Hypothiocyanite

Advances in Inorganic Chemistry

Volumn 64, Issue , 2012, Pages 263-303

  Ashby, Michael T ^a  

^a UNIVERSITY OF OKLAHOMA   (United States)

Author keywords

Antimicrobial; Hypothiocyanite; Kinetics; Lactoperoxidase; Mechanism; Myeloperoxidase; Peroxidase; Pseudohalide; Thiocyanate

Indexed keywords

EID: 84857580738     PISSN: 08988838     EISSN: None     Source Type: Book Series    
DOI: 10.1016/B978-0-12-396462-5.00008-8     Document Type: Chapter

References (136)

1. Bjerrum N., Kirschner A. Kgl. Danske Videnskabernes Selskab. 1918, 8:76.
2. Lecher H., Wittwer M., Speer W. Ber. Dtsch. Chem. Ges. B 1923, 56B:1104.
3. " The Lactoperoxidase System: Chemistry and Biological Significance. Immunology Series 1985, Vol. 27. Dekker, New York, 257pp. K.M. Pruitt, J.O. Tenovuo (Eds.).
4. Below J.F., Connick R.E., Coppel C.P. J. Am. Chem. Soc. 1958, 80:2961.
5. Clark C.R. J. Chem. Educ. 1997, 74:1214.
6. Wrobel M., Jurkowska H., Sliwa L., Srebro Z. Toxicol. Mech. Methods 2004, 14:331.
7. Weuffen W., Franzke C., Thuerkow B. Nahrung 1984, 28:341.
8. Moir D., Rickert W.S., Levasseur G., Larose Y., Maertens R., White P., Desjardins S. Chem. Res. Toxicol. 2008, 21:494.
9. Zgliczynski J.M., Stelmaszynska T. Biochim. Biophys. Acta Enzymol. 1979, 567:309.
10. Conner G.E., Wijkstrom-Frei C., Randell S.H., Fernandez V.E., Salathe M. FEBS Lett. 2007, 581:271.
11. Ryall B., Davies J.C., Wilson R., Shoemark A., Williams H.D. Eur. Respir. J. 2008, 32:740.
12. Broderick K.E., Chan A., Balasubramanian M., Feala J., Reed S.L., Panda M., Sharma V.S., Pilz R.B., Bigby T.D., Boss G.R. J. Infect. Dis. 2007, 197:457.
13. Askeland R.A., Morrison S.M. Appl. Environ. Microbiol. 1983, 45:1802.
14. Pessi G., Haas D. J. Bacteriol. 2000, 182:6940.
15. Chung J., Wood J.I. Arch. Biochem. Biophys. 1970, 141:73.
16. Aune T.M., Thomas E.L. Eur. J. Biochem. 1977, 80:209.
17. Fragoso M.A., Fernandez V., Forteza R., Randell S.H., Salathe M., Conner G.E. J. Physiol. 2004, 561:183.
18. Valdes M.G., Diaz-Garcia M.E. Crit. Rev. Anal. Chem. 2004, 34:9.
19. Chemistry and Biochemistry of Thiocyanic Acid and its Derivatives 1975, Academic Press, London, England, p. 351.
20. Hawkins C.L. Free Radic. Res. 2009, 43:1147.
21. Pyykko P., Runeberg N. J. Chem. Soc. Chem. Commun. 1991, 547.
22. Sundholm D. J. Am. Chem. Soc. 1995, 117:11523.
23. Dua S., Maclean M.J., Fitzgerald M., McAnoy A.M., Bowie J.H. J. Phys. Chem. A 2006, 110:4930.
24. Hogg D.M., Jago G.R. Biochem. J. 1970, 117:779.
25. Walker J.V., Butler A. Inorg. Chim. Acta 1996, 243:201.
26. Modi S., Deodhar S.S., Behere D.V., Mitra S. Biochemistry 1991, 30:118.
27. Arlandson M., Decker T., Roongta V.A., Bonilla L., Mayo K.H., MacPherson J.C., Hazen S.L., Slungaard A. J. Biol. Chem. 2001, 276:215.
28. Pollock J.R., Goff H.M. Biochim. Biophys. Acta 1992, 1159:279.
29. Pruitt K.M., Tenovuo J. Biochim. Biophys. Acta 1982, 704:204.
30. Modi S., Behere D.V., Mitra S. Biochim. Biophys. Acta 1991, 1080:45.
31. Nagy P., Alguindigue S.S., Ashby M.T. Biochemistry 2006, 45:12610.
32. Boehland H., Golub A.M., Koehler H., Lisko T.P., Samoilenko V.M., Skopenko V.V., Cincadze G.V. Chemistry of Pseudohalides 1979, Dr. Alfred Huethig Verlag, Heidelberg, p. 440.
33. Okulik N.B., Jubert A.H., Castro E.A. Adv. Quantum Chem. Bond. Struct. 2008, 119.
34. Okulik N.B., Jubert A.H., Castro E.A. J. Struct. Chem. 2008, 49:922.
35. Chemistry of Halides, Pseudo-Halides and Azides, Part 2 1995, Wiley, Chichester, p. 916.
36. Chemistry of Halides, Pseudo-Halides and Azides, Part I 1995, Wiley, Chichester, p. 860.
37. Morgan T.D.B., Stedman G., Whincup P.A.E. J. Chem. Soc. 1965, 4813.
38. Krishnan P. J. Solid State Electrochem. 2007, 11:1327.
39. Loucka T., Janos P. Electrochim. Acta 1996, 41:405.
40. Hughes M.N. General Chemistry [of Thiocyanic Acid and its Derivatives]. Chem. Biochem. Thiocyanic Acid Deriv. 1975, 1-67. Academic Press, New York. A.A. Newman (Ed.).
41. Pruitt K.M., Tenovuo J., Andrews R.W., McKane T. Biochemistry 1982, 21:562.
42. Ashby M.T., Carlson A.C., Scott M.J. J. Am. Chem. Soc. 2004, 126:15976.
43. Nagy P., Beal J.L., Ashby M.T. Chem. Res. Toxicol. 2006, 19:587.
44. Wood J.L. Org. React. (N. Y.) 1946, 240.
45. Zeng Y., Zheng S., Meng L. Inorg. Chem. 2004, 43:5311.
46. Li Y., Qiao Z., Qiao S., Zhao J., Li H., Wang D. Inorg. Chem. 2003, 42:8446.
47. Guy R.G., Pearson I. J. Chem. Soc. Perkin Trans. 1 1973, 281.
48. Burchell C.J., Kilian P., Slawin A.M.Z., Woollins J.D., Tersago K., Van Alsenoy C., Blockhuys F. Inorg. Chem. 2006, 45:710.
49. Krishnan P., Gurjar V.G. J. Appl. Electrochem. 1995, 25:792.
50. Cataldo F. Polyhedron 2000, 19:681.
51. Nelson M.J., Pullin A.D.E. J. Chem. Soc. 1960, 604.
52. Bacon R.G.R., Irwin R.S. J. Chem. Soc. 1958, 778.
53. Hoogendoorn H., Piessens J.P., Scholtes W., Stoddard L.A. Caries Res. 1977, 11:77.
54. Xulu B.A., Ashby M.T. Biochemistry 2010, 49:2068.
55. Wilson I.R., Harris G.M. J. Am. Chem. Soc. 1960, 82:4515.
56. Christy A.A., Egeberg P.K. Talanta 2000, 51:1049.
57. Wilson I.R., Harris G.M. J. Am. Chem. Soc. 1961, 83:286.
58. Figlar J.N., Stanbury D.M. Inorg. Chem. 2000, 39:5089.
59. Slungaard A., Mahoney J.R. J. Biol. Chem. 1991, 266:4903.
60. van Dalen C.J., Whitehouse M.W., Winterbourn C.C., Kettle A.J. Biochem. J. 1997, 327:487.
61. Ashby M.T. J. Dent. Res. 2008, 87:900.
62. Michot J.L., Osty J., Nunez J. Eur. J. Biochem. 1980, 107:297.
63. Pintus F., Spano D., Bellelli A., Angelucci F., Scorciapino A.M., Anedda R., Medda R., Floris G. Biochemistry 2010, 49:8739.
64. Wojciechowski G., Huang L., Ortiz de Montellano P.R. J. Am. Chem. Soc. 2005, 127:15871.
65. Adak S., Mazumdar A., Banerjee R.K. J. Biol. Chem. 1997, 272:11049.
66. Wever R., Kast W.M., Kasinoedin J.H., Boelens R. Biochim. Biophys. Acta 1982, 709:212.
67. Pruitt K.M., Mansson-Rahemtulla B., Baldone D.C., Rahemtulla F. Biochemistry 1988, 27:240.
68. Figlar J.N., Stanbury D.M. J. Phys. Chem. A 1999, 103:5732.
69. Ashby M.T. Synthesis and Use of Hypothiocyanite 2006, The Board of Regents of the University of Oklahoma, USA, US Patent 7238334 10pp.
70. Mokhtari B., Azadi R., Rahmani-Nezhad S. Tetrahedron Lett. 2009, 50:6588.
71. Falck J.R., Gao S., Prasad R.N., Koduru S.R. Bioorg. Med. Chem. Lett. 2008, 18:1768.
72. Toste F.D., De Stefano V., Still I.W.J. Synth. Commun. 1995, 25:1277.
73. Ashby M., Aneetha H., Carlson A., Scott M., Beal J. Phosphorus Sulfur Silicon Relat. Elem. 2005, 180:1369.
74. Nagy P., Ashby M.T. J. Am. Chem. Soc. 2007, 129:14082.
75. Pearson R.G. J. Chem. Educ. 1968, 45:643.
76. Pearson R.G. J. Chem. Educ. 1968, 45:581.
77. Nagy P., Jameson G.N.L., Winterbourn C.C. Chem. Res. Toxicol. 2009, 22:1833.
78. Skaff O., Pattison D.I., Davies M.J. Biochem. J. 2009, 422:111.
79. Lemma K., Ashby M.T. Chem. Res. Toxicol. 2009, 22:1622.
80. Ashby M.T., Aneetha H. J. Am. Chem. Soc. 2004, 126:10216.
81. Nagy P., Lemma K., Ashby M.T. Inorg. Chem. 2007, 46:285.
82. Lemma K., Ashby M.T. J. Org. Chem. 2008, 73:3017.
83. Wang X., Ashby M.T. Chem. Res. Toxicol. 2008, 21:2120.
84. Nagy P., Wang X., Lemma K., Ashby M.T. J. Am. Chem. Soc. 2007, 129:15756.
85. Hawkins C.L., Pattison D.I., Stanley N.R., Davies M.J. Biochem. J. 2008, 416:441.
86. Barnett J.J., McKee M.L., Stanbury D.M. Inorg. Chem. 2004, 43:5021.
87. Barnett J.J., Stanbury D.M. Inorg. Chem. 2002, 41:164.
88. Lengyel I., Epstein I.R., Kustin K. Inorg. Chem. 1993, 32:5880.
89. Wang T.X., Margerum D.W. Inorg. Chem. 1994, 33:1050.
90. Beckwith R.C., Wang T.X., Margerum D.W. Inorg. Chem. 1996, 35:995.
91. Sebok-Nagy K., Koertvelyesi T. Int. J. Chem. Kinet. 2004, 36:596.
92. Schmitz G. Int. J. Chem. Kinet. 2004, 36:480.
93. Phan T.B., Breugst M., Mayr H. Angew. Chem. Int. Ed. 2006, 45:3869.
94. Loos R., Kobayashi S., Mayr H. J. Am. Chem. Soc. 2003, 125:14126.
95. Koskikallio J. Acta Chem. Scand. 1969, 23:1477.
96. Pattison D.I., Davies M.J. Biochemistry 2004, 43:4799.
97. Pattison D.I., Davies M.J. Chem. Res. Toxicol. 2001, 14:1453.
98. Gerritsen C.M., Margerum D.W. Inorg. Chem. 1990, 29:2757.
99. Gerritsen C.M., Gazda M., Margerum D.W. Inorg. Chem. 1993, 32:5739.
100. Rayson M.S., Mackie J.C., Kennedy E.M., Dlugogorski B.Z. Inorg. Chem. 2011, 50:7440.
101. Mamman S., Iyun J.F. Int. J. Pure Appl. Chem. 2007, 2:429.
102. Thomas E.L. Biochemistry 1981, 20:3273.
103. Walden P., Audrieth L.F. Chem. Rev. 1928, 5:339.
104. Kornath A., Blecher O., Ludwig R. J. Am. Chem. Soc. 1999, 121:4019.
105. Kornath A., Blecher O. Z. Anorg. Allg. Chem. 2002, 628:625.
106. Jander G., Gruttner B., Scholz G. Chem. Ber. 1947, 80:279.
107. Palmer D.A., Van Eldik R. Inorg. Chem. 1986, 25:928.
108. Truesdale V.W., Luther G.W., Greenwood J.E. Phys. Chem. Chem. Phys. 2003, 5:3428.
109. Martell A.E., Smith R.M. Critical Stability Constants. Inorganic Complexes 1976, Vol. 4. Plenum Press, New York.
110. Kitching W., Smith R.H., Wilson I.R. Aust. J. Chem. 1962, 15:211.
111. Nimmo S.L.A., Lemma K., Ashby M.T. Heteroatom. Chem. 2007, 18:467.
112. Kettenhofen N.J., Wood M.J. Chem. Res. Toxicol. 2010, 23:1633.
113. Rehder D.S., Borges C.R. Biochemistry 2010, 49:7748.
114. Aune T.M., Thomas E.L., Morrison M. Biochemistry 1977, 16:4611.
115. Furtmuller P.G., Burner U., Obinger C. Biochemistry 1998, 37:17923.
116. Miyasaki K.T. J. Dent. Res. 1990, 69:1780.
117. Miyasaki K.T., Zambon J.J., Jones C.A., Wilson M.E. Infect. Immun. 1987, 55:1029.
118. Britigan B.E., Ratcliffe H.R., Buettner G.R., Rosen G.M. Biochim. Biophys. Acta Gen. Subj. 1996, 1290:231.
119. Wright C.D., Nelson R.D. Biochem. Biophys. Res. Commun. 1988, 154:809.
120. Henderson W.R., Jong E.C., Klebanoff S.J. J. Immunol. 1980, 124:1383.
121. Gomez-Mejiba S.E., Zhai Z., Gimenez M.S., Ashby M.T., Chilakapati J., Kitchin K., Mason R.P., Ramirez D.C. J. Biol. Chem. 2010, 285:20062.
122. Hoogendoorn H. Protides Biol. Fluids 1985, 32:133.
123. Pattison D.I., Hawkins C.L., Davies M.J. Biochemistry 2007, 46:9853.
124. Pattison D.I., Hawkins C.L., Davies M.J. Chem. Res. Toxicol. 2009, 22:807.
125. Wang Z., Nicholls S.J., Rodriguez E.R., Kummu O., Hoerkkoe S., Barnard J., Reynolds W.F., Topol E.J., DiDonato J.A., Hazen S.L. Nat. Med. 2007, 13:1176.
126. Pattison D.I., Hawkins C.L., Davies M.J. Chem. Res. Toxicol. 2003, 16:439.
127. Hawkins C.L., Pattison D.I., Davies M.J. Amino Acids 2003, 25:259.
128. Nagy P., Ashby M.T. Chem. Res. Toxicol. 2007, 20:79.
129. Winterbourn C.C., Hampton M.B., Livesey J.H., Kettle A.J. J. Biol. Chem. 2006, 281:39860.
130. Cayley S., Record M.T. Biochemistry 2003, 42:12596.
131. Garcia-Perez A.I., Lopez-Beltran E.A., Kluner P., Luque J., Ballesteros P., Cerdan S. Arch. Biochem. Biophys. 1999, 362:329.
132. Ribeiro A.C.F., Lobo V.M.M., Leaist D.G., Natividade J.J.S., Verissimo L.P., Barros M.C.F., Cabral A.M.T.D.P.V. J. Solut. Chem. 2005, 34:1009.
133. Konopka M.C., Shkel I.A., Cayley S., Record M.T., Weisshaar J.C. J. Bacteriol. 2006, 188:6115.
134. Shin K., Hayasawa H., Lonnerdal B. J. Appl. Microbiol. 2001, 90:489.
135. Hurst J.K., Barrette W.C., Michel B.R., Rosen H. Eur. J. Biochem. 1991, 202:1275.
136. Sermon J., Vanoirbeek K., De Spiegeleer P., Van Houdt R., Aertsen A., Michiels C.W. Res. Microbiol. 2005, 156:225.