hydroxylamines

Summary

Summary: Organic compounds that contain the (-NH2OH) radical.

Top Publications

  1. Conejo Garcia A, Schofield C. A prodrug system for hydroxylamines based on esterase catalysis. Bioorg Med Chem Lett. 2005;15:4004-9 pubmed
    ..Gamma-hydroxy hydroxamates were found to enable hydroxylamine release via lactonisation. Hydroxamates were found to undergo esterase catalysed hydrolysis...
  2. Wood P, Khan M, Kulow S, Mahmood S, Moskal J. Neurotoxicity of reactive aldehydes: the concept of "aldehyde load" as demonstrated by neuroprotection with hydroxylamines. Brain Res. 2006;1095:190-9 pubmed
    ..To this end, we evaluated hydroxylamines as aldehyde-trapping agents in an in vitro model of neurodegeneration induced by the reactive aldehyde, 3-..
  3. Dikalov S, Kirilyuk I, Voinov M, Grigor ev I. EPR detection of cellular and mitochondrial superoxide using cyclic hydroxylamines. Free Radic Res. 2011;45:417-30 pubmed publisher
    ..Cyclic hydroxylamines rapidly react with O???, producing stable nitroxides and allowing site-specific cO??? detection in ..
  4. Liu L, Nakatsuru Y, Gerson S. Base excision repair as a therapeutic target in colon cancer. Clin Cancer Res. 2002;8:2985-91 pubmed
    ..DNA BER may be a useful pharmacological target through which tumor cells can be sensitized to alkylating therapeutic agents...
  5. Zhao J, Ross J, Hao Y, Spate L, Walters E, Samuel M, et al. Significant improvement in cloning efficiency of an inbred miniature pig by histone deacetylase inhibitor treatment after somatic cell nuclear transfer. Biol Reprod. 2009;81:525-30 pubmed publisher
    ..05). In conclusion, the extremely low cloning efficiency in the NIH miniature pig may be caused by its inbred genetic background and can be improved by alteration of genomic histone acetylation patterns...
  6. Lu J, Verkruyse L, Hofmann S. Lipid thioesters derived from acylated proteins accumulate in infantile neuronal ceroid lipofuscinosis: correction of the defect in lymphoblasts by recombinant palmitoyl-protein thioesterase. Proc Natl Acad Sci U S A. 1996;93:10046-50 pubmed
    ..These data support a role for palmitoyl-protein thioesterase in the lysosomal degradation of S-acylated proteins and define a major new pathway for the catabolism of acylated proteins in the lysosome...
  7. Rümer S, Gupta K, Kaiser W. Plant cells oxidize hydroxylamines to NO. J Exp Bot. 2009;60:2065-72 pubmed publisher
    ..Unexpectedly, the addition of superoxide dismutase (SOD) to cell suspensions stimulated NO formation from hydroxylamines, and SOD alone (without cells) also catalysed the production of NO from HA or SHAM...
  8. Frazier C, Bugarin A, Engelking J, Read de Alaniz J. Copper-catalyzed aerobic oxidation of N-substituted hydroxylamines: efficient and practical access to nitroso compounds. Org Lett. 2012;14:3620-3 pubmed publisher
    A general and efficient aerobic oxidation of N-substituted hydroxylamines is described...
  9. Yan L, Bulgar A, Miao Y, Mahajan V, Donze J, Gerson S, et al. Combined treatment with temozolomide and methoxyamine: blocking apurininc/pyrimidinic site repair coupled with targeting topoisomerase IIalpha. Clin Cancer Res. 2007;13:1532-9 pubmed
    ..When located within topoisomerase IIalpha (topo II) cleavage sites in DNA, MX-AP sites act as dual lethal targets, not only functionally disrupting the base excision repair (BER) pathway but also potentially poisoning topo II...

More Information

Publications62

  1. Xavier S, Yamada K, Samuni A, Samuni A, DeGraff W, Krishna M, et al. Differential protection by nitroxides and hydroxylamines to radiation-induced and metal ion-catalyzed oxidative damage. Biochim Biophys Acta. 2002;1573:109-20 pubmed
    ..damage using plasmid DNA, genomic DNA, and cell survival, by three nitroxides and their corresponding hydroxylamines, were examined...
  2. Rinne M, Caldwell D, Kelley M. Transient adenoviral N-methylpurine DNA glycosylase overexpression imparts chemotherapeutic sensitivity to human breast cancer cells. Mol Cancer Ther. 2004;3:955-67 pubmed
    ..These data establish transient MPG overexpression as a potential therapeutic approach for increasing cellular sensitivity to alkylating agent chemotherapy...
  3. Taverna P, Hwang H, Schupp J, Radivoyevitch T, Session N, Reddy G, et al. Inhibition of base excision repair potentiates iododeoxyuridine-induced cytotoxicity and radiosensitization. Cancer Res. 2003;63:838-46 pubmed
    ..Thus, a genetic or biochemical impairment of BER results in increased IdUrd-induced cytotoxicity and radiosensitization in mammalian cells...
  4. Fishel M, He Y, Smith M, Kelley M. Manipulation of base excision repair to sensitize ovarian cancer cells to alkylating agent temozolomide. Clin Cancer Res. 2007;13:260-7 pubmed
  5. Bobko A, Kirilyuk I, Grigor ev I, Zweier J, Khramtsov V. Reversible reduction of nitroxides to hydroxylamines: roles for ascorbate and glutathione. Free Radic Biol Med. 2007;42:404-12 pubmed
    ..The rapid reduction of NR in biological samples into hydroxylamines (HA) significantly limits their application...
  6. Whitworth K, Zhao J, Spate L, Li R, Prather R. Scriptaid corrects gene expression of a few aberrantly reprogrammed transcripts in nuclear transfer pig blastocyst stage embryos. Cell Reprogram. 2011;13:191-204 pubmed publisher
    ..0003). Scriptaid treatment significantly affected gene expression in 7 of the 14 transcripts evaluated and returned 3 genes to BLIVV levels...
  7. Hanson K, VandenBrink B, Babu K, Allen K, Nelson W, Kunze K. Sequential metabolism of secondary alkyl amines to metabolic-intermediate complexes: opposing roles for the secondary hydroxylamine and primary amine metabolites of desipramine, (s)-fluoxetine, and N-desmethyldiltiazem. Drug Metab Dispos. 2010;38:963-72 pubmed publisher
    ..S)-fluoxetine [(S)-FLX], and N-desmethyldiltiazem (MA) undergo N-hydroxylation to the corresponding secondary hydroxylamines [N-hydroxydesipramine, (S)-N-hydroxyfluoxetine, and N-hydroxy-N-desmethyldiltiazem] by cytochromes P450 2C11, ..
  8. Jones K, Porzelle A, Hall A, Woodrow M, Tomkinson N. Copper-catalyzed coupling of hydroxylamines with aryl iodides. Org Lett. 2008;10:797-800 pubmed publisher
    An efficient method for the copper-catalyzed N-arylation of hydroxylamines with aryl iodides is described...
  9. Cudkowicz M, Shefner J, Simpson E, Grasso D, Yu H, Zhang H, et al. Arimoclomol at dosages up to 300 mg/day is well tolerated and safe in amyotrophic lateral sclerosis. Muscle Nerve. 2008;38:837-44 pubmed publisher
    ..Arimoclomol CSF levels increased with dose. Arimoclomol was shown to be safe, and it crosses the blood-brain barrier. Serum pharmacokinetic profiles support dosing of three times per day. An efficacy study in ALS is planned...
  10. Hill D, Hsiao C, Kurukulasuriya R, Wittenberger S. 2,2,2-trifluoroethyl formate: a versatile and selective reagent for the formylation of alcohols, amines, and N-hydroxylamines. Org Lett. 2002;4:111-3 pubmed
    reaction: see text] Treatment of a variety of alcohols, amines, and N-hydroxylamines with 2,2,2-trifluoroethyl formate gave the corresponding formylated adducts in high yields.
  11. Atamna H, Robinson C, Ingersoll R, Elliott H, Ames B. N-t-Butyl hydroxylamine is an antioxidant that reverses age-related changes in mitochondria in vivo and in vitro. FASEB J. 2001;15:2196-204 pubmed
    ..NtBHA is an antioxidant that is recycled by mitochondrial electron transport chain and prevents radical-induced toxicity to mitochondria...
  12. Park C, Jeong Y, Jeong Y, Lee S, Jeong Y, Shin T, et al. X-linked gene transcription patterns in female and male in vivo, in vitro and cloned porcine individual blastocysts. PLoS ONE. 2012;7:e51398 pubmed publisher
  13. Kieran D, Kalmar B, Dick J, Riddoch Contreras J, Burnstock G, Greensmith L. Treatment with arimoclomol, a coinducer of heat shock proteins, delays disease progression in ALS mice. Nat Med. 2004;10:402-5 pubmed
    ..Pharmacological activation of the heat shock response may therefore be a successful therapeutic approach to treating ALS, and possibly other neurodegenerative diseases...
  14. Kalmar B, Novoselov S, Gray A, Cheetham M, Margulis B, Greensmith L. Late stage treatment with arimoclomol delays disease progression and prevents protein aggregation in the SOD1 mouse model of ALS. J Neurochem. 2008;107:339-50 pubmed publisher
  15. Kurian J, Bajad S, Miller J, Chin N, Trepanier L. NADH cytochrome b5 reductase and cytochrome b5 catalyze the microsomal reduction of xenobiotic hydroxylamines and amidoximes in humans. J Pharmacol Exp Ther. 2004;311:1171-8 pubmed
    ..These results indicate a novel direct role for NADH cytochrome b5 reductase and cytochrome b5 in xenobiotic metabolism and suggest that pharmacogenetic variability in either of these proteins may effect drug reduction capacity...
  16. Samuni A, Goldstein S, Russo A, Mitchell J, Krishna M, Neta P. Kinetics and mechanism of hydroxyl radical and OH-adduct radical reactions with nitroxides and with their hydroxylamines. J Am Chem Soc. 2002;124:8719-24 pubmed
    ..Surprisingly, the reduced forms of cyclic nitroxides, cyclic hydroxylamines, are better reductants yet have no radioprotective activity...
  17. Porzelle A, Woodrow M, Tomkinson N. Palladium-catalyzed coupling of hydroxylamines with aryl bromides, chlorides, and iodides. Org Lett. 2009;11:233-6 pubmed publisher
    The bis-pyrazole phosphine ligand BippyPhos is effective for the palladium-catalyzed cross-coupling of hydroxylamines with aryl bromides, chlorides, and iodides...
  18. Matsuda N, Hirano K, Satoh T, Miura M. Copper-catalyzed direct amination of electron-deficient arenes with hydroxylamines. Org Lett. 2011;13:2860-3 pubmed publisher
    The C-H amination of electron-deficient arenes such as polyfluoroarenes and azole compounds with O-acylated hydroxylamines effectively proceeds in the presence of a copper catalyst even at room temperature to provide the corresponding ..
  19. Chen K, Swartz H. The products of the reduction of doxyl stearates in cells are hydroxylamines as shown by oxidation by 15N-perdeuterated Tempone. Biochim Biophys Acta. 1989;992:131-3 pubmed
    ..paper presents data indicating the value of 15N-perdeuterated Tempone specifically to indicate the amount of hydroxylamines that are present in a cellular system...
  20. Bergström M, Isin E, Castagnoli N, Milne C. Bioactivation pathways of the cannabinoid receptor 1 antagonist rimonabant. Drug Metab Dispos. 2011;39:1823-32 pubmed publisher
    ..In view of these findings, it is noteworthy that, to date, no toxicity findings related to the formation of reactive metabolites from rimonabant have been reported...
  21. Sibi M, Prabagaran N, Ghorpade S, Jasperse C. Enantioselective synthesis of alpha,beta-disubstituted-beta-amino acids. J Am Chem Soc. 2003;125:11796-7 pubmed
    ..These reactions proceed in 60-96% ee with 93-99% de's using 5 mol % of Mg(NTf2)2 and ligand 18. The product isoxazolidinones can be hydrogenolyzed directly to provide alpha,beta-disubstituted-beta-amino acids...
  22. Sacco J, Trepanier L. Cytochrome b5 and NADH cytochrome b5 reductase: genotype-phenotype correlations for hydroxylamine reduction. Pharmacogenet Genomics. 2010;20:26-37 pubmed publisher
    ..The aim of this study was to characterize variability in SMX-HA reduction in 111 human livers, and investigate its association with single nucleotide polymorphisms (SNPs) in b5 and b5R cDNA...
  23. Fishel M, Kelley M. The DNA base excision repair protein Ape1/Ref-1 as a therapeutic and chemopreventive target. Mol Aspects Med. 2007;28:375-95 pubmed
    ..In this review, we will provide an overview of Ape1/Ref-1's activities and explore the potential of this protein as a target in cancer treatment as well as its role in chemoprevention...
  24. Lu C, Petzold A, Kalmar B, Dick J, Malaspina A, Greensmith L. Plasma neurofilament heavy chain levels correlate to markers of late stage disease progression and treatment response in SOD1(G93A) mice that model ALS. PLoS ONE. 2012;7:e40998 pubmed publisher
    ..Neither specific investigative tools nor reliable biomarkers are currently available to enable an early diagnosis or monitoring of disease progression, hindering the design of treatment trials...
  25. Zapata J, Mateo Vivaracho L, Cacho J, Ferreira V. Comparison of extraction techniques and mass spectrometric ionization modes in the analysis of wine volatile carbonyls. Anal Chim Acta. 2010;660:197-205 pubmed publisher
    ..Recovery experiments show that in the case of SPE, uncertainties are lower than 12% in all cases, while with the SPME method the imprecision plus the existence of matrix effects make the global uncertainty to be higher than 15%...
  26. Harned A, Hanson P. Capture-ROMP-release: application for the synthesis of O-alkylhydroxylamines. Org Lett. 2002;4:1007-10 pubmed
    ..Treatment of the polymer with hydrazine releases the substrate from the water-soluble polymer, producing a variety of O-alkylhydroxylamines with good purity...
  27. Kudo W, Yamato M, Yamada K, Kinoshita Y, Shiba T, Watanabe T, et al. Formation of TEMPOL-hydroxylamine during reaction between TEMPOL and hydroxyl radical: HPLC/ECD study. Free Radic Res. 2008;42:505-12 pubmed publisher
    ..Finally, it was clarified that TEMPOL-H was generated during dopamine metabolism, which is believed to be one of the (*)OH sources in pathological processes such as Parkinson's disease...
  28. Miyamoto Y, Wada N, Soeta T, Fujinami S, Inomata K, Ukaji Y. One-pot stereoselective synthesis of 2-acylaziridines and 2-acylpyrrolidines from N-(propargylic)hydroxylamines. Chem Asian J. 2013;8:824-31 pubmed publisher
    The stereoselective direct transformation of N-(propargylic)hydroxylamines into cis-2-acylaziridines was achieved by the combined use of AgBF4 and CuCl...
  29. Rees M, Bottle S, Fairfull Smith K, Malle E, Whitelock J, Davies M. Inhibition of myeloperoxidase-mediated hypochlorous acid production by nitroxides. Biochem J. 2009;421:79-86 pubmed publisher
    ..Overall, these data indicate that nitroxides have considerable promise as therapeutic agents for the inhibition of MPO-mediated damage in inflammatory diseases...
  30. Lim E, Rhee Y, Park M, Shim B, Ahn K, Kang H, et al. DMNQ S-64 induces apoptosis via caspase activation and cyclooxygenase-2 inhibition in human nonsmall lung cancer cells. Ann N Y Acad Sci. 2007;1095:7-18 pubmed
    ..Taken together, DMNQ S-64 may exhibit cytotoxicity against A549 cells via caspase activation and COX-2 inhibition...
  31. Yang S, Savvides P, Liu L, Gerson S, Xu Y. Development and validation of an LC-MS/MS method for pharmacokinetic study of methoxyamine in phase I clinical trial. J Chromatogr B Analyt Technol Biomed Life Sci. 2012;901:25-33 pubmed publisher
    ..The method developed had been applied to the determination of plasma MX concentrations in the first-in-human phase I clinical trial, and PK data were presented...
  32. Noorwez S, Kuksa V, Imanishi Y, Zhu L, Filipek S, Palczewski K, et al. Pharmacological chaperone-mediated in vivo folding and stabilization of the P23H-opsin mutant associated with autosomal dominant retinitis pigmentosa. J Biol Chem. 2003;278:14442-14450 pubmed publisher
    ..These properties suggest that 11-cis-7-ring retinal may be a useful therapeutic agent for the rescue of P23H-opsin and the prevention of retinal degeneration...
  33. She M, Guo K, Niu X, Lu X. [Effects of manumycin combined with methoxyamine on apoptosis in myeloid leukemia U937 cells]. Ai Zheng. 2008;27:835-9 pubmed
    ..This study was to investigate apoptosis induced by manumycin combined with methoxyamine in myeloid leukemia cell line U937, and to explore the role of mitochondrial apoptotic pathway in apoptosis induction of the two drugs...
  34. Tang M, Helsby N, Wilson W, Tingle M. Aerobic 2- and 4-nitroreduction of CB 1954 by human liver. Toxicology. 2005;216:129-39 pubmed
    ..These studies demonstrate that human liver is capable of aerobic reductive bioactivation of CB 1954 to cytotoxic metabolites in vitro, possibly involving multiple enzymes, which may account for the clinical hepatotoxicity observed...
  35. Weng S, Weaver W, Afifi M, Blatchley T, Cramer J, Chen J, et al. Dynamics of gas-phase trichloramine (NCl3) in chlorinated, indoor swimming pool facilities. Indoor Air. 2011;21:391-9 pubmed publisher
    ..The nature of swimmer activities also influenced air quality, presumably because of the effects of these activities on mixing near the gas-liquid interface...
  36. Kalmar B, Edet Amana E, Greensmith L. Treatment with a coinducer of the heat shock response delays muscle denervation in the SOD1-G93A mouse model of amyotrophic lateral sclerosis. Amyotroph Lateral Scler. 2012;13:378-92 pubmed publisher
    ..In conclusion, our results indicate that pharmacological targeting of muscles at early stages of disease may be a successful strategy to ameliorate disease progression in ALS...
  37. Meerman J, Ringer D, Coughtrie M, Bamforth K, Gilissen R. Sulfation of carcinogenic aromatic hydroxylamines and hydroxamic acids by rat and human sulfotransferases: substrate specificity, developmental aspects and sex differences. Chem Biol Interact. 1994;92:321-8 pubmed
    ..No such sex or age difference was found for the sulfation of aromatic hydroxylamines. In cytosols of adult human livers, sulfation activity towards aromatic hydroxamic acids and hydroxylamines ..
  38. Stepánková S, Vránová M, Zdrazilová P, Komers K, Komersová A, Cegan A. Two new methods monitoring kinetics of hydrolysis of acetylcholine and acetylthiocholine. Z Naturforsch C. 2005;60:943-6 pubmed
    ..Practical determinations are shown, comparison with known (above all Ellman's and pH-stat) methods, advantages and disadvantages are discussed...
  39. El Zoeiby A, Beaumont M, Dubuc E, Sanschagrin F, Voyer N, Levesque R. Combinatorial enzymatic assay for the screening of a new class of bacterial cell wall inhibitors. Bioorg Med Chem. 2003;11:1583-92 pubmed
    ..This approach yielded interesting lead compounds for the development of novel antibacterial agents...
  40. Clement B, Behrens D, Moller W, Cashman J. Reduction of amphetamine hydroxylamine and other aliphatic hydroxylamines by benzamidoxime reductase and human liver microsomes. Chem Res Toxicol. 2000;13:1037-45 pubmed
    ..It was not known if this enzyme system was also capable of reducing aliphatic hydroxylamines. The N-hydroxylation of aliphatic amines is a well-known metabolic process...
  41. Shah M, Campbell J. Transformation of nitrobenzene by ferredoxin NADP oxidoreductase from spinach leaves. Biochem Biophys Res Commun. 1997;241:794-6 pubmed
    ..Nitrobenzene was reduced in a solution containing ferredoxin NADP oxidoreductase (FNR) from spinach leaves and NADPH generating system. The product of nitrobenzene was identified as phenylhydroxylamine (PHA) on 1:1 basis...
  42. Yang S, Lagu B, Wilson L. Mild and efficient Lewis acid-promoted detritylation in the synthesis of N-hydroxy amides: a concise synthesis of (-)-Cobactin T. J Org Chem. 2007;72:8123-6 pubmed
    ..An application of this methodology for a concise synthesis of (-)-Cobactin T (18) is also demonstrated...
  43. Voloboueva L, Killilea D, Atamna H, Ames B. N-tert-butyl hydroxylamine, a mitochondrial antioxidant, protects human retinal pigment epithelial cells from iron overload: relevance to macular degeneration. FASEB J. 2007;21:4077-86 pubmed
    ..NtBHA might be useful in AMD due to its potential to reduce oxidative stress, mitochondrial damage, and age-related iron accumulation, which may damage normal RPE function and lead to loss of vision...
  44. Fukutsu N, Kawasaki T, Saito K, Nakazawa H. An approach for decontamination of beta-lactam antibiotic residues or contaminants in the pharmaceutical manufacturing environment. Chem Pharm Bull (Tokyo). 2006;54:1340-3 pubmed
    ..Therefore, hydroxylamine was considered an appropriate decontamination agent for beta-lactam antibiotics...
  45. Berman A, Johnson J. Copper-catalyzed electrophilic amination of organozinc nucleophiles: documentation of O-benzoyl hydroxylamines as broadly useful R2N(+) and RHN(+) synthons. J Org Chem. 2006;71:219-24 pubmed
    ..paper details new copper-catalyzed electrophilic amination reactions of diorganozinc reagents using O-benzoyl hydroxylamines as electrophilic nitrogen sources that may be accessed in one step...
  46. Johnson J, Hunter R, McElveen R, Qian X, Baliga B, Pace B. Fetal hemoglobin induction by the histone deacetylase inhibitor, scriptaid. Cell Mol Biol (Noisy-le-grand). 2005;51:229-38 pubmed
    ..8-fold increase in gamma-globin mRNA transcripts. The potential for scriptaid as a treatment option for sickle cell disease will be discussed...
  47. Chapman E, Blasi J, An S, Brose N, Johnston P, Sudhof T, et al. Fatty acylation of synaptotagmin in PC12 cells and synaptosomes. Biochem Biophys Res Commun. 1996;225:326-32 pubmed
    ..In addition, hydroxylamine-induced mobility shifts were also apparent for synaptotagmins II and III, suggesting that posttranslational palmitoylation via thioester bonds may be a general modification of all synaptotagmins...
  48. Wall D, Zylicz M, Georgopoulos C. The NH2-terminal 108 amino acids of the Escherichia coli DnaJ protein stimulate the ATPase activity of DnaK and are sufficient for lambda replication. J Biol Chem. 1994;269:5446-51 pubmed
    ..These results may be applicable to other eukaryotic proteins that contain this conserved J domain as proteins that interact and stimulate the hydrolysis of ATP by their cognate HSP70 proteins...
  49. Pacchiarotta T, Derks R, Hurtado Fernández E, van Bezooijen P, Henneman A, Schiewek R, et al. Online spectral library for GC-atmospheric pressure chemical ionization-ToF MS. Bioanalysis. 2013;5:1515-25 pubmed publisher
    ..However, the general acceptance of GC-APCI-MS is certainly constrained by the lack of spectral libraries, which make the traditional GC-MS approaches so powerful...
  50. Noya Y, Seki K, Asano H, Mai Y, Horinouchi T, Higashi T, et al. Identification of stable cytotoxic factors in the gas phase extract of cigarette smoke and pharmacological characterization of their cytotoxicity. Toxicology. 2013;314:1-10 pubmed publisher
  51. Kiyatkin E. Brain temperature homeostasis: physiological fluctuations and pathological shifts. Front Biosci (Landmark Ed). 2010;15:73-92 pubmed
    ..While different adaptive mechanisms could, within some limits, compensate for altered intra-brain heat balance, these mechanisms could fail in real-life situations, resulting in life-threatening health complications. ..
  52. An H, Yang L, Zhou Y, Liu J. [Blood toxicity assessment of subchronic exposure to hydroxylammonium nitrate in wistar rats ]. Wei Sheng Yan Jiu. 2007;36:505-7 pubmed
    ..To investigate the effects of hydroxylammonium nitrate (HAN) on the blood system in rats...
  53. Chakravarti D, Badawi A, Venugopal D, Meza J, Crandall L, Rogan E, et al. Improved measurement of dibenzo[a,l]pyrene-induced abasic sites by the aldehyde-reactive probe assay. Mutat Res. 2005;588:158-65 pubmed
    ..In summary, the inclusion of ARP in the DB[a,l]P-DNA adduct-forming reaction traps and protects the nascent abasic sites, allowing an improved quantification of abasic sites...