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At least 19 recordsLinked to original sources
PubMed1992

X-ray studies on anti-tumour triazenes. Structures of 1-(4-carbamoylphenyl)-3,3-dimethyltriazene 1-oxide and 3,3-dimethyl-1-(4-nitrophenyl)triazene.

The molecular structures of the title compounds have been determined by X-ray crystallographic methods. The analyses revealed differences in the geometry, and by inference the bond delocalization in these two triazenes owing to the presence in the 1-oxide structure of an N-O bond. The geometries are compared to the crystal structures of the isomeric 3-oxides [Kuroda & Wilman (1985). Acta Cryst. C41, 1543-1545; Neidle, Webster, Kuroda & Wilman (1987). Acta Cryst. C43, 674-676] which shows the dominance of an alternative tautomeric equilibrium for the triazene groups.

Computer Graphics↗
PubMed1987

DNA methylating activity in murine lymphoma cells xenogenized by triazene derivatives.

We investigated whether epigenetic rather than mutational events may be involved in the induction of novel immunogenicity ("xenogenization") in murine lymphoma treated with triazene derivatives. To this end, we assessed the DNA methylation pattern of tumor cells during the course of in vivo or in vitro xenogenization by 2 triazenes, and compared it with the changes induced by the DNA hypomethylating agent 5-azacytidine (5-aza). While all of the tested agents were able to increase tumor cell immunogenicity, their effects on DNA methylating activity were opposite. In particular, the novel immunogenicity conferred by 5-aza treatment correlated well with the extent of hypomethylation induced, whereas xenogenization by triazenes was accompanied by a limited increase in DNA methylating activity. Interestingly, the antimutagenic compound quinacrine, which is known to block the xenogenizing activity of triazenes, was incapable of hypermethylating effects, whereas the hypermethylating agent cytosine arabinoside (ara-C) was apparently unable to interfere with the induction of novel immunogenicity by triazenes.

Animals↗
PubMed1979

Aryl-monoalkyl and cyclic triazenes: direct-acting mutagens.

An aryl-monoalkyl triazene, methyl-p-tolyl triazene (MTT) and a cyclic triazene (delta2-triazoline) are direct-acting mutagens for Salmonella typhimurium bacteria and for cell-free Hemophilus influenzae DNA. MTT causes reversion of the hisG46 base-substitution mutation, but no reversion of the hisD3052 frameshift mutation. Induced mutation frequency is not strongly influenced by modifications in the genetic background of the S. typhimurium Ames tester strains, but is mildly enhanced by the addition of a pool of amino acids to the plating medium and is strongly enhanced by liquid preincubation before plating.

Base Sequence↗
PubMed1978

Antimetastatic action of some triazene derivatives against the Lewis lung carcinoma in mice.

Two dimethyltriazenoimidazoles, DTIC and BRL 51308, and a benzenoid dimethyltriazene, CB 10286, have been examined for their effects in mice bearing Lewis lung carcinoma. A slight reduction of primary tumor growth was found after treatment with DTIC and BRL 51308, whereas CB 10286 caused no significant effect. On the contrary, all the tested compounds sharply reduced the number of lung metastases and also resulted in a high proportion of animals free of metastases at death. No significant cytotoxic effect of the triazenes was observed in small established pulmonary tumors, as determined by evaluating the effects of treatment on the fractional incorporation of 3H-TdR into DNA of the lung colonies. These results are in contrast to those obtained with a purely cytotoxic agent, cyclophosphamide, and indicate that all three triazene derivatives tested have selective antimetastatic properties.

Animals↗
PubMed1991

Comparison of the cytotoxicity in vitro of temozolomide and dacarbazine, prodrugs of 3-methyl-(triazen-1-yl)imidazole-4-carboxamide.

The present study tested the hypothesis that the experimental antineoplastic imidazotetrazinone temozolomide degrades in the biophase to 3-methyl-(triazen-1-yl)imidazole-4-carboxamide (MTIC) and exerts its cytotoxicity via this species. MTIC is a metabolite of the antimelanoma agent dacarbazine and is thought to be responsible for the antineoplastic activity of the latter. Cytotoxicity in vitro was investigated in TLX5 murine lymphoma cells. MTIC and temozolomide were cytotoxic in the absence of mouse-liver microsomes, whereas dacarbazine required metabolic activation. The generation of MTIC from either dacarbazine, its primary metabolite 5-[3-(hydroxymethyl)-3-methyl-triazen-1-yl]-imidazole-4-carboxamid e (HMMTIC) or temozolomide was studied by reversed-phase high-performance liquid chromatography in incubation mixtures under the conditions of the cytotoxicity assay. MTIC was found in incubations of temozolomide with or without microsomes. Dacarbazine yielded MTIC (and HMMTIC) only when microsomes were included in the incubation mixture. Although the mode of action of temozolomide seems to be similar to that of dacarbazine, the results obtained in this study show that these agents differ markedly in their ability to generate the active species MTIC.

Animals↗
PubMed1976

Use of cluster analysis in the development of structure-activity relations for antitumor triazenes.

A series of antitumor triazenes in which the members of the series are physicochemically distinct was designed using the cluster analysis approach as proposed by Hansch and his co-workers. The series that resulted was tested against Sarcoma 180 in the mouse and the antitumor activities were analyzed using regression techniques. The structure-activity relations that resulted are discussed in terms of proposed mechanisms of action.

Animals↗
PubMed1990

Metabolism of 1,3-di-(4-[N-(4,6-dimethyl-2-pyrimidinyl)sulphamoyl] phenyl)triazene (DDPSPT) in the rat.

1. Six hours after rats were orally dosed with 1,3-di-(4-[N-(4,6-dimethyl-2-pyrimidinyl)sulphamoyl][U-14C]phenyl) triazene (14C-DDPSPT), approx. 81% of the 14C remained in the gastrointestinal tract (gut) and less than 3% was excreted in the urine. 2. Six hours after dosing, more than half of the 14C in the gut was present as DDPSPT. 14C-Labelled metabolites in the gut included 4-amino-N-(4,6-dimethyl-2-pyrimidinyl)-benzenesulphonamide (Sulmet), N4-glucosyl-N-(4,6-dimethyl-2-pyrimidinyl)benzenesulphonamide (N4-gluc-Sulmet), 4-acetamido-N-(4,6-dimethyl-2-pyrimidinyl)benzenesulphonamide (N4-acetyl-Sulmet), and [N-4,6-dimethyl-2-pyrimidinyl) benzenesulphonamide] (desamino-Sulmet). 3. 14C-Labelled compounds in the blood, liver and skeletal muscle included DDPSPT, Sulmet, N4-gluc-Sulmet, N4-acetyl-Sulmet and desamino-Sulmet. 4. There was little or no reaction of DDPSPT with cysteine, bovine serum albumin, AMP, GMP, or calf thymus deoxyribonucleic acid in vitro (pH 3, 5, 7 or 8).

Administration, Oral↗
PubMed1976

[Phytotoxic activity of triazene derivatives. VI. 1-aryl-3-arylalkyl-3-alkyltriazene derivatives].

A series of of 1-aryl-3-arylalkyl-3-alkyltriazenes (B) was prepared and studied for phytotoxic activity. The previously unknown substances [Table I: substances (I leads to XVI)] were prepared by condensation of the appropriate diazonium salt with the required secondary amine in an alkaline medium and were tested against five representative plant species in both pre- and post-emergence tests at a dose of 6 kg/ha. All the substances studied were inactive in pre-emergence tests. However most of the compounds showed phytotoxic activity by absorption through the foliage. This activity was not very pronounced and always lower than triazene analogs previously studied (type A compounds) which have no aralkyl residue on nitrogen 3.

Herbicides↗
PubMed1975

[Local and metastatic growth of Lewis lung carcinoma as a function of its transplantation site. Application to the study of the pharmacology of sulphadiazine triazene].

The presence of a local tumour and pulmonary metastases is studied after the administration of the Lewis Lung Carcinoma at different sites of transplantation. The intravenous administration routes, in the tail vein and in the portal vein, injections in the liver and in the muscle of the left hindleg are used. The injection in the tail vein induces pulmonary "metastases". The injection in the portal vein is followed by multiple tumours in the whole liver and pulmonary metastases. An unilobar hepatic tumour and early pulmonary metastases appear after transplantation in the liver. Intra-muscular injection gives a local tumour which can be weighed after amputation of the leg and pulmonary metastases. A test of treatment by Sulphadiazine Triazene points out a weak action on the primary tumour and a larger one on the metastases.

Animals↗
PubMed1990

[Synthesis and anticonvulsant properties of sugar triazene N-oxides].

In this paper we describe a high-yielding method leading to a novel family of sugars: the sugar triazene N-oxides. The anticonvulsant effect of one of these compounds was tested. It showed a promising activity indicating the potential therapeutic usefulness of this class of carbohydrate derivatives.

Animals↗