TY  - JOUR
A1  - Ban, Željka
A1  - Karačić, Zrinka
A1  - Tomić, Sanja
A1  - Amini, Hashem
A1  - Marder, Todd B.
A1  - Piantanida, Ivo
T1  - Triarylborane dyes as a novel non-covalent and non-inhibitive fluorimetric markers for DPP III enzyme
JF  - Molecules
N2  - Novel dyes were prepared by simple “click CuAAC” attachment of a triarylborane–alkyne to the azide side chain of an amino acid yielding triarylborane dye 1 which was conjugated with pyrene (dye 2) forming a triarylborane–pyrene FRET pair. In contrast to previous cationic triarylboranes, the novel neutral dyes interact only with proteins, while their affinity to DNA/RNA is completely abolished. Both the reference triarylborane amino acid and triarylborane–pyrene conjugate bind to BSA and the hDPP III enzyme with high affinities, exhibiting a strong (up to 100-fold) fluorescence increase, whereby the triarylborane–pyrene conjugate additionally retained FRET upon binding to the protein. Furthermore, the triarylborane dyes, upon binding to the hDPP III enzyme, did not impair its enzymatic activity under a wide range of experimental conditions, thus being the first non-covalent fluorimetric markers for hDPP III, also applicable during enzymatic reactions with hDPP III substrates.
KW  - triarylborane
KW  - pyrene
KW  - click CuAAC synthesis
KW  - DPP III enzyme
KW  - BSA
KW  - fluorescence
Y1  - 2021
U6  - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-245046
SN  - 1420-3049
VL  - 26
IS  - 16
ER  - 
TY  - JOUR
A1  - Berger, Sarina M.
A1  - Rühe, Jessica
A1  - Schwarzmann, Johannes
A1  - Phillipps, Alexandra
A1  - Richard, Ann-Katrin
A1  - Ferger, Matthias
A1  - Krummenacher, Ivo
A1  - Tumir, Lidija-Marija
A1  - Ban, Željka
A1  - Crnolatac, Ivo
A1  - Majhen, Dragomira
A1  - Barišić, Ivan
A1  - Piantanida, Ivo
A1  - Schleier, Domenik
A1  - Griesbeck, Stefanie
A1  - Friedrich, Alexandra
A1  - Braunschweig, Holger
A1  - Marder, Todd B.
T1  - 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
JF  - Chemistry—A European Journal
N2  - 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.
KW  - singlet oxygen
KW  - boron
KW  - bioimaging
KW  - luminescence
KW  - nucleic acid
Y1  - 2021
U6  - http://nbn-resolving.de/urn/resolver.pl?urn:nbn:de:bvb:20-opus-256963
VL  - 27
IS  - 56
ER  - 
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  -