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PubMed1979

Binding of N-methyl isatin beta-thiosemicarbazone-copper complexes to proteins and nucleic acids.

N-Methyl isatin beta-thiosemicarbazone-copper complexes interact with nucleic acids and proteins as shown by ultraviolet (UV) and visible spectroscopy and Sephadex exclusion chromatography. The Cu++ ions are most effective; Co++ ions have less albeit significant activity. Chelating agents, such as Tris and histidine, high NaCl concentration, and dimethyl sulfoxide reduce the binding of the drug-metal complex. The binding constant of the drug-copper complex to calf-thymus DNA was calculated to range between 6.9 x 10(4) and 2.7 x 10(5) M-1.

Chelating Agents↗
PubMed2001

Synthesis, structure and biological activity of nickel(II) complexes of 5-methyl 2-furfural thiosemicarbazone.

5-Methyl 2-furfuraldehyde thiosemicarbazone (M5HFTSC) with nickel(II) leads to three types of complexes: [Ni(M5HFTSC)(2)X(2)], [Ni(M5FTSC)(2)] and [Ni(M5FTSC)(2)] x 2DMF. In the first type the ligand remains in thione form, while in the two other, the anionic thiolato form is involved. The species [Ni(M5HFTSC)(2)X(2)] has been characterized spectroscopically. The structures of [Ni(M5FTSC)(2)] x 2DMF and [Ni(M5FTSC)(2)] have been solved using X-ray diffraction. Biological studies of [Ni(M5HFTSC)(2)Cl(2)] have been carried out in vitro for antifungal activity on human pathogenic fungi, Aspergillus fumigatus and Candida albicans, and in vivo for toxicity on mice. The results are compared to those of the ligand, the metal salt and a similar copper complex [Cu(M5HFTSC)Cl(2)].

Animals↗
PubMed2001

Platinum(II) complexes with 2-acetyl pyridine thiosemicarbazone. Synthesis, crystal structure, spectral properties, antimicrobial and antitumour activity.

An interesting series of new platinum complexes has been synthesized by the reaction of Na(2)PtCl(4) with 2-acetyl pyridine thiosemicarbazone, HAcTsc. The new complexes, [Pt(AcTsc)Cl], [Pt(HAcTsc)(2)]Cl(2) and [Pt(AcTsc)(2)], have been characterized by elemental analyses and spectroscopic studies. The crystal structure of the complex [Pt(AcTsc)Cl] has been solved by single-crystal X-ray diffraction. The anion of HAcTsc coordinates in a planar conformation to the central platinum(II) through the pyridyl N, azomethine N and thiolato S atoms. Double intermolecular hydrogen bonds (NH-Cl), pi-pi and weak Pt-Pt and Pt-pi contacts lead to aggregation and to a two-dimensional supramolecular assembly. The antibacterial and antifungal effect of the novel platinum(II) complexes and the related palladium(II) complexes, [Pd(AcTsc)Cl], [Pd(HAcTsc)(2)]Cl(2) and [Pd(AcTsc)(2)], were studied in vitro. The complexes were found to have a completely lethal effect on Gram+ bacteria, while the same complexes showed no bactericidal effect on Gram- bacteria. Additionally, the complexes [Pt(AcTsc)(2)] and [Pd(AcTsc)(2)] showed effective antifungal activity towards yeast. Among these compounds [33], the most effective in inducing antitumour and cytogenetic effects are the complexes [Pt(AcTsc)(2)] and [Pd(AcTsc)(2)] while the rest, display marginal cytogenetic and antitumour effects.

Anti-Bacterial Agents↗
PubMed2001

New methyl pyruvate thiosemicarbazones and their copper and zinc complexes: synthesis, characterization, X-ray structures and biological activity.

By reacting thiosemicarbazides substituted on the aminic nitrogen with both alkyl or aryl groups, and methyl pyruvate a new group of methylpyruvate thiosemicarbazones (Hmpt) derivatives was obtained. These ligands were then treated with copper and zinc inorganic salts. All isolated compounds were characterized using spectroscopic methods. The single crystal structural analysis of the ligands Me-Hmpt x 0.5H2O 1, Et-Hmpt x H2O 2, Ph-Hmpt 5, Meph-Hmpt 6 showed that only compound 6 presents significant deviation from planarity. The X-ray structure of [Zn(Me-Hmpt)Cl2] x H2O 8 showed that in this complex Me-Hmpt behaves as a neutral ligand SNO terdentate and that the penta coordination is achieved by chloride ions according to spectroscopic and elemental analyses. On the basis of the analytical data the same behavior is proposed for the other zinc complexes. All the ligands in copper complexes seem to be monodeprotonated; nevertheless the same SNO behavior is expected. Tests on cell proliferation of human leukemic cell line U937 showed that the copper complex Cu(Et-mpt)Cl x H2O is the most active compound among those reported even though it is not able to induce apoptosis.

Apoptosis↗
PubMed2002

Synthesis, characterization and X-ray structures of new antiproliferative and proapoptotic natural aldehyde thiosemicarbazones and their nickel(II) and copper(II) complexes.

Synthesis and characterization of new thiosemicarbazones derived from natural aldehydes (1-9) have been investigated in order to develop a research program aimed at the development of compounds with antiviral, antibacterial, and antitumor properties. These substances contain both a chain with N and S nucleophilic centers with tuberculostatic activity, and an alkyl or terpenic moiety. In addition, a few nickel(II) and copper(II) complexes (10-18), derived also from the previously studied ligands, were synthesized and characterized by means of NMR and IR techniques. The trans-2-octenal N(1)-phenylthiosemicarbazone and its nickel complex were also characterized by X-ray diffractometry. Biological studies, performed with some of these compounds, have involved both inhibition of cell proliferation and apoptosis tests in vitro on human leukemia cell line U937 to deepen our knowledge on the way these substances interfere with biological processes in leukemic cells.

Apoptosis↗
PubMed2003

Transition metal complexes of phenanthrenequinone thiosemicarbazone as potential anticancer agents: synthesis, structure, spectroscopy, electrochemistry and in vitro anticancer activity against human breast cancer cell-line, T47D.

The thiosemicarbazone derivative of 9,10-phenanthrenequinone, 1, and its metal complexes were synthesized. The X-ray crystal structure for 1 confirms the presence of the E tautomeric arrangement in this compound. Its copper complex shows 1:1 stoichiometry while nickel and cobalt compounds show 1:2 stoichiometry. The X-ray crystal structure of the nickel complex indicates two tridentate ligands coordinating in the thiolato form yielding an octahedral geometry for the 'mer' isomer. The copper complex exhibits maximum antiproliferative activity against human breast cancer cell-line, T47D probably due to inhibition of steroid binding to the cognitive receptor or by preventing dimerization of the estrogen receptor.

Antineoplastic Agents↗
PubMed1997

Acenaphthenequinone thiosemicarbazone and its transition metal complexes: synthesis, structure, and biological activity.

The reaction of iron, nickel, copper, and zinc chlorides or acetates with acenaphthenequinone thiosemicarbazone, Haqtsc leads to the formation of novel complexes that have been characterized by spectroscopic studies (NMR, IR) and biological properties. The crystal structures of the free ligand Haqtsc 1 and of the compound [Ni(aqtsc)2].DMF 2, have also been determined by X-ray methods from diffractometer data. In 1, the conformation of the two nonequivalent molecules is governed by intramolecular hydrogen bonds, while an intermolecular hydrogen bond is responsible for dimer-like groups formation. In 2, the coordination geometry about nickel is distorted octahedral, and the two ligand molecules are terdentate monodeprotonated. Biological studies have shown that, for the first time at least up the used doses, a free ligand is active both in the inhibition of cell proliferation and in the induced differentiation on Friend erythroleukemia cells (FLC).

Acenaphthenes↗
PubMed1997

Palladium(II) complexes of 2-acetylpyridine N(4)-methyl, N(4)-ethyl and N(4)-phenyl-thiosemicarbazones. Crystal structure of chloro(2-acetylpyridine N(4)-methylthiosemicarbazonato) palladium(II). Synthesis, spectral studies, in vitro and in vivo antitumour activity.

The reactions of 2-acetylpyridine N(4)-methyl, (HAc4Me) N(4)-ethyl (HAc4Et) and N(4)-Phenyl (HAc4Ph) thiosemicarbazone with palladium(II) were studied. The ligands and the palladium(II) complexes have been characterized by spectroscopic techniques. The structure of [Pd(Ac4Me)Cl] has been determined by single-crystal x-ray diffraction. The protonation constants of HAc4Me and HAc4Et, Ka1 and Ka2, were determined by spectrophotometry. The effect of palladium compounds on DNA synthesis of P388 and L1210 cell cultures is also reported. Some of these compounds increased the life span of mice bearing tumors.

Animals↗
PubMed1998

Synthesis, characterisation and biological activity of three copper (II) complexes with a modified nitrogenous base: 5-formyluracil thiosemicarbazone.

Three Cu(II) co-ordination compounds with a novel ligand, 5-formyluracil thiosemicarbazone (H3ut), have been synthesised and characterised by single-crystal X-ray diffraction and subsequently tested in vitro on human leukemic cells. The crystal structures revealed, in all three cases, a square pyramidal co-ordination geometry of the copper atom with the ligand lying on the basal plane and behaving as an SNO terdentate ligand. These three compounds have been tested on human leukemic cell line K562 and CEM. In these experiments the complexes have demonstrated to inhibit cell growth and one of them to induce apoptosis. In the paper we also report the spectrophotometric characterization of the free ligand.

Apoptosis↗
PubMed1999

A cycloplatinated compound of p-isopropylbenzaldehyde thiosemicarbazone and its chloro-bridged derivative induce apoptosis in cis-DDP resistant cells which overexpress the H-ras oncogene.

cis-Diamminedichloroplatinum(II) (cis-DDP) is a widely used antitumour drug which produces important damage on the DNA inducing apoptosis in several cell lines. We have analyzed the cytotoxic activity of novel cyclometallated complexes of p-isopropylbenzaldehyde thiosemicarbazone (p-is.TSCN) and their dimeric chloro-bridged derivatives in murine keratinocytes transformed by the H-ras oncogene which are resistant to cis-DDP (Pam-ras cells). The data show that, in contrast with cis-DDP, the tetrameric cycloplatinated complex [Pt(p-is.TSCN)]4 and its dimeric chloro-bridged derivative [Pt(microCl)(p-is.TSCN)]2 have a good in vitro therapeutic index when comparing the cytotoxicity in Pam-ras cells to normal murine keratinocytes (Pam 212 cells) since they induce cell death in Pam-ras cells at drug concentrations significantly lower than those needed to kill Pam 212 cells. At equitoxic doses (IC90), both complexes produce characteristic features of apoptosis in Pam-ras cells together with a drastic decrease in levels of H-ras protein. These effects are not observed when the cells are treated with the IC90 of the cis-DDP drug nor the p-is.TSCN ligand. Altogether, these results suggest that the platinum compounds [Pt(p-is.TSCN)]4 and [Pt(microCl)(p-is.TSCN)]2 might have potential as antitumour agents in view of their specific induction of apoptosis in cis-DDP resistant cells.

Animals↗
PubMed2000

Synthesis, characterization, and antibacterial activity of novel Mn(II), Co(II), Ni(II), Cu(II), and Zn(II) complexes with vitamin K3-thiosemicarbazone.

Vitamin K3-thiosemicarbazone (C12H11N3NaO4S2 x 5H2O, abbreviated as VT), a new Schiff base derivative, has been synthesized. Its crystal structure, determined by X-ray diffraction, is triclinic, space group P1. We have also prepared five novel complexes of VT with transition metals: [M(VT)(2)2H2O] x nH2O, (n = 1 and 2 for M = Cu(II) and Zn(II), respectively) and [M'(HVT)2Cl2] x mH2O, (m = 4, 5, and 7 for M' = Co(II), Mn(II), and Ni(II), respectively). These compounds were characterized by IR and UV-Vis spectroscopy, molar conductivity, thermal analyses, complexometric titration, and elemental analysis. In all the complexes, the VT ligand coordinates through sulfur and oxygen atoms, and the geometry around metal atom is best described as octahedral. In vitro tests of antibacterial activity showed that VT and its complexes with Mn(II), Co(II), Ni(II), Cu(II), and Zn(II) all had strong inhibitory actions against G(+) Staphylococcus aureus, G(+) Hay bacillus, and G(-) Escherichia coli.

Anti-Bacterial Agents↗
PubMed2000

Synthesis, spectroscopic characterization and biological properties of new natural aldehydes thiosemicarbazones.

As part of a research programme aimed at the synthesis of compounds with antiviral, antibacterial and antitumor properties and their spectroscopic characterization, new thiosemicarbazones deriving from natural aldehydes have been investigated. These substances contain in the same molecule both a chain with nucleophilic centres N, S with tubercolostatic activity, and a glycosidic or alkyl moiety (modified glycosides and nucleosides have recently received a great deal of attention in the fields of neoplastic diseases and viral infections). In this paper the synthesis and the characterization of these compounds by means of 1H NMR, IR, and MS techniques is reported. Biological studies have involved both inhibition of cell proliferation and apoptosis tests on human leukemia cell line U937.

Apoptosis↗
PubMed2003

Spectral studies and structure of a 2-hydroxyacetophenone 3-hexamethyleneiminyl thiosemicarbazonate(-2) copper(II) complex containing 1,10-phenanthroline.

The spectral studies and structure of a ternary complex of copper(II) with 2-hydroxyacetophenone 3-hexamethyliminylthiosemicarbazonate (L(2-)) and 1,10-phenanthroline (phen) are reported. The thiosemicarbazone binds to the metal as a dianionic ONS-donor (L(2-)) ligand, and forms a complex of the stoichiometry [CuLphen]. The copper(II) complex was characterized by IR and UV/Vis spectroscopies, as well as by solid state room-temperature magnetic susceptibility. Spin Hamiltonian and bonding parameters of the compound are calculated from the EPR spectra. Computer simulation of EPR spectrum in DMF at 77 K aided the calculation of magnetic and bonding parameters of the compound. The structure of the compound is solved by single crystal X-ray diffraction. The geometry around copper is distorted square pyramidal.

Acetophenones↗
PubMed2003

Spectrofluorimetric determination of both hydrogen peroxide and -O-O-H in polyethylene glycols (PEGs) using 2-hydroxy-1-naphthaldehyde thiosemicarbazon (HNT) as the substrate for horseradish peroxidase (HRP).

2-Hydroxy-1-naphthaldehyde thiosemicarbazon (HNT) had been synthesized and used as a new kind of substrate for horseradish peroxidase (HRP) in spectrofluorimetric determination of hydrogen peroxide (H(2)O(2)). The oxidation reaction of HNT with H(2)O(2) under the catalysis of HRP was studied in detail. The possible reaction mechanism was discussed. Under optimum experimental conditions, the oxidized product of HNT had excitation and emission maxima at 260 and 450 nm, respectively. The linear range of this method was 1.30 x 10(-9)-1.25 x 10(-5) mol l(-1) with a detection limit of 3.89 x 10(-10) mol l(-1). The effect of interferences, surfactants and organic solvents on the determination of H(2)O(2) had been investigated. A study to prove the existence of -O-O-H in PEGs was carried out. The proposed method was successfully applied to the determination of -O-O-H in polyethylene glycols.

Horseradish Peroxidase↗
PubMed2003

Cu(II) complexes with heterocyclic substituted thiosemicarbazones: the case of 5-formyluracil. Synthesis, characterization, x-ray structures, DNA interaction studies, and biological activity.

Two new 5-formyluracil thiosemicarbazone (H(3)ut) derivatives, Me-H(3)ut (1) and Me(2)-H(3)ut (2), were synthesized by reacting thiosemicarbazides, mono- and dimethylated on the aminic nitrogen, with 5-formyluracil and were subsequently characterized. These ligands, treated with copper chloride and nitrate, afforded three complexes: [Cu(Me-H(3)ut)Cl(2)].H(2)O (3), [Cu(Me(2)-H(3)ut)Cl(2)].H(2)O (4), and [Cu(Me-H(3)ut)(NO(3))(OH(2))(2)]NO(3) (5). The crystal structures of these complexes have been determined by single-crystal X-ray diffraction. In 3 and 4, a similar pentacoordination is present; the copper atom is surrounded by the ligand SNO donor atoms and by two chloride ions. The structure of 5 consists of [Cu(Me-H(3)ut)(NO(3))(OH(2))(2)](+) cations and nitrate anions. The copper coordination (4 + 2) involves the SNO ligand atoms and a water oxygen in the basal plane; the apical positions are occupied by a second water oxygen and by an oxygen of a monodentate nitrate group. Two biochemical techniques, namely DNA titration in the UV-vis region and thermal denaturation, have been employed to probe the details of DNA binding of these compounds. Analysis of the results suggests that our compounds are able to interact with DNA by electrostatic and groove binding but not by intercalation. The compounds have been also tested in vitro on human leukemic cell line U937, but they are not able to inhibit significantly cell proliferation.

Copper↗
PubMed2005

Antitumor metallothiosemicarbazonates: structure and antitumor activity of palladium complex of phenanthrenequinone thiosemicarbazone.

The crystal structure of the potential antitumor metal compound, viz. chloro, mono(phenanthrenequinone thiosemicarbazonato) palladium(II) dimethyl formamide solvate, is reported. The central palladium(II) atom is in a square planar environment provided by the tridentate, monoanionic thiosemicarbazone ligand and the ancillary chloride ion. The compound exhibited remarkable activity against drug-sensitive and drug-resistant breast cancer cell lines and was relatively nontoxic toward the normal mammary epithelial cells. The drug-induced killing effect against breast cancer cell lines was predominantly mediated via apoptosis, a physiologic form of cell death.

Antineoplastic Agents↗
PubMed2004

Copper(II) complexes with substituted thiosemicarbazones of alpha-ketoglutaric acid: synthesis, X-ray structures, DNA binding studies, and nuclease and biological activity.

New alpha-ketoglutaric acid thiosemicarbazone (H(3)ct) derivatives and their copper complexes were synthesized and characterized by analytical and spectroscopic (IR and NMR) methods. For two of the ligands, Me-H(3)ct and Allyl-H(3)ct, and for a complex, [Cu(Me-Hct)(OH(2))](n) x 2nH(2)O, the X-ray structures were also determined. In the latter the copper atom shows a 4 + 1 pyramidal coordination, a water oxygen appears in the apical position, and three of the basal positions are occupied by the SNO tridentate ligand and the fourth by a carboxylic oxygen of an adjacent molecule that gives rise to a polymeric chain. DNA binding constants were determined, and studies of thermal denaturation profiles and nuclease activity were also performed. Tests in vitro on human leukemia cell line U937 were carried out on cell growth inhibition, cell cycle, and apoptosis induction.

Antineoplastic Agents↗
PubMed2006

Copper complexes of thiosemicarbazone-pyridylhydrazine (THYNIC) hybrid ligands: a new versatile potential bifunctional chelator for copper radiopharmaceuticals.

Two new thiosemicarbazone-pyridylhydrazine (THYNIC) hybrid ligands have been synthesized. Copper(II) and copper(I) complexes of the ligands have been prepared and characterized by X-ray crystallography. Cyclic voltammetry measurements show that the copper(II) complexes undergo quasi-reversible reductions at biologically accessible potentials. One of the ligands, bearing a pendant carboxylate arm, has been conjugated to N-alpha-(tert-butoxycarbonyl)-L-lysine.

Chelating Agents↗