TY  - JOUR
A1  - Ferger, Matthias
A1  - Ban, Željka
A1  - Krošl, Ivona
A1  - Tomić, Sanja
A1  - Dietrich, Lena
A1  - Lorenzen, Sabine
A1  - Rauch, Florian
A1  - Sieh, Daniel
A1  - Friedrich, Alexandra
A1  - Griesbeck, Stefanie
A1  - Kenđel, Adriana
A1  - Miljanić, Snežana
A1  - Piantanida, Ivo
A1  - Marder, Todd B.
T1  - Bis(phenylethynyl)arene Linkers in Tetracationic Bis-triarylborane Chromophores Control Fluorimetric and Raman Sensing of Various DNAs and RNAs
JF  - Chemistry-A European Journal
N2  - We report four new luminescent tetracationic bis-triarylborane DNA and RNA sensors that show high binding affinities, in several cases even in the nanomolar range. Three of the compounds contain substituted, highly emissive and structurally flexible bis(2,6-dimethylphenyl-4-ethynyl)arene linkers (3: arene=5,5′-2,2′-bithiophene; 4: arene=1,4-benzene; 5: arene=9,10-anthracene) between the two boryl moieties and serve as efficient dual Raman and fluorescence chromophores. The shorter analogue 6 employs 9,10-anthracene as the linker and demonstrates the importance of an adequate linker length with a certain level of flexibility by exhibiting generally lower binding affinities than 3–5. Pronounced aggregation–deaggregation processes are observed in fluorimetric titration experiments with DNA for compounds 3 and 5. Molecular modelling of complexes of 5 with AT-DNA, suggest the minor groove as the dominant binding site for monomeric 5, but demonstrate that dimers of 5 can also be accommodated. Strong SERS responses for 3–5 versus a very weak response for 6, particularly the strong signals from anthracene itself observed for 5 but not for 6, demonstrate the importance of triple bonds for strong Raman activity in molecules of this compound class. The energy of the characteristic stretching vibration of the C≡C bonds is significantly dependent on the aromatic moiety between the triple bonds. The insertion of aromatic moieties between two C≡C bonds thus offers an alternative design for dual Raman and fluorescence chromophores, applicable in multiplex biological Raman imaging.
KW  - boranes
KW  - Raman probes
KW  - molecular modelling
KW  - fluorescent probes
KW  - DNA/RNA sensors
Y1  - 2021
U6  - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-256717
VL  - 27
IS  - 16
ER  - 
TY  - JOUR
A1  - Ban, Željka
A1  - Griesbeck, Stefanie
A1  - Tomić, Sanja
A1  - Nitsch, Jörn
A1  - Marder, Todd  B.
A1  - Piantanida, Ivo
T1  - A Quadrupolar Bis-Triarylborane Chromophore as a Fluorimetric and Chirooptic Probe for Simultaneous and Selective Sensing of DNA, RNA and Proteins
JF  - Chemistry - A European Journal
N2  - A water‐soluble tetracationic quadrupolar bis‐triarylborane chromophore showed strong binding to ds‐DNA, ds‐RNA, ss‐RNA, as well as to the naturally most abundant protein, BSA. The novel dye can distinguish between DNA/RNA and BSA by fluorescence emission separated by Δv =3600 cm\(^{-1}\), allowing for the simultaneous quantification of DNA/RNA and protein (BSA) in a mixture. The applicability of such fluorimetric differentiation in vitro was demonstrated, strongly supporting a protein‐like target as a dominant binding site of 1 in cells. Moreover, our dye also bound strongly to ss‐RNA, with the unusual rod‐like structure of the dye, decorated by four positive charges at its termini and having a hydrophobic core, acting as a spindle for wrapping A, C and U ss‐RNAs, but not poly G, the latter preserving its secondary structure. To the best of our knowledge, such unmatched, multifaceted binding activity of a small molecule toward DNA, RNA, and proteins and the selectivity of its fluorimetric and chirooptic response makes the quadrupolar bis‐triarylborane a novel chromophore/fluorophore moiety for biochemical applications.
KW  - boranes
KW  - circular dichrosism
KW  - fluorescent probes
KW  - luminescence
KW  - sensors
Y1  - 2020
U6  - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-208154
VL  - 26
IS  - 10
ER  -