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PubMed1990

[Antineoplastic activity and toxicity of dihydroambazone in comparison with ambazone (1,4-benzoquinone-guanylhydrazone-thiosemicarbazone)].

Dihydroambazone 1, a soluble derivative of ambazone, was tested with an admixture of ascorbic acid (0.1, 0.25, or 0.5% in distilled water) for antineoplastic activity by different routes (i.p., p.o., s.c., i.v.) against leukemia P388, and by s.c. application against Lewis lung carcinoma on B6D2F1-mice. The results were compared with that of ambazone. 1 was as active as ambazone upon the per os d 1-4 schedule only. Ascorbic acid, added for stabilization of 1, had no significant influence on the results. Intravenously given 1 was of low activity. It proved to be toxic at 100 mg/kg body mass. The i.v. toxicity was estimated approximately on B6D2F1-mice (LD50: 150 mg/kg; LD100: 175 mg/kg; maximum tolerated dose (MTD): 100 mg/kg. A comparison between the MTD's of 1 and ambazone in mice and rats (Wistar) showed partly a somewhat better p.o. compatibility of 1. The expectation of a favourable i.v. applicable derivative from the otherwise in water nearly insoluble ambazone could not be realized.

Animals↗
PubMed2003

A new approach to suppress nonlinearity-transparency trade-off through coordination chemistry: syntheses and spectroscopic study on second-order nonlinear optical properties of a series of square-pyramidal zinc(II) complexes.

Five new square-pyramidal coordination compounds L x Zn(acac)(2) (1-5) (acac = acetylacetonate; L is a variety of thiosemicarbazones: p-dimethylaminobenzaldehyde thiosemicarbazone (1), p-hydroxy-o-methoxybenzaldehyde thiosemicarbazone (2), p-methoxybenzaldehyde thiosemicarbazone (3), p-hydroxybenzaldehyde thiosemicarbazone (4), o-hydroxybenzaldehyde thiosemicarbazone (5)) have been synthesized and characterized by 1H NMR, IR, and elemental analysis. All of these compounds exhibit pretty wide transparent ranges in the visible region. Their electronic absorption spectra have been studied experimentally, and theoretically by ZINDO/S calculation. The latter has also been utilized to estimate the extent of intramolecular charge transfer. The MOPAC software package has been used to evaluate their first-order molecular hyperpolarizabilities (beta). All beta values of the five coordination compounds are larger than those of the corresponding thiosemicarbazones. And complex 1 shows the largest beta(0) (39.1 x 10(-30) esu) in the series.

Magnetic Resonance Spectroscopy↗
PubMed1962

The chemotherapy of variola major infection.

In view of earlier work which suggested that certain derivatives of isatin beta-thiosemicarbazone might be of possible clinical use in smallpox infections, several such derivatives have been tested for antiviral effect in infant mice inoculated intracerebrally with up to 10(3) LD(50) (up to 10(6.5) pock-forming units) of the Harvey strain of variola major virus.Survival of 100% was obtained in mice treated twice daily with N-methylisatin beta-thiosemicarbazone in a dose level of 10 mg/kg, isatin beta-thiosemicarbazone in a dose level of 25 mg/kg and 7-methylisation beta-thiosemicarbazone at 10 mg/kg, the treatment beginning immediately after infection. No evidence of toxicity was observed at these dose levels. At lower dose levels of these and other related compounds complete protection was not obtained, but a chemotherapeutic effect was demonstrated by a prolongation of the mean survival time. Mice which had survived variola infection after treatment with an adequate dose of chemotherapeutic agent were immune when challenged with 10(5) pock-forming units of rabbitpox virus.

Animals↗
PubMed1983

Fluorescent probes for opioid receptors.

Naloxone, naltrexone and oxymorphone were labeled in position 6 with fluorescein by coupling their hydrazone analogs with fluorescein isothiocyanate. Naloxone was also coupled in a similar way with rhodamine-B. The compounds thus obtained were: "6-FN", [1-(N)-fluoresceinyl naloxone thiosemicarbazone]; "6-FNX", [1-(N)-fluoresceinyl naltrexone thiosemicarbazone]; "6-FO", [1-(N)-fluoresceinyl oxymorphone thiosemicarbazone]; "6-RN", [1-(N)-tetramethylrhodaminyl-B naloxone thiosemicarbazone]. These compounds were tested for opioid receptor binding in rat brain synaptosomal plasma membranes and for biological activity on the guinea pig ileum. All compounds retained activity, showing some changes in affinity and binding profile compared to their parent compounds. "6-FN", for example, showed decreased (approximately 10x) affinity compared to naloxone in opiate displacement analysis but retained potency in displacement of opioid peptides. Antagonist activity of "6-FN" in the guinea pig ileum bioassay was about ten-fold less than that of naloxone.

Animals↗
PubMedDate not supplied

Effects of some ruthenium chelates on MCa mammary carcinoma and on TLX5 lymphoma in mice.

A group of four Ruthenium chelates of the mixed hard/soft N-S donor ligands 2-formylpyridine (4-H/4-phenyl)thiosemicarbazone has been studied in the experimental models of MCa mammary carcinoma and TLX5 lymphoma in the CBA mouse. Although all the four tested complexes, bis-[2-formylpyridine(4- phenyl)thiosemicarbazone]ruthenium(II)chloride]Ru(L1)(L1H)Cl, 1], [2-formylpyridine(4-phenyl)thiosemicarbazone]ruthenium(II)-mu- trichloro chloro(imidazole)ruthenium(III)monomethanolate [Ru2(L1)(imz)Cl4.CH3OH, 9]. [2-formylpyridine(4-phenyl)thiosemicarbazone]dichloroimidazoler uthenium(II) [Ru(L1H)(imz)Cl2,10] and bis[2- formylpyridinethiosemicarbazone]ruthenium(II) perchlorate, dihydrate [Ru(L)(LH)ClO4.2H2O, 16], reduced the formation of lung metastases at the same extent only compound 1 caused parallel inhibition of the growth of the primary tumor. The chemical nature of the tested compounds seems to determine the nature of the antitumor effects and the bis-chelates are found to be endowed with greater cytotoxic properties towards primary tumor than the monochelates. This opens up a very interesting point, whether it is the presence of two chelate rings around the Ruthenium(II)/(III) acceptor centre or the increase in the number of the soft (S) donor centers that generates greater cytotoxic properties in the corresponding ruthenium complexes. As far as the reduction of the metastasis formation is concerned, it appears that among the four Ruthenium chelates tested, it is possible to identify structures capable of controlling the spread of tumor to the lungs in the absence of significant cytotoxicity for tumor cells. This finding appears of importance in that it indicates the possibility of a specific mechanism of interaction with cells of the metastatic tumor. In this context it appears necessary to investigate other congeners of this "family" with more sulfur donor sites and particularly those with better water solubility.

Animals↗
PubMed1990

Structure-activity relationships for metal-labeled blood flow tracers: comparison of keto aldehyde bis(thiosemicarbazonato)copper(II) derivatives.

Radiocopper-labeled pyruvaldehyde bis(N4-methylthiosemicarbazonato)copper(II), Cu[PTSM], is under investigation as a radiopharmaceutical for evaluation of regional blood flow in the brain, heart, and kidneys because it affords relatively high levels of radioactivity in these organs upon intravenous injection, followed by prolonged tissue retention of the radiolabel. To probe and differentiate the physicochemical properties that are critical for blood-brain barrier (BBB) penetration and tissue retention in complexes of this type, 17 67Cu-labeled copper(II) bis(thiosemicarbazone) derivatives of Cu[PTSM] have been prepared and characterized, focusing on the bis(thiosemicarbazone), bis(N4-methylthiosemicarbazone), bis(N4-dimethylthiosemicarbazone), and bis(N4-ethylthiosemicarbazone) derivatives of several alkylglyoxals (R(1) = Me, Et, n-Pr, i-Pr, n-Bu, or Me(EtO)CH) and phenylglyoxal. The compounds studied varied in lipophilicity from log P = 0.75 to log P = 3.5 (where P is the octanol/water partition coefficient). In rat biodistribution studies the N4-methylthiosemicarbazone (R(1)TSM) and N4-dimethylthiosemicarbazone (R(1)TSM2) complexes always show comparable cerebral uptake at 1 min postinjection (iv) for any given R(1) group, while the thiosemicarbazone (R(1)TS) complex always penetrates the BBB less efficiently. Comparison of the various Cu[R(1)TS] derivatives shows that their brain uptake does tend to increase with increasing lipophilicity over the range 0.75 less than log P less than 2.4, although it never reaches that of the N4-alkylated derivatives. The Cu[R(1)TS] and Cu[R(1)TSM] complexes are found to exhibit prolonged cerebral retention of activity, consistent with their known susceptibility to reductive decomposition by intracellular sulfhydryl groups, while the more inert Cu[R(1)TSM2] complexes clear from the brain relatively rapidly. Tracer clearance kinetics in the heart and kidney are similar to those observed for the brain with each of the tracers examined.

Animals↗
PubMed2002

Synthesis and primary cytotoxicity evaluation of new 5-nitroindole-2,3-dione derivatives.

A new series of 5-nitro-1H-indole-2,3-dione-3-thiosemicarbazones (3a-k) obtained by condensation of 5-nitro-1H-indole-2,3-dione (1) with N-substituted-thiosemicarbazides (2a-k) were treated with morpholine or piperidine and formaldehyde to yield 1-morpholino/piperidinomethyl-5-nitroindole-2,3-dione-3-thiosemicarbazones (4a-m). The structures of all the compounds were determined by analytical and spectral (IR, 1H-NMR, EIMS) methods. Compounds 3b, 3c, 3f, 3k, 4a, 4c, 4f and 4l chosen as prototypes were evaluated in the National Cancer Institute's 3-cell line, one dose in vitro primary cytotoxicity assay. All the compounds that passed the criteria for activity in this assay were scheduled automatically for evaluation against the full panel of 60 human tumour cell lines at a minimum of five concentrations at 10-fold dilutions. Sulphorhodamine B (SRB) protein assay was used to estimate cell stability or growth. The most active compound was found to be 1-morpholinomethyl-5-nitroindole-2,3-dione-3-N-(chlorophenyl)thiosemicarbazone (4l). This compound demonstrated the most marked effects in the National Cancer Institute's 60 human tumour cell line in vitro screen on a non-small cell lung cancer cell line (HOP-62, log(10)GI(50) value <-8.00) and on leukaemia cell lines (HL-60(TB), log(10)GI(50) value -6.30; MOLT-4, log(10)GI(50) value -6.18).

Antineoplastic Agents↗
PubMed2004

Synthesis, anticancer and antibacterial activity of some novel mononuclear Ru(II) complexes.

In search of potential anticancer drug candidates in ruthenium complexes, a series of mononuclear ruthenium complexes of the type [Ru(phen)(2)(nmit)]Cl(2) (Ru1), [Ru(bpy)(2)(nmit)]Cl(2) (Ru2), [Ru(phen)(2)(icpl)]Cl(2) (Ru3), Ru(bpy)(2)(icpl)]Cl(2) (Ru4) (phen=1,10-phenanthroline; bpy=2,2'-bipyridine; nmit=N-methyl-isatin-3-thiosemicarbazone, icpl=isatin-3-(4-Cl-phenyl)thiosemicarbazone) and [Ru(phen)(2)(aze)]Cl(2) (Ru5), [Ru(bpy)(2)(aze)]Cl(2) (Ru6) (aze=acetazolamide) and [Ru(phen)(2)(R-tsc)](ClO(4))(2) (R=methyl (Ru7), ethyl (Ru8), cyclohexyl (Ru9), 4-Cl-phenyl (10), 4-Br-phenyl (Ru11), and 4-EtO-phenyl (Ru12), tsc=thiosemicarbazone) were prepared and characterized by elemental analysis, FTIR, (1)H-NMR and FAB-MS. Effect of these complexes on the growth of a transplantable murine tumor cell line (Ehrlich Ascites Carcinoma) and their antibacterial activity were studied. In cancer study the effect of hematological profile of the tumor hosts have also been studied. In the cancer study, the complexes Ru1-Ru4, Ru10 and Ru11 have remarkably decreased the tumor volume and viable ascitic cell count as indicated by trypan blue dye exclusion test (p<0.05). Treatment with the ruthenium complexes prolonged the lifespan of Ehrlich Ascites Carcinoma (EAC) bearing mice. Tumor inhibition by the ruthenium chelates was followed by improvements in hemoglobin, RBC and WBC values. All the complexes showed antibacterial activity, except Ru5 and Ru6. Thus, the results suggest that these ruthenium complexes have significant antitumor property and antibacterial activity. The results also reflect that the drug does not adversely affect the hematological profiles as compared to that of cisplatin on the host.

Animals↗
PubMed1977

Anti-tumor virus activity of copper-binding drugs.

Several, structurally different, copper-binding ligands can inhibit the RNA-dependent DNA polymerase of Rous sarcoma virus (RSV) and can inactivate the ability of the virus to malignantly transform chick embryo cells. These ligands include the anti-microbial agents, thiosemicarbazones, 8-hydroxyquinolines, isonicotinic acid hydrazide, and others. Many of these compounds bind to DNA and RNA in the presence of copper, which may play a role in their anti-viral activity. However, not all agents active against RSV bind to nucleic acids and not all ligands that bind to nucleic acids are active against RSV. Some copper-binding ligands are neither active against RSV, nor bind nucleic acids. It appears that there is no simple relationship between the anti-viral activity of copper-binding ligands and their nucleic acid-binding ability. The biological importance of thiosemicarbazone-copper complex binding to nucleic acids is supported by the observation that treatment of intact RSV virions with the complex causes the genome 70S RNA to sediment abnormally in velocity sucrose gradient analysis.

Anti-Bacterial Agents↗
PubMed1976

Computer-based approach to chelation therapy: a theoretical study of some chelating agents for the selective removal of toxic metal ions from plasma.

COMICS is a computer programme for calculating equilibrium concentrations of metal complexes and reactive species in multi-metal-multi-ligand systems. Its usefulness for analysing metal ion equilibria in blood plasma has been improved by including albumin as a ligand. Using this model system the distribution and removal of copper(II) and zinc ions in histidinaemia, lead poisoning and Wilson's disease have been examined. The efficacy of TRIEN in removing excess copper(II) is shown. The use of specific tripeptides such as Gly-Gly-His methyl ester for the selective removal of copper(II) is suggested. A possible chemoprophylaxis of influenza based on complexation of zinc is discussed. Calculations confirm that thiosemicarbazones such as methisazone and 2-acetylpyridine thiosemicarbazone are effective competitors for heavy metal ions under physiological conditions.

Amino Acid Metabolism, Inborn Errors↗