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Chemical Compound Review

hydroxylamine     hydroxylamine

Synonyms: Nitroxide, Azanol, Oxammonium, Oxyammonia, Hydroxyazane, ...
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Disease relevance of hydroxylamine


Psychiatry related information on hydroxylamine


High impact information on hydroxylamine

  • We provide a review of current electron spin resonance (ESR) techniques for studying basic molecular mechanisms in membranes and proteins by using nitroxide spin labels [7].
  • At added LF levels ranging from 4 to 15 micrograms/10(7) PMN there was a dose-dependent reduction in PMN surface charge reaching 4 mV, when the partitioning into the membrane of a charged amphipathic nitroxide spin label was measured by electron spin resonance spectroscopy, whereas transferrin was without effect [8].
  • Erythrocytes were labeled with the nitroxide-substituted analogue of stearic acid, 2-(3-carboxypropyl)-4,4-dimethyl-2-tridecyl-3-oxazolidinyloxyl, and ESR spectra were obtained [9].
  • To identify sites in arrestin involved in receptor interaction, a nitroxide-containing side chain was introduced at each of 28 different positions in visual arrestin, and the dynamics of the side chain was used to monitor arrestin interaction with phosphorylated forms of its cognate receptor, rhodopsin [10].
  • Derivatives of monomeric PLB were synthesized, each of which contained a single spin-labeled 2,2,6,6,-Tetramethyl-piperidine-N-oxyl-4-amino-4-carboxylic acid amino acid, with the nitroxide-containing ring covalently and rigidly attached to the alpha-carbon, providing direct insight into the conformational dynamics of the peptide backbone [11].

Chemical compound and disease context of hydroxylamine


Biological context of hydroxylamine

  • A weak dipolar interaction is detected between the nitroxide and paramagnetic transition ions, indicating this position is approximately 19 A from the nearest high affinity binding site [17].
  • Direct measurement of nitroxide pharmacokinetics in isolated hearts situated in a low-frequency electron spin resonance spectrometer: implications for spin trapping and in vivo oxymetry [18].
  • PSTV was inactivated by ribonuclease digestion, psoralen photoadduct formation, Zn2+ -catalyzed hydrolysis, and chemical modification with NH2OH [19].
  • The use of molecular genetics to introduce both a metal ion binding site and a nitroxide spin label into the same protein opens the use of paramagnetic metalnitroxyl interactions to estimate intramolecular distances in a wide variety of proteins [20].
  • Analysis of the orientation-dependent information thus obtained has clearly shown that the lignad moieties in all 4 respective complexes are accommodated in adjacent base-pair layers of the DNA with the nitroxide reporter oriented in 1 preferential direction [21].

Anatomical context of hydroxylamine


Associations of hydroxylamine with other chemical compounds

  • To investigate the interaction of HA with membranes, two 40-residue, cysteine-substituted peptides comprising the loop region and the first part of the coiled-coil stem were synthesized and modified with a nitroxide spin label [27].
  • To characterize the mechanism by which receptors propagate conformational changes across membranes, nitroxide spin labels were attached at strategic positions in the bacterial aspartate receptor [28].
  • The results indicate that the dismutation of .O2- is catalyzed by the oxoammonium/nitroxide redox couple for carbocyclic nitroxide derivatives [29].
  • The high-field EPR spectra from random dispersions of the cholesterol-containing membranes display very little axial averaging of the nitroxide g-tensor anisotropy for lipids spin labeled toward the carboxyl end of the sn-2 chain (down to the 8-C atom) [30].
  • Thiouridine at position 8 (s4U8) of tRNAf1Met was spin-labeled with the nitroxide free radical, N-(1-oxyl-2,2,5,5-Tetramethyl-3-pyrrolidinyl) bromacetamide, for proton nuclear magnetic resonance spectroscopic studies [31].

Gene context of hydroxylamine

  • We tested this hypothesis by determining whether the well-described nitroxide antioxidant, tempol (4-hydroxy-2,2,6,6-tetramethylpiperidine-N-oxyl), acts as a chemopreventative agent in Atm mutant mice, a model of the human cancer prone syndrome ataxia-telangiectasia [5].
  • Line shape broadening resulting from spin-spin coupling of nitroxide pairs introduced into the membrane-binding helices of PGHS-2 was used to calculate the inter-helical distances and changes in these distances that occur in response to binding various ligands [32].
  • The nitroxide tempol induces oxidative stress, p21(WAF1/CIP1), and cell death in HL60 cells [33].
  • The antiproliferative effect of Tempol, a stable nitroxide free radical, was investigated on the p53-negative human leukemia cell line HL60 [33].
  • The determination of the NMR structure of the sterol carrier protein-2 (SCP2), analysis of backbone (15)N spin relaxation parameters and NMR studies of nitroxide spin-labeled substrate binding are presented as a new basis for investigations of the mode of action of SCP2 [34].

Analytical, diagnostic and therapeutic context of hydroxylamine

  • The boundaries and structures of membrane-embedded domains in integral membrane proteins can be determined by a method based on a combination of site-specific mutagenesis and nitroxide spin labeling [35].
  • Time domain pulsed saturation recovery and electron-electron double resonance spectroscopies were used to measure the spin-lattice relaxation rates of the electron and the nitrogen nucleus in nitroxide spin labels in liquids [36].
  • Cardiac reperfusion damage prevented by a nitroxide free radical [3].
  • Specific IgG antibodies directed against the spin-label nitroxide group present as a lipid hapten in single-compartment lipid vesicles have been visualized by using freeze-etch electron microscopy [37].
  • Experiments were performed using low-frequency (1.3 GHz) in vivo EPR spectroscopy and imaging techniques with a nitroxide redox probe [38].


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  2. Oxidative damage to brain proteins, loss of glutamine synthetase activity, and production of free radicals during ischemia/reperfusion-induced injury to gerbil brain. Oliver, C.N., Starke-Reed, P.E., Stadtman, E.R., Liu, G.J., Carney, J.M., Floyd, R.A. Proc. Natl. Acad. Sci. U.S.A. (1990) [Pubmed]
  3. Cardiac reperfusion damage prevented by a nitroxide free radical. Gelvan, D., Saltman, P., Powell, S.R. Proc. Natl. Acad. Sci. U.S.A. (1991) [Pubmed]
  4. Cancer chemoprevention by the antioxidant tempol acts partially via the p53 tumor suppressor. Erker, L., Schubert, R., Yakushiji, H., Barlow, C., Larson, D., Mitchell, J.B., Wynshaw-Boris, A. Hum. Mol. Genet. (2005) [Pubmed]
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  6. Hydrophobic interactions between spin-label 5-SASL and humic acid as revealed by ESR spectroscopy. Ferreira, J.A., Nascimento, O.R., Martin-Neto, L. Environ. Sci. Technol. (2001) [Pubmed]
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  8. Membrane-bound lactoferrin alters the surface properties of polymorphonuclear leukocytes. Boxer, L.A., Haak, R.A., Yang, H.H., Wolach, J.B., Whitcomb, J.A., Butterick, C.J., Baehner, R.L. J. Clin. Invest. (1982) [Pubmed]
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  10. Differential interaction of spin-labeled arrestin with inactive and active phosphorhodopsin. Hanson, S.M., Francis, D.J., Vishnivetskiy, S.A., Kolobova, E.A., Hubbell, W.L., Klug, C.S., Gurevich, V.V. Proc. Natl. Acad. Sci. U.S.A. (2006) [Pubmed]
  11. Phospholamban structural dynamics in lipid bilayers probed by a spin label rigidly coupled to the peptide backbone. Karim, C.B., Kirby, T.L., Zhang, Z., Nesmelov, Y., Thomas, D.D. Proc. Natl. Acad. Sci. U.S.A. (2004) [Pubmed]
  12. Mössbauer, EPR, and optical studies of the P-460 center of hydroxylamine oxidoreductase from Nitrosomonas. A ferrous heme with an unusually large quadrupole splitting. Andersson, K.K., Kent, T.A., Lipscomb, J.D., Hooper, A.B., Münck, E. J. Biol. Chem. (1984) [Pubmed]
  13. Topography of the prostaglandin endoperoxide h2 synthase-2 in membranes. Mirafzali, Z., Leipprandt, J.R., McCracken, J.L., Dewitt, D.L. J. Biol. Chem. (2006) [Pubmed]
  14. The nitroxide Tempol modulates anthracycline resistance in breast cancer cells. Gariboldi, M.B., Terni, F., Ravizza, R., Meschini, S., Marra, M., Condello, M., Arancia, G., Monti, E. Free Radic. Biol. Med. (2006) [Pubmed]
  15. Base dynamics of nitroxide-labeled thymidine analogues incorporated into (dA-dT)n by DNA polymerase I from Escherichia coli. Pauly, G.T., Thomas, I.E., Bobst, A.M. Biochemistry (1987) [Pubmed]
  16. Nebivolol improves coronary flow reserve in hypertensive patients without coronary heart disease. Galderisi, M., Cicala, S., D'Errico, A., de Divitiis, O., de Simone, G. J. Hypertens. (2004) [Pubmed]
  17. Overexpression, purification, and site-directed spin labeling of the Nramp metal transporter from Mycobacterium leprae. Reeve, I., Hummel, D., Nelson, N., Voss, J., Hummell, D. Proc. Natl. Acad. Sci. U.S.A. (2002) [Pubmed]
  18. Direct measurement of nitroxide pharmacokinetics in isolated hearts situated in a low-frequency electron spin resonance spectrometer: implications for spin trapping and in vivo oxymetry. Rosen, G.M., Halpern, H.J., Brunsting, L.A., Spencer, D.P., Strauss, K.E., Bowman, M.K., Wechsler, A.S. Proc. Natl. Acad. Sci. U.S.A. (1988) [Pubmed]
  19. Viroids and prions. Diener, T.O., McKinley, M.P., Prusiner, S.B. Proc. Natl. Acad. Sci. U.S.A. (1982) [Pubmed]
  20. A method for distance determination in proteins using a designed metal ion binding site and site-directed spin labeling: evaluation with T4 lysozyme. Voss, J., Salwiński, L., Kaback, H.R., Hubbell, W.L. Proc. Natl. Acad. Sci. U.S.A. (1995) [Pubmed]
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  23. Spin trapping evidence for the lack of significant hydroxyl radical production during the respiration burst of human phagocytes using a spin adduct resistant to superoxide-mediated destruction. Britigan, B.E., Coffman, T.J., Buettner, G.R. J. Biol. Chem. (1990) [Pubmed]
  24. Depalmitylation with hydroxylamine alters the functional properties of rhodopsin. Morrison, D.F., O'Brien, P.J., Pepperberg, D.R. J. Biol. Chem. (1991) [Pubmed]
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  28. A piston model for transmembrane signaling of the aspartate receptor. Ottemann, K.M., Xiao, W., Shin, Y.K., Koshland, D.E. Science (1999) [Pubmed]
  29. Oxoammonium cation intermediate in the nitroxide-catalyzed dismutation of superoxide. Krishna, M.C., Grahame, D.A., Samuni, A., Mitchell, J.B., Russo, A. Proc. Natl. Acad. Sci. U.S.A. (1992) [Pubmed]
  30. High-frequency, spin-label EPR of nonaxial lipid ordering and motion in cholesterol-containing membranes. Gaffney, B.J., Marsh, D. Proc. Natl. Acad. Sci. U.S.A. (1998) [Pubmed]
  31. Proton nuclear magnetic resonance of spin-labeled Escherichia coli tRNAf1MET. Daniel, W.E., Cohn, M. Proc. Natl. Acad. Sci. U.S.A. (1975) [Pubmed]
  32. Arachidonic acid and nonsteroidal anti-inflammatory drugs induce conformational changes in the human prostaglandin endoperoxide H2 synthase-2 (cyclooxygenase-2). Smith, T., McCracken, J., Shin, Y.K., DeWitt, D. J. Biol. Chem. (2000) [Pubmed]
  33. The nitroxide tempol induces oxidative stress, p21(WAF1/CIP1), and cell death in HL60 cells. Gariboldi, M.B., Rimoldi, V., Supino, R., Favini, E., Monti, E. Free Radic. Biol. Med. (2000) [Pubmed]
  34. NMR structure of the sterol carrier protein-2: implications for the biological role. García, F.L., Szyperski, T., Dyer, J.H., Choinowski, T., Seedorf, U., Hauser, H., Wüthrich, K. J. Mol. Biol. (2000) [Pubmed]
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  37. Visualization of specific antibody and C1q binding to hapten-sensitized lipid vesicles. Henry, N., Parce, J.W., McConnell, H.M. Proc. Natl. Acad. Sci. U.S.A. (1978) [Pubmed]
  38. Noninvasive imaging of tumor redox status and its modification by tissue glutathione levels. Kuppusamy, P., Li, H., Ilangovan, G., Cardounel, A.J., Zweier, J.L., Yamada, K., Krishna, M.C., Mitchell, J.B. Cancer Res. (2002) [Pubmed]
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