Biocoordination chemistry of bismuth: Recent advances

Coordination Chemistry Reviews

Volumn 251, Issue 17-20, 2007, Pages 2354-2366

  Yang, Nan ^a   Sun, Hongzhe ^a  

^a UNIVERSITY OF HONG KONG   (Hong Kong)

Author keywords

Bismuth; Cancer; Enzyme; Protein; Ulcer

Indexed keywords

EID: 34548543539     PISSN: 00108545     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.ccr.2007.03.003     Document Type: Review

References (139)

1. http://en.wikipedia.org/wiki/Bismuth
2. In: Suzuki H., and Matano Y. (Eds). Organobismuth Chemistry (2001), Elsevier, Amsterdam
3. Norman N.C. Chemistry of Arsenic, Antimony and Bismuth (1998), Blackie Academic and Professional, London
4. Mehring M. Coord. Chem. Rev. 251 (2007) 974
5. Sadler P.J., Li H., and Sun H. Coord. Chem. Rev. 185/186 (1999) 689
6. Sun H., and Sadler P.J. Top. Biol. Inorg. Chem. 2 (1999) 159
7. de Marcillac P., Coron N., Dambier G., Leblanc J., and Moalic J.P. Nature 422 (2003) 876
8. Luckay R., Cukrowski I., Mashishi J., Reibenspies J.H., Bond A.H., Rogers R.D., and Hancock R.D. J. Chem. Soc. Dalton Trans. (1997) 901
9. Stavila V., Davidovich R.L., Gulea A., and Whirmire K.H. Coord. Chem. Rev. 250 (2006) 2782
10. Sadler P.J., Sun H., and Li H. Chem. Eur. J. 2 (1996) 701
11. Burford N., Eelman M.D., Mahony D.E., and Morash M. Chem. Commun. (2003) 146
12. Burford N., Eelman M.D., and Groom K. J. Inorg. Biochem. 99 (2005) 1992
13. Cotton F.A., Wilkinson G., Murillo C.A., and Bochmann M. Advanced Inorganic Chemistry. 6th ed. (1999), John Wiley & Sons Inc., USA
14. Levason W., and Reid G. In: Lever A.B.P. (Ed). Comprehensive Coordination Chemistry II: Coordination Chemistry of the S, P, and F Metals vol. 3 (2004), Elsevier Pergamon, Amsterdam 465
15. Lazarini F. Cryst. Struct. Comm. 8 (1979) 69
16. Summers S., Abboud K.A., Farrah S.R., and Palenik G.J. Inorg. Chem. 33 (1994) 88
17. Michaudet L., Richard P., and Boitrel B. Chem. Commun. (2000) 1589
18. Hassfjell S., Kongshaug K.O., and Rømming C. J. Chem. Soc. Dalton Trans. (2003) 1433
19. Näslund J., Persson I., and Sandström M. Inorg. Chem. 39 (2000) 4012
20. Hassan A., and Wang S. J. Chem. Soc. Dalton Trans. (1997) 2009
21. Suzuki H., Ikegami T., Matano Y., and Azuma N. J. Chem. Soc. Perkin Trans. 1 (1993) 2411
22. Dittes U., Keppler B.K., and Nuber B. Angew. Chem. Int. Ed. Engl. 35 (1996) 67
23. Odier L. J. Med. Chir. Pharm. 68 (1986) 49
24. Baxter G.F. Chem. Brit. (1992) 445
25. Briand G.G., and Burford N. Chem. Rev. 99 (1999) 2601
26. Me Y.Q., Li Y.Y., Wu H.S., Sha W.H., Du H., Dai S.J., Wang H., and Li Q.L. Helicobacter 4 (1999) 128
27. Beales I.L.P. BMC Gastroenterol. 1 (2001) 7
28. Domenico P., Salo R.J., Novick S.G., Schoch P.E., Horn K.V., and Cunha B.A. Antimicrob. Agents Chemother. 41 (1997) 1697
29. Brogan A.P., Verghese J., Widger W.R., and Kohn H. J. Inorg. Biochem. 99 (2005) 841
30. Kotani T., Nagai D., Asahi K., Suzuki H., Yamao F., Kataoka N., and Yagura T. Antimicrob. Agents Chemother. 49 (2005) 2729
31. Murafuji T., Miyoshi Y., Ishibashi M., Mustafizur Rahman A.F.M., Sugihara Y., Miyakawa I., and Uno H. J. Inorg. Biochem. 98 (2004) 547
32. Salata O.V. J. Nanobiotechnol. 2 (2004) 3
33. Stoimenov P.K., Klinger R.L., Marchin G.L., and Klabunde K.J. Langmuir 18 (2002) 6679
34. Kwak S.Y., and Kim S.H. Environ. Sci. Technol. 35 (2001) 2388
35. Mah C., Zolotukhin I., Fraites T.J., Dobson J., Batich C., and Byrne B.J. Mol. Ther. 1 (2000) S239
36. Panatarotto D., Prtidos C.D., Hoebeke J., Brown F., Kramer E., Briand J.P., Muller S., Prato M., and Bianco A. Chem. Biol. 10 (2003) 961
37. Edelstein R.L., Tamanaha C.R., Sheehan P.E., Miller M.M., Baselt D.R., Whitman L.J., and Colton R.J. Biosens. Bioelectron. 14 (2000) 805
38. Yoshida J., and Kobayashi T. J. Magn. Magn. Mater. 194 (1999) 176
39. Weissleder R., Elizondo G., Wittenburg J., Rabito C.A., Bengele H.H., and Josephson L. Radiology 175 (1990) 489
40. Chen R., So M.H., Yang J., Deng F., Che C.M., and Sun H. Chem. Comm. (2006) 2265
41. Hassfjell S., and Brechbiel M.W. Chem. Rev. 101 (2001) 2019
42. Imam S.K. Int. J. Radial Oncol. Biol. Phys. 51 (2001) 271
43. Kozak R.W., Waldmann T.A., Atcher R.W., and Gansow O.A. Trends Biotechnol. 4 (1986) 259
44. Burke J.M., Jurcic J.G., and Scheinberg D.A. Cancer Contr. 9 (2002) 106
45. Jurcic J.G. Crit. Rev. Oncol./Hematol. 38 (2001) 37
46. McDevitt M.R., Nikula T.N., Finn R.D., Curcio M.J., Gansow O.A., Geerlings Sr. M.W., Larson S.M., and Scheinberg D.A. Tumor Target. 2 (1996) 182
47. McDevitt M.R., Finn R.D., Ma D., Larson S.M., and Scheinberg D.A. J. Nucl. Med. 40 (1999) 1722
48. Halime Z., Michaudet L., Lachkar M., Brossier P., and Boitrel B. Bioconj. Chem. 15 (2004) 1193
49. Mulford D.A., Scheinberg D.A., and Jurcic J.G. J. Nucl. Med. 46 (2005) 199s
50. Abbas Rizvi S.M., Li Y., Song E.Y., Qu C.F., Raja C., Morgenstern A., Apostolidis C., and Allen B.J. Cancer Biol. Ther. 5 (2006) 386
51. Nikula T.K., McDevitt M.R., Finn R.D., Wu C., Kozak R.W., Garmestani K., Brechbiel M.W., Curcio M.J., Pippin C.G., Tiffany-Jones L., Geerlings Jr. M.W., Gansow O.A., and Scheinberg D.A. J. Nucl. Med. 4 (1999) 166
52. Sandmaier B.M., Bethge W.A., Wilbur D.S., Hamlin D.K., Santos E.B., Brechbiel M.W., Fisher D.R., and Storb R. Blood 100 (2002) 318
53. McDevitt M.R., Barendswaard E., Ma D., Lai L., Curcio M.J., Sgouros G., Ballangrud A.M., Yang W.-H., Finn R.D., Pellegrini V., Geerlings Jr. M.W., Lee M., Brechbiel M.W., Bander N.H., Cordon-Cardo C., and Scheinberg D.A. Cancer Res. 60 (2000) 6095
54. Ballangrud A.M., Yang W.-H., Charlton D.E., McDevitt M.R., Hamacher K.A., Panageas K.S., Ma D., Bander N.H., Scheinberg D.A., and Sgouros G. Cancer Res. 61 (2001) 2008
55. Jurcic J.G., McDevitt M.R., Sgouros G., Ballangrud A.M., Finn R.D., Ma D., Hamacher K., Geerlings Sr. M.W., Humm J.L., Brechbiel M.W., Molinet R., Apostolidis C., Larson S.M., and Scheinberg D.A. Proc. Am. Soc. Clin. Oncol. 18 (1999) 17a
56. Mulford D.A., and Jurcic J.G. Expert Opin. Biol. Ther. 4 (2004) 1
57. Qu C.F., Song Y.J., Rizvil S.M.A., Li Y., Smith R., Perkins A.C., Morgenstern A., Brechbiel M., and Allen B.J. Cancer Biol. Ther. 4 (2005) 849
58. Zhang M., Yao Z., Germestani K., Axworthy D.B., Zhang Z., Mallett R.W., Theodore L.J., Goldman C.K., Brechbiel M.W., Carrasquillo J.A., and Waldmann T.A. Blood 100 (2002) 208
59. Yao Z., Zhang M., Germestani K., Axworthy D.B., Mallett R.W., Fritzberg A.R., Theodore L.J., Plascjak P.S., Eckelman W.C., Waldmann T.A., Pastan I., Paik C.H., Brechbiel M.W., and Carrasquillo J.A. Clin. Cancer Res. 10 (2004) 3137
60. Huang R., Wallqvist A., and Covell D.G. Biochem. Pharmacol. 69 (2005) 1009
61. Kirschner S., Wei Y., Francis D., and Bergman J.G. J. Med. Chem. 9 (1966) 369
62. Skinner S.M., Swatzell J.M., and Lewis R.W. Res. Comm. Chem. Pathol. Pharmacol. 17 (1978) 165
63. Köpf-Maier P., and Klapötke T. Inorg. Chim. Acta 152 (1988) 49
64. Smith K.A., Deacon G.B., Jackson W.R., Tiekink E.R.T., Rainone S., and Webster L.K. Metal-Based Drugs 5 (1998) 295
65. Wang X.Y., Zhang X.M., Lin J., Chen J.W., Xu Q., and Guo Z.J. J. Chem. Soc. Dalton Trans. (2003) 2379
66. Daugaard G. Dan. Med. Bull. 37 (1990) 1
67. Schweitzer V.G. Laryngoscope 103 (1993) 1
68. Shibuya K., Cherian M.G., and Satoh M. Radiat. Res. 148 (1997) 235
69. Verweij J., de Wit R., and de Mulder P.H. Oncology 53 Suppl. 1 (1996) 56
70. Kondo Y., Satoh M., Imura N., and Akimoto M. Cancer Chemother. Pharmacol. 29 (1991) 19
71. Kondo Y., Himeno S., Satoh M., Naganuma A., Nishimura T., and Imura N. Cancer Chemother. Pharmacol. 53 (2004) 33
72. Hamer D.H. Annu. Rev. Biochem. 55 (1986) 913
73. Kägi J.H., and Schaffer A. Biochemistry 27 (1988) 8509
74. Kelley S.L., Basu A., Teicher B.A., Hacker M.P., Hamer D.H., and Lazo J.S. Science 241 (1988) 1813
75. Lazo J.S., Kondo Y., Dellapiazza D., Michalska A.E., Choo K.H.A., and Pitt B.R. J. Biol. Chem. 270 (1995) 5506
76. Sato M., Kondoh M., and Tohoku. J. Exp. Med. 196 (2002) 9
77. Magnusson N.E., Larsen A., Rungby J., Kruhøffer M., Ørntoft T.F., and Stoltenberg M. Cell Tissue Res. 321 (2005) 195
78. Suarez F.L., Furne J., Stiehm J., Garten C., and Levitt M.D. Dig. Dis. Sci. 45 (2000) 1444
79. Iffland R. Bismuth, Handbook on Metals in Clinical and Analytical Chemistry (1994), Marcel Dekker, New York
80. DuPont H.L., and Ericeeon C.D. N. Engl. J. Med. 328 (1993) 1821
81. Figueroa-Quintanilla D., Salazar-Lindo E., and Sack R.B. N. Engl. J. Med. 328 (1993) 1653
82. Bierer D.W., and Klapötke T. Biol. Met. 1 (1988) 69
83. Thurston J.H., Marlier E.M., and Whitmire K.H. Chem. Commun. (2002) 2834
84. Burford N., Eelman M.D., and Cameron T.S. Chem. Commun. (2002) 1402
85. Andrews P.C., Deacon G.B., Jackson E.R., Maguire M., Scott N., Skelton B.W., and White A.H. J. Chem. Soc. Dalton Trans. (2002) 4634
86. Thurston J.H., and Whitmire K.H. Inorg. Chem. 41 (2002) 4194
87. Andrews P.C., Deacon G.B., Forsyth C.M., Junk P.C., Kumar I., and Maguire M. Angew. Chem. Int. Ed. 45 (2006) 5638
88. Suerbaum S., and Mchetti P. N. Engl. J. Med. 347 (2003) 1175
89. Sun H., Zhang L., and Szeto K.Y. Met. Ions Biol. Syst. 41 (2004) 333
90. Lambert J.R., and Midolo P. Aliment. Pharmacol. Ther. 11 Suppl. (1997) 27
91. Merck Index. 11th ed. (1989), Merck, Rahway, NJ, USA p. 197
92. Merck Index. 14th ed. (2006), Merck, Whitehouse, NJ, USA. http://library.dialog.com/bluesheets/html/b10304.html online version: http://library.dialog.com/bluesheets/html/b10304.html
93. Li W., Jin L., Zhu N., Hou X., Deng F., and Sun H. J. Am. Chem. Soc. 125 (2003) 12408
94. Asato E., Katsura K., Mikuriya M., Turpeinen U., Mutikainen I., and Reedijk J. Inorg. Chem. 34 (1995) 2447
95. Briand G.G., Burford N., Eelman M.D., Aumeerally N., Chen L., Cameron T.S., and Robertson K.N. Inorg. Chem. 43 (2004) 6495
96. Phillips H.A., Eelman M.D., and Burford N. J. Inorg. Biochem. 101 (2007) 736
97. Gyurasics A., Koszorús L., Varga F., and Gregus Z. Biochem. Pharmacol. 44 (1992) 1275
98. Chowers M.Y., Keller N., Tal R., Barshack I., Lang R., Bar-Meir S., and Chowers Y. Gastroenterology 117 (1999) 1113
99. Chowers M.Y., Keller N., Meir S.B., and Chowers Y. FEMS Microbiol. Lett. 217 (2002) 231
100. Pannequin J., Kovac S., Tantiongco J.P., Norton R.S., Shulkes A., Barnham K.J., and Baldwin G.S. J. Biol. Chem. 279 (2004) 2453
101. Aisen P., Enns C., and Wessling-Resnick M. Int. J. Biochem. Cell Biol. 33 (2001) 940
102. Cheng Y., Zak O., Aisen P., Harrison S.C., and Walz T. Cell 116 (2004) 565
103. Sun H., Li H., and Sadler P.J. Chem. Rev. 99 (1999) 2817
104. Sun H., and Szeto K.Y. J. Inorg. Biochem. 94 (2003) 114
105. Li H., Sadler P.J., and Sun H. J. Biol. Chem. 271 (1996) 9483
106. Sun H., Li H., Mason A.B., Woodworth R.C., and Sadler P.J. Biochem. J. 337 (1999) 105
107. Sun H., Cox M.C., Li H., Mason A.B., Woodworth R.C., and Sadler P.J. FEBS Lett. 422 (1998) 315
108. Mizutani K., Mikami B., Aibara S., and Hirose M. Acta Crystallogr. D Biol. Crystallogr. 61 (2005) 1636
109. Miquel G., Nekaa T., Kahn P.H., Hemadi M., and El Hage Chaine J.M. Biochemistry 43 (2004) 14722
110. Lönnerdal B., and Iyer S. Annu. Rev. Nutr. 15 (1995) 93
111. Levay P.F., and Viljoen M. Haematologica 80 (1995) 252
112. Aisen P., and Leibman A. Biochim. Biophys. Acta 257 (1972) 314
113. Bullen J.J., Rogers M.J., and Griffiths E. In: Neilands J.B. (Ed). Microbial Iron Metabolism (1974), Academic Press, New York
114. Zhang L., Szeto K.Y., Wong W.B., Loh T.T., Sadler P.J., and Sun H. Biochemistry 40 (2001) 13281
115. Britigan B.E., Lewis T.S., McCormick M.L., and Wilson M.E. Adv. Exp. Med. Biol. 443 (1998) 135
116. Davidson L.A., and Lönnerdal B. Am. J. Physiol. 257 (1989) 930
117. Slikkerveer A., and de Wolff F.A. Med. Toxicol. Adverse Drug Exp. 4 (1989) 303
118. Noach L.A., Eekhof J.L.A., Bour L.J., Posthumus M., Keyjes F.E., Tytgat G.N.J., and Ongerboer de Visser B.W. Hum. Toxicol. 14 (1995) 349
119. Vanhoe H., Versieck J., Vanballenberghe L., and Dams R. Clin. Chim. Acta 219 (1993) 79
120. Braun W., Vašák M., Robbins A.H., Stout C.D., Wagner G., Kägi J.H.R., and Wüthrich K. Proc. Natl. Acad. Sci. U.S.A. 89 (1992) 10124
121. Vašák M., and Hasler D.W. Curr. Opin. Chem. Biol. 4 (2000) 177
122. Park J.D., Liu Y., and Klaassen C.D. Toxicology 163 (2001) 93
123. Sun H., Li H., Harvey I., and Sadler P.J. J. Biol. Chem. 274 (1999) 29094
124. Busenlehner L.S., Apuy J.L., and Giedroc D.P. J. Biol. Inorg. Chem. 7 (2002) 551
125. Apuy J.L., Busenlehner L.S., Russell D.H., and Giedroc D.P. Biochemistry 43 (2004) 3824
126. Matzapetakis M., Ghosh D., Weng T., Penner-Hahn J.E., and Pecoraro V.L. J. Biol. Inorg. Chem. 11 (2006) 876
127. Tomb J.F., White O., Kerlavage A.R., Clayton R.A., Sutton G.G., et al. Nature 388 (1997) 539
128. Ge R., Watt R.M., Sun X., Tanner J.A., He Q.Y., Huang J.D., and Sun H. Biochem. J. 393 (2006) 285
129. Mobley H.L., Garner R.M., Chippendale G.R., Gilbert J.V., Kane A.V., and Plaut A.G. Helicobacter 4 (1999) 162
130. Ge R., Zhang Y., Sun X., Watt R.M., He Q.Y., Huang J.D., Wilcox D.E., and Sun H. J. Am. Chem. Soc. 128 (2006) 11330
131. Turkez H., Geyikoglu F., and Keles M.S. Biol. Trace. Elem. Res. 105 (2005) 151
132. Salaspuro M. Helicobacter pylori alcohol dehydrogenase. In: Jansson B., Jörnvall H., Rydberg U., Terenius L., and Vallee B.L. (Eds). Toward a Molecular Basis of Alcohol Use and Abuse (1994), Birkhäuser Verlag, Basel, Switzerland 185
133. Jin L., Szeto K.Y., Zhang L., Du W., and Sun H. J. Inorg. Biochem. 98 (2004) 1331
134. Mulrooney S.B., and Hausinger R.P. FEMS Microbiol. Rev. 27 (2003) 239
135. Asato E., Kamamuta K., Akamine Y., Fukami T., Nukada R., Mikuriya M., Deguchi S., and Yokota Y. Bull. Chem. Soc. Jpn. 70 (1997) 639
136. Murafuji T., Azuma T., Myoshi Y., Ishibashi M., Rahman A.F.M.M., Migita K., Sugthara Y., and Mikata Y. Bioorg. Med. Chem. Lett. 16 (2006) 1510
137. Zhang L., Mulrooney S.B., Leung A.F.K., Zeng Y., Ko B.B.C., Hausinger R.P., and Sun H. Biometals 19 (2006) 503
138. Kulkarni P.P., She Y., Smith S.D., Roberts E.A., and Sarkar B. Chem. Eur. J. 12 (2006) 2410
139. Ge R., and Sun H. Accts. Chem. Res. 40 (2007) 10.1021/ac6000016