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

Research output: Contribution to journalArticlepeer-review

174 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)8957-8962
Number of pages6
JournalAngewandte Chemie - International Edition
Volume59
Issue number23
DOIs
Publication statusPublished - 2020 Jun 2

Bibliographical note

Funding Information:
This study was supported by grants from the National Research Foundation of Korea (NRF) funded by the Korean government (MSIP) (No. 2012R1A3A2048814 for J.Y. and No. 2019R1A6A1A11044070 for S.P.) Mass spectral data were obtained from the Korea Basic Science Institute (Daegu) on a Jeol JMS 700 high‐resolution mass spectrometer. The authors were also thankful to Dr. H. J. Lee (Korea Basic Science Institute) for her assistance in the SC‐XRD analysis.

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

Keywords

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

ASJC Scopus subject areas

  • Catalysis
  • General Chemistry

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