Bismuth(III) Complexes of 2-Mercaptoethanol: Preparation, Structural and Spectroscopic Characterization, Antibactericidal Activity toward Helicobacter pylori, and Inhibitory Effect toward H. pylory-Produced Urease

Bulletin of the Chemical Society of Japan

Volumn 70, Issue 3, 1997, Pages 639-648

  Asato, Eiji ^a   Kamamuta, Koji ^a   Akamine, Yasutoshi ^a   Fukami, Takanori ^a   Nukada, Ryoji ^b   Mikuriya, Masahiro ^b   Deguchi, Shuhei ^c   Yokota, Yoshiko ^c  

^a UNIVERSITY OF THE RYUKYUS   (Japan)

^b KWANSEI GAKUIN UNIVERSITY   (Japan)

^c ASTELLAS PHARMA INC   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0012437706     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.70.639     Document Type: Article

References (53)

1. a) P. Ehrlich, Ber. Klin. Wochenschr., 47, 1910 (1996);
2. b) G. O. Doak and C. D. Freedman, in "Medical Chemistry," 3rd ed, ed by A. Burger; Wiley-Interscience, New York (1970), Part I, Chap. 25;
3. c) S. C. Harvey, in "The Pharmaceutical Basis of Therapeutics," 5th ed, ed by L. S. Goodman and A. Gilman, Macmillan Publishing Co., Inc., New York (1975), Chap. 46;
4. d) G. Alonzo, N. Bertazzi, and M. Consiglio, Inorg. Chim. Acta, 85, L35 (1984).
5. For examples: a) A. J. Wagstaff, P. Benfield, and J. P. Monk, Drugs, 36, 132 (1988); b) G. N. J. Tytget, "Digestion, Suppl. 2," 1987, p. 31; c) J. P. Miller and E. B. Faragher, Br. Med. J., 293, 1117 (1986); d) A. T. R. Axon, Br. Med. J., 293, 772 (1986); e) C. S. Goodwin, J. A. Armstrong, and B. J. Marshall, J. Clin. Pathol., 39, 353 (1986); f) G. N. J. Tytget, Afr. Med. J., 70, 31 (1986); g) B. J. Marshall, J. Infect. Dis., 53, 650 (1986); h) R. Pickard, Proc. Cairo, 1985, 55; i) K. Vogt, M. Warrelmann, and H. Hahn, Zentralbl. Bakteriol., Abt. 1, Orig. A, 273, 33 (1990).
6. For examples: a) A. J. Wagstaff, P. Benfield, and J. P. Monk, Drugs, 36, 132 (1988); b) G. N. J. Tytget, "Digestion, Suppl. 2," 1987, p. 31; c) J. P. Miller and E. B. Faragher, Br. Med. J., 293, 1117 (1986); d) A. T. R. Axon, Br. Med. J., 293, 772 (1986); e) C. S. Goodwin, J. A. Armstrong, and B. J. Marshall, J. Clin. Pathol., 39, 353 (1986); f) G. N. J. Tytget, Afr. Med. J., 70, 31 (1986); g) B. J. Marshall, J. Infect. Dis., 53, 650 (1986); h) R. Pickard, Proc. Cairo, 1985, 55; i) K. Vogt, M. Warrelmann, and H. Hahn, Zentralbl. Bakteriol., Abt. 1, Orig. A, 273, 33 (1990).
7. For examples: a) A. J. Wagstaff, P. Benfield, and J. P. Monk, Drugs, 36, 132 (1988); b) G. N. J. Tytget, "Digestion, Suppl. 2," 1987, p. 31; c) J. P. Miller and E. B. Faragher, Br. Med. J., 293, 1117 (1986); d) A. T. R. Axon, Br. Med. J., 293, 772 (1986); e) C. S. Goodwin, J. A. Armstrong, and B. J. Marshall, J. Clin. Pathol., 39, 353 (1986); f) G. N. J. Tytget, Afr. Med. J., 70, 31 (1986); g) B. J. Marshall, J. Infect. Dis., 53, 650 (1986); h) R. Pickard, Proc. Cairo, 1985, 55; i) K. Vogt, M. Warrelmann, and H. Hahn, Zentralbl. Bakteriol., Abt. 1, Orig. A, 273, 33 (1990).
8. For examples: a) A. J. Wagstaff, P. Benfield, and J. P. Monk, Drugs, 36, 132 (1988); b) G. N. J. Tytget, "Digestion, Suppl. 2," 1987, p. 31; c) J. P. Miller and E. B. Faragher, Br. Med. J., 293, 1117 (1986); d) A. T. R. Axon, Br. Med. J., 293, 772 (1986); e) C. S. Goodwin, J. A. Armstrong, and B. J. Marshall, J. Clin. Pathol., 39, 353 (1986); f) G. N. J. Tytget, Afr. Med. J., 70, 31 (1986); g) B. J. Marshall, J. Infect. Dis., 53, 650 (1986); h) R. Pickard, Proc. Cairo, 1985, 55; i) K. Vogt, M. Warrelmann, and H. Hahn, Zentralbl. Bakteriol., Abt. 1, Orig. A, 273, 33 (1990).
9. For examples: a) A. J. Wagstaff, P. Benfield, and J. P. Monk, Drugs, 36, 132 (1988); b) G. N. J. Tytget, "Digestion, Suppl. 2," 1987, p. 31; c) J. P. Miller and E. B. Faragher, Br. Med. J., 293, 1117 (1986); d) A. T. R. Axon, Br. Med. J., 293, 772 (1986); e) C. S. Goodwin, J. A. Armstrong, and B. J. Marshall, J. Clin. Pathol., 39, 353 (1986); f) G. N. J. Tytget, Afr. Med. J., 70, 31 (1986); g) B. J. Marshall, J. Infect. Dis., 53, 650 (1986); h) R. Pickard, Proc. Cairo, 1985, 55; i) K. Vogt, M. Warrelmann, and H. Hahn, Zentralbl. Bakteriol., Abt. 1, Orig. A, 273, 33 (1990).
10. For examples: a) A. J. Wagstaff, P. Benfield, and J. P. Monk, Drugs, 36, 132 (1988); b) G. N. J. Tytget, "Digestion, Suppl. 2," 1987, p. 31; c) J. P. Miller and E. B. Faragher, Br. Med. J., 293, 1117 (1986); d) A. T. R. Axon, Br. Med. J., 293, 772 (1986); e) C. S. Goodwin, J. A. Armstrong, and B. J. Marshall, J. Clin. Pathol., 39, 353 (1986); f) G. N. J. Tytget, Afr. Med. J., 70, 31 (1986); g) B. J. Marshall, J. Infect. Dis., 53, 650 (1986); h) R. Pickard, Proc. Cairo, 1985, 55; i) K. Vogt, M. Warrelmann, and H. Hahn, Zentralbl. Bakteriol., Abt. 1, Orig. A, 273, 33 (1990).
11. For examples: a) A. J. Wagstaff, P. Benfield, and J. P. Monk, Drugs, 36, 132 (1988); b) G. N. J. Tytget, "Digestion, Suppl. 2," 1987, p. 31; c) J. P. Miller and E. B. Faragher, Br. Med. J., 293, 1117 (1986); d) A. T. R. Axon, Br. Med. J., 293, 772 (1986); e) C. S. Goodwin, J. A. Armstrong, and B. J. Marshall, J. Clin. Pathol., 39, 353 (1986); f) G. N. J. Tytget, Afr. Med. J., 70, 31 (1986); g) B. J. Marshall, J. Infect. Dis., 53, 650 (1986); h) R. Pickard, Proc. Cairo, 1985, 55; i) K. Vogt, M. Warrelmann, and H. Hahn, Zentralbl. Bakteriol., Abt. 1, Orig. A, 273, 33 (1990).
12. For examples: a) A. J. Wagstaff, P. Benfield, and J. P. Monk, Drugs, 36, 132 (1988); b) G. N. J. Tytget, "Digestion, Suppl. 2," 1987, p. 31; c) J. P. Miller and E. B. Faragher, Br. Med. J., 293, 1117 (1986); d) A. T. R. Axon, Br. Med. J., 293, 772 (1986); e) C. S. Goodwin, J. A. Armstrong, and B. J. Marshall, J. Clin. Pathol., 39, 353 (1986); f) G. N. J. Tytget, Afr. Med. J., 70, 31 (1986); g) B. J. Marshall, J. Infect. Dis., 53, 650 (1986); h) R. Pickard, Proc. Cairo, 1985, 55; i) K. Vogt, M. Warrelmann, and H. Hahn, Zentralbl. Bakteriol., Abt. 1, Orig. A, 273, 33 (1990).
13. For examples: a) A. J. Wagstaff, P. Benfield, and J. P. Monk, Drugs, 36, 132 (1988); b) G. N. J. Tytget, "Digestion, Suppl. 2," 1987, p. 31; c) J. P. Miller and E. B. Faragher, Br. Med. J., 293, 1117 (1986); d) A. T. R. Axon, Br. Med. J., 293, 772 (1986); e) C. S. Goodwin, J. A. Armstrong, and B. J. Marshall, J. Clin. Pathol., 39, 353 (1986); f) G. N. J. Tytget, Afr. Med. J., 70, 31 (1986); g) B. J. Marshall, J. Infect. Dis., 53, 650 (1986); h) R. Pickard, Proc. Cairo, 1985, 55; i) K. Vogt, M. Warrelmann, and H. Hahn, Zentralbl. Bakteriol., Abt. 1, Orig. A, 273, 33 (1990).
14. E. Asato, W. L. Driessen, R. A. G. De Graaff, F. B. Hulsbergen, and J. Reedijk, Inorg. Chem., 30, 4210 (1991).
15. E. Asato, C. M. Hol, F. B. Hulsbergen, N. T. M. Klooster, and J. Reedijk, Inorg. Chim. Acta, 214, 159 (1993).
16. E. Asato, K. Katsura, M. Mikuriya, T. Fujii, and J. Reedijk, Inorg. Chem., 32, 5322 (1993).
17. E. Asato, K. Katsura, M. Mikuriya, U. Turpeinen, I. Mutikainen, and J. Reedijk, Inorg. Chem., 34, 2447 (1995).
18. W. A. Herrmann, E. Herdtweck, and L. Pajdla, Inorg. Chem., 30, 2579 (1991).
19. W. A. Herrmann, E. Herdtweck, and L. Pajdla, Z. Kristallogr., 198, 257 (1992).
20. S. P. Summers, K. A. Abboud, S. R. Farrah, and G. J. Palenik, Inorg. Chem., 33, 88 (1944).
21. a) C. A. M. McNulty, J. Dent, and R. Wise, Antimicrob. Agents Chemother., 28, 837 (1985);
22. b) G. N. J. Tytgat, E. Rauws, and M. L. Langenberg, Scand. J. Gastroenterol., 21, 22 (1986);
23. c) K. Berstad and A. Berstad, Scand. J. Gastroenterol., 28, 561 (1993).
24. a) J. R. Warren and B. J. Marshall, Lancet, I, 1273 (1983);
25. b) J. R. Warren and B. J. Marshall, Lancet, I, 1311 (1984);
26. c) H. J. O'Connor, J. L. Wyatt, M. F. Dixton, and A. T. R. Axon, J. Clin. Pathol., 35, 531 (1986);
27. d) M. L. Langenberg, G. N. J. Tyget, M. E. I. Schipper, P. J. G. M. Rietra, and H. C. Zanen, Lancet, I, 1348 (1984);
28. e) J. Berkowicz and A. Lee, Lancet, II, 680 (1987).
29. H. L. T. Mobley, L.-T. Hu, and P. A. Foxall, Scand. J. Gastroenterol., Suppl., 26, 39 (1991).
30. A. T. R. Axon, Scand. J. Gastroenterol., Suppl., 31, 47 (1996).
31. a) J. E. F. Reynolds, "Martindale, The Extra Pharmacopoeia," 20 th ed, The Pharmaceutical Press, London (1982);
32. b) M. D. Manhart, Rev. Infect. Dis., 12, S11 (1990).
33. E. Bayerdorffer and R. Ottenjann, Scand. J. Gastroenterol., 23, 93 (1988), and references cited therein.
34. E. Asato, K. Katsura, T. Arakaki, M. Mikuriya, and T. Kotera, Chem. Lett., 1994, 2123.
35. H. L. T. Mobley and R. P. Housinger, Microbiol. Rev., 53, 85 (1989).
36. a) M. J. Todd and P. R. Housinger, J. Biol. Chem., 264, 15835 (1989);
37. b) N. E. Dixon, R. L. Blakeley, and B. Zerner, Can. J. Biochem., 58, 481 (1980);
38. c) R. L. Blakeley, N. E. Dixon, and B. Zerner, Biochim. Biophys. Acta, 744, 219 (1983);
39. d) P. A. Clark and N. E. Dixon, Inorg. Chem., 28, 1326 (1989);
40. e) P. A. Clark, D. E. Wilcox, and R. A. Scott, Inorg. Chem., 29, 579 (1990).
41. I. G. Dance, R. G. Garbutt, and D. C. Craig, Inorg. Chem., 26, 3732 (1987).
42. A closely related Bi complex having the same stoichiometry (Bi : ligand : perchlorate ion=1 : 2 : 1) has been reported in the reference: G. E. Jackson and R. D. Hancock, Polyhedron, 3, 71 (1984). Although these authors carried out an X-ray structural analysis for the complex, no structural detail was described in the reference.
43. C. K. Fair, "MolEN Structure Determination System," Delft Instruments, Delft, The Netherlands (1990).
44. E. Asato, T. Arakaki, M. Mikuriya, and T. Fujii, unpublished result. Its structural information is available from the author E. A.
45. H. Wullens, M. Devillers, B. Tinant, and J.-P. Declercq, J. Chem. Soc., Dalton Trans., 1996, 2023.
46. a) R. D. Rogers, A. H. Bond, and S. Aguinaga, J. Am. Chem. Soc., 114, 2960 (1992);
47. b) R. D. Rogers, A. H. Bond, S. Aguinaga, and A. Reyes, J. Am. Chem. Soc., 114, 2967 (1992).
48. N. W. Alcock, in "Advances in Inorganic Chemistry and Radiochemistry," ed by H. J. Emeleus and A. G. Sharpe, Academic Press, New York (1972), pp. 1-58.
49. E. Block, G. Ofori-Okai, H. Kang, J. Wu, and J. Zubieta, Inorg. Chem., 30, 4784 (1991).
50. D. A. Atwood, A. H. Cowley, R. D. Hernandez, , R. A. Jones, L. L. Rand, S. G. Bott, and J. L. Atwood, Inorg. Chem., 32, 2972 (1993).
51. C. L. Raston and A. H. White, J. Chem. Soc., Dalton Trans., 1976, 791.
52. Estimated from values in the reference: A. F. Wells, "Structural Inorganic Chemistry," Clarendon Press, Oxford, England (1982).
53. W. J. Geary, Coord. Chem. Rev., 7, 81 (1971).