Synthesis, characterization and investigation of biological properties of phenylboronic acid functionalized N-heterocycic carbene precursors

N-heterocyclic carbenes (NHC) are heterocyclic compounds consisting of singlet carbenes and containing nitrogen atoms. In this thesis, the synthesis, characterization, determination of anticancer, genotoxicity, antibacterial and enzyme inhibition properties of benzimidazolium salts bearining phenylboronic acid functional group were investigated. Within the scope of the study, benzimidazolium salts (1a-f) with meta-phenylboronic acid substituted were synthesized. The IC50 µg/mL values of the synthesized for the 1a-f salts on the breast cancer cell line MCF-7 and for the cisplatin drug were measured 37.40±1.70, 54.17±2.77, 29.57±3.04, 32.27±4.24, 29.90±2,89, 38.97±2.44 and 82.02±6.19, respectively. On the lung cancer cell line A549, the IC50 µg/mL values of 1a-f salts and cisplatin were determined as 38.83±3.17, 51.17±5.84, 17.14±3.72, 31.86±3.53, 29.24±2.86, 24.18±3.99 and 91.31±3.65, respectively. The IC50 µg/mL values of salts 1a-f for colon cancer HCT116 cell line and for cisplatin were 29.20±2.33, 52.78±2.22, 34.29±1.97, 30.42±4.52, 15.31±3.81, 36.04±1.38 and 106.57±6.77, respectively. In genotoxic studies, no effect was observed on the pBR322 plasmid despite increasing concentration. It did not show comparable effect with standard antibiotic on B. subtilis and E. coli bacteria. In the enzyme inhibition test, the IC50 µg/mL values of salts 1a-f and for allopurinol were found as 1.062±0.038, 1.226±0.021, 0.761±0.024, 0.811±0.033, 0.637±0.011, 0.591±0.016 and 1.685±0.051, respectively. It showed more inhibition of acetylcholine esterase enzyme than donepezil, and these values of IC50 µg/mL for 1a-f salts and donepezil drug were 0.861±0.045, 1.088±0.049, 0.976±0.058, 0.862±0.033, 0.903±0.011, 1.029±0.089 and 3.172±0.661, respectively. As a result, it has been determined that phenylboronic acid functionalized NHC precursors are biologically active compounds and exhibit biological activity on cells, especially through enzyme inhibitions.