A New Isoindoline Based Schiff Base Derivative as Cu(II) Chemosensor: Synthesis, Photophysical, DNA Binding and Molecular Docking Studies

• Published in: Journal of fluorescence Vol. 25; no. 6; pp. 1763 - 1773
• Main Authors: Nayab, Pattan Sirajuddin, Pulaganti, Madhusudana, Chitta, Suresh Kumar, Rahisuddin
• Format: Journal Article
• Language: English
• Published: New York Springer US 01.11.2015
• Subjects: Analytical Chemistry; Biochemistry; Biological and Medical Physics; Biomedical and Life Sciences; Biomedicine; Biophysics; Biotechnology; Chemistry Techniques, Analytical - instrumentation; Chemistry Techniques, Synthetic; Copper - analysis; Copper - chemistry; DNA - chemistry; Electrochemistry; Ethanol - chemistry; Hydrodynamics; Hydrogen-Ion Concentration; Isoindoles - chemical synthesis; Isoindoles - chemistry; Molecular Docking Simulation; Nucleic Acid Conformation; Original Article; Phthalimides - chemical synthesis; Phthalimides - chemistry; Schiff Bases - chemical synthesis; Schiff Bases - chemistry; Phthalimide; Cu(II) sensor; Ct-DNA binding studies; Molecular modeling; pH sensor
• ISSN: 1053-0509; 1573-4994
• DOI: 10.1007/s10895-015-1664-4

A new chemo sensor 2-(4-methylbenzylideneamino)-isoindoline-1,3-dione (PDB) was synthesized and characterized by UV–Vis., IR, 1 H NMR, 13 C NMR spectral and elemental analysis. Its photophysical properties in organic solvents with different polarity were studied. The sensitivity of the PDB in different pH solutions was investigated and the results indicated that PDB would be able to act as an efficient “off–on–off” switch for pH. This chemosensor displayed high selectivity towards Cu 2+ in the presence of metal ions Ba 2+ , Cd 2+ , Co 2+ , Hg 2+ , Ni 2+ , Pb 2+ , K + and Zn 2+ in DMF/H 2 O solution. Furthermore DNA binding and molecular docking studies were also carried out to investigate the biological potential of the test compound. The interaction of compound (PDB) with Ct-DNA was examined by absorption, CD spectroscopy, cyclic voltammetry and viscosity measurements. In silico studies revealed that the test compound (PDB) showed good affinity towards the target receptor d (CGCGAATTCGCG) 2 with the binding energy of −7.70 kcal/mol.