Structure, chemical and photochemical reactivity and biological activity of some ruthenium amine nitrosyl complexes

Coordination Chemistry Reviews

Volumn 236, Issue 1-2, 2003, Pages 57-69

  Tfouni, Elia ^a   Krieger, Marta ^b   McGarvey, Bruce R ^c   Franco, Douglas W ^a  

^a UNIVERSITY OF SÃO PAULO   (Brazil)

^b UNIVERSITY OF CAMPINAS   (Brazil)

^c UNIVERSITY OF WINDSOR   (Canada)

Author keywords

Biological activity; Chemical and photochemical reactivity; Nitric oxide donors; Nitric oxide scavengers; Ruthenium amine and ruthenium ammine nitrosyl complexes

Indexed keywords

AMINE; ANTIHYPERTENSIVE AGENT; COORDINATION COMPOUND; METAL COMPLEX; NITRIC OXIDE; RUTHENIUM DERIVATIVE;

ACIDITY; ANIMAL CELL; ANTIHYPERTENSIVE ACTIVITY; CALCULATION; COMPLEX FORMATION; CYCLIC POTENTIOMETRY; DIFFERENTIAL PULSE POLAROGRAPHY; DISSOCIATION; DRUG EFFECT; DRUG STRUCTURE; DRUG SYNTHESIS; ELECTROCHEMISTRY; ELECTRON SPIN RESONANCE; HYPERTENSION; INFRARED SPECTROSCOPY; ISOMER; LOW TEMPERATURE; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; OXIDATION REDUCTION REACTION; PHOTOCHEMISTRY; PROTON NUCLEAR MAGNETIC RESONANCE; QUANTUM MECHANICS; RAT; REVIEW; SOLID STATE; STRUCTURE ACTIVITY RELATION; STRUCTURE ANALYSIS; ULTRAVIOLET SPECTROSCOPY; X RAY ANALYSIS;

EID: 0037264316     PISSN: 00108545     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0010-8545(02)00177-7     Document Type: Review

References (129)

1. (a) G.B. Richter-Addo, P. Legzdins, Metal Nytrosyls (and references therein), Oxford University Press, New York, 1992;
2. (b) F. Bottomley, in: P.S. Braterman (Ed.), Reactions of Coordinated Ligands, vol. 2 (references therein), Plenum Press, New York, 1989;
3. (c) J.H. Enemark, R.D. Feltham, Chem. Rev. 13 (1974) 339;
4. (d) A.F. Schreiner, P.J. Hauser, J.W. Lin, E.A. Hopcus, D.J. Hamm, J.B. Gunter, Inorg. Chem. 11 (1972) 880;
5. (e) J.N. Armor, M.Z. Hoffman, Inorg. Chem. 13 (1974) 339;
6. (f) D.W. Pipes, T.J. Meyer, Inorg. Chem. 23 (1984) 2466;
7. (g) J.H. Swinehart, W.G. Schmidt, Inorg. Chem. 6 (1967) 232;
8. (h) V.S. Ozkon, U.S. Agarwal, S.W. Marcelin (Eds.), Reduction of Nitrogen Oxide Emissions; ACS Symposium Series 587, American Chemical Society, Washington, DC, 1995.
9. (a) R.M.J. Palmer, D.S. Ashtom, S. Moncada, Nature (1998) 326;
10. (b) M. Marletta, P.S. Yoan, R. Ivengar, J.S. Wishnok, Biochemistry 27 (1988) 8706;
11. (c) S. Waldman, F. Murad, Pharm. Rev. 39 (1987) 163;
12. (d) D.E. Koshland, Jr., Science 258 (1992) 1861;
13. (e) L.J. Ignarro, G.M. Burga, K.S. Wood, R.E. Byrns, G. Chaudhuri, Proc. Natl. Acad. Sci. USA 84 (1987) 9265;
14. (f) M. Feelisch, J.S. Stamler (Eds.), Methods in Nitric Oxide Research, Wiley, Dorset, UK, 1996;
15. (g) L.J. Ignarro (Eds.), Nitric Oxide Biology and Pathology, Academic Press, San Diego, USA, 2000;
16. (h) J. Lancaster, Jr. (Eds.), Nitric Oxide, Principles and Actions, Academic Press, San Diego, USA, 1996.
17. (a) P.C. Ford, D.A. Wink, D.M. Stanbury, FEBS Lett. 326 (1993) 1;
18. (b) M. Hoshino, L. Laverman, P.C. Ford, Coord. Chem. Rev. 187 (1999) 75 (and references therein);
19. (c) M.J. Clarke, J.B. Gaul, Struct. Bonding 81 (1993) 147;
20. (d) P.J. Sadler, Adv. Inorg. Chem. 36 (1991) 1;
21. (e) N.A. Davies, M.T. Wilson, E. Slade, S.P. Fricker, B.A. Murrer, N.A. Powell, R. Henderson, Chem. Commun. (1997) 47;
22. (f) A.R. Butler, D.L.H. Williams, Chem. Soc. Rev. 233 (1993);
23. (g) Y. Chen, F.T. Lin, R.E. Shepherd, Inorg. Chem. 38 (1999) 973;
24. (h) Y. Chen, R. Shepherd, J. Inorg. Biochem. 68 (1997) 18;
25. (i) L.M. Baraldo, M.S. Bessega, G.E. Rigotti, J.A. Olabe, Inorg. Chem. 33 (1991) 5890;
26. (j) E. Walldhor, W. Kaim, J.A. Olabe, L.D. Slep, J. Fiedler, Inorg. Chem. 36 (1997) 2969;
27. (k) D. Jourd'heuil, K.M. Miranda, S.M. Kim, M.G. Espey, Y. Vodovotz, S. Laroux, C.T. Mai, A.M. Miles, M.B. Grisham, D.A. Wink, Arch. Biochem. Biophys. 365 (1999) 92;
28. (l) I.A Bagatin, H.E. Toma, Spectrosc. Lett. 29 (1996) 1409;
29. (m) J.F. Kervin, Jr., J.R. Lancaster, Jr., P.L. Feldman, J. Med. Chem. 38 (1995) 4333;
30. (n) J.C. Toledo, Jr., L.G.F. Lopes, A.A. Alves, L.P. de Silva, D.W. Franco, J. Inorg. Biochem. 89 (2002) 267;
31. (o) M. Feelisch, J. Cardiovasc. Pharmacol. 17 (1991) 525;
32. (p) C.S. Allardyce, P.J. Dyson, Plat. Met. Rev. 45 (2001) 62.
33. (a) M.G. Gomes, C.V. Davanzo, S.C. da Silva, L.G.F. Lopes, P.S. Santos, D.W. Franco, J. Chem. Soc. Dalton Trans. (1998) 601;
34. (b) S.S.S. Borges, C.V. Davanzo, E.E. Castellano, J.Z. Schpector, S.C. Silva, D.W. Franco, Inorg. Chem. 37 (1998) 2670;
35. (c) L.G.F. Lopes, M.G. Gomes, S.S.S. Borges, D.W. Franco, Aust. J. Chem. 51 (1998) 865;
36. (d) S.S. Silva, D.W. Franco, Spectrochim. Acta A 55 (1999) 1515;
37. (e) M.G. Gomes, S.S.S. Borges, D.W. Franco, An. Assoc. Bras. Quim. 47 (1998) 154;
38. (f) C.W.B. Bezerra, S.C. Silva, M.T.P. Gambardella, R.H.A Santos, E. Tfouni, D.W. Franco, Inorg. Chem. 38 (1999) 5660;
39. (g) L. Lang, J. Davis, L.G.F. Lopes, A.A. Ferro, L.C.G. Vasconcellos, A. Prock, D.W. Franco, E. Tfouni, A Wierasko, M.J. Clarke, Inorg. Chem. 39 (2000) 2394;
40. (h) B.R. MacGarvey, A.A Ferro, E. Tfouni, C.W. Bezerra, I. Bagatin, D.W. Franco, Inorg. Chem. 39 (2000) 3577;
41. (i) S.I. Gorelsky, S. Silva, A.B.P. Lever, D.W. Franco, Inorg. Chim. Acta 300-302 (2000) 698;
42. (j) I.A. Bagatin, A. Magalhães, A.G. Ferreira, D.W. Franco, Inorg. Chim. Acta 333 (2002) 109;
43. (k) A.P.B. Guidorzi, L.G.F. Lopes, D.W. Franco, 20a Reunião Anual da Sociedade Brasileira de Química, Poços de Caldas, MG, 1997. This was wrongly cited in reference [4h];
44. (l) M.G. Gomes, S.S.S. Borges, A.A. Ferro, H.A. Silva, E. Tfouni, P.C. Ford, S. Borges, D.W. Franco, M.C. Rose, manuscript in preparation;
45. (m) A. Wierasko, M.J. Clarke, D.R. Lang, L.G. Lopes, D.W. Franco, Life Sci. 68 (2001) 1535;
46. (n) L.G.F. Lopes, A. Wieraszko, E.E. Castellano, J.Z. Schpector, A.G. Ferreira, C.V. Davanzo, M.J. Clarke, D.W. Franco, manuscript in preparation;
47. (o) J.C. Toledo Jr., L.P. da Silva, D.W Franco, J. Inorg. Biochem. 000 (2002);
48. (p) J.C. Toledo Jr., H.A. dos Santos, V. Mori, M. Bertotti, D.W. Franco, manuscript in preparation;
49. (q) E.E. Castellano, R.Z. Osti, D.W. Franco, manuscript in preparation.
50. (a) P.C. Ford, Coord. Chem. Rev. 5 (1970) 75;
51. (b) H. Taube, Pure Appl. Chem. 51 (1979) 901 (and references therein);
52. (c) H. Taube, Comments Inorg. Chem. 1 (1981) 17;
53. (d) H. Taube, Surv. Prog. Chem. (1973) 1;
54. (e) D.W. Franco, Coord. Chem. Rev. 119 (1992) 199;
55. (f) R.S. Silva, M.T.P. Gambardella, R.H.A. Santos, B.E. Mann, E. Tfouni, Inorg. Chim. Acta 245 (1996) 215 (and references therein).
56. (a) E.S. Dodsworth, A.A. Vleck, A.B.P. Lever, Inorg. Chem. 33 (1994) 1045;
57. (b) A.B.P. Lever, Inorg. Chem. 29 (1990) 1271.
58. J. Mastone, J. Armor, J. Inorg. Nucl. Chem. 37 (1975) 473.
59. R. Brambley, B.N. Figgis, R.S. Nyholm, J. Chem. Soc. A (1967) 861.
60. L.K. Bell, J. Mason, D.M. Mingos, D.W. Tew, Inorg. Chem. 22 (1983) 3497.
61. C.W.B. Bezerra, B.R. McGarvey, D.W. Franco, work in progress.
62. J. Bordini, D.L. Hughes, J.D. Da Motta Neto, C.G.Cunha, Inorg. Chem., in press.
63. (a) F.J. Bottomley, J. Chem. Soc. Dalton Trans. (1974) 1600;
64. (b) J.F. Bottomley, J. Chem Soc. Dalton Trans (1972) 2148.
65. H.A. Santos, R.A. Santos, C.M.C. Picchi, D.W. Franco, manuscript in preparation.
66. (a) J.T. Veal, D.J. Hogdson, Inorg. Chem. 11 (1972) 1420;
67. (b) H. Nagao, H. Nishimura, H. Funato, Y. Ichikmura, F.S. Howell, M. Mukaida, H. Kakihano, Inorg. Chem. 28 (1989) 3955;
68. (c) M.M. Taqui Khan, K. Venkata-Subramarian, Z. Shirim, M.M. Bhaadhada, J. Chem Soc. Dalton Trans. (1992) 1031;
69. (d) C.K. Prout, H.M. Powell, J. Chem. Soc. (1962) 137.
70. (a) G.M. Coleman, J.W. Gesler, F.A. Shirley, J.R Kuempel, Inorg. Chem. 12 (1973) 1036;
71. (b) H.S. Lim, D.J. Baclay, F. Anson, Inorg. Chem. 11 (1972) 1460.
72. C. Kuehn, H. Taube, J. Am. Chem. Soc. 98 (1976) 689.
73. L.G.F. Lopes, A. Nieraszko, Y. El-Sherif, M.J. Clarke, Inorg. Chim. Acta 312 (2001) 15.
74. M.F. Tweedle, H. Taube, Inorg. Chem. 21 (1982) 3361.
75. (a) K. Gleu, W. Brewel, K.Z. Rehm, Anorg. Allg. Chem. 235 (1938) 201;
76. (b) L.H. Vogt, J.L. Katz, S.E. Wiberley, Inorg. Chem. 4 (1965) 1157.
77. S.S. Isied, H. Taube, Inorg. Chem. 13 (1974) 1545.
78. E. Tfouni, Coord. Chem. Rev. 196 (2000) 281.
79. P.C. Ford, R.E. Hintze, J.D. Petersen, in: A.W. Adamson, P.D. Fleischauer (Eds.), Concepts of Inorganic Photochemistry (Chapter 5), Wiley, New York, 1975.
80. P.C. Ford, D.F.P. Rudd, R. Gaunder, H. Taube, J. Am. Chem. Soc. 150 (1968) 1187.
81. (a) P.C. Ford, J.D. Petersen, R.E. Hintze, Coord. Chem. Rev. 14 (1974) 67;
82. (b) P.C. Ford, G. Malouf, J.D. Petersen, V.A. Durante, ACS Adv. Chem. 150 (1976) 187;
83. (c) P.C. Ford, ACS Adv. Chem. 168 (1978) 73;
84. (d) P.C. Ford, Rev. Chem. Interm. 2 (1979) 267;
85. (e) P.C. Ford, D. Wink, J. Dibenedetto, Prog. Inorg. Chem. 30 (1983) 213.
86. (a) R.S. Silva, E. Tfouni, Inorg. Chem. 31 (1992) 3313;
87. (b) M.L. Bento, E. Tfouni, Inorg. Chem. 27 (1988) 3410;
88. (c) M.L. Bento, D.Sc. Thesis, Instituto de Quimica, UNESP, Araraquara, SP, Brazil, 1993;
89. (d) M.L. Bento, S.I. Klein, E. Tfouni, manuscript in preparation.
90. R.E. Hintze, P.C. Ford, J. Am. Chem. Soc. 97 (1975) 2664.
91. (a) D.W. Franco, H. Taube, Inorg. Chem. 17 (1978) 571;
92. (b) J.C. Nascimento Filho, J.M. Rezende, B.S. Lima Neto, D.W. Franco, Inorg. Chim. Acta 145 (1988) 111;
93. (c) R.L. Sernaglia, D.W. Franco, Inorg. Chem. 28 (1989) 3485;
94. (d) D.W. Franco, Inorg. Chim. Acta 48 (1981) 1;
95. (e) D.W. Franco, Coord. Chem. Rev. 119 (1992) 199.
96. S.E. Mazzetto, E. Tfouni, D.W. Franco, Inorg. Chem. 35 (1996) 3513.
97. S.E. Mazzetto, L.M.A. Plicas, E. Tfouni, D.W. Franco, Inorg. Chem. 31 (1992) 516.
98. P.T. Manoharan, H.B. Gray, J. Am. Chem. Soc. 87 (1965) 3340.
99. P.T. Manoharan, H.B. Gray, Inorg. Chem. 5 (1966) 823.
100. (a) G. Malouf, P.C. Ford, J. Am. Chem. Soc. 99 (1977) 7213;
101. (b) G. Malouf, Ph.D. Thesis, University of California, Santa Barbara, CA, USA, 1977.
102. A.A. Ferro, D.Sc Thesis, Departamento de Química, Faculdade de Filosofia, Ciências e Letras de Ribeirão Preto, Universidade de São Paulo, Ribeirão Preto, SP, Brazil, 2000.
103. (a) M.A. DeLeo, P.C. Ford, Coord. Chem. Rev. 208 (2000) 47;
104. (b) J.L. Bourassa, P.C. Ford, Coord. Chem. Rev. 200 (2000) 887;
105. (c) C.F. Works, P.C. Ford, J. Am. Chem. Soc. 122 (2000) 7592;
106. (d) N. Bettache, T. Carter, J.E.T. Corrie, D. Ogden, D.R. Trentham, Meth. Enzym. 268 (1996) 266;
107. (e) K. Szacilowski, W. Macyk, G. Stochel, Z. Stasicka, S. Sostero, O. Traverso, Coord. Chem. Rev. 208 (2000) 277;
108. (f) M.G. DeOliveira, G.J. Langley, A.J. Rest, J. Chem. Soc. Dalton (1995) 2013;
109. (g) W.I.K. Bisset, M.G. Burdon, A.R. Butler, C. Glidwell, J. Reglinski, J. Chem. Res. (1981) 299;
110. (h) S.K. Wolfe, J.H. Swinehart, Inorg. Chem. 14 (1975) 1049;
111. (i) J. Sykora, J. Sima, Coord. Chem. Rev. 107 (1990) 1;
112. (j) E.A. Seddon, K.R. Seddon, The Chemistry of Ruthenium, Elsevier, Amsterdam, 1984.
113. (a) U. Hauser, V. Oestreich, H.D. Rohrewck, Z. Phys. A280 (1977) 17;
114. (b) T. Woike, H. Zöllner, W. Krasser, S. Haussühl, Solid State Commun. 73 (1990) 149;
115. (c) J.A. Guida, O.K. Piro, P.J. Aymonino, Solid State Commun. 57 (1986) 175;
116. (d) D.V. Fomitchev, P. Coppens, Inorg. Chem. 35 (1996) 7021;
117. (e) H. Zöllner, T. Woike, W. Krasser, S. Haussühl, J. Chem. Phys. Lett. 161 (1989) 497;
118. (f) T. Woike, W. Krasser, P.S. Bechthold, S. Haussühl, Phys. Rev. Lett. 53 (1984) 1767;
119. (g) M. Kawano, A. Ishikawa, Y. Morioka, H. Tomigawa, E. Miki, Y. Ohashi, J. Chem. Soc. Dalton 2425 (2000);
120. (h) Y. Morioka, A. Ishikawa, H. Tomigawa, E. Miki, J. Chem. Soc. Dalton (2000) 781.
121. (a) D.V. Fomitchev, I. Novozhilova, P. Coppens, Tetrahedron 56 (2000) 6813;
122. (b) C. Kim, I. Novozhilova, M.S. Goodman, K.A. Bagley, P. Coppens, Inorg. Chem. 39 (2000) 5791.
123. S.I. Gorelsky, A.B.P. Lever, Intern. J. Quant. Chem. 80 (2000) 636.
124. A.B. Nikolski, V.Y. Kotov, Vestn. Lenin U. Fiz. Kh. 3 (1986) 54.
125. A.S. Torsoni, B.F. Barros, J.C. Toledo Jr., M. Haun, M.H. Krieger, E. Tfouni, D.W. Franco, Nitric Oxide 6 (2002) 247. In this reference, the correct concentrations in p3 and table 1 are μmol/kg and not mol/kg.
126. F.G. Marcondes, A.A. Ferro, A. Souza-Torsoni, M. Sumitani, M.J. Clarke, D.W. Franco, E. Tfouni, M.H. Krieger, Life Sci. 70 (2002) 2735.
127. B. Mayer, F. Brunner, X. Schmidt, Biochem. Pharmacol. 45 (1993) 367.
128. T. Akaike, M. Yoshida, Y. Miyamoto, K. Sato, M. Kohno, K. Sasamoto, K. Miyazaki, S. Ueda, H. Maeda, Biochemistry 32 (1993) 827.
129. E.A. Kowaluk, P. Seth, H-L. Fung, J. Pharm. Exp. Ther. 262 (1992) 916.