Substitution of PPh3+ as a lipophilic cation on new water-soluble Co(II) and Zn(II) Schiff base complexes: Effect of central metal and substitutional group of ligand on DNA-complex interaction

[Display omitted] •New series of water soluble complexes were synthesized and characterized.•DNA binding potency of these complexes was investigated with different methods.•Cytotoxicity of these complexes against Raji, Jurkat and A549 cell lines were studied.•Docking studies were performed to furthe...

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Published inJournal of photochemistry and photobiology. A, Chemistry. Vol. 337; pp. 140 - 150
Main Authors Asadi, Zahra, Haddadi, Elahe, Sedaghat, Moslem
Format Journal Article
LanguageEnglish
Published Lausanne Elsevier B.V 15.03.2017
Elsevier BV
Subjects
Absorption spectroscopy
Anticancer activity
Binding
Cadmium
Cations
Cell lines
Circular dichroism
Cisplatin
Cobalt
Coordination compounds
Cytotoxicity
Deoxyribonucleic acid
DFT
DNA
Docking
Docking study
Fluorescence
Fluorescence spectroscopy
Gravimetric analysis
Gravimetry
Imines
Infrared radiation
Ligands
Lipophilic
Metal complexes
NMR
Nuclear magnetic resonance
Phenylenediamine
Schiff base complex
Toxicity
Viscosity
Water soluble
Zinc
Water soluble
Docking study
DFT
Schiff base complex
DNA
Anticancer activity
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Abstract [Display omitted] •New series of water soluble complexes were synthesized and characterized.•DNA binding potency of these complexes was investigated with different methods.•Cytotoxicity of these complexes against Raji, Jurkat and A549 cell lines were studied.•Docking studies were performed to further investigate the DNA binding interactions. New series of water soluble Schiff base complexes by conjugating the lipophilic triphenylphosphonium cation to aromatic moiety of Schiff base ligand, aiming to increase the water solubility and passing through cell membrane were synthesized and characterized. Four new complexes; [N,N′-bis{5-[(triphenylphosphoniumchloride)-methyl]salicylidine}-phenylenediamine] with the formula [Zn(5-CH2PPh3-4-H-1,2-salphen)] (ClO4)2 (1), [Zn(5-CH2PPh3-4-CH3-1,2-salphen)](ClO4)2 (2), [Zn(5-CH2PPh3-4-Cl-1,2-salphen)](ClO4)2 (3), [Co(5-CH2PPh3-4-CH3-1,2-salphen)](ClO4)2 (4) were characterized by elemental analysis, FT-IR, 1H NMR, 13C NMR, 31P NMR and UV–vis spectroscopy. Cobalt(II) complex also characterized by thermal gravimetry analysis (TG). DNA interaction studies were investigated by UV–vis absorption spectroscopy, viscosity measurements, circular dichroism (CD) spectroscopy and fluorescence spectroscopy. The DNA binding affinity (Kb) obtained from absorption spectroscopy had this order: 2>3>4>1>ligand(L) which revealed that metal complexes had more propensities to interact with DNA. In comparing the metal complexes; Zn(II) complexes revealed DNA binding stronger than the corresponding Co(II) analogue. All the complexes displayed cytotoxicity against Raji, Jurkat and A549 cell lines with potency more than that of cisplatin and thus they are good candidate to act as promising anticancer drug. Finally, docking studies were performed to further investigate the DNA binding interactions.
AbstractList New series of water soluble Schiffbase complexes by conjugating the lipophilic triphenylphosphonium cation to aromatic moiety of Schiffbase ligand, aiming to increase the water solubility and passing through cell membrane were synthesized and characterized. Four new complexes; [N,N'-bis{5-[(triphenylphosphoniumchloride)-methyl]salicylidine}-phenylenediamine] with the formula [Zn(5-CH2PPh3-4-H-1,2-salphen)] (ClO4)2 (1), [Zn(5-CH2PPh3-4-CH3-1,2-salphen)](ClO4)2 (2), [Zn(5-CH2PPh3-4-Cl-1,2-salphen)](ClO4)2 (3), [Co(5-CH2PPh3-4-CH3-1,2-salphen)](ClO4)2 (4) were characterized by elemental analysis, FT-IR, 1H NMR, 13C NMR, 31P NMR and UV-vis spectroscopy. Cobalt(II) complex also characterized by thermal gravimetry analysis (TG). DNA interaction studies were investigated by UV-vis absorption spectroscopy, viscosity measurements, circular dichroism (CD) spectroscopy and fluorescence spectroscopy. The DNA binding affinity (Kb) obtained from absorption spectroscopy had this order: 2 > 3 > 4 > 1 > ligand(L) which revealed that metal complexes had more propensities to interact with DNA. In comparing the metal complexes; Zn(II) complexes revealed DNA binding stronger than the corresponding Co(II) analogue. All the complexes displayed cytotoxicity against Raji, Jurkat and A549 cell lines with potency more than that of cisplatin and thus they are good candidate to act as promising anticancer drug. Finally, docking studies were performed to further investigate the DNA binding interactions.
[Display omitted] •New series of water soluble complexes were synthesized and characterized.•DNA binding potency of these complexes was investigated with different methods.•Cytotoxicity of these complexes against Raji, Jurkat and A549 cell lines were studied.•Docking studies were performed to further investigate the DNA binding interactions. New series of water soluble Schiff base complexes by conjugating the lipophilic triphenylphosphonium cation to aromatic moiety of Schiff base ligand, aiming to increase the water solubility and passing through cell membrane were synthesized and characterized. Four new complexes; [N,N′-bis{5-[(triphenylphosphoniumchloride)-methyl]salicylidine}-phenylenediamine] with the formula [Zn(5-CH2PPh3-4-H-1,2-salphen)] (ClO4)2 (1), [Zn(5-CH2PPh3-4-CH3-1,2-salphen)](ClO4)2 (2), [Zn(5-CH2PPh3-4-Cl-1,2-salphen)](ClO4)2 (3), [Co(5-CH2PPh3-4-CH3-1,2-salphen)](ClO4)2 (4) were characterized by elemental analysis, FT-IR, 1H NMR, 13C NMR, 31P NMR and UV–vis spectroscopy. Cobalt(II) complex also characterized by thermal gravimetry analysis (TG). DNA interaction studies were investigated by UV–vis absorption spectroscopy, viscosity measurements, circular dichroism (CD) spectroscopy and fluorescence spectroscopy. The DNA binding affinity (Kb) obtained from absorption spectroscopy had this order: 2>3>4>1>ligand(L) which revealed that metal complexes had more propensities to interact with DNA. In comparing the metal complexes; Zn(II) complexes revealed DNA binding stronger than the corresponding Co(II) analogue. All the complexes displayed cytotoxicity against Raji, Jurkat and A549 cell lines with potency more than that of cisplatin and thus they are good candidate to act as promising anticancer drug. Finally, docking studies were performed to further investigate the DNA binding interactions.
Author Sedaghat, Moslem
Haddadi, Elahe
Asadi, Zahra
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Snippet [Display omitted] •New series of water soluble complexes were synthesized and characterized.•DNA binding potency of these complexes was investigated with...
New series of water soluble Schiffbase complexes by conjugating the lipophilic triphenylphosphonium cation to aromatic moiety of Schiffbase ligand, aiming to...
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SubjectTerms Absorption spectroscopy
Anticancer activity
Binding
Cadmium
Cations
Cell lines
Circular dichroism
Cisplatin
Cobalt
Coordination compounds
Cytotoxicity
Deoxyribonucleic acid
DFT
DNA
Docking
Docking study
Fluorescence
Fluorescence spectroscopy
Gravimetric analysis
Gravimetry
Imines
Infrared radiation
Ligands
Lipophilic
Metal complexes
NMR
Nuclear magnetic resonance
Phenylenediamine
Schiff base complex
Toxicity
Viscosity
Water soluble
Zinc
Title Substitution of PPh3+ as a lipophilic cation on new water-soluble Co(II) and Zn(II) Schiff base complexes: Effect of central metal and substitutional group of ligand on DNA-complex interaction
URI https://dx.doi.org/10.1016/j.jphotochem.2017.01.022
https://www.proquest.com/docview/1937407190/abstract/
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