Insight into the effect of Ca2+, Mg2+ and Zn2+ on serum albumin interaction of benzimidazole-type new isopropyl substituted N-heterocyclic carbene molecules

• Published in: Journal of photochemistry and photobiology. A, Chemistry. Chemistry., 2024-01, Vol.447, p.115282, Article 115282
• Main Authors: Üstün, Elvan, Şahin, Neslihan
• Format: Article
• Language: English
• Subjects: BSA-binding; Fluorescence spectroscopy; Molecular docking; N-heterocyclic carbenes
• ISSN: 1010-6030
• DOI: 10.1016/j.jphotochem.2023.115282

[Display omitted] •Novel isopropyl substituted benzimidazole type N-heterocyclic carbenes were synthesized.•The molecules were fully characterized by 1H and 13C NMR, FT-IR, elemental analysis, UV–Vis spectroscopy and DFT- and TDDFT-based methods.•BSA-binding properties of the molecules were analyzed with fluorescence spectroscopy.•BSA interactions of molecules were analyzed in the presence of Ca2+, Mg2+ and Zn2+.•The molecules were investigated by molecular docking methods against of BSA and DNA. N-heterocyclic carbenes are not only revolutionary catalysts in organic synthesis but also well-known anthelmintics, fungicides, antacids, and antibiotics. Serum albumin transports various substances in the body such as hormones, fatty acids, bilirubin, certain drugs, and is also crucial in the maintenance of health and bodily functions. For that reason, in this study five novel benzimidazole-type N-heterocyclic carbenes, 1- Isopropyl-3-benzyl-5,6-dimethylbenzimidazolium chloride (2a), 1- Isopropyl-3-(2-chlorobenzyl)-5,6-dimethylbenzimidazolium chloride (2b), 1- Isopropyl-3-(2-methylbenzyl)-5,6-dimethylbenzimidazolium chloride (2c), 1- Isopropyl-3-(2,3,4,5,6-pentamethylbenzyl)-5,6-dimethylbenzimidazolium chloride (2d), 1- Isopropyl-3-naphthyl-5,6-dimethylbenzimidazolium chloride (2e) were gained in 74–85 % yields. The molecules were fully characterized 1H and 13C NMR, elemental analysis, UV–Vis spectroscopy, FT-IR, and DFT- and TDDFT-based in-silico methods. Additionally, Stern-Volmer methods with fluorescence spectroscopy were performed in order to analyze the BSA-binding properties of these molecules. BSA interactions of molecules were evaluated with specific concentrations of Ca2+, Mg2+ and Zn2+. The detailed interaction analyses were also surveyed by molecular docking methods against the BSA and DNA.