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

被引:27
作者
Nayab, Pattan Sirajuddin [1 ]
Pulaganti, Madhusudana [2 ]
Chitta, Suresh Kumar [2 ]
Rahisuddin [1 ]
机构
[1] Jamia Millia Islamia, Dept Chem, New Delhi 110025, India
[2] Sri Krishnadevraya Univ, Dept Biochem, Ananthapuram 515003, India
关键词
Phthalimide; pH sensor; Cu(II) sensor; Molecular modeling; Ct-DNA binding studies; CIRCULAR-DICHROISM; FLUORESCENT SENSOR; CRYSTAL-STRUCTURE; COPPER(II); COMPLEXES; LIGAND; IONS; SPECTROMETRY; CLEAVAGE; DESIGN;
D O I
10.1007/s10895-015-1664-4
中图分类号
Q5 [生物化学];
学科分类号
071010 ; 081704 ;
摘要
A new chemo sensor 2-(4-methylbenzylideneamino)-isoindoline-1,3-dione (PDB) was synthesized and characterized by UV-Vis., IR, H-1 NMR, C-13 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 Cu2+ in the presence of metal ions Ba2+, Cd2+, Co2+, Hg2+, Ni2+, Pb2+, K+ and Zn2+ in DMF/H2O 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.
引用
收藏
页码:1763 / 1773
页数:11
相关论文
共 43 条
[1]   Novel and versatile methodology for synthesis of cyclic imides and evaluation of their cytotoxic, DNA binding, apoptotic inducing activities and molecular modeling study [J].
Abdel-Aziz, Alaa A. -M. .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2007, 42 (05) :614-626
[2]   A highly sensitive and selective fluorescent sensor for the determination of copper(II) based on a schiff base [J].
Aksuner, Nur ;
Henden, Emuer ;
Yilmaz, Ibrahim ;
Cukurovali, Alaaddin .
DYES AND PIGMENTS, 2009, 83 (02) :211-217
[3]   Quantitative imaging of selenium, copper, and zinc in thin sections of biological tissues (Slugs-Genus arion) measured by laser ablation inductively coupled of plasma mass spectrometry [J].
Becker, J. S. ;
Matusch, A. ;
Depboylu, C. ;
Dobrowolska, J. ;
Zoriy, M. V. .
ANALYTICAL CHEMISTRY, 2007, 79 (16) :6074-6080
[4]   Design and Synthesis of Highly Photostable Yellow-Green Emitting 1,8-Naphthalimides as Fluorescent Sensors for Metal Cations and Protons [J].
Bojinov, Vladimir B. ;
Georgiev, Nikolai I. ;
Bosch, Paula .
JOURNAL OF FLUORESCENCE, 2009, 19 (01) :127-139
[5]   VOLTAMMETRIC STUDIES OF THE INTERACTION OF METAL-CHELATES WITH DNA .2. TRIS-CHELATED COMPLEXES OF COBALT(III) AND IRON(II) WITH 1,10-PHENANTHROLINE AND 2,2'-BIPYRIDINE [J].
CARTER, MT ;
RODRIGUEZ, M ;
BARD, AJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1989, 111 (24) :8901-8911
[6]   Experimental and theoretical studies on the DNA-binding and spectral properties of water-soluble complex [Ru(MeIm)4(dpq)]2+ [J].
Chen, Lan-Mei ;
Liu, Jie ;
Chen, Jin-Can ;
Shi, Shuo ;
Tan, Cai-Ping ;
Zheng, Kang-Cheng ;
Ji, Liang-Nian .
JOURNAL OF MOLECULAR STRUCTURE, 2008, 881 (1-3) :156-166
[7]   Atom transfer radical polymerization of vinyl monomers mediated by a new class of neutral and cationic ruthenium alkylidene catalysts containing a 1,3-dimesityl-4,5-dihydroimidazol-2-ylidene and a Schiff base ligand [J].
De Clercq, B ;
Verpoort, F .
POLYMER BULLETIN, 2003, 50 (03) :153-160
[8]   Peat as a natural solid-phase for copper preconcentration and determination in a multicommuted flow system coupled to flame atomic absorption spectrometry [J].
Gonzales, A. P. S. ;
Firmino, M. A. ;
Nomura, C. S. ;
Rocha, F. R. P. ;
Oliveira, P. V. ;
Gaubeur, I. .
ANALYTICA CHIMICA ACTA, 2009, 636 (02) :198-204
[9]   Single chemosensor for highly selective colorimetric and fluorometric dual sensing of Cu(II) as well as 'NIRF' to acetate ion [J].
Goswami, Shyamaprosad ;
Maity, Sibaprasad ;
Das, Avijit Kumar ;
Maity, Annada C. .
TETRAHEDRON LETTERS, 2013, 54 (48) :6631-6634
[10]   Copper(II) complexes of 1,10-phenanthroline-derived ligands: Studies on DNA binding properties and nuclease activity [J].
Hirohama, T ;
Kuranuki, Y ;
Ebina, E ;
Sugizaki, T ;
Arii, H ;
Chikira, M ;
Selvi, PT ;
Palaniandavar, M .
JOURNAL OF INORGANIC BIOCHEMISTRY, 2005, 99 (05) :1205-1219