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Chemical Compound Review

Hydrazoate     azide

Synonyms: Azide ion, Azide(1-), CHEMBL79455, AGN-PC-00OW22, CCRIS 1791, ...
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Disease relevance of Azide Bound At Distal Site


High impact information on Azide Bound At Distal Site

  • In the structure of bovine F1-ATPase determined at 1.95-A resolution with crystals grown in the presence of ADP, 5'-adenylyl-imidodiphosphate, and azide, the azide anion interacts with the beta-phosphate of ADP and with residues in the ADP-binding catalytic subunit, betaDP [3].
  • Interactions of azide ion with bovine heart cytochrome c oxidase (CcO) at five redox levels (IV) to (0), obtained by zero to four electron reduction of fully oxidized enzyme CcO(IV), were monitored by infrared and visible/Soret spectra [4].
  • In both enzyme subunits, the azide anion, which is a competitive inhibitor expected to mimic the superoxide binding mode, is observed directly coordinated to the Cu2+ at the place of the metal-bound water molecule, forming an ion pair with the conserved active site residue Arg141 [5].
  • No significant changes were observed in the presence of methyl beta-D-glucoside, but with azide anion the half-life of reactivation was found to be reduced to t1/2 = 20 h [6].
  • These data show that the E461G mutation causes a more than 8000-fold increase in the equilibrium constant for transfer of the beta-D-galactopyranosyl group from beta-galactosidase to azide ion [7].

Biological context of Azide Bound At Distal Site

  • The data suggest a significant stabilization of nonproductive complexes formed by binding of glucose to the galactosylated enzyme. beta-Galactosidase catalyzes the hydrolysis of beta-D-galactopyranosyl azide, but not the synthesis of this compound by reaction of azide ion with the galactosylated enzyme.(ABSTRACT TRUNCATED AT 400 WORDS)[1]
  • 2,3,4,6-Tetra-O-acetyl-beta-D-glucopyranosyl azide is available on large scale from D-glucose by means of a three-step sequence involving acetylation, activation as the glycosyl bromide, and stereospecific displacement with azide anion [8].
  • The pseudo-first-order reaction kinetics with protection by azide ion are consistent with a Type II mechanism mediated by singlet oxygen [9].

Anatomical context of Azide Bound At Distal Site

  • Reaction of cyanide or azide ion with native thyroid peroxidase resulted in the loss of the axial EPR signal within several hours [10].

Associations of Azide Bound At Distal Site with other chemical compounds

  • The mechanism of N-tetrazole ring formation at the distal histidyl imidazole of sperm whale myoglobin (Mb) has been studied by nitrogen-15 (15N) NMR spectroscopy by utilizing 15N-labeled cyanogen bromide (BrCN) and azide ion (N3-) [11].
  • The enzyme binds the substrate-analogue azide (N3-), which displaces one water molecule, with near normal affinity, whereas the enzyme activity with the O2- substrate is reduced to less than 1% of wild-type levels at pH 7 [12].
  • The effects of azide ion, 1,4-diazabicyclo(2.2.2)octane, and superoxide dismutase on photosensitized inactivation of lysozyme in 0.5% Triton X-100 indicate that singlet oxygen is the major inactivating intermediate with a contribution from superoxide [13].
  • Alkaline phosphatase appears to be resistant to free radical attack (particularly to OH radicals) since hydrogen peroxide alone or in presence of ferrous ions did not reduce the enzyme activity and mannitol or azide anion gave no significant protection when alkaline phosphatase was irradiated with Co-60 gamma rays up to 2 K Gy [14].
  • A new high oxidation state Mn(III/IV)(11) carboxylate complex has been prepared and then converted to a Mn(II/III)(25) azide/carboxylate cluster with Me(3)SiN(3); the Mn(25) product is the initial example of a higher oxidation state Mn azide complex not stabilized by any chelate ligands [15].
  • In H(2)O-CHCl(3), the phosphonium borane [ortho-(Mes(2)B)C(6)H(4)(PMePh(2))](+) selectively complexes azide anions to afford ortho-(Mes(2)(N(3))B)C(6)H(4)(PMePh(2)) in which the boron-bound azide anion is stabilized by an interaction with the adjacent phosphorus atom [16].

Gene context of Azide Bound At Distal Site

  • Experiments with certain inhibitors showed that catalase and azide ion strongly inhibited DNA binding, while superoxide dismutase had a slight stimulatory effect on binding [17].
  • Interaction of azide ion with hemin and cytochrome c immobilized on Au and Ag nanoparticles [18].
  • Lignin peroxidases from the wood-rotting fungus Phanerochaete chrysosporium are also inactivated when they catalyze oxidation of azide ion [Tuisel et al. (1991) Arch. Biochem. Biophys. 288, 456-462; DePillis et al. (1990) Arch. Biochem. Biophys. 280, 217-223] [19].
  • The effect of multiple binding of azide, N3-, on the structural and functional properties of ceruloplasmin (CP) has been reinvestigated by means of both spectroscopic and enzymatic techniques [20].

Analytical, diagnostic and therapeutic context of Azide Bound At Distal Site

  • The affinities of the individual subunits in human adult and fetal hemoglobins to azide ion have been determined from the combined analysis of NMR and optical titration data [21].
  • In the azide-inhibited system, reaction of azide anion with H2O2-activated endogenous peroxidase and spin-trapping of the resulting azidyl radical is a convenient monitor of H2O2 production [22].
  • Studies with inhibitors such as catalase, superoxide dismutase and azide ion further suggest that these two related cell cultures metabolize 2-AF in similar manner [23].
  • Application of a new analytical method using gas chromatography and gas chromatography-mass spectrometry for the azide ion to human blood and urine samples of an actual case [24].


  1. Structure-reactivity relationships for beta-galactosidase (Escherichia coli, lac Z). 2. Reactions of the galactosyl-enzyme intermediate with alcohols and azide ion. Richard, J.P., Westerfeld, J.G., Lin, S., Beard, J. Biochemistry (1995) [Pubmed]
  2. Hydrogen ion control of autolysin-dependent functions in Bacillus subtilis. Jolliffe, L.K., Langemeier, S.O., Doyle, R.J. Microbios (1983) [Pubmed]
  3. How azide inhibits ATP hydrolysis by the F-ATPases. Bowler, M.W., Montgomery, M.G., Leslie, A.G., Walker, J.E. Proc. Natl. Acad. Sci. U.S.A. (2006) [Pubmed]
  4. Infrared evidence of azide binding to iron, copper, and non-metal sites in heart cytochrome c oxidase. Yoshikawa, S., Caughey, W.S. J. Biol. Chem. (1992) [Pubmed]
  5. Crystallographic study of azide-inhibited bovine Cu,Zn superoxide dismutase. Djinović-Carugo, K., Polticelli, F., Desideri, A., Rotilio, G., Wilson, K.S., Bolognesi, M. J. Mol. Biol. (1994) [Pubmed]
  6. Mechanism-based inhibition and stereochemistry of glucosinolate hydrolysis by myrosinase. Cottaz, S., Henrissat, B., Driguez, H. Biochemistry (1996) [Pubmed]
  7. Structure-reactivity relationships for beta-galactosidase (Escherichia coli, lac Z). 4. Mechanism for reaction of nucleophiles with the galactosyl-enzyme intermediates of E461G and E461Q beta-galactosidases. Richard, J.P., Huber, R.E., Heo, C., Amyes, T.L., Lin, S. Biochemistry (1996) [Pubmed]
  8. N-glycoside neoglycotrimers from 2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyl azide. Temelkoff, D.P., Zeller, M., Norris, P. Carbohydr. Res. (2006) [Pubmed]
  9. Photosensitization of aqueous model systems by hypericin. Senthil, V., Longworth, J.W., Ghiron, C.A., Grossweiner, L.I. Biochim. Biophys. Acta (1992) [Pubmed]
  10. Electron paramagnetic resonance spectroscopy of thyroid peroxidase. Lukat, G.S., Jabro, M.N., Rodgers, K.R., Goff, H.M. Biochim. Biophys. Acta (1988) [Pubmed]
  11. Modification of the distal histidyl imidazole in myoglobin to N-tetrazole-substituted imidazole and its effects on the heme environmental structure and ligand binding properties. Adachi, S., Morishima, I. Biochemistry (1992) [Pubmed]
  12. Mutation of the metal-bridging proton-donor His63 residue in human Cu, Zn superoxide dismutase. Biochemical and biophysical analysis of the His63-->Cys mutant. Banci, L., Bertini, I., Borsari, M., Viezzoli, M.S., Hallewell, R.A. Eur. J. Biochem. (1995) [Pubmed]
  13. Hypericin photosensitization in aqueous model systems. Senthil, V., Jones, L.R., Senthil, K., Grossweiner, L.I. Photochem. Photobiol. (1994) [Pubmed]
  14. A simple in vitro method to detect singlet oxygen and to compare photodynamic activity using alkaline phosphatase. Yadav, H.S., Jain, V. Indian J. Biochem. Biophys. (1994) [Pubmed]
  15. Azide groups in high oxidation state Mn carboxylate chemistry: a new Mn(11) complex and its conversion to a Mn(25) azide complex with Me(3)SiN(3). Stamatatos, T.C., Vinslava, A., Abboud, K.A., Christou, G. Chem. Commun. (Camb.) (2009) [Pubmed]
  16. Azide ion recognition in water-CHCl(3) using a chelating phosphonium borane as a receptor. Kim, Y., Hudnall, T.W., Bouhadir, G., Bourissou, D., Gabbaï, F.P. Chem. Commun. (Camb.) (2009) [Pubmed]
  17. The covalent binding of acetaminophen to cellular nucleic acids as the result of the respiratory burst of neutrophils derived from the HL-60 cell line. Corbett, M.D., Corbett, B.R., Hannothiaux, M.H., Quintana, S.J. Toxicol. Appl. Pharmacol. (1992) [Pubmed]
  18. Interaction of azide ion with hemin and cytochrome c immobilized on Au and Ag nanoparticles. Tom, R.T., Pradeep, T. Langmuir : the ACS journal of surfaces and colloids. (2005) [Pubmed]
  19. Further studies on the inactivation by sodium azide of lignin peroxidase from Phanerochaete chrysosporium. Tatarko, M., Bumpus, J.A. Arch. Biochem. Biophys. (1997) [Pubmed]
  20. The multifunctional oxidase activity of ceruloplasmin as revealed by anion binding studies. Musci, G., Bellenchi, G.C., Calabrese, L. Eur. J. Biochem. (1999) [Pubmed]
  21. A 1H NMR comparative study of human adult and fetal hemoglobins. Yamamoto, Y., Nagaoka, T. FEBS Lett. (1998) [Pubmed]
  22. Spin trapping of azidyl and hydroxyl radicals in azide-inhibited rat brain submitochondrial particles. Partridge, R.S., Monroe, S.M., Parks, J.K., Johnson, K., Parker, W.D., Eaton, G.R., Eaton, S.S. Arch. Biochem. Biophys. (1994) [Pubmed]
  23. A comparison of the HL-60 cell line and human granulocytes to effect the bioactivation of arylamines and related xenobiotics. The binding of 2-aminofluorene to nucleic acids as the result of the respiratory burst. Corbett, M.D., Hannothiaux, M.H., Corbett, B.R., Quintana, S.J. Chem. Biol. Interact. (1991) [Pubmed]
  24. Application of a new analytical method using gas chromatography and gas chromatography-mass spectrometry for the azide ion to human blood and urine samples of an actual case. Kikuchi, M., Sato, M., Ito, T., Honda, M. J. Chromatogr. B Biomed. Sci. Appl. (2001) [Pubmed]
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