Investigation of the complex structure, comparative DNA-binding and DNA cleavage of two water-soluble mono-nuclear lanthanum(III) complexes and cytotoxic activity of chitosan-coated magnetic nanoparticles as drug delivery for the complexes.
Two water-soluble mono-nuclear macrocyclic lanthanum(III) complexes of 2,6-diformyl-4-methylphenol with 1,3-diamino-2-propanol (C1) or 1,3-propylenediamine (C2) were synthesized and characterized by UV-Vis, FT-IR,13C and1H NMR spectroscopy and elemental analysis. C1complex was structurally characterized by single-crystal X-ray diffraction, which revealed that the complex was mononuclear and ten-coordinated. The coordination sites around lanthanum(III) were occupied with a five-dentate ligand, two bidentate nitrates, and one water molecule. The interaction of complexes with DNA was studied in buffered aqueous solution at pH7.4. UV-Vis absorption spectroscopy, emission spectroscopy, circular dichroism (CD) and viscometric measurements provided clear evidence of the intercalation mechanism of binding. The obtained intrinsic binding constants (Kb) 9.3×103and 1.2×103M-1for C1and C2, respectively confirmed that C1is better intercalator than C2. The DNA docking studies suggested that the complexes bind with DNA in a groove binding mode with the binding affinity of C1>C2. Moreover, agarose gel electrophoresis study of the DNA-complex for both compounds revealed that the C1intercalation cause ethidium bromide replacement in a competitive manner which confirms the suggested mechanism of binding. Finally, the anticancer experiments for the treated cancerous cell lines with both synthesized compounds show that these hydrophilic molecules need a suitable carrier to pass through the hydrophobic nature of cell membrane efficiently.
Department of Chemistry, Faculty of Sciences, Shiraz University, Shiraz 71454, Iran. Electronic address: zasadi@shirazu.ac.ir.
Zahra
Z
Asadi
Department of Chemistry, Faculty of Sciences, Shiraz University, Shiraz 71454, Iran.
Neda
N
Nasrollahi
Molecular Biotechnology Laboratory, Department of Biology, Faculty of Sciences, Shiraz University, Shiraz 71454, Iran.
Hamidreza
H
Karbalaei-Heidari
Institute of Physics ASCR, v.v.i, Na Slovance 2, Praha 821182, Czech Republic.
Vaclav
V
Eigner
Institute of Physics ASCR, v.v.i, Na Slovance 2, Praha 821182, Czech Republic.
Michal
M
Dusek
Department of Chemistry, Faculty of Sciences, Shiraz University, Shiraz 71454, Iran.
Nabiallah
N
Mobaraki
Molecular Biotechnology Laboratory, Department of Biology, Faculty of Sciences, Shiraz University, Shiraz 71454, Iran.
Roya
R
Pournejati
D016923:Cell Death / Q000187:drug effects; D045744:Cell Line, Tumor; D002470:Cell Survival / Q000187:drug effects; D048271:Chitosan / Q000737:chemistry*; D002942:Circular Dichroism; D056831:Coordination Complexes / Q000737:chemistry* / Q000494:pharmacology*; D018360:Crystallography, X-Ray; D004247:DNA / Q000378:metabolism*; D053837:DNA Cleavage; D016503:Drug Delivery Systems; D004583:Electrons; D006801:Humans; D007454:Iodides / Q000737:chemistry; D007700:Kinetics; D007811:Lanthanum / Q000737:chemistry*; D058185:Magnetite Nanoparticles / Q000737:chemistry*; D008968:Molecular Conformation; D062105:Molecular Docking Simulation; D009994:Osmolar Concentration; D013050:Spectrometry, Fluorescence; D014783:Viscosity; D014867:Water / Q000737:chemistry
D056831:Coordination Complexes; D007454:Iodides; D058185:Magnetite Nanoparticles; D014867:Water; D007811:Lanthanum; D004247:DNA; D048271:Chitosan
Binding constant; Chitosan; Cytotoxicity; DNA cleavage; Lanthanum(III); Molecular docking