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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
Author(s) -
Berger Sarina M.,
Rühe Jessica,
Schwarzmann Johannes,
Phillipps Alexandra,
Richard AnnKatrin,
Ferger Matthias,
Krummenacher Ivo,
Tumir LidijaMarija,
Ban Željka,
Crnolatac Ivo,
Majhen Dragomira,
Barišić Ivan,
Piantanida Ivo,
Schleier Domenik,
Griesbeck Stefanie,
Friedrich Alexandra,
Braunschweig Holger,
Marder Todd B.
Publication year - 2021
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202102308
Subject(s) - chromophore , tris , chemistry , dna , polymer chemistry , photochemistry , biochemistry
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. 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.