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

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 betwee...

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Vydáno v:Angewandte Chemie International Edition Ročník 59; číslo 23; s. 8957 - 8962
Hlavní autoři: Nguyen, Van‐Nghia, Yim, Yubin, Kim, Sangin, Ryu, Bokyeong, Swamy, K. M. K., Kim, Gyoungmi, Kwon, Nahyun, Kim, C‐Yoon, Park, Sungnam, Yoon, Juyoung
Médium: Journal Article
Jazyk:angličtina
Vydáno: WEINHEIM Wiley 02.06.2020
Wiley Subscription Services, Inc
Vydání:International ed. in English
Témata:
aggregation-induced emission
Aqueous solutions
Atomic energy levels
BODIPY
Boron Compounds - chemistry
Boron Compounds - pharmacology
Boron Compounds - therapeutic use
Cell Line, Tumor
Chemistry
Chemistry, Multidisciplinary
Drug Design
Energy gap
heavy-atom-free photosensitizers
Humans
In vivo methods and tests
Medical imaging
Molecular Imaging - methods
Photochemotherapy - methods
Photodynamic therapy
Photosensitizing Agents - chemistry
Photosensitizing Agents - pharmacology
Photosensitizing Agents - therapeutic use
Physical Sciences
reactive oxygen species
Science & Technology
Singlet oxygen
Triplet state
BODIPY
ELECTRON-TRANSFER
DYES
photodynamic therapy
reactive oxygen species
PHOTOSENSITIZERS
aggregation-induced emission
heavy-atom-free photosensitizers
GENERATION
DYADS
EXCITED-STATES
ISSN:1433-7851, 1521-3773, 1521-3773
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Popis
Shrnutí: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. Twisted sensitizers: Twisted D‐BODIPY π‐conjugated systems with a phenyl linker as novel heavy‐atom‐free triplet BODIPY photosensitizers were prepared for imaging‐guided photodynamic therapy. BDP‐5 NPs were successfully applied in vitro and in vivo and exhibited a high potential for photodynamic cancer therapy and bioimaging.
Bibliografie:These authors contributed equally to this work.
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ISSN:1433-7851
1521-3773
1521-3773
DOI:10.1002/anie.202002843