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

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 differ...

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Bibliographic Details
Published in:Journal of fluorescence 2015-11, Vol.25 (6), p.1763-1773
Main Authors: Nayab, Pattan Sirajuddin, Pulaganti, Madhusudana, Chitta, Suresh Kumar, Rahisuddin
Format: Article
Language:English
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
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Summary: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.
ISSN:1053-0509
1573-4994
DOI:10.1007/s10895-015-1664-4