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- W4294770603 endingPage "110711" @default.
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- W4294770603 abstract "Neutral and water soluble anionic carborane derivatives of 4,4-difluoro-4-bora- 3a , 4a -diaza- s -indacene (BODIPY) were efficiently synthesized via nucleophilic aromatic substitution of p -fluorine atom in meso -8-pentafluorophenyl-substituted BODIPYs with carborane S-nucleophiles. Using this synthetic approach a series of thiocarboranyl-BODIPYs was generated in good yields under mild reaction conditions such as room temperature and a short reaction time. Individual carborane-BODIPY conjugates formed stable complexes with serum albumin and generated singlet oxygen. In cell based experiments compounds 6 (8-[4-(( m -carboran-9-yl)thio)-2,3,5,6-tetrafluorophenyl]-4,4-difluoro-4-bora- 3a,4a -diaza- s -indacene) and 11 ({8-[4-((1-carba- closo -dodecaboran-1-yl)thio)-2,3,5,6-tetrafluorophenyl]-1,3,5,7-tetramethyl-4,4-difluoro-4-bora- 3a,4a -diaza- s -indacene} caesium) were negligibly cytotoxic in the dark whereas the plasma membrane photodamage and cell death were registered rapidly after illumination. Thus, the new chemotype of boronated BODIPYs emerges as a biocompatible and efficient tool for binary therapeutic modalities. • Neutral and water-soluble anionic carborane BODIPY derivatives were synthesized. • Compounds demonstrated high fluorescence quantum yields and formed complexes with albumin. • Photoactivation of tumor cells loaded with selected compounds triggered rapid necrosis." @default.
- W4294770603 created "2022-09-06" @default.
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- W4294770603 date "2022-11-01" @default.
- W4294770603 modified "2023-10-16" @default.
- W4294770603 title "A straightforward approach to carborane-substituted BODIPY derivatives via nucleophilic aromatic substitution: Synthesis and photodynamic properties" @default.
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- W4294770603 doi "https://doi.org/10.1016/j.dyepig.2022.110711" @default.
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