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1.
ACS Appl Bio Mater ; 6(6): 2358-2369, 2023 06 19.
Article in English | MEDLINE | ID: mdl-37259943

ABSTRACT

2,3-Dihydro-4-hydroxy-chromene-4(N)-ethyl thiosemicarbazone (probe F4) is used as a chemosensor, and it selectively detected Cu2+ ions among the metal ions by showing fluorescence "TURN ON" behavior. The stoichiometric binding of the probe with Cu2+ (CF4) was confirmed by Job's plot and mass spectroscopy. Further, CF4 was used as a sensor for the detection of l-amino acids and N-heterocyclic compounds. Among them, CF4 selectively detected l-histidine by showing fluorescence "TURN-OFF" behavior and selectively detected indazole by showing fluorescence "TURN-ON" behavior. These behaviors were further confirmed by in vivo live cell imaging studies by using Caenorhabditis elegans as a model. In vitro cytotoxicity was assayed for probe F4, complex CF4, and CF4 with l-histidine and indazole. The IC50 concentration was used for confocal imaging studies by using the MDA-MB-231 cell line (breast cancer cell line).


Subject(s)
Benzopyrans , Histidine , Spectrometry, Fluorescence/methods , Schiff Bases/chemistry , Indazoles/pharmacology , Ions
2.
Eur J Med Chem ; 50: 405-15, 2012 Apr.
Article in English | MEDLINE | ID: mdl-22397923

ABSTRACT

Four new 2-oxo-1,2-dihydrobenzo[h]quinoline-3-carbaldehyde N-substituted thiosemicarbazone ligands (H(2)-LR, where R = H, Me, Et or Ph) and their corresponding new cobalt(III) complexes have been synthesized and characterized. The structures of the complexes 2 and 3 were determined by single crystal X-ray diffraction analysis. The interactions of the new complexes with DNA were investigated by absorption, emission and viscosity studies which indicated that the complexes bind to DNA via intercalation. Antioxidant studies of the new complexes showed that the significant antioxidant activity against DPPH radical. In addition, the in vitro cytotoxicity of complexes 1-4 against A549 cell line was assayed which showed higher cytotoxic activity with lower IC(50) values indicating their efficiency in killing the cancer cells even at very low concentrations.


Subject(s)
Antineoplastic Agents/chemical synthesis , Antineoplastic Agents/pharmacology , Antioxidants/chemical synthesis , Antioxidants/pharmacology , Cell Proliferation/drug effects , Cobalt/chemistry , DNA/metabolism , Thiosemicarbazones/chemistry , Binding, Competitive , Biphenyl Compounds/pharmacology , Cell Line, Tumor , Crystallography, X-Ray , Ethidium/metabolism , Ferric Compounds/chemistry , Humans , Indicators and Reagents/pharmacology , L-Lactate Dehydrogenase/metabolism , Lung Neoplasms/drug therapy , Lung Neoplasms/metabolism , Models, Molecular , Molecular Structure , Nitric Oxide/metabolism , Organometallic Compounds/chemical synthesis , Organometallic Compounds/pharmacology , Picrates/pharmacology , Structure-Activity Relationship
3.
Inorg Chem ; 51(6): 3525-32, 2012 Mar 19.
Article in English | MEDLINE | ID: mdl-22376179

ABSTRACT

Unprecedented selective cleavage of the carbon-sulfur bond of the ferrocenylthiosemicarbazone moiety has been observed for the first time, resulting in the formation of mixed geometrical binuclear copper complex [(PPh(3))Cu(µ-S)(2)Cu(PPh(3))(2)]. Upon trying direct synthesis of the title complex, an unusual tetranuclear [Cu(4)(µ(3)-Cl)(4)(PPh(3))(4)] cubane resulted.


Subject(s)
Carbon/chemistry , Copper/chemistry , Sulfur/chemistry , Thiosemicarbazones/chemistry , Hydrolysis , Models, Molecular
4.
Metallomics ; 4(2): 218-27, 2012 Feb.
Article in English | MEDLINE | ID: mdl-22101384

ABSTRACT

New complexes, [Ni(HL)(PPh(3))]Cl (1), [Pd(L)(PPh(3))](2), and [Pd(L)(AsPh(3))](3), were synthesized from the reactions of 4-chloro-5-methyl-salicylaldehyde thiosemicarbazone [H(2)L] with [NiCl(2)(PPh(3))(2)], [PdCl(2)(PPh(3))(2)] and [PdCl(2)(AsPh(3))(2)]. They were characterized by IR, electronic, (1)H-NMR spectral data. Further, the structures of the complexes have been determined by single crystal X-ray diffraction. While the thiosemicarbazone coordinated as binegative tridentate (ONS) in complexes 2 and 3, it is coordinated as mono negative tridentate (ONS) in 1. The interactions of the new complexes with calf thymus DNA was examined by absorption and emission spectra, and viscosity measurements. Moreover, the antioxidant properties of the new complexes have also been tested against DPPH radical in which complex 1 exhibited better activity than that of the other two complexes 2 and 3. The in vitro cytotoxicity of complexes 1-3 against A549 and HepG2 cell lines was assayed, and the new complexes exhibited higher cytotoxic activity with lower IC(50) values indicating their efficiency in killing the cancer cells even at very low concentrations.


Subject(s)
Aldehydes/chemistry , Antineoplastic Agents/chemistry , Coordination Complexes/chemistry , Nickel/chemistry , Palladium/chemistry , Thiosemicarbazones/chemistry , Aldehydes/pharmacokinetics , Aldehydes/pharmacology , Animals , Antineoplastic Agents/pharmacokinetics , Antineoplastic Agents/pharmacology , Antioxidants/chemistry , Antioxidants/pharmacokinetics , Antioxidants/pharmacology , Biphenyl Compounds/chemistry , Cattle , Cell Line , Cell Survival/drug effects , Coordination Complexes/pharmacokinetics , Coordination Complexes/pharmacology , Crystallography, X-Ray , DNA/drug effects , DNA/metabolism , Hep G2 Cells , Humans , L-Lactate Dehydrogenase/metabolism , Models, Molecular , Nickel/pharmacokinetics , Nickel/pharmacology , Nitric Oxide/metabolism , Palladium/pharmacokinetics , Palladium/pharmacology , Picrates/chemistry , Spectrometry, Fluorescence , Thiosemicarbazones/pharmacokinetics , Thiosemicarbazones/pharmacology , Viscosity
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