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

Please always quote using this URN: urn:nbn:de:bvb:20-opus-256963
  • 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 Cat\(^{1+}\), Cat\(^{2+}\), Cat(i)\(^{2+}\), and Cat\(^{3+}\). Comparison with the mono-triarylboranes reveals the large influence of the bridging unit on the properties of the bis-triarylboranes, especially those of the cationic compounds. BasedThe 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 Cat\(^{1+}\), Cat\(^{2+}\), Cat(i)\(^{2+}\), and Cat\(^{3+}\). Comparison with the mono-triarylboranes reveals the large influence of the bridging unit on the properties of the bis-triarylboranes, especially those of the cationic compounds. Based on these preliminary investigations, the interactions of Cat\(^{1+}\), Cat\(^{2+}\), Cat(i)\(^{2+}\), and Cat\(^{3+}\) 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.show moreshow less

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Author: Sarina M. Berger, Jessica Rühe, Johannes Schwarzmann, Alexandra Phillipps, Ann-Katrin Richard, Matthias Ferger, Ivo Krummenacher, Lidija-Marija Tumir, Željka Ban, Ivo Crnolatac, Dragomira Majhen, Ivan Barišić, Ivo Piantanida, Domenik Schleier, Stefanie Griesbeck, Alexandra Friedrich, Holger BraunschweigORCiD, Todd B. MarderORCiD
URN:urn:nbn:de:bvb:20-opus-256963
Document Type:Journal article
Faculties:Fakultät für Chemie und Pharmazie / Institut für Anorganische Chemie
Language:English
Parent Title (English):Chemistry—A European Journal
Year of Completion:2021
Volume:27
Issue:56
Pagenumber:14057–14072
Source:Chemistry—A European Journal 2021, 27(56):14057–14072. DOI: 10.1002/chem.202102308
DOI:https://doi.org/10.1002/chem.202102308
Dewey Decimal Classification:5 Naturwissenschaften und Mathematik / 54 Chemie / 546 Anorganische Chemie
Tag:bioimaging; boron; luminescence; nucleic acid; singlet oxygen
Release Date:2022/03/08
Licence (German):License LogoCC BY: Creative-Commons-Lizenz: Namensnennung 4.0 International