NO-group transfer (transnitrosation) between S-nitrosothiols and thiols. Part 2
Abstract
The kinetics of NO-group transfer have been measured for the reaction between a nitrosothiol (HOCH2CH2SNO) and nine thiols, mostly based on the cysteine structure. The reaction is second-order and there is evidence for a steric effect for thiols containing 1,1-dimethyl substituents (penicillamine derivatives). Reaction occurs via the thiolate anion as shown by the pH-rate constant profile, and a full kinetic analysis for the reactions of two thiols (N-acetylcysteine and glutathione) is quantitatively in agreement with this mechanism. Variation of the nitrosothiol structure for reaction with N-acetylcysteine shows that electron-withdrawing substituents in the nitrosothiol promote reaction; there is a similarity with the corresponding reactions of alkyl nitrites.
Integrity signals
Registry
Cites
Statistics
Claims the paper makes
Claims other papers make about this one
Each is checked against this paper’s own text: does it say what the citing paper says it does?
The reaction of transnitrosation between nitrosothiols and thiols is very fast, requiring stopped-flow techniques for kinetics.
“They found the reaction to be very fast, requiring stopped-flow techniques for investigating the kinetics.”
From On the chemical biology of the nitrite/sulfide interaction (2015) · cites this paper as [97]
Nitrosation favors thiols with a lower pKa.
“Their data showed that the nitrosation favored thiols with a lower pKa.”
From On the chemical biology of the nitrite/sulfide interaction (2015) · cites this paper as [97]
Cites
Nitric oxide: physiology, pathophysiology, and pharmacology.
Moncada, S., Palmer, R. M., & Higgs, E. A. (1991) · Pharmacological Reviews · doi:10.1016/s0031-6997(25)06663-3 · Cited by 15,525 · see citing works
The physiological role of nitric oxide
Butler, A. R., & Williams, D. L. H. (1993) · Chemical Society Reviews · doi:10.1039/cs9932200233 · Cited by 555 · see citing works
Meyer, D. J., Kramer, H., Özer, N., Coles, B., & KETTERER, B. (1994) · FEBS Letters · doi:10.1016/0014-5793(94)00429-3 · Cited by 156 · see citing works
Reaction of S-nitrosoglutathione with sulfhydryl groups in protein
Park, J. (1988) · Biochemical and Biophysical Research Communications · doi:10.1016/s0006-291x(88)80127-x · Cited by 113 · see citing works
Small Ring Heterocyclic Nitrosoamines1
Bumgardner, C. L., McCallum, K. S., & Freeman, J. P. (1961) · Journal of the American Chemical Society · doi:10.1021/ja01482a028 · Cited by 65 · see citing works
Reaction of thiol anions with benzene oxide and malachite green
Reuben, D. M. E., & Bruice, T. C. (1976) · Journal of the American Chemical Society · doi:10.1021/ja00417a020 · Cited by 60 · see citing works
Flagged first, then by citations
Cited by
Sorted by citations
Nitric oxide donors: chemical activities and biological applications
Wang, P. G., Xian, M., Tang, X., Wu, X., Wen, Z., Cai, T., & Janczuk, A. J. (2002) · Chemical Reviews · doi:10.1021/cr000040l · Cited by 1,337 · see citing works
Forman, H., Fukuto, J., & Torres, M. (2004) · American Journal of Physiology - Cell Physiology · doi:10.1152/ajpcell.00516.2003 · Cited by 538 · see citing works
“, transfer) of the equivalent of NO from one thiol to another (7, 8).”
BackgroundMechanism of Nitric Oxide Release from S-Nitrosothiols
Singh, R. J., Hogg, N., Joseph, J., & Kalyanaraman, B. (1996) · Journal of Biological Chemistry · doi:10.1074/jbc.271.31.18596 · Cited by 600 · see citing works
Free radical biology and medicine: it's a gas, man!
Pryor, W. A., Houk, K. N., Foote, C. S., Fukuto, J. M., Ignarro, L. J., Squadrito, G. L., & Davies, K. J. A. (2006) · American Journal of Physiology-Regulatory, Integrative and Comparative Physiology · doi:10.1152/ajpregu.00614.2005 · Cited by 465 · see citing works
Chemistry, Analysis, and Biological Roles ofS-Nitrosothiols
Anthony, A. R., & Rhodes, P. (1997) · Analytical Biochemistry · doi:10.1006/abio.1997.2129 · Cited by 182 · see citing works
On the chemical biology of the nitrite/sulfide interaction
Cortese-Krott, M. M., Fernandez, B. O., Kelm, M., Butler, A. R., & Feelisch, M. (2015) · Nitric Oxide · doi:10.1016/j.niox.2014.12.009 · Cited by 115 · see citing works
SMITH, J. N. M., & Dasgupta, T. P. (2000) · Nitric Oxide · doi:10.1006/niox.2000.0272 · Cited by 110 · see citing works
Inhibition of Papain by S-Nitrosothiols
Xian, M., Chen, X., Liu, Z., Wang, K., & Wang, P. G. (2000) · Journal of Biological Chemistry · doi:10.1074/jbc.m001054200 · Cited by 95 · see citing works
Firouzabadi, H., Iranpoor, N., & Zolfigol, M. A. (1998) · Synthetic Communications · doi:10.1080/00397919808005959 · Cited by 92 · see citing works
The Chemical Properties of Nitric Oxide and Related Nitrogen Oxides
Fukuto, J. M., Cho, J. Y., & Switzer, C. H. (2000) · Elsevier eBooks · doi:10.1016/b978-012370420-7/50003-4 · Cited by 78 · see citing works
S-Nitrosothiols: Materials, Reactivity and Mechanisms
Szacilowski, K. T., & Stasicka, Z. (2001) · Progress in Reaction Kinetics and Mechanism · doi:10.3184/007967401103165181 · Cited by 76 · see citing works
Iranpoor, N., Firouzabadi, H., & Zolfigol, M. A. (1998) · Synthetic Communications · doi:10.1080/00397919808005729 · Cited by 71 · see citing works
Equilibrium and kinetics studies of transnitrosation between S-nitrosothiols and thiols
Wang, K., Wen, Z., Zhang, W., Xian, M., Cheng, J., & Wang, P. G. (2001) · Bioorganic & Medicinal Chemistry Letters · doi:10.1016/s0960-894x(00)00688-0 · Cited by 51 · see citing works
New insights into the S-nitrosothiol–ascorbate reaction. The formation of nitroxyl
Kirsch, M., Büscher, A.-M., Aker, S., Schulz, R., & de GROOT, H. (2009) · Organic & Biomolecular Chemistry · doi:10.1039/b901046g · Cited by 48 · see citing works
The kinetics of thiol-mediated decomposition of S-nitrosothiols
Hu, T., & Chou, T.-C. (2006) · The AAPS Journal · doi:10.1208/aapsj080357 · Cited by 48 · see citing works
Thiol redox biochemistry: insights from computer simulations
Zeida, A., Guardia, C. M. A., Lichtig, P., Perissinotti, L. L., Defelipe, L. A., Turjanski, A. G., Radí, R., Trujillo, M., & Estrin, D. A. (2014) · Biophysical Reviews · doi:10.1007/s12551-013-0127-x · Cited by 45 · see citing works
“The reaction rate depends on pH, suggesting that the RS- is the reactive species (Barnett et al. 1994, 1995; Munro and Williams 2000; Wang et al. 2001).”
BackgroundHeikal, L., Martin, G. P., & Dailey, L. A. (2008) · Nitric Oxide · doi:10.1016/j.niox.2008.11.001 · Cited by 43 · see citing works
Glyco-S-nitrosothiols, a novel class of no donor compounds
Ramirez, J., Yu, L., Li, J., Braunschweiger, P. G., & Wang, P. G. (1996) · Bioorganic & Medicinal Chemistry Letters · doi:10.1016/0960-894x(96)00484-2 · Cited by 43 · see citing works
A Novel Family of S-Nitrosothiols: Chemical Synthesis and Biological Actions
Al‐Sa'doni, H. H., Khan, I. Y., Poston, L., Fisher, I. B., & Ferro, A. (2000) · Nitric Oxide · doi:10.1006/niox.2000.0315 · Cited by 41 · see citing works
Caro's Acid Supported on Silica Gel. Part 1: Oxidative Coupling of Thiols to Disulfides
Movassagh, B., Lakouraj, M. M., & Ghodrati, K. (1999) · Synthetic Communications · doi:10.1080/00397919908085994 · Cited by 41 · see citing works
Photodelivery of Nitric Oxide from a Nitrosothiol-Derivatized Surface
Etchenique, R., Furman, M., & Olabe, J. A. (2000) · Journal of the American Chemical Society · doi:10.1021/ja9939845 · Cited by 40 · see citing works
Assessments of Thiyl Radicals in Biosystems: Difficulties and New Applications
Stoyanovsky, D. A., Maeda, A., Atkins, J. L., & Kagan, V. E. (2011) · Analytical Chemistry · doi:10.1021/ac200418s · Cited by 40 · see citing works
The reaction of S-nitrosothiols with thiols at high thiol concentration
Dicks, A. P., Li, E., Munro, A. P., Swift, H. R., & Williams, D. L. H. (1998) · Canadian Journal of Chemistry · doi:10.1139/v98-062 · Cited by 36 · see citing works
Noble, D. R., & Williams, D. L. H. (2000) · Nitric Oxide · doi:10.1006/niox.2000.0291 · Cited by 35 · see citing works
Namiki, S., Kaneda, F., Ikegami, M., Arai, T., Fujimori, K., Asada, S., Hama, H., Kasuya, Y., & Goto, K. (1999) · Bioorganic & Medicinal Chemistry · doi:10.1016/s0968-0896(99)00084-x · Cited by 34 · see citing works
Nitrosating Agents: Is Peroxynitrite a Likely Candidate?
Williams, D. L. H. (1997) · Nitric Oxide · doi:10.1006/niox.1997.0159 · Cited by 34 · see citing works
Amperometric S-nitrosothiol sensor with enhanced sensitivity based on organoselenium catalysts
Cha, W., Anderson, M. R., Zhang, F., & Meyerhoff, M. E. (2008) · Biosensors and Bioelectronics · doi:10.1016/j.bios.2008.12.022 · Cited by 29 · see citing works
“The reaction rate for transnitrosation depends on the pKa of thiol species; as a result, the rate constants reported for transnitrosation with cysteine are 2-4 times higher than those for GSH (Barnett et al. 1994;Barnett et al. 1995;Hogg 1999).”
BackgroundFluorophore-Labeled S-Nitrosothiols
Chen, X., Wen, Z., Xian, M., Wang, K., Ramachandran, N., Tang, X., Schlegel, H. B., Mutus, B., & Wang, P. G. (2001) · The Journal of Organic Chemistry · doi:10.1021/jo015658p · Cited by 28 · see citing works
Kinetic studies of the reaction of S-nitroso-L-cysteine with L-cysteine
Komiyama, T., & Fujimori, K. (1997) · Bioorganic & Medicinal Chemistry Letters · doi:10.1016/s0960-894x(96)00608-7 · Cited by 24 · see citing works
IRMPD spectroscopy of protonated S-nitrosocaptopril, a biologically active, synthetic amino acid
Coletti, C., Re, N., Scuderi, D., Maı̂tre, P., Chiavarino, B., Fornarini, S., Lanucara, F., Sinha, R. K., & Crestoni, M. E. (2010) · Physical Chemistry Chemical Physics · doi:10.1039/c0cp00671h · Cited by 22 · see citing works
S-Nitrosothiol and Nitric Oxide Reactivity at Zinc Thiolates
Varonka, M. S., & Warren, T. H. (2009) · Inorganic Chemistry · doi:10.1021/ic900664r · Cited by 21 · see citing works
Yi, J., Khan, M. A., Lee, J., & Richter-Addo, G. B. (2005) · Nitric Oxide · doi:10.1016/j.niox.2005.03.005 · Cited by 18 · see citing works
Synthesis and kinetics of decomposition of some novel S-nitrosothiols
Munro, A. P., & Williams, D. L. H. (1999) · Canadian Journal of Chemistry · doi:10.1139/v99-026 · Cited by 17 · see citing works
Reaction of the XPA Zinc Finger with S-Nitrosoglutathione
Smirnova, J., Zhukova, L., Witkiewicz-Kucharczyk, A., Kopera, E., Olędzki, J., Wysłouch‐Cieszyńska, A., Palumaa, P., Hartwig, A., & Bal, W. (2008) · Chemical Research in Toxicology · doi:10.1021/tx700297f · Cited by 15 · see citing works
SMITH, J. N. M., & Dasgupta, T. P. (2002) · Inorganic Reaction Mechanisms · doi:10.1080/10286620210352 · Cited by 14 · see citing works
Reactions of S-nitrosothiols with l-ascorbic acid in aqueous solution
Dasgupta, T. P., & SMITH, J. N. M. (2002) · Methods in enzymology on CD-ROM/Methods in enzymology · doi:10.1016/s0076-6879(02)59186-2 · Cited by 13 · see citing works
First Kinetic Discrimination Between Carbon and Oxygen Reactivity of Enols
García‐Río, L., Mejuto, J. C., Parajo, M., & Pérez‐Lorenzo, M. (2008) · The Journal of Organic Chemistry · doi:10.1021/jo801183y · Cited by 12 · see citing works
PS-SNAP, a practical polymer-supported nitrosation reagent in organic synthesis
Roche, D., Lardy, C., Tournier, L., Prunier, M., & Valeur, E. (2010) · Tetrahedron Letters · doi:10.1016/j.tetlet.2010.02.135 · Cited by 12 · see citing works
Li, J., Wang, G., & Schlegel, H. B. (2006) · Organic & Biomolecular Chemistry · doi:10.1039/b600177g · Cited by 11 · see citing works
Firouzabadi, H., Iranpoor, N., & Heydari, R. (2002) · Phosphorus, sulfur, and silicon and the related elements · doi:10.1080/10426500210273 · Cited by 9 · see citing works
The theoretical comparison between two model NO carriers, MeSNO and MeSeNO
Lai, C., & Chou, P. (2007) · Journal of Molecular Modeling · doi:10.1007/s00894-007-0246-z · Cited by 7 · see citing works
Li, X., Deng, H., Zhu, X., Wang, X., Liang, H., & Cheng, J. (2009) · The Journal of Organic Chemistry · doi:10.1021/jo900732b · Cited by 7 · see citing works
The Biological Chemistry of NO
Hogg, N., & Griffith, O. W. (1997) · Springer eBooks · doi:10.1007/978-1-4615-6039-5_1 · Cited by 7 · see citing works
Volatile S-nitrosothiols and the typical smell of cancer
Schroeder, W. (2015) · Journal of Breath Research · doi:10.1088/1752-7155/9/1/016010 · Cited by 6 · see citing works
“Subsequent publications dealt with the apparent instability of these compounds towards heat [32, 44], decomposition during pH changing [33, 45], reactivity towards photodissociation [46, 47], fast reaction by reduction [35], reaction with other molecules (trans nitrosation with thiols) [36, 48] and their remarkable in…”
BackgroundAquart, D. V., & Dasgupta, T. P. (2005) · Organic & Biomolecular Chemistry · doi:10.1039/b500915d · Cited by 6 · see citing works
Eilertsen, M., Allin, S. M., & Pearson, R. J. (2018) · Bioorganic & Medicinal Chemistry Letters · doi:10.1016/j.bmcl.2018.01.059 · Cited by 6 · see citing works
S ‐ Nitroso Compounds, Formation, Reactions and Biological Activity
Williams, D. L. H. (2009) · Patai's chemistry of functional groups · doi:10.1002/9780470682531.pat0084 · Cited by 6 · see citing works
Transfer of nitric oxide from nitrovasodilators to free thiols—Evidence of two distinct stages
Dasgupta, T. P., & Aquart, D. V. (2005) · Biochemical and Biophysical Research Communications · doi:10.1016/j.bbrc.2005.07.126 · Cited by 4 · see citing works
Alimoradi, H., Thomas, A., Lyth, D. D. B., Barzegar‐Fallah, A., Matikonda, S. S., Gamble, A. B., & Giles, G. I. (2022) · Nanotechnology · doi:10.1088/1361-6528/ac4eb0 · Cited by 2 · see citing works
“Assuming a second order reaction [ 74 ] , with initial concentrations of BmobaSNO ( 1.17 mM ) and GSH ( 5 mM ) the derived rate constant k GSH was 360 M − 1 s − 1 .”
InfluentialMolecular Mechanisms of Action of Nitric Oxide in Heart Muscle
Balligand, J. (1998) · Yearbook of intensive care and emergency medicine · doi:10.1007/978-3-642-72038-3_10 · Cited by 2 · see citing works
Hydrogen Sulfide, Reactive Nitrogen Species, and “The Joy of the Experimental Play*”
Cortese-Krott, M. M. (2022) · Wiley eBooks · doi:10.1002/9781119799900.ch4 · Cited by 2 · see citing works
Brown, R. F. G., Dasgupta, T. P., Maragh, P. T., & Holder, A. A. (2009) · Biophysical Chemistry · doi:10.1016/j.bpc.2009.01.014
Plasmodium-Induced Nitrosative Stress in Anopheles stephensi: The Cost of Host Defense
Marie, T., & Peterson, L. (2005) · VTechWorks (Virginia Tech)
(2004) · Elsevier eBooks · doi:10.1016/b978-044451721-0/50016-5
- Authors
- Barnett, D. J., Rios, A., & Williams, D. L. H.
- Venue
- Journal of the Chemical Society Perkin Transactions 2
- Publisher
- Royal Society of Chemistry (RSC)
- Published
- 1995
- Issue
- 7
- Pages
- 1279
- ISSN
- 0300-9580 (ISSN-L)
- 1364-5471
- OpenAlex
- W2061745954
- Cited by
- 55
- References
- 6
- Citations by year
- 2022: 2 · 2018: 1 · 2015: 1 · 2014: 2
- FWCI
- 3.03
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Journal of the Chemical Society Perkin Transactions 2 (publishedVersion)
- Funders
- Xunta de Galicia
- Engineering and Physical Sciences Research Council
- Topics
- Physical Sciences › Chemistry › Organic Chemistry › Chemical Reaction Mechanisms
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Molecular Biology › Redox biology and oxidative stress
- Health Sciences › Medicine › Physiology › Nitric Oxide and Endothelin Effects
- Keywords
- transnitrosation, S-nitrosothiols, thiols, reaction kinetics, steric effects, thiolate anion, N-acetylcysteine, glutathione, electron-withdrawing substituents, alkyl nitrites, pH-rate profile
About these checks
Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.
Statistics and arithmetic are recomputed, not judged.
Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.
What counts as a claim ›How we measure confidence ›How we check this ›
Are you an author, or do you see a problem with this page? Request a review
