Berger, Sarina M.; Rühe, Jessica; Schwarzmann, Johannes; Phillipps, Alexandra; Richard, Ann-Katrin; Ferger, Matthias; Krummenacher, Ivo; Tumir, Lidija-Marija; Ban, Željka; Crnolatac, Ivo; Majhen, Dragomira; Barišić, Ivan; Piantanida, Ivo; Schleier, Domenik; Griesbeck, Stefanie; Friedrich, Alexandra; Braunschweig, Holger; Marder, Todd B. (2021) Bithiophene-Cored, mono-, bis-, and tris-(Trimethylammonium)- Substituted, bis-Triarylborane Chromophores: Effect of the Number and Position of Charges on Cell Imaging and DNA/RNA Sensing. Chemistry : a European journal, 27 . pp. 14057-14072. ISSN 0947-6539
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Abstract
The synthesis, photophysical, and electrochemical properties of selectively mono-, bis- and tris-dimethylamino- and trimethylammonium-substituted bis-triarylborane bithiophene chromophores are presented along with the water solubility and singlet oxygen sensitizing efficiency of the cationic compounds Cat1+, Cat2+, Cat(i)2+, and Cat3+. Comparison with the mono- triarylboranes reveals the large influence of the bridging unit on the properties of the bistriarylboranes, especially those of the cationic compounds. Based on these preliminary investigations, the interactions of Cat1+, Cat2+, Cat(i)2+, and Cat3+ with DNA, RNA, and DNApore were investigated in buffered solutions. The same compounds were investigated for their ability to enter and localize within organelles of human lung carcinoma (A549) and normal lung (WI38) cells showing that not only the number of charges but also their distribution over the chromophore influences interactions and staining properties.
| Item Type: | Article | ||||||||
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| Uncontrolled Keywords: | boron ; bioimaging ; luminescence ; singlet oxygen ; nucleic acid | ||||||||
| Subjects: | NATURAL SCIENCES > Chemistry | ||||||||
| Divisions: | Division of Molecular Biology Division of Organic Chemistry and Biochemistry |
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| Depositing User: | Ivo Piantanida | ||||||||
| Date Deposited: | 29 Oct 2021 11:46 | ||||||||
| URI: | http://fulir.irb.hr/id/eprint/6590 | ||||||||
| DOI: | 10.1002/chem.202102308 |
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