Summary: Conversion into nitroso compounds. An example is the reaction of nitrites with amino compounds to form carcinogenic N-nitrosamines.

Top Publications

  1. Chiranand W, McLeod I, Zhou H, Lynn J, Vega L, Myers H, et al. CTA4 transcription factor mediates induction of nitrosative stress response in Candida albicans. Eukaryot Cell. 2008;7:268-78 pubmed
    ..albicans ssu1 mutants were not sensitive to NO, in contrast to findings in Saccharomyces cerevisiae. Cta4p is the first protein found to be necessary for initiating NO response in C. albicans. ..
  2. Foster M, Hess D, Stamler J. Protein S-nitrosylation in health and disease: a current perspective. Trends Mol Med. 2009;15:391-404 pubmed publisher
  3. Benhar M, Forrester M, Stamler J. Protein denitrosylation: enzymatic mechanisms and cellular functions. Nat Rev Mol Cell Biol. 2009;10:721-32 pubmed publisher
    ..In addition, they protect from nitrosative stress in microorganisms, mammals and plants, thereby exerting profound effects on host-microbe interactions and innate immunity. ..
  4. Basu S, Keszler A, Azarova N, Nwanze N, Perlegas A, Shiva S, et al. A novel role for cytochrome c: Efficient catalysis of S-nitrosothiol formation. Free Radic Biol Med. 2010;48:255-63 pubmed publisher
    ..Here, we demonstrate a novel mechanism by which cytochrome c may represent an efficient catalyst of S-nitrosation in vivo...
  5. Zenser T, Lakshmi V, Schut H, Zhou H, Josephy P. Activation of aminoimidazole carcinogens by nitrosation: mutagenicity and nucleotide adducts. Mutat Res. 2009;673:109-15 pubmed
    ..In summary, these N-nitrosamines are genotoxic and might be alternatives to their hydroxylamine analogues as activated intermediates leading to initiation of colon cancer in individuals with colitis. ..
  6. Nakamura T, Lipton S. Cell death: protein misfolding and neurodegenerative diseases. Apoptosis. 2009;14:455-68 pubmed publisher
    ..We discuss how memantine/NitroMemantine can inhibit excessive NMDA receptor activity to ameliorate NO production, protein misfolding, and neurodegeneration. ..
  7. Bechtold E, Reisz J, Klomsiri C, Tsang A, Wright M, Poole L, et al. Water-soluble triarylphosphines as biomarkers for protein S-nitrosation. ACS Chem Biol. 2010;5:405-14 pubmed publisher
    ..Several regulatory proteins are now verified targets of cellular S-nitrosation, and the direct detection of S-nitrosated residues in proteins has become essential to better understand RSNO-..
  8. Lopez Sanchez L, Corrales F, Lopez Pedrera C, Aranda E, Rodriguez Ariza A. Pharmacological impairment of s-nitrosoglutathione or thioredoxin reductases augments protein S-Nitrosation in human hepatocarcinoma cells. Anticancer Res. 2010;30:415-21 pubmed
    ..Mithramycin interfered with GSNOR induction resulting in an increased cellular sensitivity to protein S-nitrosation. Moreover, the thioredoxin reductase inhibitor auranofin also increased cellular susceptibility to S-..
  9. Zhou X, Han P, Li J, Zhang X, Huang B, Ruan H, et al. ESNOQ, proteomic quantification of endogenous S-nitrosation. PLoS ONE. 2010;5:e10015 pubmed publisher
    S-nitrosation is a post-translational protein modification and is one of the most important mechanisms of NO signaling. Endogenous S-nitrosothiol (SNO) quantification is a challenge for detailed functional studies...

More Information


  1. Stavniichuk R, Drel V, Shevalye H, Vareniuk I, Stevens M, Nadler J, et al. Role of 12/15-lipoxygenase in nitrosative stress and peripheral prediabetic and diabetic neuropathies. Free Radic Biol Med. 2010;49:1036-45 pubmed publisher
    ..Its presence in human Schwann cells and upregulation by high glucose suggest a potential involvement in human disease. ..
  2. Hill B, Darley Usmar V. S-nitrosation and thiol switching in the mitochondrion: a new paradigm for cardioprotection in ischaemic preconditioning. Biochem J. 2008;412:e11-3 pubmed publisher
    ..the Biochemical Journal in 2006, Burwell and colleagues addressed this issue and provided direct evidence for S-nitrosation of complex I of the mitochondrial electron transport chain...
  3. Dunn J, Gutbrod S, Webb A, Pak A, Jandu S, Bhunia A, et al. S-nitrosation of arginase 1 requires direct interaction with inducible nitric oxide synthase. Mol Cell Biochem. 2011;355:83-9 pubmed publisher
    ..Here, we demonstrate that a direct interaction of Arg1 with NOS2 is necessary for its S-nitrosation. The specific domain of NOS2 that mediates this interaction is identified...
  4. Chaki M, Valderrama R, Fern ndez Oca a A, Carreras A, G mez Rodr guez M, L pez Jaramillo J, et al. High temperature triggers the metabolism of S-nitrosothiols in sunflower mediating a process of nitrosative stress which provokes the inhibition of ferredoxin-NADP reductase by tyrosine nitration. Plant Cell Environ. 2011;34:1803-18 pubmed publisher
    ..Taken together, these results suggest that HT augments SNOs, which appear to mediate protein tyrosine nitration, inhibiting FNR, which is involved in the photosynthesis process...
  5. Raines K, Bonini M, Campbell S. Nitric oxide cell signaling: S-nitrosation of Ras superfamily GTPases. Cardiovasc Res. 2007;75:229-39 pubmed
    ..This article reviews the mechanism of free radical-mediated GTPase regulation and shows nitric oxide can serve as important regulator of small GTPase proteins (i.e. Ras and RhoA) through protein modifications such as S-nitrosation.
  6. Koppenol W. Nitrosation, thiols, and hemoglobin: energetics and kinetics. Inorg Chem. 2012;51:5637-41 pubmed publisher
    ..2) The electrode potential of the RSNO, H(+)/RSH, NO(•)(aq) couple is -0.20 ± 0.06 V at pH 7. (3) Thiol nitrosation by NO(2)(-) is favorable by 37 ± 5 kJ mol(-1) at pH 7...
  7. Chouchani E, Methner C, Nadtochiy S, Logan A, Pell V, Ding S, et al. Cardioprotection by S-nitrosation of a cysteine switch on mitochondrial complex I. Nat Med. 2013;19:753-9 pubmed publisher
    ..Here we used a mitochondria-selective S-nitrosating agent, MitoSNO, to determine how mitochondrial S-nitrosation at the reperfusion phase of myocardial infarction is cardioprotective in vivo in mice...
  8. Keszei A, Goldbohm R, Schouten L, Jakszyn P, van den Brandt P. Dietary N-nitroso compounds, endogenous nitrosation, and the risk of esophageal and gastric cancer subtypes in the Netherlands Cohort Study. Am J Clin Nutr. 2013;97:135-46 pubmed publisher
    Dietary N-nitroso compounds and endogenous nitrosation are important carcinogenic factors, but human evidence of their role is scarce for esophageal cancer and inconsistent for gastric cancer...
  9. Ropelle E, Pauli J, Cintra D, da Silva A, De Souza C, Guadagnini D, et al. Targeted disruption of inducible nitric oxide synthase protects against aging, S-nitrosation, and insulin resistance in muscle of male mice. Diabetes. 2013;62:466-70 pubmed publisher
    Accumulating evidence has demonstrated that S-nitrosation of proteins plays a critical role in several human diseases...
  10. Qu J, Liu G, Huang B, Chen C. Nitric oxide controls nuclear export of APE1/Ref-1 through S-nitrosation of cysteines 93 and 310. Nucleic Acids Res. 2007;35:2522-32 pubmed
    ..This nuclear-cytoplasmic translocation was dependent on S-nitrosation modification of APE1, as simultaneous mutation of S-nitrosation target sites Cys93 and Cys310 completely ..
  11. Nadtochiy S, Burwell L, Brookes P. Cardioprotection and mitochondrial S-nitrosation: effects of S-nitroso-2-mercaptopropionyl glycine (SNO-MPG) in cardiac ischemia-reperfusion injury. J Mol Cell Cardiol. 2007;42:812-25 pubmed
    ..Acknowledging the role of nitric oxide (NO()) in IPC, it was hypothesized that mitochondrial protein S-nitrosation may be a cardioprotective mechanism...
  12. Fernhoff N, Derbyshire E, Underbakke E, Marletta M. Heme-assisted S-nitrosation desensitizes ferric soluble guanylate cyclase to nitric oxide. J Biol Chem. 2012;287:43053-62 pubmed publisher
    ..of NO desensitization and find that sGC undergoes a reductive nitrosylation reaction that is coupled to the S-nitrosation of sGC cysteines...
  13. Pullan S, Gidley M, Jones R, Barrett J, Stevanin T, Read R, et al. Nitric oxide in chemostat-cultured Escherichia coli is sensed by Fnr and other global regulators: unaltered methionine biosynthesis indicates lack of S nitrosation. J Bacteriol. 2007;189:1845-55 pubmed
    ..demonstrated the expression of nitric oxide (NO)-protective mechanisms, and obtained evidence of critical thiol nitrosation. The present study was the first to examine the transcriptome of NO-exposed E. coli in a chemostat...
  14. Zhang X, Huang B, Zhang L, Zhang Y, Zhao Y, Guo X, et al. SNObase, a database for S-nitrosation modification. Protein Cell. 2012;3:929-33 pubmed publisher
    ..Here we developed a database named SNObase ( ), which collected S-nitrosation targets extracted from literatures up ..
  15. Duran W, Beuve A, Sánchez F. Nitric oxide, S-nitrosation, and endothelial permeability. IUBMB Life. 2013;65:819-26 pubmed publisher
    S-Nitrosation is rapidly emerging as a regulatory mechanism in vascular biology, with particular importance in the onset of hyperpermeability induced by pro-inflammatory agents...
  16. Thomas D, JOURD HEUIL D. S-nitrosation: current concepts and new developments. Antioxid Redox Signal. 2012;17:934-6 pubmed publisher
    The S-nitrosation (also referred to as S-nitrosylation) of cysteine residues is an important post-translational protein modification that regulates protein function and cell signaling...
  17. Seven A, Aslan M, Incir S, Altintas A. Evaluation of oxidative and nitrosative stress in relapsing remitting multiple sclerosis: effect of corticosteroid therapy. Folia Neuropathol. 2013;51:58-64 pubmed
    ..As to nitrosative stress, nitrotyrosine and nitrite-nitrate levels were increased in CSF and decreased in serum. ..
  18. Joosen A, Lecommandeur E, Kuhnle G, Aspinall S, Kap L, Rodwell S. Effect of dietary meat and fish on endogenous nitrosation, inflammation and genotoxicity of faecal water. Mutagenesis. 2010;25:243-7 pubmed publisher
    ..We investigated the influence of isocaloric replacement of red meat with fatty fish on endogenous nitrosation, inflammation and genotoxicity of faecal water in apparently healthy human volunteers on controlled diets...
  19. Combet E, Preston T, McColl K. Development of an in vitro system combining aqueous and lipid phases as a tool to understand gastric nitrosation. Rapid Commun Mass Spectrom. 2010;24:529-34 pubmed publisher
    ..Ascorbic acid inhibits nitrosation by converting the nitrosative species into nitric oxide (NO)...
  20. Huang B, Chen C. Detection of protein S-nitrosation using irreversible biotinylation procedures (IBP). Free Radic Biol Med. 2010;49:447-56 pubmed publisher
    The biotin switch assay for detection of protein S-nitrosation has been widely used in the field of nitric oxide and redox signaling...
  21. Sinha V, Wijewickrama G, Chandrasena R, Xu H, Edirisinghe P, Schiefer I, et al. Proteomic and mass spectroscopic quantitation of protein S-nitrosation differentiates NO-donors. ACS Chem Biol. 2010;5:667-80 pubmed publisher
    Protein S-nitrosation has been argued to be the most important signaling pathway mediating the bioactivity of NO. This post-translational modification of protein thiols is the result of chemical nitrosation of cysteine residues...
  22. Helbo S, Fago A. Allosteric modulation by S-nitrosation in the low-O? affinity myoglobin from rainbow trout. Am J Physiol Regul Integr Comp Physiol. 2011;300:R101-8 pubmed publisher
    ..S-nitrosation at reactive cysteines may generate S-nitroso Mb (Mb-SNO) and contribute further to NO homeostasis...
  23. Wang H, Xian M. Chemical methods to detect S-nitrosation. Curr Opin Chem Biol. 2011;15:32-7 pubmed publisher
    ..Modification of cysteine residues by NO (or NO metabolites), that is S-nitrosation, changes the function of a broad spectrum of proteins...
  24. Joosen A, Kuhnle G, Aspinall S, Barrow T, Lecommandeur E, Azqueta A, et al. Effect of processed and red meat on endogenous nitrosation and DNA damage. Carcinogenesis. 2009;30:1402-7 pubmed publisher
    ..11 females), we investigated whether processing of meat might increase colorectal cancer risk by stimulating nitrosation and DNA damage. Meat diets contained 420 g (males) or 366 g (females) meat/per day...
  25. Wenzl M, Beretta M, Griesberger M, Russwurm M, Koesling D, Schmidt K, et al. Site-directed mutagenesis of aldehyde dehydrogenase-2 suggests three distinct pathways of nitroglycerin biotransformation. Mol Pharmacol. 2011;80:258-66 pubmed publisher
    ..Although the latter reaction accounts for less than 10% of total turnover of GTN metabolism catalyzed by wild-type ALDH2, it is most likely essential for vascular GTN bioactivation...
  26. Santhanam L, Gucek M, Brown T, Mansharamani M, Ryoo S, Lemmon C, et al. Selective fluorescent labeling of S-nitrosothiols (S-FLOS): a novel method for studying S-nitrosation. Nitric Oxide. 2008;19:295-302 pubmed publisher
    Protein S-nitrosation is a reversible post-translation modification critical for redox-sensitive cell signaling that is typically studied using the Biotin Switch method...
  27. Mitchell D, Morton S, Fernhoff N, Marletta M. Thioredoxin is required for S-nitrosation of procaspase-3 and the inhibition of apoptosis in Jurkat cells. Proc Natl Acad Sci U S A. 2007;104:11609-14 pubmed
    S-nitrosation is a posttranslational, oxidative addition of NO to cysteine residues of proteins that has been proposed as a cGMP-independent signaling pathway [Hess DT, Matsumoto A, Kim SO, Marshall HE, Stamler JS (2005) Nat Rev Mol Cell ..
  28. Kuhnle G, Bingham S. Dietary meat, endogenous nitrosation and colorectal cancer. Biochem Soc Trans. 2007;35:1355-7 pubmed
    ..Nitrosyl haem and other nitroso compounds can then form under the alkaline and reductive conditions of the small and large bowel. ..
  29. Reinartz M, Ding Z, Flogel U, Gödecke A, Schrader J. Nitrosative stress leads to protein glutathiolation, increased s-nitrosation, and up-regulation of peroxiredoxins in the heart. J Biol Chem. 2008;283:17440-9 pubmed publisher
    ..Another mechanism by which NO exerts biological effects is mediated through S-nitrosation of target proteins...
  30. Pullan S, Monk C, Lee L, Poole R. Microbial responses to nitric oxide and nitrosative stress: growth, "omic," and physiological methods. Methods Enzymol. 2008;437:499-519 pubmed publisher
    ..A key to the literature describing methods suitable for assessing toxicity to microbes of NO and reactive nitrogen species is given. ..
  31. Backhaus C, Rahman H, Scheffler S, Laatsch H, Hardeland R. NO scavenging by 3-hydroxyanthranilic acid and 3-hydroxykynurenine: N-nitrosation leads via oxadiazoles to o-quinone diazides. Nitric Oxide. 2008;19:237-44 pubmed publisher
    ..b>Nitrosation of the non-hydroxylated analogs did not lead to colored products within the period of observation...
  32. Derakhshan B, Hao G, Gross S. Balancing reactivity against selectivity: the evolution of protein S-nitrosylation as an effector of cell signaling by nitric oxide. Cardiovasc Res. 2007;75:210-9 pubmed
  33. Martínez Ruiz A, Lamas S. Signalling by NO-induced protein S-nitrosylation and S-glutathionylation: convergences and divergences. Cardiovasc Res. 2007;75:220-8 pubmed
  34. Mayer B, Kleschyov A, Stessel H, Russwurm M, Munzel T, Koesling D, et al. Inactivation of soluble guanylate cyclase by stoichiometric S-nitrosation. Mol Pharmacol. 2009;75:886-91 pubmed publisher
    ..Based on the proposal that desensitization of sGC through S-nitrosation contributes to vascular NO resistance ( Proc Natl Acad Sci U S A 104: 12312-12317, 2007 ), we exposed purified ..
  35. Yanagimoto T, Toyota T, Matsuki N, Makino Y, Uchiyama S, Ohwada T. Transnitrosation of thiols from aliphatic N-nitrosamines: S-nitrosation and indirect generation of nitric oxide. J Am Chem Soc. 2007;129:736-7 pubmed
  36. Kawano T, Zoga V, Kimura M, Liang M, Wu H, Gemes G, et al. Nitric oxide activates ATP-sensitive potassium channels in mammalian sensory neurons: action by direct S-nitrosylation. Mol Pain. 2009;5:12 pubmed publisher
    ..NO-dependent mechanisms modulate both KATP channels and participate in the pathophysiology and pharmacology of neuropathic pain. Therefore, we investigated NO modulation of KATP channels in control and axotomized DRG neurons...
  37. Cecconi D, Orzetti S, Vandelle E, Rinalducci S, Zolla L, Delledonne M. Protein nitration during defense response in Arabidopsis thaliana. Electrophoresis. 2009;30:2460-8 pubmed publisher
    ..These findings shed new light on the signaling functions of nitric oxide and reactive oxygen species, paving the way on studies on the role of this post-translational modification in plants. ..
  38. Selvakumar B, Huganir R, Snyder S. S-nitrosylation of stargazin regulates surface expression of AMPA-glutamate neurotransmitter receptors. Proc Natl Acad Sci U S A. 2009;106:16440-5 pubmed publisher
    ..NMDAR stimulation, well known to activate neuronal nitric oxide synthase, increases both nitrosylation of stargazin and its binding to AMPAR. Thus, S-nitrosylation of stargazin is a physiologic regulator of AMPAR surface expression. ..
  39. Martínez Ruiz A, Lamas S. Proteomic identification of S-nitrosylated proteins in endothelial cells. Methods Mol Biol. 2007;357:215-23 pubmed NO have been increasingly studied and, among them, cysteine modification by S-nitrosylation (also called S-nitrosation) has been hypothesized to represent a relevant mechanism for cell signaling...
  40. Sengupta R, Ryter S, Zuckerbraun B, Tzeng E, Billiar T, Stoyanovsky D. Thioredoxin catalyzes the denitrosation of low-molecular mass and protein S-nitrosothiols. Biochemistry. 2007;46:8472-83 pubmed
    While most proteins have critical thiols whose oxidation affects their activity, it has been suggested that S-nitrosation and denitrosation of cellular thiols are fundamental processes similar to protein phosphorylation and ..
  41. Tannenbaum S, White F. Regulation and specificity of S-nitrosylation and denitrosylation. ACS Chem Biol. 2006;1:615-8 pubmed
    ..A paper in this issue of the journal dissects the regulatory system involved in SNO of caspase-3 and highlights the need for more direct investigations of the complex biological regulation by NO signaling. ..
  42. Barglow K, Knutson C, Wishnok J, Tannenbaum S, Marletta M. Site-specific and redox-controlled S-nitrosation of thioredoxin. Proc Natl Acad Sci U S A. 2011;108:E600-6 pubmed publisher
    Protein S-nitrosation on cysteine residues has emerged as an important posttranslational modification in mammalian cells. Previous studies have suggested a primary role for thioredoxin (Trx) in controlling protein S-nitrosation reactions...
  43. Suzuki T. Nitrosation of uric acid induced by nitric oxide under aerobic conditions. Nitric Oxide. 2007;16:266-73 pubmed
    ..These results indicate that under aerobic conditions nitric oxide can convert uric acid into its nitroso derivative, which can give a nitroso group to glutathione. Uric acid may act as a vehicle of nitric oxide in humans. ..
  44. Sumbayev V. PI3 kinase and direct S-nitrosation are involved in down-regulation of apoptosis signal-regulating kinase 1 during LPS-induced Toll-like receptor 4 signalling. Immunol Lett. 2008;115:126-30 pubmed
    ..In addition, nitric oxide produced in response to exposure of THP-1 cells to LPS was found to S-nitrosate and therefore, down-regulate ASK1 activity. ..
  45. Lancaster J. Protein cysteine thiol nitrosation: maker or marker of reactive nitrogen species-induced nonerythroid cellular signaling?. Nitric Oxide. 2008;19:68-72 pubmed publisher
    ..Much recent interest in the effects of ()NO in the setting of cancer has centered on the possible role of nitrosation (specifically, formation of nitrosothiol, RSNO) as a mechanism of protein-mediated signaling transduction...
  46. Maes M, Galecki P, Chang Y, Berk M. A review on the oxidative and nitrosative stress (O&NS) pathways in major depression and their possible contribution to the (neuro)degenerative processes in that illness. Prog Neuropsychopharmacol Biol Psychiatry. 2011;35:676-92 pubmed publisher
    ..It is concluded that aberrations in O&NS pathways are--together with the inflammatory processes--key components of depression. All in all, the results suggest that depression belongs to the spectrum of (neuro)degenerative disorders. ..
  47. Lopez Sanchez L, Corrales F, Gonzalez R, Ferrín G, Munoz Castaneda J, Ranchal I, et al. Alteration of S-nitrosothiol homeostasis and targets for protein S-nitrosation in human hepatocytes. Proteomics. 2008;8:4709-20 pubmed publisher
    ..of cellular function and disease, and this study was aimed to identify potential targets for protein S-nitrosation during alteration of SNO homeostasis in human hepatocytes...
  48. Coles S, Easton P, Sharrod H, Hutson S, Hancock J, Patel V, et al. S-Nitrosoglutathione inactivation of the mitochondrial and cytosolic BCAT proteins: S-nitrosation and S-thiolation. Biochemistry. 2009;48:645-56 pubmed publisher
    ..with reactive thiol(ate) groups are susceptible to nitric oxide (NO) modification, which can result in S-nitrosation, S-thiolation, or disulfide bond formation...
  49. Lam Y, Yuan Y, Isaac J, Babu C, Meller J, Ho S. Comprehensive identification and modified-site mapping of S-nitrosylated targets in prostate epithelial cells. PLoS ONE. 2010;5:e9075 pubmed publisher
    ..To our knowledge, this is the first report identifying SNO targets in prostate epithelial cells. ..
  50. 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. ..
  51. Alencar J, Lobysheva I, Geffard M, Sarr M, Schott C, Schini Kerth V, et al. Role of S-nitrosation of cysteine residues in long-lasting inhibitory effect of nitric oxide on arterial tone. Mol Pharmacol. 2003;63:1148-58 pubmed
    S-Nitrosation of cysteine residues plays an important role in nitric oxide (NO) signaling and transport...
  52. Carvalho Filho M, Ueno M, Carvalheira J, Velloso L, Saad M. Targeted disruption of iNOS prevents LPS-induced S-nitrosation of IRbeta/IRS-1 and Akt and insulin resistance in muscle of mice. Am J Physiol Endocrinol Metab. 2006;291:E476-82 pubmed
    ..iNOS) induction in two different models of obesity, diet-induced obesity and the ob/ob mice, is mediated by S-nitrosation of proteins involved in insulin signal transduction: insulin receptor beta-subunit (IRbeta), insulin receptor ..
  53. Kim J, Tannenbaum S. S-Nitrosation regulates the activation of endogenous procaspase-9 in HT-29 human colon carcinoma cells. J Biol Chem. 2004;279:9758-64 pubmed
    ..We show in this paper that cytokines and nitric-oxide synthase (NOS) inhibitors regulate S-nitrosation of an initiator caspase, procaspase-9, in a human colon adenocarcinoma cell line, HT-29...