nitroso compounds


Summary: Organic compounds containing the nitroso (-N=O) group attached to an organic moiety.

Top Publications

  1. Morales Helguera A, Perez Gonzalez M, Dias Soeiro Cordeiro M, Cabrera Pérez M. Quantitative structure-carcinogenicity relationship for detecting structural alerts in nitroso compounds: species, rat; sex, female; route of administration, gavage. Chem Res Toxicol. 2008;21:633-42 pubmed publisher
    ..MOlecular DEsign (TOPS-MODE) approach, aimed at predicting the rodent carcinogenicity of a set of nitroso compounds selected from the Carcinogenic Potency Data Base (CPDB)...
  2. Gerik K, Bhimireddy S, Ryerse J, Specht C, Lodge J. PKC1 is essential for protection against both oxidative and nitrosative stresses, cell integrity, and normal manifestation of virulence factors in the pathogenic fungus Cryptococcus neoformans. Eukaryot Cell. 2008;7:1685-98 pubmed publisher
    ..Notably, this is the first time that Pkc1 has been implicated in protection against nitrosative stress in any organism. ..
  3. 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 catalytic and sustainable alternative to stoichiometric oxidation methods to gain access to a range of nitroso compounds, such as acylnitroso, nitrosoformate, nitrosoformamide, iminonitroso, arylnitroso, and P-nitrosophosphine ..
  4. Lo Conte M, Carroll K. Chemoselective ligation of sulfinic acids with aryl-nitroso compounds. Angew Chem Int Ed Engl. 2012;51:6502-5 pubmed publisher
    Making a comeback: The inefficient condensation of sulfinic acid and aryl nitroso compounds has been transformed into a chemoselective process that converts sulfinic acid into stable cyclic sulfonamide analogues (see scheme)...
  5. Shoman M, DuMond J, Isbell T, Crawford J, Brandon A, Honovar J, et al. Acyloxy nitroso compounds as nitroxyl (HNO) donors: kinetics, reactions with thiols, and vasodilation properties. J Med Chem. 2011;54:1059-70 pubmed publisher
    Acyloxy nitroso compounds hydrolyze to nitroxyl (HNO), a nitrogen monoxide with distinct chemistry and biology...
  6. Bellinger A, Reiken S, Carlson C, Mongillo M, Liu X, Rothman L, et al. Hypernitrosylated ryanodine receptor calcium release channels are leaky in dystrophic muscle. Nat Med. 2009;15:325-30 pubmed publisher
  7. Derakhshan B, Wille P, Gross S. Unbiased identification of cysteine S-nitrosylation sites on proteins. Nat Protoc. 2007;2:1685-91 pubmed
    ..The protocol requires approximately 2 days for sample processing, including the incubation time for proteolysis. An additional 1-2 days is needed for sample analysis by nLC-MS/MS and data analysis/interpretation. ..
  8. Ishima Y, Yoshida F, Kragh Hansen U, Watanabe K, Katayama N, Nakajou K, et al. Cellular uptake mechanisms and responses to NO transferred from mono- and poly-S-nitrosated human serum albumin. Free Radic Res. 2011;45:1196-206 pubmed publisher
    ..Thus, increasing the number of SNO groups on HSA does not simply intensify the cellular responses to the product but can also result in very different effects. ..
  9. Katayama N, Nakajou K, Komori H, Uchida K, Yokoe J, Yasui N, et al. Design and evaluation of S-nitrosylated human serum albumin as a novel anticancer drug. J Pharmacol Exp Ther. 2008;325:69-76 pubmed publisher
    ..These results suggest that NO-HSA has the potential for chemopreventive and/or chemotherapeutic activity with few side effects. ..

More Information


  1. Ishima Y, Hara M, Kragh Hansen U, Inoue A, Suenaga A, Kai T, et al. Elucidation of the therapeutic enhancer mechanism of poly-S-nitrosated human serum albumin against multidrug-resistant tumor in animal models. J Control Release. 2012;164:1-7 pubmed publisher
    ..Thus, in addition to its proapoptotic effect Poly-SNO-HSA can in an efficient manner revert drug resistance both in vitro and in vivo, and two pathways for this effect have been identified. ..
  2. Kuhnle G, Story G, Reda T, Mani A, Moore K, Lunn J, et al. Diet-induced endogenous formation of nitroso compounds in the GI tract. Free Radic Biol Med. 2007;43:1040-7 pubmed
    ..The endogenous formation of nitroso compounds is a possible explanation, as red or processed meat--but not white meat or fish--causes a dose-dependent ..
  3. Wang Y, Liu T, Wu C, Li H. A strategy for direct identification of protein S-nitrosylation sites by quadrupole time-of-flight mass spectrometry. J Am Soc Mass Spectrom. 2008;19:1353-60 pubmed publisher
    ..We have successfully applied this method to thioredoxin, a key antioxidant protein, and identified within it an S-nitrosylation site at Cys73. ..
  4. Hebels D, Jennen D, Kleinjans J, de Kok T. Molecular signatures of N-nitroso compounds in Caco-2 cells: implications for colon carcinogenesis. Toxicol Sci. 2009;108:290-300 pubmed publisher
    N-nitroso compounds (NOC) are genotoxic, carcinogenic to animals, and may play a role in human cancer development...
  5. Nagai H, Yasuda H, Hatachi Y, Xue D, Sasaki T, Yamaya M, et al. Nitric oxide (NO) enhances pemetrexed cytotoxicity via NO?cGMP signaling in lung adenocarcinoma cells in vitro and in vivo. Int J Oncol. 2012;41:24-30 pubmed publisher
    ..These findings suggest that NO donors, such as NOC-18 and GTN, enhance the anticancer effects of PEM by increasing the RFC1 and FPGS expression and stimulating cGMP signaling pathways in cancer cells. ..
  6. Fahrer J, Kaina B. O6-methylguanine-DNA methyltransferase in the defense against N-nitroso compounds and colorectal cancer. Carcinogenesis. 2013;34:2435-42 pubmed publisher
    ..A growing body of evidence suggests that N-nitroso compounds (NOC) play a pivotal role in the etiology of CRC...
  7. Cormary B, Ladeira S, Jacob K, Lacroix P, Woike T, Schaniel D, et al. Structural influence on the photochromic response of a series of ruthenium mononitrosyl complexes. Inorg Chem. 2012;51:7492-501 pubmed publisher
    ..DFT calculations have been performed to confirm the influence of the counterions. Additionally, we found that the lower the donating character of the ligand trans to NO the higher the photoconversion yield. ..
  8. Katayama N, Nakajou K, Ishima Y, Ikuta S, Yokoe J, Yoshida F, et al. Nitrosylated human serum albumin (SNO-HSA) induces apoptosis in tumor cells. Nitric Oxide. 2010;22:259-65 pubmed publisher
    ..These results suggest that SNO-HSA has potential as a chemopreventive and/or chemotherapeutic agent because it induces apoptosis in tumor cells. ..
  9. Tsang A, Lee Y, Ko H, Savitt J, Pletnikova O, Troncoso J, et al. S-nitrosylation of XIAP compromises neuronal survival in Parkinson's disease. Proc Natl Acad Sci U S A. 2009;106:4900-5 pubmed publisher
  10. Hogg N. Red meat and colon cancer: heme proteins and nitrite in the gut. A commentary on "diet-induced endogenous formation of nitroso compounds in the GI tract". Free Radic Biol Med. 2007;43:1037-9 pubmed
  11. Leal E, Aveleira C, Castilho A, Serra A, Baptista F, Hosoya K, et al. High glucose and oxidative/nitrosative stress conditions induce apoptosis in retinal endothelial cells by a caspase-independent pathway. Exp Eye Res. 2009;88:983-91 pubmed publisher
    ..NOC-18 and H(2)O(2) also activate a caspase-independent apoptotic pathway, although H(2)O(2) can also induce caspase-mediated apoptosis. ..
  12. Liebeskind S, Korth H, de Groot H, Kirsch M. Dependence of product formation from decomposition of nitroso-dithiols on the degree of nitrosation. Evidence that dinitroso-dithiothreitol acts solely as an nitric oxide releasing compound. Org Biomol Chem. 2008;6:2560-73 pubmed publisher
    ..The identified pathways are proposed to be of general importance for physiological systems because control experiments showed that the physiological dithiol thioredoxin reacts in a similar manner...
  13. Mirvish S, Davis M, Lisowyj M, Gaikwad N. Effect of feeding nitrite, ascorbate, hemin, and omeprazole on excretion of fecal total apparent N-nitroso compounds in mice. Chem Res Toxicol. 2008;21:2344-51 pubmed publisher
    It was proposed that colon cancer induced by red and nitrite-preserved meat is due to meat-derived N-nitroso compounds in the colonic contents...
  14. Wong F, Patra P, Seayad J, Zhang Y, Ying J. N-heterocyclic carbene (NHC)-catalyzed direct amidation of aldehydes with nitroso compounds. Org Lett. 2008;10:2333-6 pubmed publisher
    NHC-catalyzed direct amidation of aldehydes with nitroso compounds is a powerful method for the synthesis of N-arylhydroxamic acids...
  15. Lefievre L, Chen Y, Conner S, Scott J, Publicover S, Ford W, et al. Human spermatozoa contain multiple targets for protein S-nitrosylation: an alternative mechanism of the modulation of sperm function by nitric oxide?. Proteomics. 2007;7:3066-84 pubmed
    ..Potential targets for S-nitrosylation in human sperm include physiologically significant proteins not previously reported in other cells. Their identification will provide novel insight into the mechanism of action of NO in spermatozoa. ..
  16. Ozawa K, Whalen E, Nelson C, Mu Y, Hess D, Lefkowitz R, et al. S-nitrosylation of beta-arrestin regulates beta-adrenergic receptor trafficking. Mol Cell. 2008;31:395-405 pubmed publisher
    ..Thus, beta-arrestin subserves the functional coupling of eNOS and GPCRs, and dynamic S-nitrosylation/denitrosylation of beta-arrestin 2 regulates stimulus-induced GPCR trafficking. ..
  17. Sha X, Isbell T, Patel R, Day C, King S. Hydrolysis of acyloxy nitroso compounds yields nitroxyl (HNO). J Am Chem Soc. 2006;128:9687-92 pubmed
    ..acetate, whereas oxidation of oximes in the presence of excess carboxylic acid gives various acyloxy nitroso compounds. These bright blue compounds exist as monomers as indicated by their infrared, proton, and carbon NMR ..
  18. Mueller B, Newton K, Holly E, Preston Martin S. Residential water source and the risk of childhood brain tumors. Environ Health Perspect. 2001;109:551-6 pubmed
    ..The N-nitroso compounds (NNC), a class of chemicals with demonstrated neurocarcinogenic potential, include substances detected in ..
  19. Brender J, Olive J, Felkner M, Suarez L, Marckwardt W, Hendricks K. Dietary nitrites and nitrates, nitrosatable drugs, and neural tube defects. Epidemiology. 2004;15:330-6 pubmed
    Amine-containing (nitrosatable) drugs can react with nitrite to form N-nitroso compounds, some of which are teratogenic...
  20. Ward M, deKok T, Levallois P, Brender J, Gulis G, Nolan B, et al. Workgroup report: Drinking-water nitrate and health--recent findings and research needs. Environ Health Perspect. 2005;113:1607-14 pubmed
    ..The contribution of drinking-water nitrate toward endogenous formation of N-nitroso compounds was evaluated with a focus toward identifying subpopulations with increased rates of nitrosation...
  21. Vermeer I, Henderson L, Moonen E, Engels L, Dallinga J, van Maanen J, et al. Neutrophil-mediated formation of carcinogenic N-nitroso compounds in an in vitro model for intestinal inflammation. Toxicol Lett. 2004;154:175-82 pubmed
    In order to study neutrophil-mediated formation of carcinogenic N-nitroso compounds as a mechanism of inflammation-related colon carcinogenesis, we designed an in vitro model for intestinal inflammation, consisting of a coincubation ..
  22. Zhong J, Cong H. [Inhibition of grape procyanidin on the expression of SSTR-2 mRNA in the hepatic cells induced by N-nitroso compounds]. Wei Sheng Yan Jiu. 2004;33:430-2 pubmed
    To study the effect of grape procyanidin (GPC) on the expression of somatostatin receptor 2 mRNA induced by N-nitroso compounds in the hepatic cells of rats...
  23. Sun J, Xu L, Eu J, Stamler J, Meissner G. Nitric oxide, NOC-12, and S-nitrosoglutathione modulate the skeletal muscle calcium release channel/ryanodine receptor by different mechanisms. An allosteric function for O2 in S-nitrosylation of the channel. J Biol Chem. 2003;278:8184-9 pubmed
    ..Our results suggest that the effect of pO(2) on RyR1 S-nitrosylation is exerted through an allosteric mechanism. ..
  24. Feelisch M, Rassaf T, Mnaimneh S, Singh N, Bryan N, JOURD HEUIL D, et al. Concomitant S-, N-, and heme-nitros(yl)ation in biological tissues and fluids: implications for the fate of NO in vivo. FASEB J. 2002;16:1775-85 pubmed
  25. Dietrich M, Block G, Pogoda J, Buffler P, Hecht S, Preston Martin S. A review: dietary and endogenously formed N-nitroso compounds and risk of childhood brain tumors. Cancer Causes Control. 2005;16:619-35 pubmed
    Maternal dietary exposure to N-nitroso compounds (NOC) or to their precursors during pregnancy has been associated with risk of childhood brain tumors. Cured meat is one source of exposure to dietary NOC and their precursors...
  26. Lunn J, Kuhnle G, Mai V, Frankenfeld C, Shuker D, Glen R, et al. The effect of haem in red and processed meat on the endogenous formation of N-nitroso compounds in the upper gastrointestinal tract. Carcinogenesis. 2007;28:685-90 pubmed
    ..cancer and it has been demonstrated that haem in red meat (RM) stimulates the endogenous production of N-nitroso compounds (NOCs) within the human intestine...
  27. Risch H. Etiology of pancreatic cancer, with a hypothesis concerning the role of N-nitroso compounds and excess gastric acidity. J Natl Cancer Inst. 2003;95:948-60 pubmed
    ..Many features of the evidence bearing on the pathophysiology of pancreatic cancer appear to support connections with N-nitroso compounds and with gastric acidity.
  28. Lin K, Shen W, Shen Z, Wu Y, Lu S. Dietary exposure and urinary excretion of total N-nitroso compounds, nitrosamino acids and volatile nitrosamine in inhabitants of high- and low-risk areas for esophageal cancer in southern China. Int J Cancer. 2002;102:207-11 pubmed
    We assessed the exposure of total N-nitroso compounds (TNOCs) in the inhabitants of high- and low-risk areas for esophageal cancer in southern China...
  29. Stoyanovsky D, Tyurina Y, Tyurin V, Anand D, Mandavia D, Gius D, et al. Thioredoxin and lipoic acid catalyze the denitrosation of low molecular weight and protein S-nitrosothiols. J Am Chem Soc. 2005;127:15815-23 pubmed
    ..We conclude that both thioredoxin and dihydrolipoic acid may be involved in the regulation of cellular S-nitrosothiols. ..
  30. Brambilla G, Martelli A. Genotoxic and carcinogenic risk to humans of drug-nitrite interaction products. Mutat Res. 2007;635:17-52 pubmed
    The large majority of N-nitroso compounds (NOC) have been found to produce genotoxic effects and to cause tumor development in laboratory animals; four NOC have been classified by the International Agency for Research on Cancer (IARC) as ..
  31. Ozhan G, Alpertunga B. Genotoxic activities of drug-nitrite interaction products. Drug Chem Toxicol. 2003;26:295-308 pubmed
    ..By the umu-test, among the nitrosation products of drugs examined 22 products showed genotoxicity at different levels. Other six products showed negative results by the umu-test. ..
  32. Mirvish S, Haorah J, Zhou L, Hartman M, Morris C, Clapper M. N-nitroso compounds in the gastrointestinal tract of rats and in the feces of mice with induced colitis or fed hot dogs or beef. Carcinogenesis. 2003;24:595-603 pubmed
    Because colonic N-nitroso compounds (NOC) may be a cause of colon cancer, we determined total NOC levels by Walters' method in the gastrointestinal tract and feces of rodents: (i) feces of C57BL mice fed chow and semi-purified diets ..
  33. Johnson M, Macdonald T, Mannick J, Conaway M, Gaston B. Accelerated s-nitrosothiol breakdown by amyotrophic lateral sclerosis mutant copper,zinc-superoxide dismutase. J Biol Chem. 2001;276:39872-8 pubmed
    ..We have identified a potentially toxic gain of function of two common FALS mutations that may contribute to neurodegeneration in FALS. ..
  34. Marley R, Patel R, Orie N, Ceaser E, Darley Usmar V, Moore K. Formation of nanomolar concentrations of S-nitroso-albumin in human plasma by nitric oxide. Free Radic Biol Med. 2001;31:688-96 pubmed
  35. Bauer J, Morrison B, Grane R, Jacobs B, Dabney S, Gamero A, et al. Effects of interferon beta on transcobalamin II-receptor expression and antitumor activity of nitrosylcobalamin. J Natl Cancer Inst. 2002;94:1010-9 pubmed
    ..NO-Cbl inhibited tumor growth in vivo by activating the extrinsic apoptotic pathway. The increased expression of TC II-R induced by IFN-beta resulted in enhanced antitumor effects with NO-Cbl both in vitro and in vivo. ..
  36. McKean Cowdin R, Pogoda J, Lijinsky W, Holly E, Mueller B, Preston Martin S. Maternal prenatal exposure to nitrosatable drugs and childhood brain tumours. Int J Epidemiol. 2003;32:211-7 pubmed
    A compelling hypothesis was proposed that childhood brain tumours are associated with maternal exposure to N-nitroso compounds during the prenatal period...
  37. Cross A, Pollock J, Bingham S. Haem, not protein or inorganic iron, is responsible for endogenous intestinal N-nitrosation arising from red meat. Cancer Res. 2003;63:2358-60 pubmed
    Many N-nitroso compounds (NOC) are carcinogens. In this controlled study of 21 healthy male volunteers, levels of NOC on a high (420 grams) red meat diet were significantly greater (P = 0...
  38. Pervin S, Singh R, Freije W, Chaudhuri G. MKP-1-induced dephosphorylation of extracellular signal-regulated kinase is essential for triggering nitric oxide-induced apoptosis in human breast cancer cell lines: implications in breast cancer. Cancer Res. 2003;63:8853-60 pubmed
    ..Our results indicate that expression of MKP-1 by NO leading to dephosphorylation of ERK1/2 is the initial essential event that commits the cells to the apoptotic pathway in breast cancer cells. ..
  39. Butler A, Megson I. Non-heme iron nitrosyls in biology. Chem Rev. 2002;102:1155-66 pubmed
  40. Rodriguez J, Maloney R, Rassaf T, Bryan N, Feelisch M. Chemical nature of nitric oxide storage forms in rat vascular tissue. Proc Natl Acad Sci U S A. 2003;100:336-41 pubmed
    ..tissues contained 10 +/- 1 microM nitrite, 42 +/- 7 microM nitrate, 40 +/- 6 nM S-nitroso, and 33 +/- 6 nM N-nitroso compounds (n = 4-8)...
  41. de Kok T, Engels L, Moonen E, Kleinjans J. Inflammatory bowel disease stimulates formation of carcinogenic N-nitroso compounds. Gut. 2005;54:731 pubmed
  42. Lewin M, Bailey N, Bandaletova T, Bowman R, Cross A, Pollock J, et al. Red meat enhances the colonic formation of the DNA adduct O6-carboxymethyl guanine: implications for colorectal cancer risk. Cancer Res. 2006;66:1859-65 pubmed
    ..As these O(6)CMG adducts are not repaired, and if other related adducts are formed and not repaired, this may explain the association of red meat with colorectal cancer. ..
  43. Heiss C, Lauer T, Dejam A, Kleinbongard P, Hamada S, Rassaf T, et al. Plasma nitroso compounds are decreased in patients with endothelial dysfunction. J Am Coll Cardiol. 2006;47:573-9 pubmed
  44. Kim D, Kadlubar F, Teitel C, Guengerich F. Formation and reduction of aryl and heterocyclic nitroso compounds and significance in the flux of hydroxylamines. Chem Res Toxicol. 2004;17:529-36 pubmed
    ..Both IQ-NHOH and IQ-N=O were mutagenic in a bacterial tester system devoid of p450 and NPR; the mutagenicity of both was decreased by expression of NPR, consistent with the reduction of these compounds observed with purified NPR. ..
  45. Martínez Ruiz A, Lamas S. Detection and proteomic identification of S-nitrosylated proteins in endothelial cells. Arch Biochem Biophys. 2004;423:192-9 pubmed
    ..We describe the identified proteins and discuss the characterization of their S-nitrosylation, confirming the validity of the methodology for approaching the description of the "nitrosylome." ..
  46. Pan X, Zhang B, Smith J, Francisco M, Anderson T, Cobb G. N-Nitroso compounds produced in deer mouse (Peromyscus maniculatus) GI tracts following hexahydro-1,3,5-trinitro-1,3,5-triazine (RDX) exposure. Chemosphere. 2007;67:1164-70 pubmed
    Given the potent carcinogenic effects of most N-nitroso compounds, the reductive transformation of the common explosive hexahydro-1,3,5-trinitro-1,3,5-triazine (RDX) to a group of N-nitroso derivatives, hexahydro-1-nitroso-3,5-dinitro-1,..
  47. Chawla Sarkar M, Bauer J, Lupica J, Morrison B, Tang Z, Oates R, et al. Suppression of NF-kappa B survival signaling by nitrosylcobalamin sensitizes neoplasms to the anti-tumor effects of Apo2L/TRAIL. J Biol Chem. 2003;278:39461-9 pubmed
    ..The use of NO-Cbl and Apo2L/TRAIL capitalizes on the tumor-specific properties of both agents and represents a promising anti-cancer combination. ..
  48. King S. N-hydroxyurea and acyl nitroso compounds as nitroxyl (HNO) and nitric oxide (NO) donors. Curr Top Med Chem. 2005;5:665-73 pubmed
    ..In general, acyl nitroso compounds, regardless of the method of their preparation, hydrolyze to form HNO and the corresponding carboxylic acid ..
  49. Foster M, McMahon T, Stamler J. S-nitrosylation in health and disease. Trends Mol Med. 2003;9:160-8 pubmed
    ..An understanding of these mechanisms is crucial for the development of an integrated model of NO biology, and for effective treatment of diseases associated with dysregulation of NO homeostasis. ..
  50. Cross A, Greetham H, Pollock J, Rowland I, Bingham S. Variability in fecal water genotoxicity, determined using the Comet assay, is independent of endogenous N-nitroso compound formation attributed to red meat consumption. Environ Mol Mutagen. 2006;47:179-84 pubmed
    Red meat consumption causes a dose-dependent increase in fecal apparent total N-nitroso compounds (ATNC)...
  51. Tang Z, Bauer J, Morrison B, Lindner D. Nitrosylcobalamin promotes cell death via S nitrosylation of Apo2L/TRAIL receptor DR4. Mol Cell Biol. 2006;26:5588-94 pubmed
    ..The C336A mutant also displayed blunted caspase-8 enzymatic activity following NO-Cbl treatment compared to the other mutants. Thus, DR4 residue C336 becomes S nitrosylated and promotes apoptosis following NO-Cbl treatment. ..
  52. Haorah J, Zhou L, Wang X, Xu G, Mirvish S. Determination of total N-nitroso compounds and their precursors in frankfurters, fresh meat, dried salted fish, sauces, tobacco, and tobacco smoke particulates. J Agric Food Chem. 2001;49:6068-78 pubmed
    Total N-nitroso compounds (NOC) and NOC precursors (NOCP) were determined in extracts of food and tobacco products...
  53. Shi Q, Feng J, Qu H, Cheng Y. A proteomic study of S-nitrosylation in the rat cardiac proteins in vitro. Biol Pharm Bull. 2008;31:1536-40 pubmed
    ..This study represents an initial attempt to characterize the S-nitrosoproteome in the heart and highlights the importance of protein S-nitrosylation in cardio function regulation. ..