Molecular Design of Highly Efficient Heavy-Atom-Free Triplet BODIPY Derivatives for Photodynamic Therapy and Bioimaging

Van Nghia Nguyen; Yubin Yim; Sangin Kim; Bokyeong Ryu; K. M.K. Swamy; Gyoungmi Kim; Nahyun Kwon; C. Yoon Kim; Sungnam Park; Juyoung Yoon

doi:10.1002/anie.202002843

Molecular Design of Highly Efficient Heavy-Atom-Free Triplet BODIPY Derivatives for Photodynamic Therapy and Bioimaging

Van Nghia Nguyen, Yubin Yim, Sangin Kim, Bokyeong Ryu, K. M.K. Swamy, Gyoungmi Kim, Nahyun Kwon, C. Yoon Kim, Sungnam Park, Juyoung Yoon

Department of Chemistry & Nanoscience

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

238 Scopus citations

Abstract

Novel BODIPY photosensitizers were developed for imaging-guided photodynamic therapy. The introduction of a strong electron donor to the BODIPY core through a phenyl linker combined with the twisted arrangement between the donor and the BODIPY acceptor is essential for reducing the energy gap between the lowest singlet excited state and the lowest triplet state (ΔE_ST), leading to a significant enhancement in the intersystem crossing (ISC) of the BODIPYs. Remarkably, the BDP-5 with the smallest ΔE_ST (ca. 0.44 eV) exhibited excellent singlet oxygen generation capabilities in both organic and aqueous solutions. BDP-5 also displayed bright emission in the far-red/near-infrared region in the condensed states. More importantly, both in vitro and in vivo studies demonstrated that BDP-5 NPs displayed a high potential for photodynamic cancer therapy and bioimaging.

Original language	English
Pages (from-to)	8957-8962
Number of pages	6
Journal	Angewandte Chemie - International Edition
Volume	59
Issue number	23
DOIs	https://doi.org/10.1002/anie.202002843
State	Published - 2 Jun 2020

Bibliographical note

Publisher Copyright:
© 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim

Keywords

BODIPY
aggregation-induced emission
heavy-atom-free photosensitizers
photodynamic therapy
reactive oxygen species

UN SDGs

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

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10.1002/anie.202002843

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title = "Molecular Design of Highly Efficient Heavy-Atom-Free Triplet BODIPY Derivatives for Photodynamic Therapy and Bioimaging",

abstract = "Novel BODIPY photosensitizers were developed for imaging-guided photodynamic therapy. The introduction of a strong electron donor to the BODIPY core through a phenyl linker combined with the twisted arrangement between the donor and the BODIPY acceptor is essential for reducing the energy gap between the lowest singlet excited state and the lowest triplet state (ΔEST), leading to a significant enhancement in the intersystem crossing (ISC) of the BODIPYs. Remarkably, the BDP-5 with the smallest ΔEST (ca. 0.44 eV) exhibited excellent singlet oxygen generation capabilities in both organic and aqueous solutions. BDP-5 also displayed bright emission in the far-red/near-infrared region in the condensed states. More importantly, both in vitro and in vivo studies demonstrated that BDP-5 NPs displayed a high potential for photodynamic cancer therapy and bioimaging.",

keywords = "BODIPY, aggregation-induced emission, heavy-atom-free photosensitizers, photodynamic therapy, reactive oxygen species",

author = "Nguyen, {Van Nghia} and Yubin Yim and Sangin Kim and Bokyeong Ryu and Swamy, {K. M.K.} and Gyoungmi Kim and Nahyun Kwon and Kim, {C. Yoon} and Sungnam Park and Juyoung Yoon",

note = "Publisher Copyright: {\textcopyright} 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim",

year = "2020",

month = jun,

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doi = "10.1002/anie.202002843",

language = "English",

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T1 - Molecular Design of Highly Efficient Heavy-Atom-Free Triplet BODIPY Derivatives for Photodynamic Therapy and Bioimaging

AU - Nguyen, Van Nghia

AU - Yim, Yubin

AU - Kim, Sangin

AU - Ryu, Bokyeong

AU - Swamy, K. M.K.

AU - Kim, Gyoungmi

AU - Kwon, Nahyun

AU - Kim, C. Yoon

AU - Park, Sungnam

AU - Yoon, Juyoung

PY - 2020/6/2

Y1 - 2020/6/2

N2 - Novel BODIPY photosensitizers were developed for imaging-guided photodynamic therapy. The introduction of a strong electron donor to the BODIPY core through a phenyl linker combined with the twisted arrangement between the donor and the BODIPY acceptor is essential for reducing the energy gap between the lowest singlet excited state and the lowest triplet state (ΔEST), leading to a significant enhancement in the intersystem crossing (ISC) of the BODIPYs. Remarkably, the BDP-5 with the smallest ΔEST (ca. 0.44 eV) exhibited excellent singlet oxygen generation capabilities in both organic and aqueous solutions. BDP-5 also displayed bright emission in the far-red/near-infrared region in the condensed states. More importantly, both in vitro and in vivo studies demonstrated that BDP-5 NPs displayed a high potential for photodynamic cancer therapy and bioimaging.

AB - Novel BODIPY photosensitizers were developed for imaging-guided photodynamic therapy. The introduction of a strong electron donor to the BODIPY core through a phenyl linker combined with the twisted arrangement between the donor and the BODIPY acceptor is essential for reducing the energy gap between the lowest singlet excited state and the lowest triplet state (ΔEST), leading to a significant enhancement in the intersystem crossing (ISC) of the BODIPYs. Remarkably, the BDP-5 with the smallest ΔEST (ca. 0.44 eV) exhibited excellent singlet oxygen generation capabilities in both organic and aqueous solutions. BDP-5 also displayed bright emission in the far-red/near-infrared region in the condensed states. More importantly, both in vitro and in vivo studies demonstrated that BDP-5 NPs displayed a high potential for photodynamic cancer therapy and bioimaging.

KW - BODIPY

KW - aggregation-induced emission

KW - heavy-atom-free photosensitizers

KW - photodynamic therapy

KW - reactive oxygen species

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DO - 10.1002/anie.202002843

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SN - 1433-7851

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JO - Angewandte Chemie - International Edition

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IS - 23

ER -

Molecular Design of Highly Efficient Heavy-Atom-Free Triplet BODIPY Derivatives for Photodynamic Therapy and Bioimaging

Abstract

Bibliographical note

Keywords

UN SDGs

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