273-13-2Relevant articles and documents
Fluorescence emission enhancement of a T-shaped benzimidazole with a mechanically-interlocked ‘suit’
Xu, Houyang,Lin, Meng-Di,Yuan, Jun,Zhou, Baiyang,Mu, Yingxiao,Huo, Yanping,Zhu, Kelong
supporting information, p. 3239 - 3242 (2021/04/06)
A fluorescent T-shaped benzimidazole was successfully designed and interlocked in a bicyclic macrocycle to form a suit[1]ane through supramolecular templated-synthesis. Compared with the bare fluorophore, suit[1]ane requires nearly two times the concentration to initialize the aggregation-caused quenching effect in solution. Furthermore, an 8-fold higher solid-state fluorescence quantum yield (21.7%) is also achieved. By taking advantage of mechanical bonding and molecular packing, such fluorescence emission enhancement through formation of a suitane opens the way to new complex fluorescent materials.
Synthesis of novel halogenated heterocycles based on o‐phenylenediamine and their interactions with the catalytic subunit of protein kinase ck2
Maciejewska, Agnieszka Monika,Paprocki, Daniel,Poznański, Jaros?aw,Speina, El?bieta,Winiewska‐szajewska, Maria
supporting information, (2021/06/09)
Protein kinase CK2 is a highly pleiotropic protein kinase capable of phosphorylating hundreds of protein substrates. It is involved in numerous cellular functions, including cell viability, apoptosis, cell proliferation and survival, angiogenesis, or ER‐stress response. As CK2 activity is found perturbed in many pathological states, including cancers, it becomes an attractive target for the pharma. A large number of low‐mass ATP‐competitive inhibitors have already been developed, the majority of them halogenated. We tested the binding of six series of halogenated heterocyclic ligands derived from the commercially available 4,5‐dihalo‐benzene‐1,2‐diamines. These ligand series were selected to enable the separation of the scaffold effect from the hydrophobic interactions attributed directly to the presence of halogen atoms. In silico molecular docking was initially applied to test the capability of each ligand for binding at the ATP‐binding site of CK2. HPLC‐derived ligand hydrophobicity data are compared with the binding affinity assessed by low‐volume differential scanning fluorimetry (nanoDSF). We identified three promising ligand scaffolds, two of which have not yet been described as CK2 inhibitors but may lead to potent CK2 kinase inhibitors. The inhibitory activity against CK2α and toxicity against four reference cell lines have been determined for eight compounds identified as the most promising in nanoDSF assay.
Between Aromatic and Quinoid Structure: A Symmetrical UV to Vis/NIR Benzothiadiazole Redox Switch
Rietsch, Philipp,Sobottka, Sebastian,Hoffmann, Katrin,Popov, Alexey A.,Hildebrandt, Pascal,Sarkar, Biprajit,Resch-Genger, Ute,Eigler, Siegfried
, p. 17361 - 17365 (2020/12/01)
Reversibly switching the light absorption of organic molecules by redox processes is of interest for applications in sensors, light harvesting, smart materials, and medical diagnostics. This work presents a symmetrical benzothiadiazole (BTD) derivative with a high fluorescence quantum yield in solution and in the crystalline state and shows by spectroelectrochemical analysis that reversible switching of UV absorption in the neutral state, to broadband Vis/NIR absorption in the 1st oxidized state, to sharp band Vis absorption in the 2nd oxidized state, is possible. For the one-electron oxidized species, formation of a delocalized radical is confirmed by electron paramagnetic resonance spectroelectrochemistry. Furthermore, our results reveal an increasing quinoidal distortion upon the 1st and 2nd oxidation, which can be used as the leitmotif for the development of BTD based redox switches.
