cyclic n oxides


Summary: Heterocyclic compounds in which an oxygen is attached to a cyclic nitrogen.

Top Publications

  1. Trnka J, Blaikie F, Smith R, Murphy M. A mitochondria-targeted nitroxide is reduced to its hydroxylamine by ubiquinol in mitochondria. Free Radic Biol Med. 2008;44:1406-19 pubmed publisher
  2. Ranguelova K, Mason R. New insights into the detection of sulfur trioxide anion radical by spin trapping: radical trapping versus nucleophilic addition. Free Radic Biol Med. 2009;47:128-34 pubmed publisher
    ..1 M and the incubations are for longer times. ..
  3. Simonsen U, Rodriguez Rodriguez R, Dalsgaard T, Buus N, Stankevicius E. Novel approaches to improving endothelium-dependent nitric oxide-mediated vasodilatation. Pharmacol Rep. 2009;61:105-15 pubmed
    ..Thus, all three approaches increase bioavailability of NO in the vascular wall, but it remains to be addressed whether these actions have any direct benefit at a clinical level. ..
  4. Matsumoto K, Hyodo F, Matsumoto A, Koretsky A, Sowers A, Mitchell J, et al. High-resolution mapping of tumor redox status by magnetic resonance imaging using nitroxides as redox-sensitive contrast agents. Clin Cancer Res. 2006;12:2455-62 pubmed
    ..067 min(-1), respectively). This study shows that MRI can be successfully used to co-register tissue redox status along with anatomic images, thus providing potentially valuable biochemical information from the region of interest. ..
  5. Hyodo F, Matsumoto K, Matsumoto A, Mitchell J, Krishna M. Probing the intracellular redox status of tumors with magnetic resonance imaging and redox-sensitive contrast agents. Cancer Res. 2006;66:9921-8 pubmed
  6. Goldstein S, Samuni A. Kinetics and mechanism of peroxyl radical reactions with nitroxides. J Phys Chem A. 2007;111:1066-72 pubmed
    ..The results demonstrate a clear correlation between the kinetic features of the nitroxides and their ability to inhibit biological damage inflicted by peroxyl radicals. ..
  7. Safarian D, Carnec X, Tsamis F, Kajumo F, Dragic T. An anti-CCR5 monoclonal antibody and small molecule CCR5 antagonists synergize by inhibiting different stages of human immunodeficiency virus type 1 entry. Virology. 2006;352:477-84 pubmed
    ..Importantly, our findings suggest that combinations of CCR5 inhibitors with different mechanisms of action will be central to controlling HIV-1 infection and slowing the emergence of resistant strains. ..
  8. Piton N, Mu Y, Stock G, Prisner T, Schiemann O, Engels J. Base-specific spin-labeling of RNA for structure determination. Nucleic Acids Res. 2007;35:3128-43 pubmed
    ..The applicability of the method to more complex biological systems is discussed. ..
  9. de Deus Teixeira L, Bersanetti P, Schreier S, Carmona A, Nakaie C. Analogues containing the paramagnetic amino acid TOAC as substrates for angiotensin I-converting enzyme. FEBS Lett. 2007;581:2411-5 pubmed
    ..In some cases, although substrates and products differ by only two residues, the difference between their EPR spectral lineshapes allows monitoring the enzymatic reaction as a function of time. ..

More Information


  1. Cotrim A, Hyodo F, Matsumoto K, Sowers A, Cook J, Baum B, et al. Differential radiation protection of salivary glands versus tumor by Tempol with accompanying tissue assessment of Tempol by magnetic resonance imaging. Clin Cancer Res. 2007;13:4928-33 pubmed
    ..These data support further development and consideration of Tempol for human clinical trials as a selective protector against radiation-induced salivary gland damage. ..
  2. Marsh D. Orientation of TOAC amino-acid spin labels in alpha-helices and beta-strands. J Magn Reson. 2006;180:305-10 pubmed
    ..The spin-label z-axes of the two mirror-image TOAC twist-boat conformers are inclined at 13+/-2 degrees and 65+/-3 degrees , respectively, to the alpha-helix axis, or at 25+/-3 degrees and 32+/-3 degrees to the beta-strand axis. ..
  3. Bernini A, Spiga O, Ciutti A, Venditti V, Prischi F, Governatori M, et al. NMR studies of BPTI aggregation by using paramagnetic relaxation reagents. Biochim Biophys Acta. 2006;1764:856-62 pubmed
    ..Some of the measured paramagnetic relaxation rates of BPTI protons exhibited a reverse dependence on protein concentration, which can be attributed to the formation of transient BPTI aggregates. ..
  4. Viswanad B, Srinivasan K, Kaul C, Ramarao P. Effect of tempol on altered angiotensin II and acetylcholine-mediated vascular responses in thoracic aorta isolated from rats with insulin resistance. Pharmacol Res. 2006;53:209-15 pubmed
  5. Kusamoto T, Kume S, Nishihara H. Realization of SOMO-HOMO level conversion for a TEMPO-dithiolate ligand by coordination to platinum(II). J Am Chem Soc. 2008;130:13844-5 pubmed publisher
    ..These findings were further supported by an investigation into a one-electron oxidized (tempodt)Pt and related complexes. ..
  6. Dymkowska D, Wojtczak L. Arachidonic acid-induced apoptosis in rat hepatoma AS-30D cells is mediated by reactive oxygen species. Acta Biochim Pol. 2009;56:711-5 pubmed
    ..They also suggest that this effect is due to arachidonic acid as such and not to its mitochondrial oxidative metabolites. ..
  7. Matsumoto K, Okajo A, Nagata K, DeGraff W, Nyui M, Ueno M, et al. Detection of free radical reactions in an aqueous sample induced by low linear-energy-transfer irradiation. Biol Pharm Bull. 2009;32:542-7 pubmed
    ..The extent of the free radical reaction, i.e., formation of reactive oxygen species, in the reaction mixture depended on the radiation energy when an identical dose was given. ..
  8. Durand G, Choteau F, Pucci B, Villamena F. Reactivity of superoxide radical anion and hydroperoxyl radical with alpha-phenyl-N-tert-butylnitrone (PBN) derivatives. J Phys Chem A. 2008;112:12498-509 pubmed publisher
    ..This supports the conclusion that the nature of HO(2)(*) addition to PBN derivatives is electrophilic, while the addition of O(2)(*-) to PBN-type compounds is only weakly electrophilic. ..
  9. Xiang L, Dearman J, Abram S, Carter C, Hester R. Insulin resistance and impaired functional vasodilation in obese Zucker rats. Am J Physiol Heart Circ Physiol. 2008;294:H1658-66 pubmed publisher
    ..These results suggest that insulin resistance and the resultant increased ROS impair functional dilation in OZRs by increasing TP-mediated vasoconstriction...
  10. Wu J, Cui X, Chen L, Jiang G, Wu Y. Palladium-catalyzed alkenylation of quinoline-N-oxides via C-H activation under external-oxidant-free conditions. J Am Chem Soc. 2009;131:13888-9 pubmed publisher
    ..The resultant N-oxide of the alkenylated quinoline can oxidize the reduced Pd(0) to regenerate the Pd(II) active species and simultaneously release the 2-alkenylated quinoline without using any external oxidants and reductants. ..
  11. Papapostolou I, Georgiou C. Superoxide radical induces sclerotial differentiation in filamentous phytopathogenic fungi: a superoxide dismutase mimetics study. Microbiology. 2010;156:960-6 pubmed publisher
    ..The production rate of O(2) *(-) and SOD levels in these fungi, as expected, were significantly lowered by the SOD mimetics, with concomitant decrease of the indirect indicator of oxidative stress, lipid peroxidation. ..
  12. Maki T, Soh N, Fukaminato T, Nakajima H, Nakano K, Imato T. Perylenebisimide-linked nitroxide for the detection of hydroxyl radicals. Anal Chim Acta. 2009;639:78-82 pubmed publisher
  13. Wang S, Zhang M, Liang B, Xu J, Xie Z, Liu C, et al. AMPKalpha2 deletion causes aberrant expression and activation of NAD(P)H oxidase and consequent endothelial dysfunction in vivo: role of 26S proteasomes. Circ Res. 2010;106:1117-28 pubmed publisher
    ..We conclude that AMPKalpha2 functions as a physiological suppressor of NAD(P)H oxidase and ROS production in endothelial cells. In this way, AMPK maintains the nonatherogenic and noninflammatory phenotype of endothelial cells. ..
  14. Ancha H, Kurella R, McKimmey C, Lightfoot S, Harty R. Luminal antioxidants enhance the effects of mesalamine in the treatment of chemically induced colitis in rats. Exp Biol Med (Maywood). 2008;233:1301-8 pubmed publisher
    ..alpha-Tocopherol plus 5-ASA exerted profound anti-inflammatory and reparative effects upon colitis induced by TNBS. ..
  15. Campeau L, Schipper D, Fagnou K. Site-selective sp2 and benzylic sp3 palladium-catalyzed direct arylation. J Am Chem Soc. 2008;130:3266-7 pubmed publisher
  16. Chang J, Sawisky G, Mitchell G, Uretsky A, Kwong P, Grey C, et al. PACAP stimulation of maturational gonadotropin secretion in goldfish involves extracellular signal-regulated kinase, but not nitric oxide or guanylate cyclase, signaling. Gen Comp Endocrinol. 2010;165:127-35 pubmed publisher
    ..These results suggest that although increased availability of NO and cGMP can lead to increased GTH-II secretion, MEK/ERK signaling, rather than NOS/NO/GC activation, mediates PACAP action on GTH-II release in goldfish. ..
  17. Carberry J, Bradford A, O Halloran K. Antioxidant treatment does not prevent chronic hypoxia-induced respiratory muscle impairment in developing rats. Adv Exp Med Biol. 2010;669:263-6 pubmed publisher
    ..Tempol treatment did not prevent hypoxia-induced muscle plasticity, suggesting that reactive oxygen species are not implicated in hypoxia-induced muscle dysfunction. ..
  18. Ranguelova K, Bonini M, Mason R. (Bi)sulfite oxidation by copper, zinc-superoxide dismutase: Sulfite-derived, radical-initiated protein radical formation. Environ Health Perspect. 2010;118:970-5 pubmed publisher
    ..The present study suggests that protein oxidative damage resulting from (bi)sulfite oxidation promoted by Cu,Zn-SOD could be involved in oxidative damage and tissue injury in (bi)sulfite-exacerbated allergic reactions. ..
  19. Skolimowski J, Cieślińska B, Zak M, Osiecka R, Błaszczyk A. Modulation of ethoxyquin genotoxicity by free radical scavengers and DNA damage repair in human lymphocytes. Toxicol Lett. 2010;193:194-9 pubmed publisher
  20. Deng X, Liu S, Shi D, Li H, Wu J, Huang Y. [Preparation of the spin trapping probe, N-tert-butyl-alpha-phenylnitrone, nanoparticle and its affinity to hepatoma cells]. Yao Xue Xue Bao. 2008;43:308-13 pubmed
    ..These results provide a potential method for early diagnosis and treatment of cancer using specific spin trapping probe targeting tumor cells. ..
  21. Garcia Alloza M, Prada C, Lattarulo C, Fine S, Borrelli L, Betensky R, et al. Matrix metalloproteinase inhibition reduces oxidative stress associated with cerebral amyloid angiopathy in vivo in transgenic mice. J Neurochem. 2009;109:1636-47 pubmed publisher
  22. Deschacht M, Horemans T, Martinet W, Bult H, Maes L, Cos P. Comparative EPR study of different macrophage types stimulated for superoxide and nitric oxide production. Free Radic Res. 2010;44:763-72 pubmed publisher
    ..In conclusion, this study established practical experimental conditions for the EPR analysis of O(2)(.-) and NO produced by different types of activated macrophages. ..
  23. Van Humbeck J, Simonovich S, Knowles R, MacMillan D. Concerning the mechanism of the FeCl3-catalyzed alpha-oxyamination of aldehydes: evidence for a non-SOMO activation pathway. J Am Chem Soc. 2010;132:10012-4 pubmed publisher
    ..The mechanistic details reported herein indicate that, as has been proposed for previously studied alcohol oxidations, complexation between TEMPO and a simple metal salt leads to electrophilic ionic reactivity. ..
  24. Lardinois O, Tomer K, Mason R, Deterding L. Identification of protein radicals formed in the human neuroglobin-H2O2 reaction using immuno-spin trapping and mass spectrometry. Biochemistry. 2008;47:10440-8 pubmed publisher
    ..Together, the data support the argument that wild-type Ngb is protected from attack by H 2O 2 by the coordinated distal His. ..
  25. Banday A, Lokhandwala M. Loss of biphasic effect on Na/K-ATPase activity by angiotensin II involves defective angiotensin type 1 receptor-nitric oxide signaling. Hypertension. 2008;52:1099-105 pubmed publisher
    ..In conclusion, oxidative stress-mediated AT1R upregulation caused a loss of NKA biphasic response and hypertension. Tempol normalized AT1R signaling and blood pressure. ..
  26. Lei R, Xu X, Xu D, Zhu G, Li N, Liu H, et al. Enhanced anodic Ru(bpy)3(2+) electrogenerated chemiluminescence by polyphenols. Anal Chim Acta. 2008;625:13-21 pubmed publisher
    ..This ECL enhancement can be used to analyze real sample and evaluate antioxidant activity of polyphenols. ..
  27. Qi X, Wu B, Cheng Y, Qu H. Simultaneous characterization of pyrrolizidine alkaloids and N-oxides in Gynura segetum by liquid chromatography/ion trap mass spectrometry. Rapid Commun Mass Spectrom. 2009;23:291-302 pubmed publisher
    ..Our results are the first comprehensive analysis of PAs and PANOs in G. segetum constituents and will be helpful for the quality control of the herb of G. segetum and its related preparations. ..
  28. Jasiewicz B. NMR spectra of sparteine N1-oxide and alpha-isosparteine N-oxide. Molecules. 2008;13:3-10 pubmed
    ..Sparteine N1-oxide and alpha-isosparteine N-oxide were prepared and their structures determined for the first time by (1)H- and (13)C-NMR spectroscopy using two-dimensional techniques. The N-oxide effects were also calculated. ..
  29. Siamilis S, Jakus J, Nyakas C, Costa A, Mihalik B, Falus A, et al. The effect of exercise and oxidant-antioxidant intervention on the levels of neurotrophins and free radicals in spinal cord of rats. Spinal Cord. 2009;47:453-7 pubmed publisher
    ..Redox alteration seems to affect the levels of GDNF and BDNF, which might have clinical consequences, as neurotrophins play an important role in cellular resistance and regeneration. ..
  30. Yang Y, Parsons K, Chi L, Malakauskas S, Le T. Glutathione S-transferase-micro1 regulates vascular smooth muscle cell proliferation, migration, and oxidative stress. Hypertension. 2009;54:1360-8 pubmed publisher
    ..Genetic variants that cause a decremental change in expression of Gstm1 may permit an environment of exaggerated oxidative stress, leading to susceptibility to vascular remodeling and atherosclerosis. ..
  31. Soto Otero R, Mendez Alvarez E, Sánchez Iglesias S, Zubkov F, Voskressensky L, Varlamov A, et al. Inhibition of 6-hydroxydopamine-induced oxidative damage by 4,5-dihydro-3H-2-benzazepine N-oxides. Biochem Pharmacol. 2008;75:1526-37 pubmed publisher
  32. Nagae A, Fujita M, Kawarazaki H, Matsui H, Ando K, Fujita T. Sympathoexcitation by oxidative stress in the brain mediates arterial pressure elevation in obesity-induced hypertension. Circulation. 2009;119:978-86 pubmed publisher
    ..In obesity-induced hypertension, increased oxidative stress in the brain, possibly via activation of NADPH oxidase, may contribute to the progression of hypertension through central sympathoexcitation. ..
  33. Yoneyama M, Kawada K, Gotoh Y, Shiba T, Ogita K. Endogenous reactive oxygen species are essential for proliferation of neural stem/progenitor cells. Neurochem Int. 2010;56:740-6 pubmed publisher
    ..These data suggest that endogenous ROS and nitric oxide are essential for the proliferation of embryonic neural stem/progenitor cells. ..
  34. Deng Bryant Y, Singh I, Carrico K, Hall E. Neuroprotective effects of tempol, a catalytic scavenger of peroxynitrite-derived free radicals, in a mouse traumatic brain injury model. J Cereb Blood Flow Metab. 2008;28:1114-26 pubmed publisher
    ..However, the modest neuroprotective effect of tempol suggests that multitarget combination strategies may be needed to interfere with posttraumatic secondary injury to a degree worthy of clinical translation. ..
  35. Harel T, Rozen S. The tetrazole 3-N-oxide synthesis. J Org Chem. 2010;75:3141-3 pubmed publisher
    ..CH(3)CN. This novel route features mild conditions and high yields. X-ray structure analysis and (15)N NMR experiments indicate that the preferred position for the incorporation of the oxygen is on the N-3 atom. ..
  36. Matsumoto T, Ozawa Y, Taguchi K, Kobayashi T, Kamata K. Chronic treatment with losartan (angiotensin II type 1 receptor antagonist) normalizes enhanced acetylcholine-induced coronary vasoconstriction in isolated perfused hearts of type 2 diabetic OLETF rats. J Smooth Muscle Res. 2009;45:197-208 pubmed
  37. Budzinska K, Ilasz R. Superoxide dismutase mimetic modulates hyperoxic augmentation of the diaphragmatic response to poikilocapnic hypoxia in non-vagotomized rats. J Physiol Pharmacol. 2008;59 Suppl 6:163-72 pubmed
    ..The abolishment is due likely to a remodeling of the respiratory pattern involving lung vagal reeptors, since in vagotomized animals, the effects of Tempol were marginal. ..
  38. Kanno H, Iwai M, Inaba S, Senba I, Nakaoka H, Sone H, et al. Improvement of glucose intolerance by combination of pravastatin and olmesartan in type II diabetic KK-A(y) mice. Hypertens Res. 2009;32:706-11 pubmed publisher
    ..The effects seem to be mediated by an increase in insulin sensitivity through the inhibition of oxidative stress. ..
  39. Fujita H, Fujishima H, Chida S, Takahashi K, Qi Z, Kanetsuna Y, et al. Reduction of renal superoxide dismutase in progressive diabetic nephropathy. J Am Soc Nephrol. 2009;20:1303-13 pubmed publisher
    ..Collectively, these results indicate that down-regulation of renal SOD1 and SOD3 may play a key role in the pathogenesis of DN. ..
  40. Scepaniak J, Young J, Bontchev R, Smith J. Formation of ammonia from an iron nitrido complex. Angew Chem Int Ed Engl. 2009;48:3158-60 pubmed publisher
    ..The mechanism likely involves hydrogen-atom transfer from TEMPO-H to the nitrido complex. Similar reaction with the triphenylmethyl radical yields [PhB(MesIm)(3)Fe[triple chemical bond]N--CPh(3)]. ..
  41. Zoia L, Argyropoulos D. Characterization of free radical spin adducts of the DIPPMPO using mass spectrometry and (31)P NMR. Eur J Mass Spectrom (Chichester). 2010;16:175-85 pubmed publisher
    ..This spin trapping technique, coupled with (31)P NMR and MS, provides a tool for the identification of short-lived and low molecular weight free radicals present in a variety of processes. ..
  42. Sengupta R, Billiar T, Stoyanovsky D. Studies toward the analysis of S-nitrosoproteins. Org Biomol Chem. 2009;7:232-4 pubmed publisher
    ..An immuno-spin trapping method for the analysis of S-nitrosoproteins based on the reaction of protein thiyl radicals with 5,5-dimethyl-1-pyrroline N-oxide has been developed. ..
  43. Fan L, Chen R, Mitchell H, Lin R, Simpson K, Rhodes P, et al. alpha-Phenyl-n-tert-butyl-nitrone attenuates lipopolysaccharide-induced brain injury and improves neurological reflexes and early sensorimotor behavioral performance in juvenile rats. J Neurosci Res. 2008;86:3536-47 pubmed publisher
  44. Wang X, Liu R, Jin Y, Liang X. TEMPO/HCl/NaNO2 catalyst: a transition-metal-free approach to efficient aerobic oxidation of alcohols to aldehydes and ketones under mild conditions. Chemistry. 2008;14:2679-85 pubmed publisher
    ..TEMPO, TEMPOH, and TEMPO(+) were observed in the redox cycle by means of ESI-MS. On the basis of these observations, a mechanism is proposed that may provide an insight into the newly developed aerobic alcohol oxidation. ..
  45. Kielland A, Blom T, Nandakumar K, Holmdahl R, Blomhoff R, Carlsen H. In vivo imaging of reactive oxygen and nitrogen species in inflammation using the luminescent probe L-012. Free Radic Biol Med. 2009;47:760-6 pubmed publisher
    ..In conclusion, L-012 is well distributed in the mouse body and mediates a strong ROS/RNS-dependent luminescent signal in vivo and is useful for monitoring the development and regulation of inflammation in living organisms. ..
  46. Sindler A, Delp M, Reyes R, Wu G, Muller Delp J. Effects of ageing and exercise training on eNOS uncoupling in skeletal muscle resistance arterioles. J Physiol. 2009;587:3885-97 pubmed publisher
  47. Ohashi N, Katsurada A, Miyata K, Satou R, Saito T, Urushihara M, et al. Role of activated intrarenal reactive oxygen species and renin-angiotensin system in IgA nephropathy model mice. Clin Exp Pharmacol Physiol. 2009;36:750-5 pubmed publisher
    ..4. These data suggest that intrarenal ROS and RAS activation play a pivotal role in the development of IgA nephropathy model mice, from the early phase, independent of blood pressure. ..
  48. Riazi S, Tiwari S, Sharma N, Rash A, Ecelbarger C. Abundance of the Na-K-2Cl cotransporter NKCC2 is increased by high-fat feeding in Fischer 344 X Brown Norway (F1) rats. Am J Physiol Renal Physiol. 2009;296:F762-70 pubmed publisher
    ..Overall, HF feeding increased the abundance of NKCC2. Inappropriately high sodium reabsorption in the thick ascending limb via NKCC2 may contribute to hypertension with insulin resistance...
  49. Neckar J, Ostadal B, Kolar F. Acute but not chronic tempol treatment increases ischemic and reperfusion ventricular arrhythmias in open-chest rats. Physiol Res. 2008;57:653-6 pubmed
    ..Acute tempol-treated rats exhibited a tendency to decrease infarct size (P = 0.087). The mechanism of proarrhythmic tempol action during ischemia and reperfusion remains to be elucidated. ..
  50. Halpern M, Weitkamp J, Mount Patrick S, Dobrenen H, Khailova L, Correa H, et al. Apical sodium-dependent bile acid transporter upregulation is associated with necrotizing enterocolitis. Am J Physiol Gastrointest Liver Physiol. 2010;299:G623-31 pubmed publisher
    ..These data confirm that BAs and upregulation of ASBT play a crucial role in NEC pathogenesis and suggest that inhibition of ASBT could be utilized as a therapeutic modality against this disease. ..
  51. Kim H, Wang J, Lu Y, Chung J, Chung K. Superoxide signaling in pain is independent of nitric oxide signaling. Neuroreport. 2009;20:1424-8 pubmed publisher
    ..Superoxide-induced hyperalgesia was not affected by inhibiting NO(.) production but was suppressed by a protein kinase C inhibitor. The data suggest that NO(.) and (.)O2 operate independently to generate pain. ..
  52. Lovett J, Hoffmann M, Cnossen A, Shutter A, Hogben H, Warren J, et al. Probing flexibility in porphyrin-based molecular wires using double electron electron resonance. J Am Chem Soc. 2009;131:13852-9 pubmed publisher
    ..Self-assembled ladder-shaped 2:2 complexes were also investigated to illustrate the scope of DEER measurements for providing structural information on synthetic noncovalent nanostructures. ..
  53. Phillips S, Pechman K, Leonard E, Friedrich J, Bian J, Beal A, et al. Increased ANG II sensitivity following recovery from acute kidney injury: role of oxidant stress in skeletal muscle resistance arteries. Am J Physiol Regul Integr Comp Physiol. 2010;298:R1682-91 pubmed publisher
    ..Taken together, this study demonstrates that AKI alters peripheral vascular responses by increasing oxidant stress, likely in the endothelium, via an undefined mechanism. ..