.1016/j.bmc.2014.02.021

@article{d425f0725b594940b1c964da4ba65661,

title = "Selective accumulation of [62Zn]-labeled glycoconjugated porphyrins as multi-functional positron emission tomography tracers in cancer cells",

abstract = "Positron-emission tomography (PET) can be used to visualize active stage cancer. Fluorine-18 ([18F])-labeled 2-([18F])2-deoxy-2- fluoroglucose (([18F])-FDG), which accumulates in glucose-dependent tissues, is a good cancer-targeting tracer. However, ([18F])-FDG is obscured in glucose-dependent normal tissues. In this study, we assessed the cancer-selective accumulation of zinc-labeled glycoconjugated 5,10,15,20-tetrakis(pentafluorophenyl)porphyrin (ZnGlc1-4), both in vitro and in vivo. Experiments using both normal and cancer cells confirmed the relationship between cancer cell-selective accumulation and the substitution numbers and orientations of glycoconjugated porphyrins. ZnGlctrans-2 accumulated at greater levels in cancer cells compared with other glycoconjugated porphyrins. PET imaging showed that ZnGlctrans-2 accumulated in tumor.",

keywords = "Cancer selective accumulation, Positron emission tomography",

author = "Masato Tamura and Hirofumi Matsui and Shiho Hirohara and Kiyomi Kakiuchi and Masao Tanihara and Naruto Takahashi and Kozi Nakai and Yasukazu Kanai and Hiroshi Watabe and Jun Hatazawa",

note = "Funding Information: Laserphyrin{\textregistered} (Laserphyrin) was kindly provided by Meiji Seika Pharma Co., Ltd (Tokyo, Japan). This study was partially supported by JSPS KAKENHI Grant number 24229008 and 236599576 , the NAIST Presidential Special Fund , Japan Science and Technology Agency (JST) , the A-Step Feasibility Study Program ( AS242Z01752P ), Grants from the Terumo Life Science Foundation , and a Grant for molecular imaging from the Japan Science Technology Agency . The authors thank Mr. Yumiko Ito, Shinji Fujiyama, Kasumi Fujitake, Taishi Tomiyama (Department of Chemical and Biological Engineering, Ube National Collage of Technology), and Dr. Hiroki Tanimoto (NAIST) for helpful discussion and kind support. ",

year = "2014",

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doi = "10.1016/j.bmc.2014.02.021",

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Tamura, M, Matsui, H, Hirohara, S, Kakiuchi, K, Tanihara, M, Takahashi, N, Nakai, K, Kanai, Y, Watabe, H & Hatazawa, J 2014, 'Selective accumulation of [⁶²Zn]-labeled glycoconjugated porphyrins as multi-functional positron emission tomography tracers in cancer cells', Bioorganic and Medicinal Chemistry, vol. 22, no. 8, pp. 2563-2570. https://doi.org/10.1016/j.bmc.2014.02.021

TY - JOUR

T1 - Selective accumulation of [62Zn]-labeled glycoconjugated porphyrins as multi-functional positron emission tomography tracers in cancer cells

AU - Tamura, Masato

AU - Matsui, Hirofumi

AU - Hirohara, Shiho

AU - Kakiuchi, Kiyomi

AU - Tanihara, Masao

AU - Takahashi, Naruto

AU - Nakai, Kozi

AU - Kanai, Yasukazu

AU - Watabe, Hiroshi

AU - Hatazawa, Jun

N1 - Funding Information: Laserphyrin® (Laserphyrin) was kindly provided by Meiji Seika Pharma Co., Ltd (Tokyo, Japan). This study was partially supported by JSPS KAKENHI Grant number 24229008 and 236599576 , the NAIST Presidential Special Fund , Japan Science and Technology Agency (JST) , the A-Step Feasibility Study Program ( AS242Z01752P ), Grants from the Terumo Life Science Foundation , and a Grant for molecular imaging from the Japan Science Technology Agency . The authors thank Mr. Yumiko Ito, Shinji Fujiyama, Kasumi Fujitake, Taishi Tomiyama (Department of Chemical and Biological Engineering, Ube National Collage of Technology), and Dr. Hiroki Tanimoto (NAIST) for helpful discussion and kind support.

PY - 2014/4/15

Y1 - 2014/4/15

N2 - Positron-emission tomography (PET) can be used to visualize active stage cancer. Fluorine-18 ([18F])-labeled 2-([18F])2-deoxy-2- fluoroglucose (([18F])-FDG), which accumulates in glucose-dependent tissues, is a good cancer-targeting tracer. However, ([18F])-FDG is obscured in glucose-dependent normal tissues. In this study, we assessed the cancer-selective accumulation of zinc-labeled glycoconjugated 5,10,15,20-tetrakis(pentafluorophenyl)porphyrin (ZnGlc1-4), both in vitro and in vivo. Experiments using both normal and cancer cells confirmed the relationship between cancer cell-selective accumulation and the substitution numbers and orientations of glycoconjugated porphyrins. ZnGlctrans-2 accumulated at greater levels in cancer cells compared with other glycoconjugated porphyrins. PET imaging showed that ZnGlctrans-2 accumulated in tumor.

AB - Positron-emission tomography (PET) can be used to visualize active stage cancer. Fluorine-18 ([18F])-labeled 2-([18F])2-deoxy-2- fluoroglucose (([18F])-FDG), which accumulates in glucose-dependent tissues, is a good cancer-targeting tracer. However, ([18F])-FDG is obscured in glucose-dependent normal tissues. In this study, we assessed the cancer-selective accumulation of zinc-labeled glycoconjugated 5,10,15,20-tetrakis(pentafluorophenyl)porphyrin (ZnGlc1-4), both in vitro and in vivo. Experiments using both normal and cancer cells confirmed the relationship between cancer cell-selective accumulation and the substitution numbers and orientations of glycoconjugated porphyrins. ZnGlctrans-2 accumulated at greater levels in cancer cells compared with other glycoconjugated porphyrins. PET imaging showed that ZnGlctrans-2 accumulated in tumor.

KW - Cancer selective accumulation

KW - Positron emission tomography

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DO - 10.1016/j.bmc.2014.02.021

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SN - 0968-0896

VL - 22

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EP - 2570

JO - Bioorganic and Medicinal Chemistry

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