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Chemical Compound Review

Diazene     diazene

Synonyms: Diimide, Diimine, Diazene, cis, AG-F-25962, CHEBI:30096, ...
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Disease relevance of diazene


High impact information on diazene

  • The nanoparticles consist of an organic photoisomerizable dye, spiropyran, as an optically responsive component and another fluorescent dye, perylene diimide, as a high-energy emitter [2].
  • The absorption band of the merocyanine matches well the fluorescence bands of perylene diimide (at 535 and 575 nm), and therefore fluorescence resonance energy transfer (FRET) converts the high-energy green emission of the perylene into low-energy red emission when the merocyanine form is present [2].
  • Flavin-catalyzed generation of diimide: an environmentally friendly method for the aerobic hydrogenation of olefins [3].
  • We tested the following design criteria: (i) binding of the diazene and subsequent reactive diyl to the DNA, (ii) sequence selectivity in the ligand binding and (iii) prevention of diyl dimerization [4].
  • RESULTS: 1H-NMR structural studies of Compound 1 bound to d(CGGTACCG)(2) confirmed a threading mode of intercalation, with four base pairs between the diimide units [5].

Biological context of diazene

  • Stopped-flow kinetics experiments demonstrate that the diimide both associates and dissociates from DNA more slowly than classical intercalators with similar binding constants [6].
  • Reduction and de-excitation then yield the corresponding diazene complex; its generation represents the essential step in a nitrogen fixation and reduction protocol [7].
  • The structure-activity relationships among three noncyclic diimide ionophores, designed to be Li+ carriers, were studied in lipid bilayer membranes [8].
  • There was no cleavage of caspase-3 in RL-337-treated samples, and the majority of cells died 6 h after the treatment through necrosis (previously, apoptosis-like cell death was detected for diazene JK-279) [9].
  • The binding affinities of N-[3-(dimethylamino)propyl amine]-1,8-naphthalenedicarboxylic imide (N-DMPrNI) and N,N'-bis [3,3'-(dimethylamino)propylamine]-naphthalene-1,4,5,8-tetracarboxylic diimide (N-BDMPrNDI) for natural DNAs of differing base composition were determined spectroscopically and by equilibrium dialysis [10].

Anatomical context of diazene


Associations of diazene with other chemical compounds

  • Herein we report the synthesis, intercalating properties, and analytical applications of an imidazole-substituted naphthalene diimide, N,N'-bis(3-propylimidazole)-1,4,5,8-naphthalene diimide (PIND), functionalized with electrocatalytic redox moieties [15].
  • A similar diazene to iron charge-transfer band is found following the reaction of diazene with ferric horseradish peroxidase and with hemin chloride but not with met-myoglobin [16].
  • The bisporphyrin host ZnH was synthesized, and its complexation with two aromatic diimide guest molecules, bis(pyridyl)naphthalenediimide NIN and bis(pyridyl)phenyldiimide PIN, was investigated by (1)H NMR and UV/Vis spectroscopy [17].
  • These titrations show that 1,4,5,8-naphthalenetetracarboxylic diimide and 1,5-dinitronaphthalene derivatives are weaker pi-acceptors than viologens, which make good pi-acceptor cyclophanes [18].
  • Immobilization of glucoamylase by adsorption, glutaraldehyde crosslinking, and covalent attachment to carbon activated by water-soluble diimide or diazotization have been examined [19].

Gene context of diazene

  • Inhibition of unwinding of G-quadruplex structures by Sgs1 helicase in the presence of N,N'-bis[2-(1-piperidino)ethyl]-3,4,9,10-perylenetetracarboxylic diimide, a G-quadruplex-interactive ligand [20].
  • Flow cytometry analysis showed that diazene JK-279 induces G(2)/M phase arrest, mediated by the increase in p21 expression, and accompanied by an alteration in the expression of survivin [21].
  • Electrochemical telomerase assay with ferrocenylnaphthalene diimide as a tetraplex DNA-specific binder [22].
  • By means of scanning tunneling microscopy (STM), the self-assembly of two organic donor-acceptor-donor triads (donor=oligo(p-phenylene vinylene) (OPV); acceptor=perylene diimide (PDI)) and their mixtures has been investigated at the liquid/solid interface [23].
  • Diazene reacts rapidly with cytochrome c oxidase to reduce cytochrome a and CuA and to form a charge-transfer complex with ferric cytochrome a3; the diazene may serve to bridge the heme iron of this cytochrome and CuB [16].

Analytical, diagnostic and therapeutic context of diazene


  1. Reduction of cyclic and acyclic diazene derivates by Azotobacter vinelandii nitrogenase: diazirine and trans-dimethyldiazene. McKenna, C.E., Simeonov, A.M., Eran, H., Bravo-Leerabhandh, M. Biochemistry (1996) [Pubmed]
  2. Reversibly photoswitchable dual-color fluorescent nanoparticles as new tools for live-cell imaging. Zhu, L., Wu, W., Zhu, M.Q., Han, J.J., Hurst, J.K., Li, A.D. J. Am. Chem. Soc. (2007) [Pubmed]
  3. Flavin-catalyzed generation of diimide: an environmentally friendly method for the aerobic hydrogenation of olefins. Imada, Y., Iida, H., Naota, T. J. Am. Chem. Soc. (2005) [Pubmed]
  4. The binding modes of a rationally designed photoactivated DNA nuclease determined by NMR. Spielmann, H.P., Fagan, P.A., Bregant, T.M., Little, R.D., Wemmer, D.E. Nucleic Acids Res. (1995) [Pubmed]
  5. Peptide bis-intercalator binds DNA via threading mode with sequence specific contacts in the major groove. Guelev, V., Lee, J., Ward, J., Sorey, S., Hoffman, D.W., Iverson, B.L. Chem. Biol. (2001) [Pubmed]
  6. Kinetic and equilibrium analysis of a threading intercalation mode: DNA sequence and ion effects. Tanious, F.A., Yen, S.F., Wilson, W.D. Biochemistry (1991) [Pubmed]
  7. A photochemical activation scheme of inert dinitrogen by dinuclear Ru(II) and Fe(II) complexes. Reiher, M., Kirchner, B., Hutter, J., Sellmann, D., Hess, B.A. Chemistry (Weinheim an der Bergstrasse, Germany) (2004) [Pubmed]
  8. Structure-activity relationships among noncyclic dicarboxamide Li(+)-selective carriers studied in lipid bilayer membranes. Zeevi, A., Margalit, R. Arch. Biochem. Biophys. (1992) [Pubmed]
  9. Structurally similar diazenes exhibit significantly different biological activity. Jakopec, S., Dubravcic, K., Brozovic, A., Polanc, S., Osmak, M. Cell Biol. Toxicol. (2006) [Pubmed]
  10. Selective DNA binding of (N-alkylamine)-substituted naphthalene imides and diimides to G+C-rich DNA. Liu, Z.R., Hecker, K.H., Rill, R.L. J. Biomol. Struct. Dyn. (1996) [Pubmed]
  11. DNA sensing on a DNA probe-modified electrode using ferrocenylnaphthalene diimide as the electrochemically active ligand. Takenaka, S., Yamashita, K., Takagi, M., Uto, Y., Kondo, H. Anal. Chem. (2000) [Pubmed]
  12. Effect of thioloxidant diazene dicarboxylic acid bis-(N'-methylpiperazide) (DIP) on 45Ca2+ net uptake into rat pancreatic islets. Ammon, H.P., Kühner, W., Youssif, N. Cell Calcium (1986) [Pubmed]
  13. Glutathione. X. Human erythrocyte membrane diffusion coefficients for diazene derivatives of the DIP series via intracellular thiol oxidation. Kosower, N.S., Kosower, E.M., Saltoun, G., Levi, L. Biochem. Biophys. Res. Commun. (1975) [Pubmed]
  14. The synthesis and screening of 1,4,5,8-naphthalenetetracarboxylic diimide-peptide conjugates with antibacterial activity. Miller, C.T., Weragoda, R., Izbicka, E., Iverson, B.L. Bioorg. Med. Chem. (2001) [Pubmed]
  15. Direct detection of DNA with an electrocatalytic threading intercalator. Tansil, N.C., Xie, H., Xie, F., Gao, Z. Anal. Chem. (2005) [Pubmed]
  16. Diazene--a not so innocent ligand for the binuclear center of cytochrome c oxidase. Liao, G.L., Palmer, G. Biochemistry (1998) [Pubmed]
  17. Photoinduced electron transfer in bisporphyrin-diimide complexes. Flamigni, L., Johnston, M.R., Giribabu, L. Chemistry (Weinheim an der Bergstrasse, Germany) (2002) [Pubmed]
  18. Modular synthesis of pi-acceptor cyclophanes derived from 1,4,5,8-naphthalenetetracarboxylic diimide and 1,5-dinitronaphthalene. Chen, G., Lean, J.T., Alcalá, M., Mallouk, T.E. J. Org. Chem. (2001) [Pubmed]
  19. Immobilization of enzymes on activated carbon: selection and preparation of the carbon support. Cho, Y.K., Bailey, J.E. Biotechnol. Bioeng. (1979) [Pubmed]
  20. Inhibition of unwinding of G-quadruplex structures by Sgs1 helicase in the presence of N,N'-bis[2-(1-piperidino)ethyl]-3,4,9,10-perylenetetracarboxylic diimide, a G-quadruplex-interactive ligand. Han, H., Bennett, R.J., Hurley, L.H. Biochemistry (2000) [Pubmed]
  21. Diazene JK-279 induces apoptosis-like cell death in human cervical carcinoma cells. Jakopec, S., Dubravcic, K., Polanc, S., Kosmrlj, J., Osmak, M. Toxicology in vitro : an international journal published in association with BIBRA. (2006) [Pubmed]
  22. Electrochemical telomerase assay with ferrocenylnaphthalene diimide as a tetraplex DNA-specific binder. Sato, S., Kondo, H., Nojima, T., Takenaka, S. Anal. Chem. (2005) [Pubmed]
  23. Scanning tunneling microscopy and spectroscopy of donor-acceptor-donor triads at the liquid/solid interface. Uji-I, H., Miura, A., Schenning, A., Meijer, E.W., Chen, Z., Würthner, F., De Schryver, F.C., Van der Auweraer, M., De Feyter, S. Chemphyschem : a European journal of chemical physics and physical chemistry. (2005) [Pubmed]
  24. Metal-catalyzed anaerobic disproportionation of hydroxylamine. Role of diazene and nitroxyl intermediates in the formation of N2, N2O, NO+, and NH3. Alluisetti, G.E., Almaraz, A.E., Amorebieta, V.T., Doctorovich, F., Olabe, J.A. J. Am. Chem. Soc. (2004) [Pubmed]
  25. Evaluation of binding of perylene diimide and benzannulated perylene diimide ligands to DNA by electrospray ionization mass spectrometry. Mazzitelli, C.L., Brodbelt, J.S., Kern, J.T., Rodriguez, M., Kerwin, S.M. J. Am. Soc. Mass Spectrom. (2006) [Pubmed]
  26. Visualization of DNA microarrays by scanning electrochemical microscopy (SECM). Yamashita, K., Takagi, M., Uchida, K., Kondo, H., Shigeori, T. The Analyst. (2001) [Pubmed]
  27. TAS+(Z)-Me3CNSN- and TAS+(E)-Me3SiNSN-: does the anion-cation interaction influence the configuration? Borrmann, T., Zibarev, A.V., Lork, E., Knitter, G., Chen, S.J., Watson, P.G., Cutin, E., Shakirov, M.M., Stohrer, W.D., Mews, R. Inorganic chemistry. (2000) [Pubmed]
  28. Cellular uptake and photocytotoxicity of glycoconjugated chlorins in HeLa cells. Hirohara, S., Obata, M., Ogata, S., Ohtsuki, C., Higashida, S., Ogura, S., Okura, I., Takenaka, M., Ono, H., Sugai, Y., Mikata, Y., Tanihara, M., Yano, S. J. Photochem. Photobiol. B, Biol. (2005) [Pubmed]
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