Synthesis, DFT calculation, and molecular docking simulation of spirooxindoles based Creatinine chemosensor of Cu2+


Mohammadi Ziarani G., Shamkhali N., Panahande Z., FEIZI DEH NAYEBI M., Badiei A.

Results in Chemistry, cilt.16, 2025 (ESCI, Scopus)

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 16
  • Basım Tarihi: 2025
  • Doi Numarası: 10.1016/j.rechem.2025.102381
  • Dergi Adı: Results in Chemistry
  • Derginin Tarandığı İndeksler: Emerging Sources Citation Index (ESCI), Scopus
  • Anahtar Kelimeler: Creatinine, Cu2+ ion chemosensor, DFT, Docking, Fluorescence spectroscopy, Multi-component reaction, SiO2-Pr-SO3H
  • Süleyman Demirel Üniversitesi Adresli: Evet

Özet

The synthesis of a Cu2+ chemosensor is developed via the multi-component reaction of isatin, malononitrile, and creatinine using SiO2-Pr-SO3H as a silica nano-catalyst under solvent-free conditions in a short reaction time and high yield. The sensing properties of 2,5-diamino-1-methyl-2-oxo-1,2-dihydro-1H-spiro[indole-3,7-pyrano[2,3-d]imidazole]-6‑carbonitrile(10−4 M) are being investigated for various metal ions in CH3CN, which selectively detects Cu2+ ions by a significant decrease in fluorescence emission with a remarkable detection limit of 18 × 10−6 M. It is evident that Cu2+ ion is one of the dangerous heavy metals for human health and the environment; therefore, it is very important to identify and detect it easily with an efficient chemosensor. The computational method (DFT) was applied to investigate the ligand's active site for Cu2+ interaction and to examine the electronic properties of the ligand and the ligand-Cu2+ complex. Furthermore, geometry optimization, MEP, HOMO-LUMO, and quantum parameters are being analyzed. Molecular docking simulation is used to investigate the synthesized compound's activity against COVID-19 main protease (PDB ID: 6LU7).