Copper() complexes with quinolone appended 1,8-naphthalimide conjugates: structural characterization, DNA and protein binding and cytotoxicity studies

A novel 1,8-naphthalimide containing ligand ( L ) and its three mononuclear complexes with different anions, [Cu(L) 2 ](NO 3 )·3(H 2 O) ( 1 ), [Cu(L) 2 ]Cl·4(H 2 O) ( 2 ), [Cu(L) 2 ]ClO 4 ·DMF ( 3 ) was synthesized and characterized by NMR, infrared spectroscopy, elemental analysis, ESI-MS and singl...

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Bibliographic Details
Published in:New journal of chemistry 2022-09, Vol.46 (35), p.1681-16812
Main Authors: Shaikh, Sabiha A, Bhat, Satish S, Revankar, Vidyanand K, Kumara, Karthik, Lokanath, N. K, Butcher, Ray J, Kumbar, Vijay, Bhat, Kishore
Format: Article
Language:English
Subjects:
Binding
Chemical analysis
Copper
Crystal structure
Crystallography
Cytotoxicity
Epithelium
Fluorescence
Infrared analysis
Ligands
NMR
Nuclear magnetic resonance
Planar structures
Serum albumin
Single crystals
Structural analysis
Titration
Toxicity
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Summary:A novel 1,8-naphthalimide containing ligand ( L ) and its three mononuclear complexes with different anions, [Cu(L) 2 ](NO 3 )·3(H 2 O) ( 1 ), [Cu(L) 2 ]Cl·4(H 2 O) ( 2 ), [Cu(L) 2 ]ClO 4 ·DMF ( 3 ) was synthesized and characterized by NMR, infrared spectroscopy, elemental analysis, ESI-MS and single crystal X-ray crystallography. Single-crystal diffraction analysis of ligand L revealed the non-planar structure of the ligand with intermolecular π π stacking interaction between naphthalimide moieties. Single-crystal X-ray studies of the complexes evidenced a seesaw geometry around the Cu( i ) center. A competitive DNA binding and absorption titration study suggests an intercalative mode of DNA binding by complex 1 . The fluorescence study of bovine serum albumin (BSA) with complex 1 revealed a dynamic quenching mechanism. A549 (adenocarcinoma human alveolar basal epithelial cells), MCF-7 (breast cancer cell line)) cell lines were used to assess the cytotoxicity of complex 1 using the MTT (3-[4,5-dimethylthiazole-2-yl]-2,5-diphenyltetrazolium bromide) assay. Complex 1 displayed improved cytotoxicity towards cancer cell lines in comparison with cis-platin. The cell accumulation study was investigated by fluorescence microscopy. Cytotoxicity, cellular uptake of copper( i ) complexes containing 1,8-naphthalimide conjugates have been investigated.
ISSN:1144-0546
1369-9261
DOI:10.1039/d2nj02655d