期刊
JOURNAL OF MATERIALS CHEMISTRY B
卷 10, 期 8, 页码 1196-1209出版社
ROYAL SOC CHEMISTRY
DOI: 10.1039/d1tb02393d
关键词
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资金
- Basic Science Research Program through the National Research Foundation of Korea (NRF) [2020R1F1A1071784]
- NRF - Korea government (MSIT) [2019R1G1A109926913]
- National Research Foundation of Korea [2020R1F1A1071784] Funding Source: Korea Institute of Science & Technology Information (KISTI), National Science & Technology Information Service (NTIS)
A series of cationic photosensitizers with mitochondrion-targeting properties were synthesized. The addition of bromine atoms in the photosensitizers increased the singlet oxygen quantum yield. The photosensitizers exhibited low cytotoxicity in the dark and high phototoxicity under light conditions.
A series of 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene-based photosensitizers (AmBXI, X = H, M, Br) featuring a cationic mitochondrion-targeting group and near-infrared (NIR) absorption was synthesized. After extending the photosensitizers' pi conjugation via Knoevenagel reaction, both the absorbance and emission maxima of AmBXI shifted to the phototherapeutic wavelength range (650-900 nm). Theoretical computations indicate that the introduction of bromine atoms promotes spin-orbit coupling, so that for each additional bromine atom in AmBXI an increase in singlet oxygen quantum yield would be expected (0.3%, 2.2%, and 4.1%, for AmBHI, AmBMI, and AmBBrI, respectively). Moreover, AmBXI photosensitizers exhibited low cytotoxicity in the dark and high phototoxicity, with the half maximal inhibitory concentrations of AmBBrI found to be 46.93 nM and 22.84 nM, while those of AmBMI were 129.7 nM and 58.34 nM in HeLa and MCF-7 cancer cells, respectively. Notably, introduction of a single bromine atom was enough to produce a cytotoxic effect. Furthermore, the presence of a quaternary ammonium group in AmBXI enabled the dyes to localize and stain the negatively charged mitochondria. The results presented herein indicate the straightforward and facile synthesis of NIR-light triggered mitochondrion-targeting photosensitizers.
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