ABSTRACT
Two isomeric dinuclear Cerium(II) complexes 1 and 2, formulated as Ce2(phen)2(NO3)2(L)4 [L=phenylacetic acid, phen=1,10-phenanthroline] was synthesized under solvothermal conditions at different pH values. The two complexes were characterized by elemental analysis, IR and single crystal X-ray diffraction. Complexes 1 and 2 were studied the binding with DNA and against cytotoxic activity. Fluorescence analysis indicated that the two complexes can bind to DNA. The changes with different gradient concentration of DNA added into the complexes in absorption spectra show a strongπ-stacking interaction between the complexes and DNA base pairs. The Cerium(II) complexes showed good cytotoxic activity against cancer cell lines, being 2 the most potent complex. Apoptotic studies of the two novel dinuclear complexes showed significant inhibitory rate on cancer cell growth line KB.
Subject(s)
Antineoplastic Agents/chemistry , Cerium/chemistry , Coordination Complexes/chemical synthesis , DNA/chemistry , Antineoplastic Agents/metabolism , Antineoplastic Agents/toxicity , Apoptosis/drug effects , Cell Line, Tumor , Coordination Complexes/chemistry , Coordination Complexes/metabolism , Coordination Complexes/toxicity , Crystallography, X-Ray , DNA/metabolism , HeLa Cells , Humans , Hydrogen Bonding , Hydrogen-Ion Concentration , Isomerism , Molecular Conformation , Phenanthrolines/chemistry , Spectrophotometry, UltravioletABSTRACT
Two new zinc complexes, namely Zn(L(1))ClCH2NO(1) and {Zn(L(2))CH2NO}nâªN(CH3)3âªClO4(2) (L(1) = 3,5-di(1H-imidazol-1-yl)pyridine L(2) = 1,3,5-tris(1-imidazolyl) benzene), have been synthesized, and characterized by IR spectra, elemental analysis, and a single crystal X-ray diffraction. Fluorescence spectroscopy indicated that two complexes presented strong DNA binding affinity constants to fish sperm DNA (FS-DNA). Gel electrophoresis assay demonstrated the ability of the complex to cleave the HL-60 DNA. Apoptotic study showed the complex exhibited significant cancer cell(KB) inhibitory rate.
Subject(s)
Antineoplastic Agents/chemical synthesis , Antineoplastic Agents/pharmacology , Coordination Complexes/chemical synthesis , Coordination Complexes/pharmacology , Imidazoles/chemistry , Zinc/chemistry , Antineoplastic Agents/chemistry , Antineoplastic Agents/metabolism , Apoptosis/drug effects , Chemistry Techniques, Synthetic , Coordination Complexes/chemistry , Coordination Complexes/metabolism , DNA/metabolism , Humans , KB Cells , Ligands , Spectrometry, FluorescenceABSTRACT
Two new complexes, Zn(L)2(H2O)2 (1) and Mn(L)2(H2O)2 (2) [L = 2-Methyl-1H-4,5-imidazoledicarboxylic acid] were synthesized and characterized by elemental analysis, infrared spectroscopy, and single crystal X-ray diffraction. Intramolecular weak interactions, such as hydrogen-bond and intermolecular interactions were presented in the complexes. The activities of the complexes binding with DNA, and cytotoxic activities were studied. The binding of complexes with fish sperm DNA (FS-DNA) was investigated by fluorescence spectra. Gel electrophoresis assay demonstrated the ability of the complexes to cleave the pBR322 plasmid DNA. The cytotoxic activities of the complexes were tested against the KB cell line. Cytotoxic activity studies showed the two complexes exhibited significant cancer cell inhibitory rate. The most active compound was complex 1 with IC50 and CC50value of 36.5, 429, with the selectivity index (SI = 11.75) among the tested compounds.
Subject(s)
Antineoplastic Agents/chemical synthesis , Antineoplastic Agents/pharmacology , Apoptosis/drug effects , Carboxylic Acids/chemistry , DNA/chemistry , Imidazoles/chemistry , Manganese/pharmacology , Organometallic Compounds/pharmacology , Zinc/pharmacology , Animals , Antineoplastic Agents/chemistry , Cell Proliferation/drug effects , Dose-Response Relationship, Drug , Drug Screening Assays, Antitumor , Fishes , Humans , Male , Manganese/chemistry , Molecular Structure , Organometallic Compounds/chemical synthesis , Organometallic Compounds/chemistry , Spermatozoa/chemistry , Structure-Activity Relationship , Tumor Cells, Cultured , Zinc/chemistryABSTRACT
A series of complexes [Pd(L1)(Phen)]·2H2O (1), [Pd(L2)(Phen)]·H2O (2), [Pd(L3)(Phen)]·H2O (3), [Pd(L4)(Phen)]·2H2O (4) and [Pd(L5)(Phen)]·2H2O (5) were prepared. The complexes were characterized by IR, (1)H NMR, elemental analysis, and single-crystal X-ray diffractometry. The binding of the complexes was investigated by fluorescence spectrum and UV spectrum, showing the ability of interaction with DNA of intercalative mode. Gel electrophoresis assay demonstrated the ability of the complexes to cleave the pBR322 DNA. Moreover, the five complexes bind to DNA with different binding affinities, in ascending order: complex 1 < 2<3 < 4 < 5. Evaluation of cytotoxic activity of the complexes against five different cancer cell lines proved that the complexes exhibited cytotoxic specificity and significant cancer cell inhibitory rate.
Subject(s)
Antineoplastic Agents/pharmacology , Carbon/chemistry , Organometallic Compounds/pharmacology , Palladium/chemistry , Antineoplastic Agents/chemical synthesis , Antineoplastic Agents/chemistry , Apoptosis/drug effects , Cell Proliferation/drug effects , Crystallography, X-Ray , Dose-Response Relationship, Drug , Drug Screening Assays, Antitumor , HeLa Cells , Humans , Models, Molecular , Molecular Structure , Organometallic Compounds/chemical synthesis , Organometallic Compounds/chemistry , Structure-Activity Relationship , Tumor Cells, CulturedABSTRACT
Four metal complexes [Pd(L(1))Cl(2)·2H(2)O] (1), [Pt(L(1))Cl(2)·2H(2)O] (2), [Pd(L(2))Cl(2)·H(2)O] (3) and [Pt(L(2))Cl(2)·H(2)O] (4) (L(1) = 2,2'-bipyridyl-5,5'-dicarboxylic acid, L(2) = 2,2'-bipyridyl-4,4'-dicarboxylic acid) have been synthesized under hydrothermal conditions and fully characterized by IR and (1)H-NMR spectra, elemental analysis, and X-ray single crystal diffraction analysis. Interactions of these complexes with fish sperm DNA (FS-DNA) were investigated using UV-Vis absorption and fluorescence spectroscopic methods. Further insight was brought by quantum chemistry calculations by means of G03 package and taking B3LYP functional Lanl2dz Gen basis set. Agarose gel electrophoresis run on pBR322 plasmid DNA gave proof that all four complexes exhibit efficient DNA cleavage. Complexes 1-4 manifested cytotoxic specificity and a significant cancer cell inhibitory rate. Independent apoptosis tests under the light microscope, performed on hematoxylin-eosin stained HeLa cells, evidenced morphological changes induced by all the complexes.
Subject(s)
Coordination Complexes/chemistry , Coordination Complexes/pharmacology , DNA/drug effects , Organoplatinum Compounds/chemistry , Organoplatinum Compounds/pharmacology , Palladium/chemistry , Pyridines/chemistry , Apoptosis/drug effects , Cell Survival/drug effects , Coordination Complexes/chemical synthesis , DNA/chemistry , DNA/metabolism , DNA Cleavage , HeLa Cells , Humans , Models, Molecular , Molecular Dynamics Simulation , Organoplatinum Compounds/chemical synthesis , Palladium/pharmacology , Pyridines/chemical synthesis , Pyridines/pharmacology , Spectrometry, Fluorescence , Spectrophotometry, Infrared , Spectrophotometry, UltravioletABSTRACT
The organic ligand Hbpmc and the polymeric complex [Mn(bpmc)(2)(4,4'-bipy)(H(2)O)(2)](n)·3H(2)O (4,4'-bipy = 4,4'-bipyridine, Hbpmc = 2,2-bis(3-phenylpropyl) malonic acid), which have both a lipophilic group (aromatic ring) and a hydrophilic group (non-coordination carboxyl), were synthesized and characterized by IR spectra, elemental analysis and X-ray single-crystal diffraction. The interaction of the complexes with HC-DNA was investigated by fluorescence spectroscopy. Gel electrophoresis assay demonstrates the ability to cleave the extracted HC-DNA. The value of IC(50) is to understand the effect of cytotoxic activity which is lower than cisplatin and higher than the ligand Hbpmc. The apoptotic tests show that the complexes apparently have an apoptotic effect on Hela cells.
Subject(s)
Carboxylic Acids/chemistry , Coordination Complexes/chemical synthesis , Malonates/chemistry , Manganese/chemistry , Apoptosis/drug effects , Cell Line, Tumor , Coordination Complexes/metabolism , Coordination Complexes/toxicity , Crystallography, X-Ray , DNA/chemistry , DNA/metabolism , HeLa Cells , Humans , Ions/chemistry , Ligands , Molecular Conformation , Pyridines/chemistryABSTRACT
Nine novel heterometallic coordination polymers [Ln(2)Ni(Hbidc)(2)(SO(4))(2)(H(2)O)(8)](n) (Ln = Pr (1), Sm (2), Eu (3), Gd (4), Tb (5), Dy (6), Ho (7), Er (8), Yb (9), H(3)bidc = 1H-benzimidazole-5,6-dicarboxylic acid) have been synthesized under hydrothermal conditions and characterized by elemental analysis, FT-IR, TG analysis and single crystal X-ray diffraction. X-ray analysis revealed that all complexes present almost identical three-dimensional (3D) structures with PtS-type topology. Complexes 1-7 are all isomorphous, and the structure variation of polymers 8 and 9 is induced by the lanthanide contraction effect. In additional, the luminescence properties of complexes 2, 3 and 5-7, and the magnetic properties of complexes 4 and 6-8 were investigated.
ABSTRACT
A series of lanthanide-organic framework coordination polymers, {[La(2)(TDC)(2)(NO(3))(H(2)O)(4)](OH)·5H(2)O}(n) (1) and [Ln(TDC)(NO(3))(H(2)O)](n) (TDC = thiophene- 2, 5- dicarboxylic acid; Ln = Nd(2), Sm(3), Eu(4), Gd(5), Tb(6), Dy(7), Ho(8), Er(9), Yb(10)) have been synthesized by solvothermal reaction and characterized by elemental analysis, FT-IR, TG analysis, single-crystal X-ray diffraction and power X-ray diffraction. The single-crystal X-ray diffraction analysis results show that 1 displays a 3-D porous framework with (3,7)-connected {4(10).6(11)}{4(3)} topology. The compounds 2-10 crystallized in the same P2(1)/c space group and exhibits a (3,6)-connected {4.6(2)}(2){4(2).6(10).8(3)} topology, Right-handed and left-handed helical chains coexist in the 2-D layer structure. The luminescence properties of 2-10 and the magnetic properties of 5,7,8,9 were investigated.
ABSTRACT
The complex [Cu4(phen)4(H2O)2]·(pyri)·3H2O(where phen=1,10-phenanthroline and pyri=3,5-pyridine dicarboxylic acid)has been synthesized and characterized. IR spectra, elemental analysis and X-ray single-crystal diffraction were carried out to determine the composition and crystal structure of the complex. The binding of the complex with HC-DNA (HeLa cells DNA, which was extracted by ourselves) was investigated by fluorescence spectrum. Gel electrophoresis assay demonstrates the ability of the complex to cleave the extracted HC-DNA. Additionally, the complex exhibited a significant cytotoxic specificity and cancer cell inhibitory rate. The apoptotic tests indicate that the complex have an apoptotic effect on HeLa cells.
Subject(s)
Antineoplastic Agents/pharmacology , Apoptosis/drug effects , Coordination Complexes/pharmacology , Organometallic Compounds/pharmacology , Antineoplastic Agents/chemical synthesis , Antineoplastic Agents/chemistry , Coordination Complexes/chemical synthesis , Coordination Complexes/chemistry , Crystallography, X-Ray , DNA/drug effects , Dose-Response Relationship, Drug , Drug Screening Assays, Antitumor , HeLa Cells , Humans , Models, Molecular , Molecular Structure , Organometallic Compounds/chemical synthesis , Organometallic Compounds/chemistry , Stereoisomerism , Structure-Activity Relationship , Tumor Cells, CulturedABSTRACT
Two novel dinuclear complexes [Co(2)(L)(2)(phen)(2)·2H(2)O](n) (1), [Co(2)(L)(2)(bipy)(2)](n) (2) (where phen=1,10-phenanthroline, bipy=2,2'-bipyridine, and L=biphenyl-2,4'-dicarboxylic acid) have been synthesized and characterized using IR, (1)H NMR, element analysis and single-crystal X-ray diffractometry. The binding of the complexes with HC-DNA (HeLa cells DNA, which was extracted by ourselves) was investigated by fluorescence spectrum. The experimental results show that the two complexes have the ability to bind with extracted HC-DNA. Gel electrophoresis assay demonstrates the ability of the complexes to cleave the extracted HC-DNA. The complexes exhibit a higher cytotoxicity against tumor cells as against normal cells in vitro. Further more, the apoptotic tests indicate that the complexes have an apoptotic effect on HeLa cells.
Subject(s)
Antineoplastic Agents/chemical synthesis , Antineoplastic Agents/metabolism , Cobalt/chemistry , Organometallic Compounds/chemical synthesis , Organometallic Compounds/metabolism , Antineoplastic Agents/chemistry , Antineoplastic Agents/pharmacology , Apoptosis/drug effects , Carboxylic Acids/chemistry , Cell Survival/drug effects , Crystallography, X-Ray , DNA/isolation & purification , DNA/metabolism , HeLa Cells , Humans , Ligands , Models, Molecular , Molecular Conformation , Organometallic Compounds/chemistry , Organometallic Compounds/pharmacology , Spectrometry, FluorescenceABSTRACT
In an attempt to establish fundamental structure-activity relationships (SAR) of Pt/Pd-based anti-tumour compounds, we have recently designed monodentate pyridyl amide ligand containing central amide units which possess external metal co-ordinating pyridyl group and internal amide functionality. It was prepared in one step from commercially available compounds in moderate to good yield. Surprisingly, treatment of K(2)[MCl(4)] [M=Pt(II), Pd(II)] with ligand N-(4-chlorophenyl)-3-pyridinecarboxamide (L) in the same reaction condition affords two different hydrogen-bonded polymers: cis-[PtL(2)Cl(2)]·CH(3)OH·DMF (1) and trans-[PdL(2)Cl(2)]·2DMF (2). Fluorescence analysis indicates that the two complexes can bind to fish sperm DNA (FS-DNA) and gel electrophoresis assay demonstrates the ability of the complexes to cleave the pBR322 plasmid DNA. The two complexes exhibit cytotoxic specificity and significant cancer cell inhibitory rate. Furthermore, cytotoxicity values are higher in the case of cis-Pt(II) complex than trans-Pd(II) complex in four different cancer cell lines.
Subject(s)
Amides/chemistry , Antineoplastic Agents/chemical synthesis , Coordination Complexes/chemical synthesis , DNA/chemistry , Palladium/chemistry , Platinum/chemistry , Pyridines/chemistry , Animals , Antineoplastic Agents/chemistry , Antineoplastic Agents/toxicity , Cell Line, Tumor , Coordination Complexes/chemistry , Coordination Complexes/toxicity , Crystallography, X-Ray , Fishes , Humans , Isomerism , Molecular Conformation , Plasmids/chemistry , Spectrometry, Fluorescence , Structure-Activity RelationshipABSTRACT
Seven novel heterometallic coordination polymers [CeAg(Hbidc)(2)(H(2)O)(2)] (1) and [LnAg(Hbidc)(2)]·3(H(2)O)[Ln = Sm (2), Gd (3), Tb (4), Dy (5), Ho (6), Er (7), H(3)bidc = 1H-benzimidazole-5,6-dicarboxylic acid] have been synthesized under hydrothermal conditions and characterized by elemental analysis, FT-IR, TG analysis, and single crystal X-ray diffraction. X-Ray analysis revealed that the seven complexes present two different types of three-dimensional (3D) structures. Complex 1 crystallized in an orthorhombic manner having a Pna2(1) space group, consisting of a 3D framework with a 1D heterometallic chain. Polymers 2-7 are isostructural and crystallized in an orthorhombic fashion having a Pccn space group existing of a two-fold interpenetrating 3D framework. The luminescence properties and the magnetic properties of all polymers were investigated.
ABSTRACT
Four novel Zn(II) complexes [Zn(L(1))(bipy)(H(2)O)(2)].4H(2)O(1), [Zn(L(1))(phen)(H(2)O)(2)].4H(2)O(2), [Zn(L(2))(bipy)(H(2)O)(2)].4H(2)O(3) and [Zn(L(2))(phen)(H(2)O)(2)].4H(2)O (4), where bipy=2,2'-bipyridine, phen=1,10-phenanthroline, L(1)=2,2'-bipyridine 5,5'-dicarboxylic acid, L(2)=2,2'-bipyridine-4,4'-dicarboxylic acid, have been synthesized and characterized using IR, (1)H NMR, element analysis and single-crystal X-ray diffractometry. The unit cell parameters for the title complex (1), a=7.9621(10)A, b=12.6853(17)A, c=13.3714(17)A, alpha=68.549(2) degrees , beta=79.065(2) degrees , gamma=88.723(2) degrees , V=1232.5(3)A(3), Z=15, space group,P-1(2).complex (4) a=9.5710(5)A, b=14.1140(7)A, c=19.0045(9)A, alpha=90 degrees , beta=99.9920(10) degrees , gamma=90 degrees , V=2528.3(2)A(3), Z=32, space group, P121/n 1(14). The binding of the complexes with fish sperm DNA (FS-DNA) was investigated by electronic absorption spectra and fluorescence spectroscopy, showing that the complexes have the ability of interaction with DNA of intercalative mode. The intrinsic binding constant K of the complexes with FS-DNA is 0.37 x 10(5)M(-1) (1) 0.73 x 10(5)M(-1) (2), 0.98 x 10(5)M(-1) (3), and 1.05 x 10(5)M(-1) (4). The results indicate that the four complexes bound to DNA with different binding affinity, in the order complex 4>3>2>1. Gel electrophoresis assay demonstrates the ability of the complexes to cleave the pBR322 plasmid DNA. The cytotoxic activity of the complexes was tested against four different cancer cell lines. The four complexes exhibited cytotoxic specificity and significant cancer cell inhibitory rate.
Subject(s)
Antineoplastic Agents/chemistry , Antineoplastic Agents/pharmacology , Coordination Complexes/chemistry , Coordination Complexes/pharmacology , Pyridines/chemistry , Pyridines/pharmacology , Zinc/chemistry , Zinc/pharmacology , Antineoplastic Agents/chemical synthesis , Cell Line, Tumor , Cell Survival/drug effects , Coordination Complexes/chemical synthesis , Crystallography, X-Ray , DNA/metabolism , Humans , Models, Molecular , Neoplasms/drug therapy , Plasmids/metabolism , Pyridines/chemical synthesisABSTRACT
A novel tetranuclear palladium(II) complex [Pd(4)(phen)(4) (micro-pydc)(4)].10H(2)O (phen = 1,10-phenanthroline, pydc = pyridine-3,4-dicarboxylate) has been synthesized and characterized. In the tetranuclear complex, two pairs of dipalladated [Pd(phen)] moieties are bridged together by four pydc, presenting a hairpin molecular shape. The binding of the title complex with fish sperm DNA (FS-DNA) has been investigated by UV spectrum and fluorescence spectrum. All the results indicate that the complex bind to DNA in an intercalative mode and considerating the molecular shape and size, the dipalladated phenanthroline moieties bisintercalate to the base pairs of DNA. Agarose gel electrophoresis assay demonstrates the ability of the complex to cleave the pBR322 plasmid DNA. Cytotoxic activity studies show the complex exhibited good cytotoxic activity against four different cancer cell lines.
Subject(s)
Antineoplastic Agents/metabolism , Antineoplastic Agents/pharmacology , DNA/metabolism , Organometallic Compounds/metabolism , Organometallic Compounds/pharmacology , Palladium/chemistry , Animals , Antineoplastic Agents/chemical synthesis , Antineoplastic Agents/chemistry , Cell Line, Tumor , Crystallography, X-Ray , Electrons , Humans , Models, Molecular , Molecular Conformation , Organometallic Compounds/chemical synthesis , Organometallic Compounds/chemistry , Solubility , Spectrum Analysis , Water/chemistryABSTRACT
The complexes [Pt(dmphen)CO3].H2O (1), [Pd(dmphen)CO3].H2O (2) (dmphen is 2,9-dimethyl-1,10-phenanthroline) have been synthesized and characterized. The binding of the complexes with FS-DNA was investigated by UV spectrum and fluorescence spectrum, showing that the complexes have the ability of interaction with DNA of intercalative mode. The intrinsic binding constant K of the complexes with FS-DNA is 1.8 x 10(5) M(-1) (1) and 1.6 x 10(4) M(-1) (2), respectively. Gel electrophoresis assay demonstrated the ability of the complexes to cleave the pBR 322 plasmid DNA. Evaluation of cytotoxic activity of the complexes against four different cancer cell lines proved that the complexes exhibited cytotoxic specificity and significant cancer cell inhibitory rate.
Subject(s)
DNA/metabolism , Organoplatinum Compounds/metabolism , Organoplatinum Compounds/pharmacology , Palladium/chemistry , Cell Line, Tumor , Cell Proliferation/drug effects , DNA/chemistry , Humans , Models, Molecular , Nucleic Acid Conformation , Organoplatinum Compounds/chemical synthesis , Organoplatinum Compounds/chemistry , Spectrum Analysis , Water/chemistryABSTRACT
Two novel complexes, namely, [Pd(pdc)(2)].(dmp).6H(2)O (1) and [Pd(pdc)(2)K(H(2)O)(5).3H(2)O]n (2) [H(2)pdc=pyridine-2,3-dicarboxylate acid, dmp=2,9-Dimethyl-1,10-phenanthroline] were synthesized and characterized as pH-dependent products. Gel electrophoresis assay demonstrated the ability of the complexes to cleave the pBR 322 plasmid DNA. Values of IC(50) calculated for complexes 1 and 2 show that the two complexes exhibit good cytotoxic activity against different cell lines tested in general, especially more effective against HL-60 and A2780(cisR) cell lines.
Subject(s)
Antineoplastic Agents/chemistry , Models, Molecular , Organoplatinum Compounds/chemistry , Palladium/chemistry , Cell Line, Tumor , Crystallography, X-Ray , DNA Cleavage , Drug Screening Assays, Antitumor , HL-60 Cells , Humans , Hydrogen Bonding , Hydrogen-Ion Concentration , Inhibitory Concentration 50 , Macromolecular Substances , Magnetic Resonance Spectroscopy , Molecular StructureABSTRACT
The novel Pd(II) complex, [Pd(2)(micro-bzta)(4)].1.5DMSO (where bzta=benzothiazole-2-thiolate) has been synthesized and structurally characterized by element analysis, IR and single-crystal X-ray diffractometry. In the binuclear complex, two palladium(II) are bridged by four deprotonated benzothiazole-2-thialate in a head to tail disposition and the distance of the two Pd(II) is 2.747 A. Three-dimensional structure of the complex was constructed though S...S (3.339 A) weak interaction and pi...pi stack. The binding of the title complex with fish sperm DNA (FS-DNA) has been investigated by absorption and fluorescence spectra. The results indicate that the complex bind to FS-DNA in an intercalative mode and the intrinsic binding constant K of the title complex with FS-DNA is about 1.2 x 10(4)M(-1). Gel electrophoresis assay demonstrates the ability of the complex to cleave the pUC19 plasmid DNA.
