N, N'‐Disubstituted Benzimidazolium Salts: Synthesis, Characterization, Micromolar Detection of Fe(III) ions in Aqueous system, Biological Evaluation and Molecular Docking Studies. Issue 48 (20th December 2022)

• Record Type: Journal Article
• Authors: Sharma, Himshikha; Chaudhary, Shweta; Nirwan, Sonam; Kakkar, Rita; Liew, HuiShan; Low, May‐Lee; Mai, Chun‐Wai; Hii, Ling‐Wei; Leong, Chee‐Onn; Daisy Milton, Marilyn
• Is Part Of: ChemistrySelect. Volume 7:Issue 48(2022)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2022-12-20
• Subjects: Breast cancer -- Doxorubicin -- Fe3+ probes -- N, N'-disubstituted benzimidazolium salts -- Pure aqueous medium; Chemistry -- Periodicals; 540.5
• DOI: 10.1002/slct.202203239
• Languages: English
• ISSNs: 2365-6549

Abstract

Abstract: A series of dicationic N, N' ‐disubstituted benzimidazolium salts with Br − and PF6 − as the counter anions were synthesized in 75–98 % yields. The single crystal X‐ray diffraction studies of one of the benzimidazolium salts confirmed the structure of these dicationic compounds. These salts exhibited a selective "turn‐off" fluorescence response toward Fe 3+ ions in aqueous solution over the other competitive metal ions such as Ag +, Al 3+, Ba 2+, Ca 2+, Co 2+, Cr 3+, Cu 2+, Fe 2+, K +, Mg 2+, Na +, Ni 2+, Pb 2+, and Zn 2+ . Upon addition of 5 equivalents Fe 3+ ions, emission intensity was quenched by 94–99 % in pure aqueous media. Detection limits for all probes with Fe 3+ ions were found in micromolar range. Further, drug combination analysis was conducted by evaluating the combinatorial treatment effects of two benzimidazolium salts with doxorubicin on breast cancer cells using the Chou‐Talalay method and the Highest Single Agent (HSA) model, and it was found that these compounds showed synergism with doxorubicin. Further, molecular docking studies revealed the best docking score (−6.11) for one of the benzimidazolium salts, and explained its binding affinity with checkpoint kinase 2 (chk2) protein. Abstract : N, N' ‐disubstituted benzimidazolium salts were synthesized in excellent yields, which exhibited selective "turn‐off" fluorescence response towards Fe 3+ ions in aqueous solution over other metal ions with the detection limits of Fe 3+ ions in the micromolar range. Two of these benzimidazolium salts could synergise doxorubicin sensitivity in breast cancer cell line (MDA‐MB‐468, MDA‐MB‐231&MCF7) as revealed by drug combination analysis.