Covalent modifications of hemoglobin by nitrite anion: Formation kinetics and properties of nitrihemoglobin

Chemical Research in Toxicology

Volumn 23, Issue 11, 2010, Pages 1786-1795

  Otsuka, Mai ^a,b   Marks, Sarah A ^a   Winnica, Daniel E ^c   Amoscato, Andrew A ^c   Pearce, Linda L ^c   Peterson, Jim ^c  

^a CARNEGIE MELLON UNIVERSITY   (United States)

^b UNIVERSITY OF SOUTH FLORIDA   (United States)

^c UNIVERSITY OF PITTSBURGH GRADUATE SCHOOL OF PUBLIC HEALTH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

FERRIC ION; FERROUS ION; HEMOGLOBIN; HEMOPROTEIN; HYDROGEN; NITRIHEMOGLOBIN; NITRITE; NITROUS ACID; OXYGEN; PROTON; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

AEROBIC REACTOR; ALKALINITY; ARTICLE; COVALENT BOND; HUMAN; KINETICS; OXYGEN AFFINITY; PROTEIN MODIFICATION; PROTEIN PROTEIN INTERACTION;

FERRIC COMPOUNDS; HEME; HEMOGLOBIN A; HUMANS; ISOELECTRIC FOCUSING; KINETICS; NITRITES; NITROUS ACID; OXYGEN; SPECTROMETRY, MASS, ELECTROSPRAY IONIZATION; SPECTROPHOTOMETRY, ULTRAVIOLET;

EID: 78649264106     PISSN: 0893228X     EISSN: 15205010     Source Type: Journal    
DOI: 10.1021/tx100242w     Document Type: Article

References (47)

1. Kim-Shapiro, D. B., Gladwin, M. T., Patel, R. P., and Hogg, N. (2005) The reaction between nitrite and hemoglobin: The role of nitrite in hemoglobin-mediated hypoxic vasodilation J. Inorg. Biochem. 99, 237-246
2. 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., Huang, K. T., Shields, H., Kim-Shapiro, D. B., Schechter, A. N., Cannon, R. O., III, and Gladwin, M. T. (2003) Nitrite reduction to nitric oxide by deoxyhemoglobin vasodilates the human circulation Nat. Med. 9, 1498-1505
3. Angelo, M., Singel, D. J., and Stamler, J. S. (2006) An S-nitrosothiol (SNO) synthase function of hemoglobin that utilizes nitrite as a substrate Proc. Natl. Acad. Sci. U.S.A. 103, 8366-8371
4. Chen, K., Piknova, B., Pittman, R. N., Schechter, A. N., and Popel, A. S. (2008) Nitric oxide from nitrite reduction by hemoglobin in the plasma and erythrocytes Nitric Oxide 18, 47-60
5. Raat, N. J., Noguchi, A. C., Liu, V. B., Raghavachari, N., Liu, D., Xu, X., Shiva, S., Munson, P. J., and Gladwin, M. T. (2009) Dietary nitrate and nitrite modulate blood and organ nitrite and the cellular ischemic stress response Free Radical Biol. Med. 47, 510-517
6. National Toxicology Program (2001) Toxicology and carcinogenesis studies of sodium nitrite (CAS NO. 7632-00-0) in F344/N rats and B6C3F1 mice (drinking water studies) Natl. Toxicol. Program Tech. Rep. Ser. 495, 7-273
7. Tilak, K. S., Veeraiah, K., and Raju, J. M. (2007) Effects of ammonia, nitrite and nitrate on hemoglobin content and oxygen consumption of freshwater fish, Cyprinus carpio (Linnaeus) J. Environ. Biol. 28, 45-47
8. Rahman, M. M., Kim, S. J., Kim, G. B., Hong, C. U., Lee, Y. U., Kim, S. Z., Kim, J. S., and Kang, H. S. (2009) Nitrite-induced methemoglobinaemia affects blood ionized and total magnesium level by hydrolysis of plasma adenosine triphosphate in rat Basic Clin. Pharmacol. Toxicol. 105, 294-300
9. Timkovich, R. and Bondoc, L. L. (1990) Diversity in the structure of hemes Adv. Biophys. Chem. 1, 203-247
10. Bondoc, L. L. and Timkovich, R. (1989) Structural characterization of nitrimyoglobin J. Biol. Chem. 264, 6134-6145
11. Antonini, E. and Brunori, M. (1971) in Hemoglobin and myoglobin in their reactions with ligands, Chapter 1, pp 1 - 12, North-Holland, Amsterdam.
12. Bonaventura, C., Godette, G., Tesh, S., Holm, D. E., Bonaventura, J., Crumbliss, A. L., Pearce, L. L., and Peterson, J. (1999) Internal electron transfer between hemes and Cu(II) bound at cysteine β93 promotes methemoglobin reduction by carbon monoxide J. Biol. Chem. 274, 5499-5507
13. Drabkin, D. L. (1946) Spectrophotometric studies. XIV. The crystallographic and optical properties of the hemoglobin of man in comparison with those of other species J. Biol. Chem. 164, 703-723
14. Fago, A., Crumbliss, A. L., Peterson, J., Pearce, L. L., and Bonaventura, C. (2003) The case of the missing NO-hemoglobin: Spectral changes suggestive of heme redox reactions reflect changes in NO-heme geometry Proc. Natl. Acad. Sci. U.S.A. 100, 12087-12092
15. Bartsch, R. G. (1971) Cytochromes: Bacterial Methods Enzymol. 23, 344-363
16. Paul, K. G., Theorell, H., and Åkeson, Å. (1953) The molar light absorption of pyridine ferroprotoporphyrin (pyridine haemochromogen) Acta Chem. Scand. 7, 1284-1287
17. Carraway, A. D., Miller, G. T., Pearce, L. L., and Peterson, J. (1998) The Alkaline Transition of Bis(N-acetylated) Heme Undecapeptide Inorg. Chem. 37, 4654-4661
18. Peng, Q. and Peterson, J. (1994) The use of near-infrared charge-transfer transitions of low-spin ferric chlorins in axial ligand assignment FEBS Lett. 356, 159-161
19. Peng, Q., Timkovich, R., Loewen, P. C., and Peterson, J. (1992) Identification of heme macrocycle type by near-infrared magnetic circular dichroism spectroscopy at cryogenic temperatures FEBS Lett. 309, 157-160
20. Troxler, H., Neuheiser, F., Kleinert, P., Kuster, T., Heizmann, C. W., Sack, R., Hunziker, P., Neuhaus, T. J., Schmid, M., and Frischknecht, H. (2002) Detection of a novel variant human hemoglobin by electrospray ionization mass spectrometry Biochem. Biophys. Res. Commun. 292, 1044-1047
21. Roberts, N. B., Green, B. N., and Morris, M. (1997) Potential of electrospray mass spectrometry for quantifying glycohemoglobin Clin. Chem. 43, 771-778
22. Doyle, M. P., Pickering, R. A., Dykstra, R. L., Nelson, C. L., and Boyer, R. F. (1982) Involvement of peroxide and superoxide in the oxidation of hemoglobin by nitrite Biochem. Biophys. Res. Commun. 105, 127-132
23. Gladwin, M. T., Grubina, R., and Doyle, M. P. (2009) The new chemical biology of nitrite reactions with hemoglobin: R-state catalysis, oxidative denitrosylation, and nitrite reductase/anhydrase Acc. Chem. Res. 42, 157-167
24. Bondoc, L. L. (1989) The structures of unusual porphyrins and hemes: Sulfmyoglobin and nitrimyoglobin. Ph.D. Dissertation, Department of Chemistry, The University of Alabama, Tuscaloosa, AL, pp 261.
25. Gouterman, M. (1978) Chapter 1: Optical spectra and electronic structure of porphyrins and related rings. In The Porphyrins: Physical Chemistry: Part A (Dolphin, D., Ed.) pp 1 - 165, Academic Press, New York.
26. Beetlestone, J. and George, P. (1964) A Magnetochemical Study of Equilibria between High and Low Spin States of Metmyoglobin Complexes Biochemistry 3, 707-714
27. Peisach, J., Blumberg, W. E., Ogawa, S., Rachmilewitz, E. A., and Oltzik, R. (1971) The effects of protein conformation on the heme symmetry in high spin ferric heme proteins as studied by electron paramagnetic resonance J. Biol. Chem. 246, 3342-3355
28. Young, L. J. and Siegel, L. M. (1988) On the reaction of ferric heme proteins with nitrite and sulfite Biochemistry 27, 2790-2800
29. Svistunenko, D. A., Sharpe, M. A., Nicholls, P., Wilson, M. T., and Cooper, C. E. (2000) A new method for quantitation of spin concentration by EPR spectroscopy: Application to methemoglobin and metmyoglobin J. Magn. Reson. 142, 266-275
30. Fago, A., Hundahl, C., Malte, H., and Weber, R. E. (2004) Functional properties of neuroglobin and cytoglobin. Insights into the ancestral physiological roles of globins IUBMB Life 56, 689-696
31. Hille, R., Olson, J. S., and Palmer, G. (1979) Spectral transitions of nitrosyl hemes during ligand binding to hemoglobin J. Biol. Chem. 254, 12110-12120
32. Benesch, R. and Benesch, R. E. (1967) The effect of organic phosphates from the human erythrocyte on the allosteric properties of hemoglobin Biochem. Biophys. Res. Commun. 26, 162-167
33. Carrico, R. J., Blumberg, W. E., and Peisach, J. (1978) The reversible binding of oxygen to sulfhemoglobin J. Biol. Chem. 253, 7212-7215
34. Park, C. M., Nagel, R. L., Blumberg, W. E., Peisach, J., and Magliozzo, R. S. (1986) Sulfhemoglobin. Properties of partially sulfurated tetramers J. Biol. Chem. 261, 8805-8810
35. Everse, J. and Grisham, M. B. (1991) Prooxidant activity of hemoglobin and myoglobin. In Peroxidases in chemistry and biology (Everse, J., Everse, K. E., and Grisham, M. B., Eds.) pp 335 - 344, CRC Press, Boca Raton, FL.
36. Everse, J., Johnson, M. C., and Marini, M. A. (1994) Peroxidatic activities of hemoglobin and hemoglobin derivatives Methods Enzymol. 231, 547-561
37. Young, J. D., Dyar, O., Xiong, L., and Howell, S. (1994) Methaemoglobin production in normal adults inhaling low concentrations of nitric oxide Intensive Care Med. 20, 581-584
38. International Committee for Standardization in Haematology (1978) International Committee for Standardization in Haematology: Protocol for type testing equipment and apparatus used for haematological analysis J. Clin. Pathol. 31, 275-279
39. Dejam, A., Hunter, C. J., Pelletier, M. M., Hsu, L. L., Machado, R. F., Shiva, S., Power, G. G., Kelm, M., Gladwin, M. T., and Schechter, A. N. (2005) Erythrocytes are the major intravascular storage sites of nitrite in human blood Blood 106, 734-739
40. Espey, M. G., Miranda, K. M., Feelisch, M., Fukuto, J., Grisham, M. B., Vitek, M. P., and Wink, D. A. (2000) Mechanisms of cell death governed by the balance between nitrosative and oxidative stress Ann. N.Y. Acad. Sci. 899, 209-221
41. 3 by the concerted nitrite reductase and anhydrase activity of hemoglobin Nat. Chem. Biol. 3, 785-794
42. 3: Quantum-chemical data J. Struct. Chem. 50, 212-218
43. The Merck Veterinary Manual (2008) Merck & Co., Inc., and Merial Ltd., Whitehouse Station, NJ.
44. Yi, J., Safo, M. K., and Richter-Addo, G. B. (2008) The nitrite anion binds to human hemoglobin via the uncommon O-nitrito mode Biochemistry 47, 8247-8249
45. Schwab, D. E., Stamler, J. S., and Singel, D. J. (2009) Nitrite-methemoglobin inadequate for hypoxic vasodilation Nat. Chem. Biol. 5, 366 (author reply p 367)
46. Flexman, A. M., Del Vicario, G., and Schwarz, S. K. (2007) Dark green blood in the operating theatre Lancet 369, 1972
47. Roberts, N. B., Green, B. N., and Morris, M. (1997) Potential of electrospray mass spectrometry for quantifying glycohemoglobin Clin. Chem. 43, 771-778