Synthesis, DNA binding of bis-naphthyl ferrocene derivatives and the application as new electroactive indicators for DNA biosensor

• Published in: Journal of inorganic biochemistry 2024-08, Vol.257, p.112615, Article 112615
• Main Authors: Deng, Ya-Ru, Li, Ya-Fei, Yang, Hao, Fan, Yan-Ru, Huang, Yu
• Format: Article
• Language: English
• Subjects: Bis-naphthyl ferrocene derivatives; DNA binding; Electrochemical DNA biosensor; Hybridization indicator; Synthesis
• ISSN: 0162-0134; 1873-3344; 1873-3344
• DOI: 10.1016/j.jinorgbio.2024.112615

A series of bis-naphthyl ferrocene derivatives were synthesized and characterized. Based on the results obtained from UV–visible absorption titration and ethidium bromide (EB) displacement experiments, it was observed that the synthesized compounds exhibited a strong binding ability to dsDNA. In comparison to the viscosity curve of EB, the tested compounds demonstrated a bisintercalation binding mode when interacting with CT-DNA. Differential pulse voltammetry (DPV) was employed to assess the binding specificity of these indicators towards ssDNA and dsDNA. All tested indicators displayed more pronounced signal differences before and after hybridization between probe nucleic acids and target nucleic acids compared to Methylene Blue (MB). Among the evaluated compounds, compound 3j containing an ether chain showed superior performance as an indicator, making it suitable for constructing DNA-based biosensors. Under optimized conditions including probe ssDNA concentration and indicator concentration, this biosensor exhibited good sensitivity, reproducibility, stability, and selectivity. The limit of detection was calculated as 4.53 × 10−11 mol/L. Furthermore, when utilizing 3j as the indicator in serum samples, the biosensor achieved satisfactory recovery rates for detecting the BRCA1 gene. Compared with Methylene Blue (MB), a commonly used electrochemical indicator, the novel indicator 3j exhibited obvious advantages in stronger peak currents and more significant signal differences between ssDNA and dsDNA. [Display omitted] •A series of bis-naphthyl ferrocene derivatives were synthesized.•These compounds exhibited an obvious advantage as electrochemical indicators over MB.•The 2-naphthyl and ether chain were beneficial in improving electrochemical activity.•The biosensor with 3j exhibited good sensitivity, reproducibility, and selectivity.