Investigation of Interactions of Anthraquinone-Derived Dyes with DNA and DNA-Related Protein Targets by Spectral, DFT, and Molecular Docking Techniques
JOURNAL OF MOLECULAR STRUCTURE, cilt.1380, 2027 (SCI-Expanded, Scopus)
- Yayın Türü: Makale / Tam Makale
- Cilt numarası: 1380
- Basım Tarihi: 2027
- Doi Numarası: 10.1016/j.molstruc.2026.147389
- Dergi Adı: JOURNAL OF MOLECULAR STRUCTURE
- Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus, Chemical Abstracts Core, Chimica, Compendex, INSPEC, Academic Search Ultimate (EBSCO), Engineering Source (EBSCO)
- Dokuz Eylül Üniversitesi Adresli: Evet
Özet
The development of efficient DNA-binding fluorescent probes and DNA-targeted therapeutic candidates remains an important research area in bioanalytical chemistry and medicinal sciences. In this study, the interactions of three anthraquinone derivatives (ANT-2, ANT-7, and ANT-11) with genomic DNA and adenine-guanine-related protein targets were investigated through spectroscopic techniques, density functional theory (DFT) calculations, and molecular docking studies. The synthesized dyes were characterized, and their photophysical properties, acidity constants, detection limits, working ranges, and interference behaviors were evaluated. All compounds exhibited selective fluorescence responses toward DNA, with detection limits of 6.2 & times; 10-6, 8.6 & times; 10-8, and 2.7 & times; 10-9 M for ANT-2, ANT-7, and ANT-11, respectively. DNA-binding studies revealed binding constants ranging from 104 to 108 M-1, indicating substantially stronger interactions for ANT-7 and ANT-11 than for the reference compound curcumin. Molecular docking analyses were consistent with an intercalative binding mode, involving favorable it-it stacking and other non-covalent interactions within DNA-binding regions. DFT calculations demonstrated reduced HOMO-LUMO energy gaps, increased electrophilicity, and enhanced electronic softness for ANT-7 and ANT-11, consistent with their experimentally observed binding affinities. Docking studies further revealed favorable interactions of the anthraquinone derivatives with adenine-guanine-related protein targets, with ANT-11 displaying the highest binding affinity. Overall, the combined experimental and computational results indicate that anthraquinone derivatives, particularly ANT-11, are promising candidates for DNA sensing applications and may provide useful molecular scaffolds for further investigation in DNA-targeted therapeutic research.