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Synthesis, characterization and molecular docking of new C,N ‐palladacycles containing pyridinium‐derived ligands: DNA and BSA interaction studies and evaluation as anti‐tumor agents
Author(s) -
Karami Kazem,
Jamshidian Nasrin,
Zakariazadeh Mostafa
Publication year - 2019
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.4728
Subject(s) - chemistry , circular dichroism , stereochemistry , bovine serum albumin , nuclear magnetic resonance spectroscopy , titration , fluorescence spectroscopy , infrared spectroscopy , crystallography , fluorescence , inorganic chemistry , organic chemistry , biochemistry , physics , quantum mechanics
Four new monomeric Pd (II) complexes with formulas [Pd(C,N)‐(2′‐NH 2 C 6 H 4 )C 6 H 4 (N 3 )(L)] ( A ), ( B ) and [Pd(C,N)‐C 6 H 4 CH 2 NH(C 4 H 9 )(N 3 )(L)] ( C ), ( D ), [L = isonicotinamide for ( A ) and ( C ), L = 4‐N,N‐dimethylaminopyridine for ( B ) and ( D )] have been synthesized using four initial dimers [Pd 2 {(C,N)‐(2′‐NH 2 C 6 H 4 )C 6 H 4 } 2 (μ‐OAc) 2 ] ( 1 ), [Pd 2 {(C,N)‐ (2′‐NH 2 C 6 H 4 )C 6 H 4 } 2 (μ‐N 3 ) 2 ] ( 3 ) for A and C , and [Pd 2 {(C,N)‐C 6 H 4 CH 2 NH(C 4 H 9 )} 2 (μ‐OAc) 2 ] ( 2 ) and [Pd 2 {(C,N)‐C 6 H 4 CH 2 NH(C 4 H 9 )} 2 (μ‐N 3 ) 2 ] ( 4 ) for B and D . Then synthesized complexes have been characterized by Fourier transform‐infrared, NMR spectroscopy and thermal gravimetric‐differential thermal analysis. Furthermore, UV–Vis spectroscopy, fluorescence spectroscopy, circular dichroism (CD) and helix melting temperature measurements have been employed to study the binding interaction of them with calf thymus‐deoxyribonucleic acid (DNA). The results reveal that all synthesized complexes can interact with DNA via groove‐binding mode. Bovine serum albumin (BSA)‐binding studies have been carried out using UV–Vis spectroscopy, emission titration and CD. However, competitive binding studies using warfarin, ibuprofen and digoxin on site markers demonstrated that the complexes bind to different sites on BSA. The results also indicated that the binding site was mainly located within site‐III for complex A , and site‐I for complexes B , C and D of BSA. In addition, molecular docking studies have been executed to determine the binding site of the DNA and BSA with complexes. Eventually, in vitro cytotoxicity of synthesized palladium complexes and cisplatin were carried out against human promyelocytic leukemia cancer (Hela) and breast cancer (MCF‐7) cell lines. Pursuant to the IC 50 values, the cytotoxicity of complexes against MCF‐7 was more than Hela.