The DOI matches its Crossref record; 37 of the 37 references it cites were found in a registry or an index.
Kinetics and mechanism of the oxidation of human deoxyhemoglobin by nitrites.
Open accessAbstract
The reactions of human hemoglobin with sodium nitrite and ethyl nitrite in deoxygenated media have been examined in kinetic detail. Nitrous acid has been identified from kinetic pH dependence studies as the principal oxidant of hemoglobin in reactions with sodium nitrite. Nitrosylhemoglobin is produced concurrently with methemoglobin as a result of reductive release of nitric oxide from nitrous acid. However, oxidation of hemoglobin by nitric oxide competes with association, and this process is proposed to arise from the action of the nitric oxide dimer on hemoglobin. Ethyl nitrite, which serves as a model for nitrous acid, reacts with hemoglobin at rates that are at least 10 times slower than those extrapolated for nitrous acid, and hydrolysis of the alkyl nitrite is not competitive with oxidation of hemoglobin. The composite experimental results are interpreted to describe alkyl nitrite, and, presumably, nitrous acid association with hemoglobin followed by rate-limiting electron transfer resulting in nitric oxide and alkoxide (or hydroxide) production. Proton transfer resulting in alcohol (or water) formation occurs subsequent to the rate-limiting step as do reactions of hemoglobin with nitric oxide.
Overview
Integrity signals
Registry
Cites
Statistics
Verification
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?
In the citing paper
“By studying the same reaction using alkyl nitrites, which do not show a pH dependence in their reaction rates with deoxyHb, it was established that the reaction of nitrite requires a proton and thus formally requires nitrous acid (247, 248). This property also makes the reaction faster in low pH conditions.”
From Sources of Vascular Nitric Oxide and Reactive Oxygen Species and Their Regulation (2019) · cites this paper as [248]
In the citing paper
“This scheme has been found to apply to virtually all the heme protein–mediated nitrite reduction reactions studied to date, including Hb (248, 447), Mb (247, 862), neuroglobin (Ngb) (932, 945), Cygb (182, 571, 780), cystathionine β-synthase (CBS) (149, 350), globin X (184), plant and cyanobacterial Hb (phytohemoglobins) (905, 946), flavohemoglobin (340), heme-albumin (43), cytochrome c (41), prot”
From Sources of Vascular Nitric Oxide and Reactive Oxygen Species and Their Regulation (2019) · cites this paper as [248]
In the citing paper
“In the acute setting, nitrite can bind to hemoglobin and oxidize the ferrous iron in heme to the ferric state, thereby forming methemoglobin (metHgb) and preventing the binding of oxygen[152].”
From Enterosalivary nitrate metabolism and the microbiome: Intersection of microbial metabolism, nitric oxide and diet in cardiac and pulmonary vascular health (2017) · cites this paper as [152]
In the citing paper
“(1)NO2−+HbFe2++H+→NO+HbFe3++OH−”
From Mechanisms of nitrite bioactivation (2014) · cites this paper as [35]
In the citing paper
“Doyle and colleagues found k0 to be 12.3 × 103 M−1s−1 [35].”
From Mechanisms of nitrite bioactivation (2014) · cites this paper as [35]
In the citing paper
“The dependence on pH is likely due to the heme actually predominately reacting with nitrous acid, HONO, rather than the nitrite anion.”
From Mechanisms of nitrite bioactivation (2014) · cites this paper as [35]
Citations
Cites
Oxidation of nitrogen-oxides by bound dioxygen in hemoproteins
Doyle, M. P., & Hoekstra, J. W. (1981) · Journal of Inorganic Biochemistry · doi:10.1016/s0162-0134(00)80291-3 · Cited by 643
Self-citationReactions of nitric oxide coordinated to transition metals
McCleverty, J. A. (1979) · Chemical Reviews · doi:10.1021/cr60317a005 · Cited by 305
METHEMOGLOBINEMIA AND METHEMOGLOBIN-PRODUCING COMPOUNDS
Bodansky, O. (1951) · Pharmacological Reviews · doi:10.1016/s0031-6997(25)07311-9 · Cited by 299
Cooperativity in the dissociation of nitric oxide from hemoglobin.
Moore, E. G., & Gibson, Q. H. (1976) · Journal of Biological Chemistry · doi:10.1016/s0021-9258(17)33557-3 · Cited by 292
Influence of globin structure on the state of the heme. I. Human deoxyhemoglobin
Perutz, M. F., Ladner, J. E., Simon, S. R., & Ho, C. (1974) · Biochemistry · doi:10.1021/bi00707a026 · Cited by 292
Conformation, co-operativity and ligand binding in human hemoglobin
Cassoly, R., & Gibson, Q. H. (1975) · Journal of Molecular Biology · doi:10.1016/0022-2836(75)90382-4 · Cited by 259
Kiese, M. (1966) · PubMed · Cited by 200
The toxicology of nitrate, nitrite and n‐nitroso compounds
SWANN, P. F. (1975) · Journal of the Science of Food and Agriculture · doi:10.1002/jsfa.2740261119 · Cited by 168
Austin, J. H., & Drabkin, D. L. (1935) · Journal of Biological Chemistry · doi:10.1016/s0021-9258(18)74966-1 · Cited by 156
Banerjee, R., Alpert, Y., Leterrier, F., & Williams, R. J. P. (1969) · Biochemistry · doi:10.1021/bi00835a025 · Cited by 111
METABOLISM OF INORGANIC NITRITE AND NITRATE ESTERS
HEPPEL, L. A., & Hilmoe, R. J. (1950) · Journal of Biological Chemistry · doi:10.1016/s0021-9258(18)56450-4 · Cited by 90
Reactions of nitric oxide with methemoglobin
Chien, J. C. W. (1969) · Journal of the American Chemical Society · doi:10.1021/ja01036a085 · Cited by 87
A mechanism for the conversion of oxyhemoglobin to methemoglobin by nitrite.
Fl, R. (1976) · Clinical Chemistry · doi:10.1093/clinchem/22.12.1986 · Cited by 78
The Functional Properties of Hemoglobin Bethesda (α2β2145 is)
Olson, J. S., & Gibson, Q. H. (1972) · Journal of Biological Chemistry · doi:10.1016/s0021-9258(19)45191-0 · Cited by 52
McDonald, M. J., & Noble, R. W. (1972) · Journal of Biological Chemistry · doi:10.1016/s0021-9258(19)45073-4 · Cited by 51
ERYTHROCYTE DPNH DEPENDENT DIAPHORASE LEVELS IN INFANTS
Bartos, H. R., & Desforges, J. F. (1966) · PEDIATRICS · doi:10.1542/peds.37.6.991 · Cited by 47
Nonequivalence of chains in hemoglobin oxidation and oxygen binding. Effect of organic phosphates
Mansouri, A., & Winterhalter, K. H. (1974) · Biochemistry · doi:10.1021/bi00713a021 · Cited by 43
Ohlsen, J. R., & Laane, J. (1978) · Journal of the American Chemical Society · doi:10.1021/ja00490a030 · Cited by 43
Reactive transition metal dinitrosyl complexes. Synthetic uses and catalytic properties
Haymore, B. L., & Ibers, J. A. (1974) · Journal of the American Chemical Society · doi:10.1021/ja00817a057 · Cited by 43
Chain equivalence in reaction of nitric oxide with hemoglobin.
Hille, R., Palmer, G., & Olson, J. S. (1977) · Journal of Biological Chemistry · doi:10.1016/s0021-9258(17)32843-0 · Cited by 42
Rates of isonitrile binding to the isolated alpha and beta subunits of human hemoglobin.
Reisberg, P., & Olson, J. S. (1980) · Journal of Biological Chemistry · doi:10.1016/s0021-9258(19)85646-6 · Cited by 40
Bonnett, R., Charalambides, A. A., Martin, R. A., Sales, K. D., & Fitzsimmons, B. W. (1975) · Journal of the Chemical Society Chemical Communications · doi:10.1039/c39750000884 · Cited by 39
Reaction between azide and nitronium ions. Formation and decomposition of nitryl azide
Doyle, M. P., Maciejko, J. J., & Busman, S. C. (1973) · Journal of the American Chemical Society · doi:10.1021/ja00784a069 · Cited by 39
Self-citationTHE ACTION OF NITRITES ON BLOOD
Marshall, W., & Marshall, C. R. (1945) · Journal of Biological Chemistry · doi:10.1016/s0021-9258(17)41605-x · Cited by 38
Thermodynamics of the Ionization of Hydroxylamine and Nitrous Acid in Water.
Lumme, P. O., Lahermo, P. W., & Tummavuori, J. L. (1965) · Acta chemica Scandinavica/Acta chemica Scandinavica. B, Organic chemistry and biochemistry/Acta chemica Scandinavica. A, Physical and inorganic chemistry/Acta chemica Scandinavica. Series B. Organic chemistry and biochemistry/Acta chemica Scandinavica. Series A, Physical and inorganic chemistry · doi:10.3891/acta.chem.scand.19-2175 · Cited by 36
XXIV. Researches on the blood.—On the action of nitrites on blood
Gamgee, A. (1868) · Philosophical Transactions of the Royal Society of London · doi:10.1098/rstl.1868.0025 · Cited by 31
Relations between optical spectrum and structure in nitrosyl hemoglobin and hybrids
Cassoly, R. (1975) · Journal of Molecular Biology · doi:10.1016/s0022-2836(75)80088-x · Cited by 29
Effect of inositol hexaphosphate on hemoglobin oxidation by nitrite and ferricyanide
Tomoda, A., Matsukawa, S., Takeshita, M., & Yoneyama, Y. (1977) · Biochemical and Biophysical Research Communications · doi:10.1016/0006-291x(77)90607-6 · Cited by 25
Nitrite and the Environment. The Nitrosation of a-Amino Acid Derivatives
Bonnett, R., & Nicolaidou, P. (1977) · Heterocycles · doi:10.3987/s-1977-01-0637 · Cited by 25
Nitroglycerin biotransformation by rat blood serum
DiCarlo, F. J., & Melgar, M. D. (1970) · Biochemical Pharmacology · doi:10.1016/0006-2952(70)90052-3 · Cited by 24
On the relationship of hemoglobin oxidation with the conformation of hemoglobin
Tomoda, A., & Yoneyama, Y. (1979) · Cellular and Molecular Life Sciences · doi:10.1007/bf01917846 · Cited by 18
Structure and stability of the nitric oxide dimer
Williams, J. E., & Murrell, J. N. (1971) · Journal of the American Chemical Society · doi:10.1021/ja00755a006 · Cited by 18
Some nitrosylsulphinate radical-anions RN(SO 2 – )O·
Mulvey, D., & Waters, W. A. (1974) · Journal of the Chemical Society Perkin Transactions 2 · doi:10.1039/p29740000772 · Cited by 16
Doyle, M. P., Doornik, F. J. V., & Funckes, C. L. (1980) · Inorganica Chimica Acta · doi:10.1016/s0020-1693(00)84156-0 · Cited by 10
Self-citationMethemoglobinemia Owing to Rectal-Probe Lubrication
SHERMAN, J. M. (1979) · Archives of Pediatrics and Adolescent Medicine · doi:10.1001/archpedi.1979.02130040093023 · Cited by 10
Absorptionsspektrum desN2O2zwischen 1850 und 2550 Å in flüssigem Argon
Buschmann, H. W. (1974) · Zeitschrift für Physikalische Chemie · doi:10.1524/zpch.1974.92.1-3.011 · Cited by 3
Study of the reaction of nitrosobenzene with haemoglobine
Holecek, V., Kopecký, J., & Škramovský, S. (1979) · Collection of Czechoslovak Chemical Communications · doi:10.1135/cccc19790981 · Cited by 2
Research works printed but not linked: 4
- Kiese, 1966, Pharmacol. Rev., 18, 1091, 10.1016/S0031-6997(25)07167-4 · DOI
- Sherman, 1979, Am. J. Dis. Child, 133, 439
- Chalamet, 1973, Ann. Chim., 8, 353
- LeMaistre, J. W. (1972) in Study Syst., Coronary Myocardial Effects of Nitrates, Proceedings Symposium, 1970, pp. 251–257
Cited by
Sorted by citations
The nitrate-nitrite-nitric oxide pathway in physiology and therapeutics
Lundberg, J. O., Weitzberg, E., & Gladwin, M. T. (2008) · Nature Reviews Drug Discovery · doi:10.1038/nrd2466 · Cited by 2,739
Nitrite reduction to nitric oxide by deoxyhemoglobin vasodilates the human circulation
Cosby, K., Partovi, K. S., Crawford, J. H., Patel, R. P., Reiter, C. D., Martyr, S., Yang, B. K., Waclawiw, M. A., Zalos, G., Xu, X., et al. (2003) · Nature Medicine · doi:10.1038/nm954 · Cited by 1,807
Nitric oxide synthase in innate and adaptive immunity: an update
Bogdan, C. (2015) · Trends in Immunology · doi:10.1016/j.it.2015.01.003 · Cited by 862
Riess, J. G. (2001) · Chemical Reviews · doi:10.1021/cr970143c · Cited by 787
Nitrate, bacteria and human health
Lundberg, J. O., Weitzberg, E., Cole, J. A., & Benjamin, N. (2004) · Nature Reviews Microbiology · doi:10.1038/nrmicro929 · Cited by 739
Metadata
- Authors
- Doyle, M. P., Pickering, R. A., DeWeert, T. M., Hoekstra, J. W., & Pater, D.
- Affiliations
- Hope College (US)
- ORCID
- Doyle, M.P.
- Venue
- Journal of Biological Chemistry
- Publisher
- Elsevier BV
- Published
- 1981-12
- Volume
- 256
- Issue
- 23
- Pages
- 12393-12398
- ISSN
- 0021-9258 (ISSN-L)
- OpenAlex
- W1589586351
- Cited by
- 334
- References
- 37
- Citations by year
- 2026: 2 · 2025: 2 · 2024: 5 · 2023: 4 · 2022: 2 · 2021: 10 · 2020: 4 · 2019: 8 · 2018: 12 · 2017: 7 · 2016: 12 · 2015: 18 · 2014: 16 · 2013: 11 · 2012: 12
- FWCI
- 0.85
- Type
- journal article
- Language
- en
- Open access
- hybrid
- doi.org
- Licence
- Locations
- Journal of Biological Chemistry (publishedVersion, cc-by)
- PubMed (publishedVersion)
- Topics
- Life Sciences › Biochemistry, Genetics and Molecular Biology › Biochemistry › Hemoglobin structure and function
- Physical Sciences › Chemistry › Inorganic Chemistry › Metal-Catalyzed Oxygenation Mechanisms
- Health Sciences › Medicine › Physiology (medical) › Nitric Oxide and Endothelin Effects
- Keywords
- nitrous acid, sodium nitrite, ethyl nitrite, nitric oxide, nitrosylhemoglobin, methemoglobin, nitric oxide dimer, electron transfer, reaction mechanism, reaction kinetics, proton transfer
- MeSH terms
- Hemoglobin A, Humans, Hydrogen-Ion Concentration, Kinetics, Nitrites, Oxidation-Reduction, Oxyhemoglobins, Sodium Nitrite, Spectrophotometry
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