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Chemical Compound Review

Triazene     triazene

Synonyms: triaz-1-ene, AG-D-97252, CHEBI:35468, CHEBI:72573, CTK0H6600, ...
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Disease relevance of triazene

  • O6-alkylguanine-DNA alkyltransferase attenuates triazene-induced cytotoxicity and tumor cell immunogenicity in murine L1210 leukemia [1].
  • Exposure in vivo of murine L5178Y lymphoma cells to cytoreductive triazene derivatives leads to the generation of immunogenic variant lines expressing new transplantation Ags recognized by CTL [2].
  • 3-Methyl-3-propyl-1-triazene and 3,3-diethyl-1-trazene analogues had comparable lipophilic-hydrophilic balance, toxicity, and antileukemic effectiveness; usual metabolic activation of the triazene N-methyl group may make little contribution to antitumor properties in the examples presented [3].
  • Compound 7a has curative activity against L-1210 and P388 leukemia and may act as a prodrug modification of the acyclic triazene 5-[3-(2-chloroethyl)triazen-1-yl]imidazole-4-carboxamide (MCTIC), since it ring opens to form the triazene in aqueous sodium carbonate [4].
  • Leukemic bone marrow cells ( > 90% blasts) of a patient with acute myeloblastic leukemia (AML), non-treated or pretreated in vitro with a mutagenic triazene compound, were infected with HTLV-I by coculture with irradiated virus-donor cells [5].

Psychiatry related information on triazene

  • The synergism between DM-COOK and PGM could be attributed to the capacity of the triazene to render the treated tumor cells more antigenic, combined with the favourable effects of PGM to restore host defense mechanisms [6].

High impact information on triazene

  • As measured by their resistance to cleavage by endoglycosidase H, the normal processing of all six carbohydrate chains on AGP to the complex form did not completely resume until nearly 24 h after triazene treatment [7].
  • DFT calculations predict a zwitterionic dehydrocinnolinium intermediate that is supported by deuterium trapping studies as well as cyclizations performed using a 2,2,6,6-tetramethylpiperidine moiety at the 3-position of the triazene [8].
  • This supports the hypothesis that the ease of initial triazene activation by cytochrome P-450 governs the mutagenicity of these compounds [9].
  • Hydrolysis studies were performed with (1)H NMR and revealed that the p-nitrophenyl substituted triazene 26 showed an optimal hydrolysis rate (t(1/2) = 23 min) and almost 100% selectivity for the desired fragmentation route [10].
  • In vitro antitumor studies in the 60 human tumor cell line panel of the National Cancer Institute confirmed the superior properties of p-nitrophenyl-protected methyl triazene 26, showing mean IC(50) values of 10 microM compared to 100 microM for temozolomide [10].

Chemical compound and disease context of triazene


Biological context of triazene


Anatomical context of triazene

  • 3. Both beta-galactosidase and beta-glucosidase activities in triazene-treated confluent fibroblast cultures recover exponentially; if zero-order enzyme production is assumed, turnover times of 10 and 5 days respectively can be estimated [20].
  • We have previously reported that depletion of OGAT activity in the human T-cell leukemic urkat line does not sensitize these cells to the cytotoxic and apoptotic effects of the methylating triazene temozolomide (Tentori et al., 1995) [21].
  • Drug-mediated changes in the susceptibility of human lymphoblastoid B cells to NK-mediated cytolysis: studies with a triazene compound [22].
  • 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 [23].
  • Triazene administration to 10-day pregnant mice gave rise to severe ear abnormalities, including middle ear ossicle malformations [24].

Associations of triazene with other chemical compounds

  • These data suggest strongly that NMA forms an unstable triazene adduct with adenine in DNA both in vitro and in vivo [25].
  • A requirement for cyclization in MeI is that the (2-alkynylphenyl)triazene must contain a suitably electron-withdrawing substituent on the phenyl ring to deactivate the triazene toward methylation-induced decomposition to an iodoarene [26].
  • Formation of triazene derivatives from sodium nitrite and sulphanilamide, sulphamethizole or sulphamethoxazole in acidic solution containing saliva or canned vegetable juice was studied using reverse-phase high-performance liquid chromatography with ultraviolet light detection at 365 nm [27].
  • The modulating effect of newly synthesized alkylating spin labeled triazene and spin labeled nitrosourea derivatives on the DOPA-oxidase activity of mushroom tyrosinase has been investigated by Bumett's spectrophotometric method (Burnett et al., 1967) [28].

Gene context of triazene

  • Therefore, it reasonable to hypothesize that combined treatment of leukaemia patients with triazene compounds along with MGMT inhibitors could lead to a better control of the disease [29].
  • The ability of these new triazenes to inhibit Pneumocystis carinii dihydrofolate reductase in vitro has been compared to that of triazene 4a [30].
  • Triazene metabolism. III. In vitro cytotoxicity towards M21 cells and in vivo antitumour activity of the proposed metabolites of the antitumour 1-aryl-3,3-dimethyltriazenes [31].
  • However, E. coli beta-galactosidase was not inactivated by these triazene derivatives [32].
  • 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 [33].

Analytical, diagnostic and therapeutic context of triazene

  • These results show a homogeneous response of melanoma lines to MRD treatment in vitro, suggesting that phase I clinical trials concerning this drug, which in vivo appears to be activated to a more cytotoxic metabolite, could be extended to metastatic melanomas, including those completely resistant to triazene compounds [11].
  • In conclusion, these results appear to provide disease-oriented rational basis to design novel clinical protocols for the treatment of acute leukaemia with combined administration of PAT and triazene compounds [29].
  • In vivo autoradiography of radioiodinated (R)-3-quinuclidinyl (S)-4-iodobenzilate [(R, S)-IQNB] and (R)-3-quinuclidinyl (R)-4-iodobenzilate [(R,R)-IQNB]. Comparison of the radiolabelled products of a novel tributylstannyl precursor with those of the established triazene and exchange methods [34].


  1. O6-alkylguanine-DNA alkyltransferase attenuates triazene-induced cytotoxicity and tumor cell immunogenicity in murine L1210 leukemia. Graziani, G., Faraoni, I., Grohmann, U., Bianchi, R., Binaglia, L., Margison, G.P., Watson, A.J., Orlando, L., Bonmassar, E., D'Atri, S. Cancer Res. (1995) [Pubmed]
  2. Multiple point mutations in an endogenous retroviral gene confer high immunogenicity on a drug-treated murine tumor. Grohmann, U., Puccetti, P., Belladonna, M.L., Fallarino, F., Bianchi, R., Binaglia, L., Sagakuchi, K., Mage, M.G., Appella, E., Fioretti, M.C. J. Immunol. (1995) [Pubmed]
  3. Potential antitumor agents. 22. Latentiated congeners of the 4'-(9-acridinylamino)methanesulfonanilides. Atwell, G.J., Cain, B.F., Denny, W.A. J. Med. Chem. (1977) [Pubmed]
  4. Antitumor imidazotetrazines. 1. Synthesis and chemistry of 8-carbamoyl-3-(2-chloroethyl)imidazo[5,1-d]-1,2,3,5-tetrazin-4(3 H)-one , a novel broad-spectrum antitumor agent. Stevens, M.F., Hickman, J.A., Stone, R., Gibson, N.W., Baig, G.U., Lunt, E., Newton, C.G. J. Med. Chem. (1984) [Pubmed]
  5. In vitro infection of leukemic bone marrow with HTLV-I generates immortalized cell lines expressing T or myeloid cell phenotype. Giuliani, A., Vernole, P., D'Atri, S., Del Poeta, G., D'Onofrio, C., Faraoni, I., Greiner, J.W., Bonmassar, E., Graziani, G. Leukemia (1995) [Pubmed]
  6. Effects of postsurgical immunotherapy with PGM in mice bearing Lewis lung carcinoma treated with p-(3,3-dimethyl-1-triazeno) benzoic acid potassium salt. Sava, G., Zorzet, S., Perissin, L., Lassiani, L., Tomasic, J. Methods and findings in experimental and clinical pharmacology. (1985) [Pubmed]
  7. Effect of alpha-D-mannopyranosylmethyl-p-nitrophenyltriazene on hepatic degradation and processing of the N-linked oligosaccharide chains of alpha 1-acid glycoprotein. Docherty, P.A., Kuranda, M.J., Aronson, N.N., BeMiller, J.N., Myers, R.W., Bohn, J.A. J. Biol. Chem. (1986) [Pubmed]
  8. Deciphering the mechanistic dichotomy in the cyclization of 1-(2-ethynylphenyl)-3,3-dialkyltriazenes: competition between pericyclic and pseudocoarctate pathways. Kimball, D.B., Weakley, T.J., Herges, R., Haley, M.M. J. Am. Chem. Soc. (2002) [Pubmed]
  9. Mutagenicity of dimethyl heteroaromatic triazenes in the Ames test: the role of hydrophobicity and electronic effects. Shusterman, A.J., Debnath, A.K., Hansch, C., Horn, G.W., Fronczek, F.R., Greene, A.C., Watkins, S.F. Mol. Pharmacol. (1989) [Pubmed]
  10. Synthesis and antitumor activity of methyltriazene prodrugs simultaneously releasing DNA-methylating agents and the antiresistance drug O(6)-benzylguanine. Wanner, M.J., Koch, M., Koomen, G.J. J. Med. Chem. (2004) [Pubmed]
  11. In vitro antitumor activity of 3'-desamino-3'(2-methoxy-4-morpholinyl) doxorubicin on human melanoma cells sensitive or resistant to triazene compounds. Alvino, E., Gilberti, S., Cantagallo, D., Massoud, R., Gatteschi, A., Tentori, L., Bonmassar, E., D'Atri, S. Cancer Chemother. Pharmacol. (1997) [Pubmed]
  12. In vitro combined effects of a triazene compound and interferon-beta on natural immunity against lymphoblastoid cells: studies at effector and target cell level. Bonmassar, L., D'Atri, S., Turriziani, M., Giuliani, A. Immunopharmacology and immunotoxicology. (1994) [Pubmed]
  13. Two spin labeled triazenes: relationship between biochemical and biological activities. Gadjeva, V.G. International journal of pharmaceutics. (2002) [Pubmed]
  14. Malignant melanoma--future prospects. Lugović, L., Situm, M., Kos, L. Acta dermatovenerologica Croatica : ADC / Hrvatsko dermatolosko drustvo. (2005) [Pubmed]
  15. Efficient synthesis of sulfonic, phosphoric, and phosphinic esters employing alkylating polymer-bound reagents. Vignola, N., Dahmen, S., Enders, D., Bräse, S. Journal of combinatorial chemistry. (2003) [Pubmed]
  16. Pyrazole derivatives. 5. Synthesis and antineoplastic activity of 3-(2-chloroethyl)-3,4-dihydro-4-oxopyrazolo[5,1-d]-1,2,3, 5-tetrazine-8-carboxamide and related compounds. Cheng, C.C., Elslager, E.F., Werbel, L.M., Priebe, S.R., Leopold, W.R. J. Med. Chem. (1986) [Pubmed]
  17. Triazene compounds induce apoptosis in O6-alkylguanine-DNA alkyltransferase deficient leukemia cell lines. Tentori, L., Graziani, G., Gilberti, S., Lacal, P.M., Bonmassar, E., D'Atri, S. Leukemia (1995) [Pubmed]
  18. Base sequence selectivity in the alkylation of DNA by 1,3-dialkyl-3-acyltriazenes. Kroeger Smith, M.B., Taneyhill, L.A., Michejda, C.J., Smith, R.H. Chem. Res. Toxicol. (1996) [Pubmed]
  19. Preparation and properties of (R)-(-)-1-azabicyclo[2.2.2]oct-3-yl- (R)-(+)-alpha-hydroxy-alpha-(4-[125I]iodophenyl)-alpha-phenyl acetate and (R)-(-)-1-azabicyclo[2.2.2]oct-3-yl-(S)-(-)-alpha-hydroxy-alpha- (4-[125I]iodophenyl)-alpha-phenyl acetate as potential radiopharmaceuticals. Cohen, V.I., Rzeszotarski, W.J., Gibson, R.E., Fan, L.H., Reba, R.C. Journal of pharmaceutical sciences. (1989) [Pubmed]
  20. Specific inactivation of lysosomal glycosidases in living fibroblasts by the corresponding glycosylmethyl-p-nitrophenyltriazenes. Van Diggelen, O.P., Galjaard, H., Sinnott, M.L., Smith, P.J. Biochem. J. (1980) [Pubmed]
  21. Mutation of the mismatch repair gene hMSH2 and hMSH6 in a human T-cell leukemia line tolerant to methylating agents. Levati, L., Marra, G., Lettieri, T., D'Atri, S., Vernole, P., Tentori, L., Lacal, P.M., Pagani, E., Bonmassar, E., Jiricny, J., Graziani, G. Genes Chromosomes Cancer (1998) [Pubmed]
  22. Drug-mediated changes in the susceptibility of human lymphoblastoid B cells to NK-mediated cytolysis: studies with a triazene compound. D'Atri, S., Bonmassar, L., Turriziani, M., Giuliani, A. Journal of chemotherapy (Florence, Italy) (1994) [Pubmed]
  23. Metabolism of 1,3-di-(4-[N-(4,6-dimethyl-2-pyrimidinyl)sulphamoyl] phenyl)triazene (DDPSPT) in the rat. Paulson, G.D., Feil, V.J., McDonald, J.J. Xenobiotica (1990) [Pubmed]
  24. Ear malformations in the mouse embryo following maternal administration of triazene, with clinical implications. Louryan, S., Heymans, O., Goffard, J.C. Surgical and radiologic anatomy : SRA. (1995) [Pubmed]
  25. Evidence for an unstable DNA adduct from N-nitroso-N-methylaniline. Koepke, S.R., Kroeger-Koepke, M.B., Michejda, C.J. Chem. Res. Toxicol. (1990) [Pubmed]
  26. Cyclization of 1-(2-alkynylphenyl)-3,3-dialkyltriazenes: a convenient, high-yield synthesis of substituted cinnolines and isoindazoles. Kimball, D.B., Weakley, T.J., Haley, M.M. J. Org. Chem. (2002) [Pubmed]
  27. Formation of triazene from sulphonamide and nitrite in acidic solution. Haraguchi, K., Masuda, Y. Food Chem. Toxicol. (1986) [Pubmed]
  28. Modulating effect of new potential antimelanomic agents, spin-labeled triazenes and nitrosoureas on the DOPA-oxidase activity of tyrosinase. Gadjeva, V., Zheleva, A., Raikova, E. Cancer Biochem. Biophys. (1999) [Pubmed]
  29. O(6)-(4-Bromothenyl)guanine (PaTrin-2), a novel inhibitor of O(6)-alkylguanine DNA alkyl-transferase, increases the inhibitory activity of temozolomide against human acute leukaemia cells in vitro. Turriziani, M., Caporaso, P., Bonmassar, L., Buccisano, F., Amadori, S., Venditti, A., Cantonetti, M., D'Atri, S., Bonmassar, E. Pharmacol. Res. (2006) [Pubmed]
  30. Structural studies on bioactive compounds. 28. Selective activity of triazenyl-substituted pyrimethamine derivatives against Pneumocystis carinii dihydrofolate reductase. Stevens, M.F., Phillip, K.S., Rathbone, D.L., O'Shea, D.M., Queener, S.F., Schwalbe, C.H., Lambert, P.A. J. Med. Chem. (1997) [Pubmed]
  31. Triazene metabolism. III. In vitro cytotoxicity towards M21 cells and in vivo antitumour activity of the proposed metabolites of the antitumour 1-aryl-3,3-dimethyltriazenes. Kohlsmith, D.J., Vaughan, K., Luner, S.J. Can. J. Physiol. Pharmacol. (1984) [Pubmed]
  32. Active-site-directed inactivation of Aspergillus oryzae beta-galactosidase with beta-D-galactopyranosylmethyl-p-nitrophenyltriazene. Mega, T., Nishijima, T., Ikenaka, T. J. Biochem. (1990) [Pubmed]
  33. 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. Neidle, S., Wilman, D.E. Acta Crystallogr., B (1992) [Pubmed]
  34. In vivo autoradiography of radioiodinated (R)-3-quinuclidinyl (S)-4-iodobenzilate [(R, S)-IQNB] and (R)-3-quinuclidinyl (R)-4-iodobenzilate [(R,R)-IQNB]. Comparison of the radiolabelled products of a novel tributylstannyl precursor with those of the established triazene and exchange methods. Sood, V.K., Lee, K.S., Boulay, S.F., Rayeq, M.R., McRee, R.C., Cohen, E.I., Zeeberg, B.R., He, X.S., Weinberger, D.R., Rice, K., Reba, R.C. Applied radiation and isotopes : including data, instrumentation and methods for use in agriculture, industry and medicine. (1997) [Pubmed]
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