tetranitromethane

Summary

Summary: Corrosive oxidant, explosive; additive to diesel and rocket fuels; causes skin and lung irritation; proposed war gas. A useful reagent for studying the modification of specific amino acids, particularly tyrosine residues in proteins. Has also been used for studying carbanion formation and for detecting the presence of double bonds in organic compounds.

Top Publications

  1. Ploug M, Rahbek Nielsen H, Ellis V, Roepstorff P, Danø K. Chemical modification of the urokinase-type plasminogen activator and its receptor using tetranitromethane. Evidence for the involvement of specific tyrosine residues in both molecules during receptor-ligand interaction. Biochemistry. 1995;34:12524-34 pubmed
    ..quot;protein-protein footprinting" study on preformed uPAR-GFD complexes by chemical modification with tetranitromethane. All six tyrosine residues in uPAR and the single tyrosine residue in GFD (Tyr24) were susceptible to ..
  2. Weinberg R. Exposure and electronic interaction of tyrosine and tryptophan residues in human apolipoprotein A-IV. Biochemistry. 1988;27:1515-21 pubmed
    ..Fluorescence studies of tetranitromethane-modified apo A-IV suggested that a significant fraction of energy transfer proceeds from the exposed ..
  3. Medda R, Padiglia A, Pedersen J, Floris G. Evidence for alpha-proton abstraction and carbanion formation involving a functional histidine residue in lentil seedling amine oxidase. Biochem Biophys Res Commun. 1993;196:1349-55 pubmed
    Lentil seedling amine oxidase catalyzes the oxidation of putrescine and in the presence of tetranitromethane gives rise to the formation of nitroform anion...
  4. McCall M, Easterbrook Smith S. Comparison of the role of tyrosine residues in human IgG and rabbit IgG in binding of complement subcomponent C1q. Biochem J. 1989;257:845-51 pubmed
    Treatment of covalently cross-linked or heat-aggregated oligomers of human IgG with 4 mM-tetranitromethane abrogated their C1q-binding activity...
  5. Li W, Wang Y. Photodegradation mechanism of two dyes: the influence of adsorption behavior on the novel TiO2 particles. J Environ Sci (China). 2004;16:328-31 pubmed
    ..of hvb+ and OH* radical potassium iodide inhibited the degradation of k-2G, free radicals scavenger tetranitromethane inhibited the photodegradation of FG...
  6. Kleinherenbrink Stins M, Schouten D, van der Boom J, Brouwer A, Knook D, van Berkel T. Nitrosylated high density lipoprotein is recognized by a scavenger receptor in rat liver. J Lipid Res. 1989;30:511-20 pubmed
    ..presence of specific recognition sites for high density lipoprotein (HDL) in vivo, HDL was nitrosylated with tetranitromethane and the decay and liver uptake were compared with that of native HDL...
  7. Kuhn D, Aretha C, Geddes T. Peroxynitrite inactivation of tyrosine hydroxylase: mediation by sulfhydryl oxidation, not tyrosine nitration. J Neurosci. 1999;19:10289-94 pubmed
    ..b>Tetranitromethane, which causes sulfhydryl oxidation at pH 6 and 8 but which nitrates tyrosines only at pH 8, inactivated TH ..
  8. Lüthy M, Schenk K, Renaud P. Synthesis of unusual oxime ethers by reaction of tetranitromethane with B-alkylcatecholboranes. Chemistry. 2010;16:10171-7 pubmed publisher
    The reaction of tetranitromethane with B-alkylcatecholboranes leads to the formation of unusual dinitrooxime ethers...
  9. Blanchardie P, Denis M, Orsonneau J, Lustenberger P. Reaction of tyrosyl-modifying reagents with the ligand- and DNA-binding domains of the rabbit liver glucocorticoid receptor. J Steroid Biochem. 1990;36:15-23 pubmed
    ..fluoride, 4-fluorosulfonyl-1-hydroxy-2-naphtoic acid, 7-chloro-4-nitrobenz-2-oxa-1,3-diazole and tetranitromethane on the glucocorticoid receptor from rabbit liver...

More Information

Publications62

  1. Ji Y, Bennett B. Activation of microsomal glutathione s-transferase by peroxynitrite. Mol Pharmacol. 2003;63:136-46 pubmed
    ..Nitration or acetylation of tyrosine residues of the enzyme using tetranitromethane and N-acetylimidazole, respectively, also resulted in increased enzyme activity, providing additional ..
  2. Cool D, Leibach F, Ganapathy V. High-affinity paroxetine binding to the human placental serotonin transporter. Am J Physiol. 1990;259:C196-204 pubmed
    ..Paroxetine inhibited NaCl gradient-dependent serotonin uptake in placental brush-border membrane vesicles both at pH 6.5 and 7.5.(ABSTRACT TRUNCATED AT 250 WORDS) ..
  3. Ma S, Nishikawa M, Yabe Y, Yamashita F, Hashida M. Role of tyrosine and tryptophan in chemically modified serum albumin on its tissue distribution. Biol Pharm Bull. 2006;29:1926-30 pubmed
    ..distribution characteristics, tyrosine (Tyr) or tryptophan (Trp) residues of BSA were chemically modified by tetranitromethane (TNM) and 2-hydroxy-5-nitrobenzyl bromide (HNB), respectively...
  4. Kilsdonk E, Van Gent T, Dorsman A, van Tol A. Binding of modified high density lipoproteins to endothelial cells: relation with cellular cholesterol efflux?. Atherosclerosis. 1992;97:131-42 pubmed
    ..Competition of binding of 5 micrograms apo E-free 125I-labelled HDL3/ml by unlabelled DMS-HDL3 and tetranitromethane-treated HDL3 (TNM-HDL3) was very poor, whereas unlabelled native HDL3 competed very effectively with 125I-..
  5. Lanzillo J, Dasarathy Y, Fanburg B. Amino acid residues essential for catalysis by peptidyl dipeptidase-4 from Pseudomonas maltophilia. Biochem Biophys Res Commun. 1989;158:45-51 pubmed
    ..Treatment with either tetranitromethane or N-acetylimidazole abolished catalytic activity...
  6. Haddad I, Zhu S, Ischiropoulos H, Matalon S. Nitration of surfactant protein A results in decreased ability to aggregate lipids. Am J Physiol. 1996;270:L281-8 pubmed
    ..SP-A was treated with various concentrations of tetranitromethane (TNM) at pH 6, 7.4, 8, or 10. Depending on the pH, TNM acts either as a nitrating (pH > or = 7...
  7. Morag E, Bayer E, Wilchek M. Reversibility of biotin-binding by selective modification of tyrosine in avidin. Biochem J. 1996;316 ( Pt 1):193-9 pubmed
  8. Guo L, Phillips A, Arteca R. Amino acid N-malonyltransferases from mung beans. Action on 1-aminocyclopropane-1-carboxylic acid and D-phenylalanine. J Biol Chem. 1993;268:25389-94 pubmed
    ..The irreversible inhibitors phenylglyoxal and tetranitromethane reduced malonyltransferase activity towards D-phenylalanine to the same extent as that for ACC...
  9. Tawfik D, Chap R, Eshhar Z, Green B. pH on-off switching of antibody-hapten binding by site-specific chemical modification of tyrosine. Protein Eng. 1994;7:431-4 pubmed
    b>Tetranitromethane (TNM) chemically mutates the binding sites of antibodies so that the nitrated antibodies exhibit pH-dependent binding near physiological pH...
  10. Wen L, Miao Z, Qing W. Chemical modification of xylanase from Trichosporon cutaneum shows the presence of carboxyl groups and cysteine residues essential for enzyme activity. J Protein Chem. 1999;18:677-86 pubmed
    ..Reaction of the enzyme with tetranitromethane and N-acetylimidazole did not result in a significant activity loss as a result of modification of tyrosine ..
  11. Batthyany C, Souza J, Duran R, Cassina A, Cerveñansky C, Radi R. Time course and site(s) of cytochrome c tyrosine nitration by peroxynitrite. Biochemistry. 2005;44:8038-46 pubmed
    ..The nitration pattern of cytochrome c in the presence of tetranitromethane (TNM) was comparable to that obtained with peroxynitrite, but with an increased relative nitration yield at ..
  12. Caine J, Macreadie I, Grunewald G, McLeish M. Recombinant human phenylethanolamine N-methyltransferase: overproduction in Escherichia coli, purification, and characterization. Protein Expr Purif. 1996;8:160-6 pubmed
    ..The enzyme could be inhibited by reagents expected to modify cysteine, arginine, tyrosine, and histidine residues, but not by methyl acetimidate, a reagent expected to modify lysine residues. ..
  13. Scholz G, Barritt G, Kwok F. Affinity labelling of the active site of brain phosphatidylinositol 4-kinase with 5'-fluorosulphonylbenzoyl-adenosine. Eur J Biochem. 1992;210:461-6 pubmed
    ..Results obtained from chemical modification experiments, which employed pyridoxal 5'-phosphate and tetranitromethane, are consistent with a catalytically-essential lysine being present within the ATP-binding site of PtdIns 4-..
  14. Koffman B, Modarress K, Beckerman T, Bashirelahi N. Evidence for involvement of tyrosine in estradiol binding by rat uterus estrogen receptor. J Steroid Biochem Mol Biol. 1991;38:135-9 pubmed
    ..Chemical modification of rER with reagents such as tetranitromethane (TNM) and N-acetylimidazole (NAcI) inhibited estradiol binding...
  15. Onal A, Lemaire D, Bothe E, Schulte Frohlinde D. Gamma-radiolysis of poly(A) in aqueous solution: efficiency of strand break formation by primary water radicals. Int J Radiat Biol Relat Stud Phys Chem Med. 1988;53:787-96 pubmed
    ..This result is considered to be due to nonhomogeneous reaction kinetics in the above-mentioned competition. The rate constants for the reaction of OH and H with poly(A) have been determined. ..
  16. Hodges G, Young M, Paul T, Ingold K. How should xanthine oxidase-generated superoxide yields be measured?. Free Radic Biol Med. 2000;29:434-41 pubmed
    The rate of formation of superoxide measured by its reduction of tetranitromethane (TNM) and by its reduction of ferric cytochrome c (Fe(III) cc) are in excellent agreement when the superoxide is generated from a simple chemical ..
  17. Plyte S, Kneale G. The role of tyrosine residues in the DNA-binding site of the Pf1 gene 5 protein. Protein Eng. 1991;4:553-60 pubmed
    ..to the DNA-binding activity of the protein, by chemical modification and protection experiments using tetranitromethane. Tyrosines 21, 30 and 55 are surface accessible in the free protein but are protected from modification in ..
  18. Trent M, Worsham L, Ernst Fonberg M. HlyC, the internal protein acyltransferase that activates hemolysin toxin: the role of conserved tyrosine and arginine residues in enzymatic activity as probed by chemical modification and site-directed mutagenesis. Biochemistry. 1999;38:8831-8 pubmed
    ..Under optimum conditions, four separate mutations of the two conserved arginine residues (R24A, R24K, R87A, and R87K) had little effect on acyltransferase activity. ..
  19. Smith S, Huang W, Chancy C, Ganapathy V. Regulation of the reduced-folate transporter by nitric oxide in cultured human retinal pigment epithelial cells. Biochem Biophys Res Commun. 1999;257:279-83 pubmed
    ..These studies suggest that NO produced during retinal disease may affect the function of RFT in adjacent RPE cells. ..
  20. Prozorovski V, Krook M, Atrian S, Gonzalez Duarte R, Jornvall H. Identification of reactive tyrosine residues in cysteine-reactive dehydrogenases. Differences between liver sorbitol, liver alcohol and Drosophila alcohol dehydrogenases. FEBS Lett. 1992;304:46-50 pubmed
    Modification of tyrosine residues with tetranitromethane and reversible sulphite protection of cysteine residues were tested on three dehydrogenases of two families...
  21. Ambler R. The amino acid sequence of Staphylococcus aureus penicillinase. Biochem J. 1975;151:197-218 pubmed
    ..K., from whom copies may be obtained on the terms given in Biochem. J. (1975) 145, 5. ..
  22. Miyagi M, Sakaguchi H, Darrow R, Yan L, West K, Aulak K, et al. Evidence that light modulates protein nitration in rat retina. Mol Cell Proteomics. 2002;1:293-303 pubmed
    ..Quantitative liquid chromatography MS/MS analyses with tetranitromethane-modified albumin demonstrated the approach capable of identifying sites of tyrosine nitration with detection ..
  23. Kuhn D, Geddes T. Molecular footprints of neurotoxic amphetamine action. Ann N Y Acad Sci. 2000;914:92-103 pubmed
    ..Protein-bound ROS or RNS may serve as molecular footprints of neurotoxic amphetamine action. ..
  24. Pavlenko A, Moroz S, Glazunov V, Vakorina T, Belogortseva N, Odinokov S, et al. Trophoblast-specific beta 1-glycoprotein: its spatial structure and localization of antigenic determinants. Tumour Biol. 1988;9:249-62 pubmed
    ..The antigenic determinants seemed to include a tryptophan residue. ..
  25. Samejima T, Tamagawa Y, Kondo Y, Hachimori A, Kaji H, Takeda A, et al. Chemical modifications of histidyl and tyrosyl residues of inorganic pyrophosphatase from Escherichia coli. J Biochem. 1988;103:766-72 pubmed
    Chemical modifications by photooxidation in the presence of rose bengal (RB) and with tetranitromethane (TNM) were carried out to elucidate the amino acid residues involved in the active site of inorganic pyrophosphatase (pyrophosphate ..
  26. Ramilo C, Braus G, Evans J. A tyrosine residue is involved in the allosteric binding of tryptophan to yeast chorismate mutase. Biochim Biophys Acta. 1993;1203:71-6 pubmed
    ..in tryptophan binding was tested by modification of tyrosine in yeast chorismate mutase by nitration with tetranitromethane. All forms of the enzyme exhibited an approx...
  27. Lundblad R, Noyes C, Featherstone G, Harrison J, Jenzano J. The reaction of bovine alpha-thrombin with tetranitromethane. Characterization of the modified protein. J Biol Chem. 1988;263:3729-34 pubmed
    Previous studies from several laboratories have shown that thrombin is inactivated by tetranitromethane with the formation of nitrotyrosine...
  28. Vertessy B, Persson R, Rosengren A, Zeppezauer M, Nyman P. Specific derivatization of the active site tyrosine in dUTPase perturbs ligand binding to the active site. Biochem Biophys Res Commun. 1996;219:294-300 pubmed
    ..coli dUTPase becomes impaired as shown by circular dichroism spectroscopy, here presented as a tool for monitoring ligand binding to the active site. ..
  29. Cymes G, Wolfenstein Todel C. Identification of a tyrosine residue in ovine placental lactogen as essential for its binding to receptors. Biochim Biophys Acta. 1996;1294:31-6 pubmed
    Nitration of ovine placental lactogen (oPL) with a 10-fold molar excess of tetranitromethane over protein content resulted in the modification of 0.8 tyrosine residue...
  30. Robertson D, Hilton S, Wong K, Koepke A, Buckley J. Influence of active site and tyrosine modification on the secretion and activity of the Aeromonas hydrophila lipase/acyltransferase. J Biol Chem. 1994;269:2146-50 pubmed
    ..Reaction of the enzyme with tetranitromethane led to modification of 2 tyrosines and a nearly 80% decline in enzyme activity...
  31. Yamanaka K, Muramatsu I, Kigoshi S. Tetranitromethane modification of the muscarinic receptors in bovine adrenal medulla. Jpn J Pharmacol. 1988;48:67-76 pubmed
    Muscarinic receptor binding was examined in bovine adrenal medullary microsomes following exposure to tetranitromethane (TNM) that modifies tyrosine and cysteine residues in proteins...
  32. Amano K, Fujihashi M, Ando A, Miki K, Nagata Y. Involvement of tyrosines at fucose-binding sites of Aleuria aurantia lectin: non-equal response to site-directed mutagenesis among five sites. Biosci Biotechnol Biochem. 2004;68:841-7 pubmed
    ..of Aleuria aurantia lectin (AAL) was proved by chemical modification using the Tyr-specific reagent tetranitromethane, site-directed mutagenesis was attempted...
  33. Asker E, Masnovi J. Charge-transfer complexations of 1,n-di(9-ethylcarbazol-3-yl)alkanes with tetracyanoethylene and tetranitromethane. Spectrochim Acta A Mol Biomol Spectrosc. 2009;71:1973-8 pubmed publisher
    ..to examine their complexation behaviors with the electron acceptors tetracyanoethylene (TCNE) and tetranitromethane (TNM)...
  34. Stratilova E, Dzúrovä M, Markovic O, Jornvall H. An essential tyrosine residue of Aspergillus polygalacturonase. FEBS Lett. 1996;382:164-6 pubmed
    ..of the proteins with all tyrosine-reactive agents tested, acetic anhydride, N-acetyl imidazole, and tetranitromethane. Furthermore, after acetylation, regeneration of enzyme activity was possible with hydroxylamine...
  35. Rauchova H, Beleznai Z, Drahota Z. Effect of chemical modification in situ on L-glycerol-3-phosphate dehydrogenase in brown adipose tissue mitochondria. J Bioenerg Biomembr. 1988;20:623-32 pubmed
    ..The SH-modifying reagents have only slight effect on the enzyme activity. The most effective chemicals were tetranitromethane and diazobenzene sulfonic acid. The enzyme activity can be abolished completely by both of them...
  36. Uversky V, Yamin G, Munishkina L, Karymov M, Millett I, Doniach S, et al. Effects of nitration on the structure and aggregation of alpha-synuclein. Brain Res Mol Brain Res. 2005;134:84-102 pubmed
    ..The addition of nitrated alpha-synuclein inhibited fibrillation of non-modified alpha-synuclein at neutral pH. Potential implications of these findings to the etiology of Parkinson's disease are discussed. ..
  37. Fang J, Zhang B, Chen N, Asai H. Chemical modification of glycerinated stalks shows tyrosine residues essential for spasmoneme contraction of Vorticella sp. Zoolog Sci. 2004;21:527-32 pubmed
    ..b>Tetranitromethane (TNM) is often employed as a specific reagent for the nitration of tyrosine residues in a protein at neutral ..
  38. Negrerie M, Martin J, Nghiêm H. Functionality of nitrated acetylcholine receptor: the two-step formation of nitrotyrosines reveals their differential role in effectors binding. FEBS Lett. 2005;579:2643-7 pubmed
    ..The presence of carbamylcholine in the agonist site prevented the effect of nitration by tetranitromethane in some conditions...
  39. Ohshima H, Friesen M, Brouet I, Bartsch H. Nitrotyrosine as a new marker for endogenous nitrosation and nitration of proteins. Food Chem Toxicol. 1990;28:647-52 pubmed
    ..5-2.5 mumol/rat) of tetranitromethane. Major urinary metabolites of NTYR, given orally to rats, were isolated and identified as 3-nitro-4-..
  40. el Kebbaj M, Latruffe N. Chemical reagents of polypeptides side chain: relationships between solubility properties and ability to cross the inner mitochondrial membrane. Cell Mol Biol (Noisy-le-grand). 1994;40:781-6 pubmed
    ..The knowledge of the properties of these reagents can be very useful to locate strategic aminoacid residues in important biological functions. ..
  41. Hodges G, Ingold K. Superoxide, amine buffers and tetranitromethane: a novel free radical chain reaction. Free Radic Res. 2000;33:547-50 pubmed
    The amine buffer Tris slowly reduces tetranitromethane (TNM) to the nitroform anion in a non-accelerating reaction...
  42. Vertessy B, Zalud P, Nyman P, Zeppezauer M. Identification of tyrosine as a functional residue in the active site of Escherichia coli dUTPase. Biochim Biophys Acta. 1994;1205:146-50 pubmed
    ..About half of them were found to be susceptible to acetylation with N-acetylimidazole or to nitration with tetranitromethane with concomitant loss of activity. Deacetylation with N-hydroxylamine leads to full reactivation...
  43. Liochev S, Fridovich I. Reversal of the superoxide dismutase reaction revisited. Free Radic Biol Med. 2003;34:908-10 pubmed
    Reversal of the superoxide dismutase (SOD) reaction was measured in terms of the reduction of tetranitromethane (TNM) by O2-. Cu,ZnSOD caused a biphasic reduction of TNM by H2O2...
  44. Yamin G, Uversky V, Fink A. Nitration inhibits fibrillation of human alpha-synuclein in vitro by formation of soluble oligomers. FEBS Lett. 2003;542:147-52 pubmed
    ..These observations suggest that nitration of soluble alpha-synuclein may be a protective factor in PD, rather than a causative one. ..
  45. ten Have R, Franssen M, Field J. Lignin peroxidase initiates O2-dependent self-propagating chemical reactions which accelerate the consumption of 1-(3',4'-dimethoxyphenyl)propene. Biochem J. 2000;347:585-91 pubmed
    ..Secondly, O(2) can prevent coupling reactions by lowering the pool of carbon-centred radicals accumulating during LiP catalysis. ..
  46. Santrucek J, Strohalm M, Kadlcik V, Hynek R, Kodicek M. Tyrosine residues modification studied by MALDI-TOF mass spectrometry. Biochem Biophys Res Commun. 2004;323:1151-6 pubmed
    ..of three model proteins with known spatial structure are modified with two tyrosine-specific reagents: tetranitromethane and iodine...
  47. Hajjou M, Le Gal Y. Catalytic site studies on tuna (Thunnus albacares) pyloric caeca aminopeptidase. Biochim Biophys Acta. 1995;1251:139-44 pubmed
    ..catalytic site of most metalloproteinases, tAP is reversibly inhibited by phenylglyoxal and inactivated by tetranitromethane in a time-dependent fashion...
  48. Maruyama T, Lin C, Yamasaki K, Miyoshi T, Imai T, Yamasaki M, et al. Binding of suprofen to human serum albumin. Role of the suprofen carboxyl group. Biochem Pharmacol. 1993;45:1017-26 pubmed
    ..The binding of SP and SPM is independent of conformational changes on HSA that accompany N-B transition. There is evidence that the carboxyl group may play a crucial role in the high affinity binding processes of SP to HSA...
  49. Woody M, DasGupta B. Effect of tetranitromethane on the biological activities of botulinum neurotoxin types A, B and E. Mol Cell Biochem. 1989;85:159-69 pubmed
    Botulinum neurotoxin serotypes A, B and E were modified at pH 7.9 with tetranitromethane, a reagent highly specific for tyrosine residues...
  50. Zhang J, Mine Y. Characterization of residues in human IgE and IgG binding site by chemical modification of ovomucoid third domain. Biochem Biophys Res Commun. 1999;261:610-3 pubmed
    ..These results suggest that hydrophilic residues appear to be more critical for human IgG binding site, whereas hydrophobic residues may be more important for IgG binding site. ..
  51. Capeillere Blandin C. Oxidation of guaiacol by myeloperoxidase: a two-electron-oxidized guaiacol transient species as a mediator of NADPH oxidation. Biochem J. 1998;336 ( Pt 2):395-404 pubmed
  52. Anderson P, Johnson W, Korte J, Xiong X, Sung Y, Fuchs J. Reversible dissociation of active octamer of cyanase to inactive dimer promoted by alteration of the sulfhydryl group. J Biol Chem. 1988;263:5674-80 pubmed
    ..b>Tetranitromethane, methyl methanethiosulfonate, N-ethylmaleimide, and Hg2+ all reacted with the sulfhydryl group to give ..
  53. Singh J, Sonnenfeld G, Doyle R. Tetranitromethane as a surface antiviral disinfectant. Antiviral Res. 1994;25:281-5 pubmed
    b>Tetranitromethane, a protein nitrating agent, was tested for its ability to disinfect surfaces from viruses...