Activatable Near-Infrared Fluorescence Imaging Using PEGylated Bacteriochlorin-Based Chlorin and BODIPY-Dyads as Probes for Detecting Cancer

Fusa Ogata; Tadanobu Nagaya; Yasuhiro Maruoka; Joshua Akhigbe; Adam Meares; Melissa Y. Lucero; Andrius Satraitis; Daiki Fujimura; Ryuhei Okada; Fuyuki Inagaki; Peter L. Choyke; Marcin Ptaszek; Hisataka Kobayashi

doi:10.1021/acs.bioconjchem.8b00820

Activatable Near-Infrared Fluorescence Imaging Using PEGylated Bacteriochlorin-Based Chlorin and BODIPY-Dyads as Probes for Detecting Cancer

Fusa Ogata, Tadanobu Nagaya, Yasuhiro Maruoka, Joshua Akhigbe, Adam Meares, Melissa Y. Lucero, Andrius Satraitis, Daiki Fujimura, Ryuhei Okada, Fuyuki Inagaki, Peter L. Choyke, Marcin Ptaszek, Hisataka Kobayashi

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

22 Citations (Scopus)

Abstract

Near infrared (NIR) fluorescent probes are attractive tools for biomedical in vivo imaging due to the relatively deeper tissue penetration and lower background autofluorescence. Activatable probes are turned on only after binding to their target, further improving target to background ratios. However, the number of available activatable NIR probes is limited. In this study, we introduce two types of activatable NIR fluorophores derived from bacteriochlorin: chlorin-bacteriochlorin energy-transfer dyads and boron-dipyrromethene (BODIPY)-bacteriochlorin energy-transfer dyads. These fluorophores are characterized by multiple narrow excitation bands with relatively strong emission in the NIR. Targeted bacteriochlorin-based antibody or peptide probes have been previously limited by aggregation after conjugation. Polyethylene glycol (PEG) chains were added to improve the hydrophilicity without altering pharmacokinetics of the targeting moieties. These PEGylated bacteriochlorin-based activatable fluorophores have potential as targeted activatable, multicolor NIR fluorescent probes for in vivo applications.

Original language	English
Pages (from-to)	169-183
Number of pages	15
Journal	Bioconjugate Chemistry
Volume	30
Issue number	1
DOIs	https://doi.org/10.1021/acs.bioconjchem.8b00820
Publication status	Published - Jan 16 2019
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biotechnology
Bioengineering
Biomedical Engineering
Pharmacology
Pharmaceutical Science
Organic Chemistry

UN SDGs

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

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10.1021/acs.bioconjchem.8b00820

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Ogata, F., Nagaya, T., Maruoka, Y., Akhigbe, J., Meares, A., Lucero, M. Y., Satraitis, A., Fujimura, D., Okada, R., Inagaki, F., Choyke, P. L., Ptaszek, M., & Kobayashi, H. (2019). Activatable Near-Infrared Fluorescence Imaging Using PEGylated Bacteriochlorin-Based Chlorin and BODIPY-Dyads as Probes for Detecting Cancer. Bioconjugate Chemistry, 30(1), 169-183. https://doi.org/10.1021/acs.bioconjchem.8b00820

Ogata, F, Nagaya, T, Maruoka, Y, Akhigbe, J, Meares, A, Lucero, MY, Satraitis, A, Fujimura, D, Okada, R, Inagaki, F, Choyke, PL, Ptaszek, M & Kobayashi, H 2019, 'Activatable Near-Infrared Fluorescence Imaging Using PEGylated Bacteriochlorin-Based Chlorin and BODIPY-Dyads as Probes for Detecting Cancer', Bioconjugate Chemistry, vol. 30, no. 1, pp. 169-183. https://doi.org/10.1021/acs.bioconjchem.8b00820

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title = "Activatable Near-Infrared Fluorescence Imaging Using PEGylated Bacteriochlorin-Based Chlorin and BODIPY-Dyads as Probes for Detecting Cancer",

abstract = "Near infrared (NIR) fluorescent probes are attractive tools for biomedical in vivo imaging due to the relatively deeper tissue penetration and lower background autofluorescence. Activatable probes are turned on only after binding to their target, further improving target to background ratios. However, the number of available activatable NIR probes is limited. In this study, we introduce two types of activatable NIR fluorophores derived from bacteriochlorin: chlorin-bacteriochlorin energy-transfer dyads and boron-dipyrromethene (BODIPY)-bacteriochlorin energy-transfer dyads. These fluorophores are characterized by multiple narrow excitation bands with relatively strong emission in the NIR. Targeted bacteriochlorin-based antibody or peptide probes have been previously limited by aggregation after conjugation. Polyethylene glycol (PEG) chains were added to improve the hydrophilicity without altering pharmacokinetics of the targeting moieties. These PEGylated bacteriochlorin-based activatable fluorophores have potential as targeted activatable, multicolor NIR fluorescent probes for in vivo applications.",

author = "Fusa Ogata and Tadanobu Nagaya and Yasuhiro Maruoka and Joshua Akhigbe and Adam Meares and Lucero, {Melissa Y.} and Andrius Satraitis and Daiki Fujimura and Ryuhei Okada and Fuyuki Inagaki and Choyke, {Peter L.} and Marcin Ptaszek and Hisataka Kobayashi",

note = "Funding Information: This research was supported by the Intramural Research Program of the National Institutes of Health, National Cancer Institute, Center for Cancer Research (ZIA-BC011512) and the National Cancer Institute of the National Institutes of Health under Award Number U01CA181628 (to M.P.). The content is solely the responsibility of the authors and does not necessarily represent the official views of the National Institutes of Health. We thank Mr. Nopondo N. Esemoto, for synthesis of compound C6. Publisher Copyright: {\textcopyright} 2018 American Chemical Society.",

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doi = "10.1021/acs.bioconjchem.8b00820",

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AU - Nagaya, Tadanobu

AU - Maruoka, Yasuhiro

AU - Akhigbe, Joshua

AU - Meares, Adam

AU - Lucero, Melissa Y.

AU - Satraitis, Andrius

AU - Fujimura, Daiki

AU - Okada, Ryuhei

AU - Inagaki, Fuyuki

AU - Choyke, Peter L.

AU - Ptaszek, Marcin

AU - Kobayashi, Hisataka

N1 - Funding Information: This research was supported by the Intramural Research Program of the National Institutes of Health, National Cancer Institute, Center for Cancer Research (ZIA-BC011512) and the National Cancer Institute of the National Institutes of Health under Award Number U01CA181628 (to M.P.). The content is solely the responsibility of the authors and does not necessarily represent the official views of the National Institutes of Health. We thank Mr. Nopondo N. Esemoto, for synthesis of compound C6. Publisher Copyright: © 2018 American Chemical Society.

PY - 2019/1/16

Y1 - 2019/1/16

N2 - Near infrared (NIR) fluorescent probes are attractive tools for biomedical in vivo imaging due to the relatively deeper tissue penetration and lower background autofluorescence. Activatable probes are turned on only after binding to their target, further improving target to background ratios. However, the number of available activatable NIR probes is limited. In this study, we introduce two types of activatable NIR fluorophores derived from bacteriochlorin: chlorin-bacteriochlorin energy-transfer dyads and boron-dipyrromethene (BODIPY)-bacteriochlorin energy-transfer dyads. These fluorophores are characterized by multiple narrow excitation bands with relatively strong emission in the NIR. Targeted bacteriochlorin-based antibody or peptide probes have been previously limited by aggregation after conjugation. Polyethylene glycol (PEG) chains were added to improve the hydrophilicity without altering pharmacokinetics of the targeting moieties. These PEGylated bacteriochlorin-based activatable fluorophores have potential as targeted activatable, multicolor NIR fluorescent probes for in vivo applications.

AB - Near infrared (NIR) fluorescent probes are attractive tools for biomedical in vivo imaging due to the relatively deeper tissue penetration and lower background autofluorescence. Activatable probes are turned on only after binding to their target, further improving target to background ratios. However, the number of available activatable NIR probes is limited. In this study, we introduce two types of activatable NIR fluorophores derived from bacteriochlorin: chlorin-bacteriochlorin energy-transfer dyads and boron-dipyrromethene (BODIPY)-bacteriochlorin energy-transfer dyads. These fluorophores are characterized by multiple narrow excitation bands with relatively strong emission in the NIR. Targeted bacteriochlorin-based antibody or peptide probes have been previously limited by aggregation after conjugation. Polyethylene glycol (PEG) chains were added to improve the hydrophilicity without altering pharmacokinetics of the targeting moieties. These PEGylated bacteriochlorin-based activatable fluorophores have potential as targeted activatable, multicolor NIR fluorescent probes for in vivo applications.

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Activatable Near-Infrared Fluorescence Imaging Using PEGylated Bacteriochlorin-Based Chlorin and BODIPY-Dyads as Probes for Detecting Cancer

Abstract

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