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Chemical Compound Review

DIMINAZENE     4-[2-(4-carbamimidoylphenyl) iminohydraziny...

Synonyms: Pirocide, berenil, Azidin, Diminazeno, Diminazine, ...
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Disease relevance of DIMINAZENE


High impact information on DIMINAZENE

  • Berenil (4,4'-diazoamino-bis-benzamidine), a parabolic competitive inhibitor of beta-trypsin, was a hyperbolic competitive inhibitor of azo-beta-trypsin [6].
  • After Berenil treatment of terminally infected mice immunocompetence was restored gradually, first to the lymph node cells and subsequently to the spleen cell population [7].
  • We observe that the binding of berenil induces characteristic responses in different helical parameters for the base-pairs around the binding site [8].
  • The technique has been applied to analyse the binding of berenil to the minor groove of a 60 base-pair sequence derived from the tyrT promoter; the results are compared with those obtained by DNAse I and hydroxyl radical footprinting on the same sequence [8].
  • Interaction of berenil with the tyrT DNA sequence studied by footprinting and molecular modelling. Implications for the design of sequence-specific DNA recognition agents [8].

Chemical compound and disease context of DIMINAZENE


Biological context of DIMINAZENE

  • Since there is evidence that Berenil binds preferentially to AT-rich DNA and seems to be involved in inhibition of DNA replication, the following hypothetical model can be proposed [14].
  • The replication of the circular kDNA molecules is discontinuous and involves the synthesis of RNA primers; when Berenil is bound to the AT-rich regions, synthesis of new RNA primers is inhibited and replication is blocked at these points, leading to the accumulation of replicating intermediates with defined branch lengths [14].
  • On binding with berenil, the ribosome is degraded faster by RNase I especially at low Mg++ concentration and its capacity to inhibit RNase I catalysed hydrolysis of ribopolymers is decreased [2].
  • Comparative pharmacokinetics of diminazene in noninfected Boran (Bos indicus) cattle and Boran cattle infected with Trypanosoma congolense [15].
  • (v) Berenil binding unwinds negative supercoils in the pBR322 plasmid, an observation consistent with an intercalative mode of binding to duplex DNA [16].

Anatomical context of DIMINAZENE

  • There is positive cooperativity in the binding of berenil to the ribosome as demonstrated by the equilibrium dialysis [2].
  • Berenil treatment abolished the immune depression against sheep erythrocytes, but did not cure the animals, which relapsed with the development of a new state of immune depression [5].
  • We also used localized spectroscopy to monitor the uptake of diminazene acturate, an antitrypanosomal agent, into compartments of a single living oocyte [17].
  • BALB/c mice infected with Trypanosoma brucei and treated seven days after inoculation with Diminazene aceturate develop polyclonal B-cell stimulation, including production of antibodies to known nephritogenic autoantigens and glomerular disease associated with severe albuminuria [18].
  • In the lymphocytes of heterozygous carriers of the rare autosomal fragile site (16)(q22) an exceptionally high frequency of sister chromatid exchanges was demonstrated at the induced fragile site by means of simultaneous berenil and BrdU treatment of the cultures [19].

Associations of DIMINAZENE with other chemical compounds


Gene context of DIMINAZENE

  • We document two unrelated normal individuals who are homozygotes for the rare fragile site FRA16B and record the patterns of induction of this fragile site with berenil [25].
  • Treatment of mice on day 21 with a subcurative dose of diminazene aceturate (Berenil), a procedure known to induce a mild PTRE, cleared the parasite from the circulation with plasma APP and liver expression of mRNA for IL-6 and TNFalpha returning to the levels in the controls [26].
  • Berenil does not bind within the triplex target sequence, and only one berenil binding sequence downstream of the triplex motif was present within the c-Ki-ras promoter fragment [27].
  • The amidine protons on berenil are also close to the H2 proton of both adenines [28].
  • Competitive electrophoretic mobility shift assays were used to show that berenil, distamycin, and mithramycin, all of which bind in the minor groove, compete with MBP-1 for binding to the MPB-1 binding site [29].

Analytical, diagnostic and therapeutic context of DIMINAZENE


  1. Subcurative chemotherapy and fatal post-treatment reactive encephalopathies in African trypanosomiasis. Hunter, C.A., Jennings, F.W., Adams, J.H., Murray, M., Kennedy, P.G. Lancet (1992) [Pubmed]
  2. The binding of berenil to Escherichia coli ribosome. Sinharay, S., Ali, Z., Burma, D.P. Nucleic Acids Res. (1977) [Pubmed]
  3. Field evaluation of the prophylactic effect of an isometamidium sustained-release device against trypanosomiasis in cattle. Diarra, B., Diall, O., Geerts, S., Kageruka, P., Lemmouchi, Y., Schacht, E., Eisler, M.C., Holmes, P. Antimicrob. Agents Chemother. (1998) [Pubmed]
  4. The trypanocide diminazene aceturate is accumulated predominantly through the TbAT1 purine transporter: additional insights on diamidine resistance in african trypanosomes. de Koning, H.P., Anderson, L.F., Stewart, M., Burchmore, R.J., Wallace, L.J., Barrett, M.P. Antimicrob. Agents Chemother. (2004) [Pubmed]
  5. Immune depression and macroglobulinemia in experimental subchronic trypanosomiasis. Baltz, T., Baltz, D., Giroud, C., Pautrizel, R. Infect. Immun. (1981) [Pubmed]
  6. Tyrosine 151 is part of the substrate activation binding site of bovine trypsin. Identification by covalent labeling with p-diazoniumbenzamidine and kinetic characterization of Tyr-151-(p-benzamidino)-azo-beta-trypsin. Oliveira, M.G., Rogana, E., Rosa, J.C., Reinhold, B.B., Andrade, M.H., Greene, L.J., Mares-Guia, M. J. Biol. Chem. (1993) [Pubmed]
  7. Lymphocyte function in experimental African trypanosomiasis. III. Loss of lymph node cell responsiveness. Wellhausen, S.R., Mansfield, J.M. J. Immunol. (1980) [Pubmed]
  8. Interaction of berenil with the tyrT DNA sequence studied by footprinting and molecular modelling. Implications for the design of sequence-specific DNA recognition agents. Laughton, C.A., Jenkins, T.C., Fox, K.R., Neidle, S. Nucleic Acids Res. (1990) [Pubmed]
  9. Effects of trypanocidal drugs on protein biosynthesis in vitro and in vivo by Trypanosoma cruzi. Gonzalez, N.S., Cazzulo, J.J. Biochem. Pharmacol. (1989) [Pubmed]
  10. Putrescine N-acetyltransferase in Onchocerca volvulus and Ascaris suum, an enzyme which is involved in polyamine degradation and release of N-acetylputrescine. Wittich, R.M., Walter, R.D. Mol. Biochem. Parasitol. (1990) [Pubmed]
  11. Susceptibility of a rodent-adapted strain of Trypanosoma vivax to Berenil, Samorin and Novidium. Arowolo, R.O., Ikede, B.O. Acta Trop. (1977) [Pubmed]
  12. Relapses in dogs experimentally infected with Trypanosoma brucei and treated with diminazene aceturate or isometamidium chloride. Kaggwa, E., Munyua, W.K., Mugera, G.M. Vet. Parasitol. (1988) [Pubmed]
  13. The experimental chemotherapy of leishmaniasis, VI. The development of rodent models for cutaneous infection with L. major and L. mexicana amazonensis. Trotter, E.R., Peters, W., Robinson, B.L. Ann. Trop. Med. Parasitol. (1980) [Pubmed]
  14. Electron-microscopic mapping of AT-rich regions and of E. coli RNA polymerase-binding sites on the circular kinetoplast DNA of Trypanosoma cruzi. Brack, C., Delain, E. J. Cell. Sci. (1975) [Pubmed]
  15. Comparative pharmacokinetics of diminazene in noninfected Boran (Bos indicus) cattle and Boran cattle infected with Trypanosoma congolense. Mamman, M., Aliu, Y.O., Peregrine, A.S. Antimicrob. Agents Chemother. (1993) [Pubmed]
  16. Berenil [1,3-bis(4'-amidinophenyl)triazene] binding to DNA duplexes and to a RNA duplex: evidence for both intercalative and minor groove binding properties. Pilch, D.S., Kirolos, M.A., Liu, X., Plum, G.E., Breslauer, K.J. Biochemistry (1995) [Pubmed]
  17. Subcellular in vivo 1H MR spectroscopy of Xenopus laevis oocytes. Lee, S.C., Cho, J.H., Mietchen, D., Kim, Y.S., Hong, K.S., Lee, C., Kang, D., Park, K.D., Choi, B.S., Cheong, C. Biophys. J. (2006) [Pubmed]
  18. Susceptibility for infection-related glomerulopathy depends on non-MHC genes. van Velthuysen, M.L., Veninga, A., Bruijn, J.A., de Heer, E., Fleuren, G.J. Kidney Int. (1993) [Pubmed]
  19. The fragile site (16)(q22). II. Sister chromatid exchanges. Schmid, M., Feichtinger, W., Haaf, T. Hum. Genet. (1987) [Pubmed]
  20. A theoretical study of the nonintercalative binding of berenil and stilbamidine to double-stranded (dA-dT)n oligomers. Gresh, N., Pullman, B. Mol. Pharmacol. (1984) [Pubmed]
  21. Crystal structure of a berenil-d(CGCAAATTTGCG) complex. An example of drug-DNA recognition based on sequence-dependent structural features. Brown, D.G., Sanderson, M.R., Garman, E., Neidle, S. J. Mol. Biol. (1992) [Pubmed]
  22. In vivo trypanocidal activities of new S-adenosylmethionine decarboxylase inhibitors. Bacchi, C.J., Brun, R., Croft, S.L., Alicea, K., Bühler, Y. Antimicrob. Agents Chemother. (1996) [Pubmed]
  23. Concerted DNA recognition and novel site-specific alkylation by duocarmycin A with distamycin A. Yamamoto, K., Sugiyama, H., Kawanishi, S. Biochemistry (1993) [Pubmed]
  24. Genetic analysis of petite mutants of Saccharomyces cerevisiae: transmissional types. Perlman, P.S. Genetics (1976) [Pubmed]
  25. Homozygotes for FRA16B are normal. Hocking, T., Feichtinger, W., Schmid, M., Haan, E.A., Baker, E., Sutherland, G.R. Chromosome Res. (1999) [Pubmed]
  26. Cytokines and the acute phase response in post-treatment reactive encephalopathy of Trypanosoma brucei brucei infected mice. Eckersall, P.D., Gow, J.W., McComb, C., Bradley, B., Rodgers, J., Murray, M., Kennedy, P.G. Parasitol. Int. (2001) [Pubmed]
  27. Influence of GC and AT specific DNA minor groove binding drugs on intermolecular triplex formation in the human c-Ki-ras promoter. Vigneswaran, N., Mayfield, C.A., Rodu, B., James, R., Kim, H.G., Miller, D.M. Biochemistry (1996) [Pubmed]
  28. Structural analysis of d(GCAATTGC)2 and its complex with berenil by nuclear magnetic resonance spectroscopy. Yoshida, M., Banville, D.L., Shafer, R.H. Biochemistry (1990) [Pubmed]
  29. The c-myc promoter binding protein (MBP-1) and TBP bind simultaneously in the minor groove of the c-myc P2 promoter. Chaudhary, D., Miller, D.M. Biochemistry (1995) [Pubmed]
  30. Suppression of antibody response to Leptospira biflexa and Brucella abortus and recovery from immunosuppression after Berenil treatment. Rurangirwa, F.R., Tabel, H., Losos, G.J., Tizard, I.R. Infect. Immun. (1979) [Pubmed]
  31. Studies in rabbits on the disposition and trypanocidal activity of the anti-trypanosomal drug, diminazene aceturate (Berenil). Gilbert, R.J. Br. J. Pharmacol. (1983) [Pubmed]
  32. Attempts to protect goats against challenge with Trypanosoma vivax by initiation of primary infections with large numbers of metacyclic trypanosomes. Vos, G.J., Moloo, S.K., Nelson, R.T., Gardiner, P.R. Parasitology (1988) [Pubmed]
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