Nitric oxide production from hydroxyurea

Free Radical Biology and Medicine

Volumn 37, Issue 6, 2004, Pages 737-744

  King, S Bruce ^a  

^a WAKE FOREST UNIVERSITY   (United States)

Author keywords

2 (4 carboxyphenyl) 4,5 dihydro 4, 4, 5, 5, tetramethyl 1H imidazolyl 1 oxy 3 oxide, potassium salt; Carboxy PTIO; cGMP; Free radicals; Heme proteins; Hydroxylamine; Hydroxyurea; Nitric oxide; Oxidation; Sickle cell disease; Urease

Indexed keywords

AMMONIA; ARGININE; CARBON DIOXIDE; CYTOCHROME C OXIDASE; DEOXYHEMOGLOBIN; FERRIC ION; FERROUS ION; FORMAMIDE; HEMOGLOBIN; HEMOPROTEIN; HYDROXYLAMINE; HYDROXYUREA; METHEMOGLOBIN; MYOGLOBIN; NITRATE; NITRIC OXIDE; NITRITE; OXYHEMOGLOBIN; PEROXIDASE; RIBONUCLEOTIDE REDUCTASE; UREASE; VASCULAR CELL ADHESION MOLECULE 1;

CHEMICAL BOND; CHEMOLUMINESCENCE; DECOMPOSITION; DIMERIZATION; DRUG METABOLISM; ELECTRON SPIN RESONANCE; HUMAN; HYDROLYSIS KINETICS; NONHUMAN; OXIDATION KINETICS; OXIDATION REDUCTION REACTION; PRIORITY JOURNAL; REVIEW; SICKLE CELL ANEMIA; STRUCTURE ACTIVITY RELATION;

ANEMIA, SICKLE CELL; FREE RADICALS; HEMOGLOBINS; HUMANS; HYDROXYLAMINE; HYDROXYUREA; IRON; MODELS, CHEMICAL; NITRATES; NITRIC OXIDE; NITRITES; OXYGEN; PEROXIDASE; TIME FACTORS; UREASE;

OXY;

EID: 4043163356     PISSN: 08915849     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.freeradbiomed.2004.02.073     Document Type: Review

References (49)

1. Steinberg M.H., et al. Effect of hydroxyurea on mortality and morbidity in adult sickle cell anemia. JAMA. 289:2003;1645-1651
2. Charache S., Terrin M.L., Moore R.D., Dover G.J., Barton F.B., Eckert S.V., McMahon R.P., Bonds D.R. the Investigators of the Multicenter Study of Hydroxyurea in Sickle Cell Anemia Effect of hydroxyurea on the frequency of painful crises in sickle cell anemia. N. Engl. J. Med. 332:1995;1317-1322
3. Charache S., Barton F.B., Moore R.D., Terrin M.L., Steinberg M.H., Dover G.J., Ballas S.K., McMahon P., Castro O., Orringer E.P. the Investigators of the Multicenter Study of Hydroxyurea in Sickle Cell Anemia Hydroxyurea and sickle cell anemia. Medicine. 75:1996;300-326
4. Halsey C., Roberts I.A.G. The role of hydroxyurea in sickle cell disease. Br. J. Haematol. 120:2003;177-186
5. King S.B. The nitric oxide producing reactions of hydroxyurea. Curr. Med. Chem. 10:2003;437-452
6. Reiter C.D., Gladwin M.T. An emerging role for nitric oxide in sickle cell disease vascular homeostasis and therapy. Curr. Opin. Hematol. 10:2003;99-107
7. Gladwin M.T., Schechter A.N. Nitric oxide therapy in sickle cell disease. Semin. Hematol. 38:2001;333-342
8. Reiter C.D., Wang X., Tanus-Santos J.E., Hogg N., Cannon R.O., Schechter A.N., Gladwin M.T. Cell-free hemoglobin limits nitric oxide bioavailability in sickle cell disease. Nat. Med. 8:2002;1383-1389
9. Aslan M., Ryan T.M., Adler B., Townes T.M., Parks D.A., Thompson J.A., Tousson A., Gladwin M.T., Patel R.P., Tarpey M.M., Batinic-Haberle I., White R.C., Freeman B.A. Oxygen radical inhibition of nitric oxide-dependent vascular function in sickle cell disease. Proc. Natl. Acad. Sci. USA. 98:2001;15215-15220
10. Aslan M., Ryan T.M., Townes T.M., Coward L., Kirk M.C., Barnes S., Alexander C.B., Rosenfeld S.S., Freeman B.A. Nitric oxide-dependent generation of reactive species in sickle cell disease. J. Biol. Chem. 278:2003;4194-4204
11. Ikuta T., Ausenda S., Cappellini M.D. Mechanism for fetal globin gene expression: role of the soluble guanylate cyclase-cGMP-dependent protein kinase pathway. Proc. Natl. Acad. Sci. USA. 98:2001;1847-1852
12. Cokic V.P., Smith R.D., Beleslin-Cokic B.B., Njoroge J.M., Miller J.L., Gladwin M.T., Schechter A.N. Hydroxyurea induces fetal hemoglobin by the nitric oxide-dependent activation of soluble guanylyl cyclase. J. Clin. Invest. 111:2003;231-239
13. Nahavandi M., Tavakkoli F., Wyche M.Q., Perlin E., Winter W.P., Castro O. Nitric Oxide and cyclic GMP levels in sickle cell patients receiving hydroxyurea. Br. J. Haematol. 119:2002;855-857
14. Jiang J., Jordan S.J., Barr D.P., Gunther M.R., Maeda H., Mason R.P. In vivo production of nitric oxide in rats after administration of hydroxyurea. Mol. Pharmacol. 52:1997;1081-1086
15. Glover R.E., Ivy E.D., Orringer E.P., Maeda H., Mason R.P. Detection of nitrosyl hemoglobin in venous blood in the treatment of sickle cell anemia with hydroxyurea. Mol. Pharmacol. 55:1999;1006-1010
16. Gladwin M.T., Shelhamer J.H., Ognibene F.P., Pease-Fye M.E., Nichols J.S., Link B., Patel D.B., Jankowski M.A., Pannell L.K., Schechter A.N., Rodgers G.P. Nitric oxide donor properties of hydroxyurea in patients with sickle cell disease. Br. J. Haematol. 116:2002;436-444
17. 2 reaction. Chem. Res. Toxicol. 6:1993;23-27
18. Morris C.R., Vichinsky E.P., van Warmerdam J., Machado L., Kepka-Lenhart D., Morris S.M., Kuypers F.A. Hydroxyurea and arginine therapy: impact on nitric oxide production in sickle cell disease. J. Pediatr. Hematol./Oncol. 25:2003;629-634
19. Sakano K., Oikawa S., Hasegawa K., Kawanishi S. Hydroxyurea induces site-specific DNA damage via formation of hydrogen peroxide and nitric oxide. Jpn. J. Cancer Res. 92:2001;1166-1174
20. Xu Y., Mull C.D., Bonifant C.L., Yasaki G., Palmer E.C., Shields H., Ballas S.K., Kim-Shapiro D.B., King S.B. Nitrosylation of sickle cell hemoglobin by hydroxyurea. J. Org. Chem. 63:1998;6452-6453
21. Fishbein W.N., Carbone P.P. Urease catalysis: inhibition of the enzyme by hydroxyurea, hydroxylamine and acetohydroxamic acid. J. Biol. Chem. 240:1965;2407-2414
22. Gale G.R. Hydroxyurea derivatives: oxamyl hydroxamic acid. Cancer Res. 26:1966;2340-2348
23. Stolze K., Nohl H. EPR Studies on the oxidation of hydroxyurea to paramagnetic compounds by oxyhemoglobins. Biochem. Pharmacol. 40:1990;799-802
24. Pacelli R., Taira J., Cook J.A., Wink D.A., Krishna M.C. Hydroxyurea reacts with heme proteins to generate nitric oxide. Lancet. 347:1996;900
25. Kim-Shapiro D.B., King S.B., Bonifant C.L., Kolibash C.P., Ballas S.K. Time resolved absorption study of the reaction of hydroxyurea with sickle cell hemoglobin. Biochimi. Biophys. Acta. 1380:1998;64-74
26. Kim-Shapiro D.B., King S.B., Shields H., Kolibash C.P., Gravatt L., Ballas S.K. The reaction of deoxy-sickle cell hemoglobin with hydroxyurea. Biochim. Biophys. Acta. 1428:1999;381-387
27. Huang J., Hadimani S.B., Rupon J.W., Ballas S.K., Kim-Shapiro D.B., King S.B. Iron nitrosyl hemoglobin formation from the reactions of hydroxyurea and hemoglobin. Biochemistry. 41:2002;2466-2474
28. Stolze K., Nohl H. Detection of free radicals as intermediates in the methemoglobin formation from oxyhemoglobin induced by hydroxylamine. Biochem. Pharmacol. 138:1989;3055-3059
29. Bazylinski D.A., Arkowitz R.A., Hollocher T.C. Decomposition of hydroxylamine by hemoglobin. Arch. Biochem. Biophys. 259:1987;520-526
30. Rupon J.W., Domingo S.R., Smith S.V., Gummadi B.K., Shields H., Ballas S.K., King S.B., Kim-Shapiro D.B. The reactions of myoglobin, normal adult hemoglobin, sickle cell hemoglobin and hemin with hydroxyurea. Biophys. Chem. 84:2000;1-11
31. Xu X., Cho M., Spencer N.Y., Patel N., Huang Z., Shields H., Kings S.B., Gladwin M.T., Hogg N., Kim-Shapiro D.B. Measurements of nitric oxide on the heme iron and β-93 thiol of human hemoglobin during cycles of oxygenation and deoxygenation. Proc. Natl. Acad. Sci. USA. 100:2003;11303-11308
32. Luchsinger B.P., Rich E.N., Gow A.J., Williams E.M., Stamler J.S., Singel D.J. Routes to S-nitroso-hemoglobin formation with heme redox and preferential reactivity in the β-subunits. Proc. Natl. Acad. Sci. USA. 100:2003;461-466
33. Huang J., Sommers E., Kim-Shapiro D.B., King S.B. Horseradish peroxidase catalyzed nitric oxide formation from hydroxyurea. J. Am. Chem. Soc. 124:2002;3473-3480
34. Bonner F.T., Hughes M.N. The aqueous solution chemistry of nitrogen in low positive oxidation states. Comments Inorg. Chem. 7:1988;215-234
35. Doyle M.P., Mahapatro S.N., Broene R.D., Guy J.K. Oxidation and reduction of hemoproteins by trioxodinitrate(II): the role of nitrosyl hydride and nitrite. J. Am. Chem. Soc. 110:1988;593-599
36. Bazylinski D.A., Goretski J., Hollocher T.C. On the reaction of trioxodinitrate(II) with hemoglobin and myoglobin. J. Am. Chem. Soc. 107:1985;7986-7989
37. Bazylinksi D.A., Hollocher T.C. Metmyoglobin and methemoglobin as efficient traps for nitrosyl hydride (nitroxyl) in neutral aqueous solutions. J. Am. Chem. Soc. 107:1985;7982-7986
38. Miranda K.M., Nims R.W., Thomas D.D., Espey M.G., Citrin D., Bartberger M.D., Paolocci N., Fukuto J.M., Feelisch M., Wink D.A. Comparison of the reactivity of nitric oxide and nitroxyl with heme proteins: a chemical discussion of the differential biological effects of these redox related products of NOS. J. Inorg. Biochem. 93:2003;52-60
39. Yonetani T., Yamamoto H., Erman J.E., Leigh J.S. Jr., Reed G.H. Electromagnetic properties of hemoproteins. J. Biol. Chem. 247:1972;2447-2455
40. Glover R.E., Koshkin V., Dunford H.B., Mason R.P. The reaction rates of NO with horseradish peroxidase compounds I and II. Nitric Oxide Biol. Chem. 3:1999;439-444
41. Stolze K., Nohl H. Reactions of reducing xenobiotics with oxymyoglobin, ferryl myoglobin and free radicals: an electron spin resonance and chemiluminescence study. Biochem. Pharmacol. 49:1995;1261-1267
42. Wang P.G., Xian M., Tang X., Wu X., Wen Z., Cai T., Janczuk A.J. Nitric oxide donors: chemical activities and biological applications. Chem. Rev. 102:2002;1091-1134
43. Kofod H. On the isomerism of hydroxyurea: VI. Paper-partition chromatography. Acta Chem. Scand. 9:1955;1575-1586
44. Kofod H., Huang T.Y. On the isomerism of hydroxyurea: III. Some physical properties of the isomers. Acta Chem. Scand. 8:1954;485-493
45. Parker G.R., Moore E.C. Solvent dependent conformational system of hydroxyureas in octanol-water and in inhibition of ribonucleotide reductase. J. Pharm. Sci. 66:1977;1040-1044
46. Fishbein W.N., Winter T.S., Davidson J.D. Urease catalysis: stoichiometry, specificity, and kinetics of a second substrate: hydroxyurea. J. Biol. Chem. 240:1965;2402-2406
47. Fishbein W.N., Carbone P.P. Hydroxyurea: mechanism of action. Science. 142:1963;1069-1070
48. Lockamy V.L., Huang J., Shields H., Ballas S.K., King S.B., Kim-Shapiro D.B. Urease enhances the formation of iron nitrosyl hemoglobin in the presence of hydroxyurea. Biochim. Biophys. Acta. 1622:2003;109-116
49. Huang J., Zou Z., Kim-Shapiro D.B., Ballas S.K., King S.B. Hydroxyurea analogs as kinetic and mechanistic probes of the nitric oxide producing reactions of hydroxyurea and oxyhemoglobin. J. Med. Chem. 46:2003;3748-3753